30+ Fun Things to Do in Chicago Alone for First-Timers + FREE Map

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So… you’re either interested in visiting Chicago or have already started planning your first trip and need help finding things to do.

Lucky for you, I’ve been five times already and, let me say, Chicago is my favorite city so far. I live in southern Illinois, just five hours of Chicago, so it’s easy to take the Amtrak and spend a few days there.

If you’ve done even just a tiny bit of planning, I can already sense how you might feel. There’s TONS to do and it can feel paralyzing deciding what to prioritize for your first trip.

But that’s where I can step in!

As a frequent visitor who has been there every season besides winter (NOT a fan of cold weather), I’ve created the perfect list of things to do in Chicago as a solo traveler. I tried not to list every possible activity because, let’s face it, you can only do so much in a few days.

I also made sure to group everything by neighborhood and include important details like pricing, opening hours, travel tips, and other decision-making tools to save you the extra time and headache of figuring out the logistics.

Alrighty. Ready, friend? Let’s travel to Chicago! (I must warn you, this is a LONG one)

THIS POST IS ALL ABOUT THINGS TO DO IN CHICAGO.

FREE INTERACTIVE CHICAGO MAP

Below you’ll find a free interactive Chicago map including all of the activities mentioned in this post (plus a TON more). Feel free to use it to plan your trip. I made sure to categorize everything by activity type to keep things neat.

HOW TO USE THIS MAP: this is an interactive map, meaning you can use two fingers to zoom in, zoom out and click on each pinned location for more information. I assigned each pin as a color to match its activity type. To view a larger map, simply click on the box in the righthand corner.

THINGS TO DO IN CHICAGO ALONE (BY NEIGHBORHOOD)

THINGS TO DO IN THE LOOP

EXPLORE MILLENNIUM PARK

A park full of art, greenery, and fun budget-friendly activities.

If you’ve done any research before finding this post, I’m almost certain you discovered a place called Millennium Park. It’s one of the most touristy areas in the city, but I think it’s worth visiting at least once.

There are several things to do and see, including:

Cloud Gate (The Bean): you’ve seen it in every Chicago photo and itinerary. While it just looks like this large, stainless steel bean, there’s more to it.

The Bean is British artist Anish Kapoor’s first public outdoor work installed in the United States. The iconic city’s skyline and clouds are reflected on the sculpture, and you can walk underneath.

That gives it the name, “Cloud Gate.” Pretty clever, eh?

Try to visit The Bean early in the morning, around 8-9AM. There won’t be as many people there, so you’ll be able to take photos without hundreds of people surrounding.

Crown Fountain: this fountain with two 50-foot video screens on each side was designed by Spanish artist Jaume Plensa.

There are holes in the towers that eject water every few minutes. The citizens projected onto the screens are real Chicago residents, which I think is neat touch.

You’ll often find kids splashing in the water and having the time of their lives. You’re never too cool or old, so join in on the fun!

If not, though, you can sit on one of the long benches and take in the scenery. I think this is a nice place to decompress for a bit.

Lurie Garden: Millennium Park’s “secret garden,” this is a beautiful place to slow down, unwind, and reflect.

Here, you’ll find all kinds of plants, including grasses, shrubs and trees. Lurie Garden is free, so it’s the perfect activity for us budget travelers.

McCormick Tribune Park: a free outdoor ice skating rank open from mid-November to mid-March.

If you don’t know how to ice skate, no worries! Free ice-skating lessons provided by the Chicago Youth Foundation are available from 9-10AM on Saturdays and Sundays for skaters of any age. Skate rental is free for the lessons.

Millennium Monument: a neoclassical colonnade that honors the 115 donors who helped fund the creation of Millennium Park. It’s a great spot to snap some photos and take in some of the park’s history.

Jay Pritzker Pavilion: various events and festivals happen at this pavilion throughout the year.

Many of them are free, making them perfect for budget travelers. Check out some of the events below.

Millennium Park Summer Film Series: an ongoing summer event where visitors and residents can gather at Jay Pritzker Pavilion and watch free movies.

The event is held every summer on Tuesdays, and the movies begin in the evening.

Some of the 2026 showings include Ratatouille, Hamilton, The Lord of the Rings, The Devil Wears Prada, and Sinner. As you can see, these aren’t random movies — they’re actually worth seeing!

If you’re visiting Chicago in the summertime, I highly recommend doing this. Bring a blanket and some snacks, and enjoy a free movie!

Be sure to arrive early, as space fills quickly. I’m currently here to see Ratatouille and ended up choosing a seat closer to the stage.

Visit Chicago’s official tourism website here for more information.

Millennium Park Summer Music Series: similar to the film series, this annual event hosts free outdoor concerts in Chicago on select Mondays and Thursdays.

If you’re anything like me, you love a good concert, and the idea of a FREE one? It can’t get better than that!

Click here for more information on these free outdoor concerts.

Millennium Park Summer Workouts: happening in Great Lawn and Wrigley Square, this is a free series of workouts on Saturdays from May to September.

During each session, you’ll engage in different 45-minute workouts like pilates, yoga, cardio kickboxing and Zumba.

Even if you aren’t interested in fitness, I think this could be a cheap, community-oriented way to get your body moving and burn off some calories from those delicious Chicago-style dogs.

Just be sure to bring your own workout mat and get there about 20-30 minutes early to secure a good spot.

And if you miss a session, don’t worry — there’s usually at least two each day!

Click here for more information on these free weekly workouts.

Bet you didn’t know all that, did you? You can easily spend a few hours in Millennium Park if you visit on the right day during the right season.

LOGISTICAL TIPS FOR MILLENNIUM PARK:

• Time Needed: 20 minutes to a few hours
• Pair With: The Art Institute of Chicago
• Other Tips:
  • Arrive early for a good spot and to give yourself enough time to set up.
  • Millennium Park is located in Grant Park, a larger area within Chicago’s Loop neighborhood. Consider visiting nearby parks and attractions like Maggie Daley Park and the Museum Campus.
  • Check the Do312 website for upcoming events and happenings at Millennium Park before your visit.There’s tons of things to enjoy during spring and summer.

SPEND A FEW HOURS AT THE ART INSTITUTE OF CHICAGO

A world-class art museum full of awe-inspiring galleries and exhibits from popular artists.

The Art Institute of Chicago is one of the largest, best art museums in America.

Here, you’ll find pieces like:

• The Shadow of Death by William Holman Hunt
• The Golden Age by Edward John Poynter
• The Bedroom by Vincent van Gogh
• Water Lillies by Claude Monet

I visited in October 2025 during a quick trip there with my brother. I was stunned by how amazing the art looked, which is really saying something since I wasn’t a huge fan of art museums at the time.

We spent two hours there, but I still felt like that wasn’t enough. Next time, I’ll probably budget around three hours to spend at the museum.

I bought individual tickets since we didn’t plan on doing anything in the CityPASS or Go City Chicago attraction passes.

If you’re interested in those other activities, though, I think it’s a great idea to get one and save money.

Consider using my Attraction Pass Decision Tool in my resource library to make sure you get the best deal.

Even if you don’t care for art or large museums, I still think it’s worth checking out The Art Institute — at least a quick sweep to see the major works.

Consider joining a guided tour like this 2.5-hour tour on Viator for a more structured visit.

It does cost around $84 and typically has only one time slot, but I think it’s worth it for a museum of this caliber.

If not, though, you can buy a general admission ticket for around $32. Please keep in mind the museum is NOT open on Tuesdays.

The museum is open until 8PM on Thursdays, which is perfect if you want to avoid the early-morning crowds.

LOGISTICAL TIPS FOR THE ART INSTITUTE:

• Admission Cost: around $32 for a general admission ticket
• Time Needed: 1-5 hours
• Pair With: Millennium Park
• Budget Tip: Buy an attraction pass like CityPASS or Go City Chicago to save money on bundled activities. Use my Attraction Comparison Tool to ensure you’re getting the best deal.
• Get Tickets Here

SEE THE BUCKINGHAM FOUNTAIN

A large fountain in Grant Park, dedicated by a sister to her art-collector brother.

Just a 14-minute walk west of Millennium Park, the Clarence F. Buckingham Memorial Fountain was donated to Chicago by philanthropist Kate Buckingham in memory of her brother, Clarence, who collected art.

French sculptor Marcel Francois Loyau sculpted the fountain, which opened to the public on May 26, 1927.

The Fountain is typically open from May to mid-October, depending on weather, so as long as you’re visiting during those seasons, you should be able to see it in action.

The “action” in question?

Every hour starting at 9AM, you’ll see a beautiful water display where a center jet shoots water 150 feet in the air. The display lasts twenty seconds and happens every hour until the last show at 10:35PM.

This is great if you have nearby activities planned and don’t want to miss the display.

LOGISTICAL TIPS FOR THE BUCKINGHAM FOUNTAIN:

• Best Time to Visit: after sunset
• Time Needed: 25-30 minutes
• Pair With: Millennium Park, The Art Institute of Chicago
• Timing Tip: be sure to get to the Fountain about 5-10 minutes early to watch the full 20-minute show. For example, arrive at 4:50PM for the 5PM display.

CHECK OUT THE CHICAGO CULTURAL CENTER

A free landmark building featuring the world’s largest stained-glass Tiffany dome, music events, art exhibitions, and more.

Right in the same area as The Art Institute and Millennium Park, the Chicago Cultural Center is a landmark building with two iconic Tiffany stained-glass domes.

Throughout the year, you can attend all kinds of events, from concerts to art exhibitions.

As the city’s first central public library, the center was designed by the Boston architectural firm Shepley, Rutan & Coolidge.

This building is nicknamed The People’s Palace because it’s a large, palace-like space for all residents and visitors to enjoy, free of charge.

It was designed to prove that Chicago had become a real, structured metropolis.

On the building’s south side (East Randolph Street), you’ll find the world’s largest stained-glass Tiffany dome. It stretches 38 feet in diameter with around 30,000 pieces of glass. Any time some mentions the Chicago Cultural Center, they’ll for sure mention this.

LOGISTICAL TIPS FOR THE CHICAGO CULTURAL CENTER:

• Admission Cost: FREE (just walk in, no ticket needed)
• Best Time to Visit: 10-11AM or 4-5PM on weekdays
• Time Needed: 1-3 hours
• Pair With: Millennium Park & Harold Washington Library Center

SEE THE CHICAGO SYMPHONY ORCHESTRA

One of the most famous orchestras in the world, based at Symphony Center.

The Chicago Symphony Orchestra is, you guessed it, a symphony orchestra that performs over 200 concerts every year.

Think genres like classical, jazz and pop. It’s considered one of the most famous orchestras in the world.

There are multiple price points for these concerts. Most start around $39 and vary depending on day, time and other factors.

Concerts are usually held from Thursday to Saturday, and each show lasts around two hours. Keep this in mind when planning your trip to Chicago!

I haven’t attended a concert yet, but based on the information I’m finding while researching, I can’t wait to go! This sounds like something you’ll want to pair with dinner at a nearby restaurant.

I’d probably choose River North since it’s only a 20-minute walk north, and there are countless solid options for dining.

PLANNING & LOGISTICAL TIPS FOR THE CHICAGO SYMPHONY ORCHESTRA:

• Sit in the Fadim Lower Balcony. Anything higher than that, and you won’t have as good of a view. The lower sections are nice if you want to splurge on a better seat, but based on my research, I don’t think that’s necessary.
• Get tickets ASAP. Tickets for The Chicago Symphony Orchestra tend to sell out, so you’ll need to buy tickets far enough in advance for a good seat.
• Utilize the virtual seat map. On the CSC website, you’ll have the option to virtually view the seat map. I suggest using this to get a better idea of your seat and view before buying your ticket.
• Arrive early. Not only will you have enough time to find your seat and get comfortable, but you’ll also enjoy the free 30-minute preconcert conversation in Orchestra Hall.
• Pair With: The Art Institute of Chicago
• Get Tickets Here

ATTEND LOLLAPALOOZA

One of the world’s most popular music festivals, held in August.

I wouldn’t usually include a music festival in my “things to do” guides, but Lollapalooza is an exception. It’s basically the Coachella of the Midwest.

And if you know anything about that festival, that’s a BIG deal.

Previous headliners include big names like Ariana Grande, SZA, Billie Eilish, and The Weeknd.

I’d argue that, in a sense, Lollapalooza is better than Coachella because you’re not in a swelteringly hot desert. And Lollapalooza lasts a day longer, so you’re getting a better deal.

I was planning to go this year (2026), but the tickets sold so quick I didn’t get a chance to see them!

Which brings me to my travel tip for this activity: try to get tickets as soon as possible. You’ll need to be on the website early and avoid refreshing, as you may lose your spot in the queue.

STROLL ALONG THE RIVERWALK

A pedestrian-only walkway with restaurants, attractions and architecture tours.

It feels like I’ve only been talking about art so far. Let’s switch it up and try another iconic Chicago experience: the Riverwalk.

The Chicago Riverwalk is a pedestrian-only walkway that stretches 1.25 miles from Lake Michigan to lake Street.

On the riverwalk — which is open from 6AM to 11PM daily — you’ll find numerous restaurants like Pizzeria Portofino and activities like boat tours.

Every night from April to December, you can see Art on theMART — the world’s largest digital art projection. It projects contemporary art across the Chicago Riverwalk.

TAKE AN ARCHITECTURE RIVER CRUISE

A must-do Chicago activity that’s enjoyed by tourists and locals alike.

It’s about time we got to my favorite Chicago activity! The architecture river cruise is something both tourists and locals enjoy, so you KNOW it’s worth doing.

During the cruise, you’ll spend anywhere from 30-150 minutes on a boat, cruising the Chicago River learning about the city’s most iconic architecture.

If you don’t do anything else in Chicago, let it be this. Even if you’re not into architecture, I think it’s a great, low-pressure way to learn about the city.

The tours usually start and finish at the Chicago Riverwalk. Throughout the tour, you’ll pass multiple buildings, including:

• Merchandise Mart
• Willis Tower
• Chicago Board of Trade Building
• Tribune Tower

Now here’s the thing: various companies run these tours at different prices and times, so it can be difficult deciding which to choose.

During my first visit, I went on the Chicago Architecture Center River Cruise aboard First Lady. I did some research beforehand and definitely chose the best option.

I mean, if you search “best Chicago architecture boat cruise” on Reddit, nearly everyone will vote for this one.

Not only did the tour last 90 minutes, but the tour guide — a trained volunteer — did an excellent job keeping us passengers entertained.

She clearly knew what she was talking about, and she was passionate about teaching us about Chicago’s history.

There are other providers for the cruise, including:

• Wendella Tours & Cruises: the mainstream provider, right behind CAC. Offers competitive pricing and cruises from 45 to 150 minutes, with the widest variety of tours. Click here for more information.
• Shoreline Sightseeing: another popular budget-friendly provider. Prices range from $33 to $65, and tours 60 to 90 minutes. Click here for more information.
• Tours & Boats Architecture Tours: a less popular provider with the smallest number of options. Offers pricing similar to CAC, around $60, with only a 90-minute tour. Click here for more information.

PLANNING TIPS FOR THE CHICAGO ARCHITECTURE RIVER CRUISES:

• Buy your ticket as soon as possible. Tours sell out fast in summer, and the architecture cruise is a can’t-miss Chicago experience.
• Arrive at the dock about 20 minutes before departure. This helps account for checking in and possible delays.
• Consider stopping by the Chicago Architecture Center before or after your tour. There are several exhibitions and tours here.
• Pair With: a meal on the Riverwalk

CHECK OUT THE THEATER DISTRICT

A world-class entertainment area full of several entertainment theaters.

Nestled in the Loop, Chicago’s Theater District offers world-class entertainment including touring Broadway musicals and concerts.

Here are some theaters you’ll find in the area:

• Chicago Theatre: inspired by the Neo-Baroque French revival style, hosting tons of concerts, Broadway shows, and comedy shows throughout the year.
• Cadillac Palace Theatre: known for its French-inspired architecture, featuring shows like The Outsiders (a Tony Award-winning Broadway musical adaptation) and The Book of Mormon (9-time Tony Award-winning musical comedy).
• James M. Nederlander Theatre: inspired by the Far East, featuring shows like Kinky Boots, a multi-award-winning musical.
• CIBC Theatre: a Beaux-Arts style theater, featuring shows like The Notebook Musical, a theatrical adaptation of the novel and film.
• Auditorium Theatre: inspired by the Richardsonian Romanesque style of architect Henry Hobson Richardson. A music and performance venue featuring shows like “& Juliet,” a critically acclaimed musical that challenges the iconic Shakespeare tragedy.
• Broadway Playhouse at Water Tower Place: features a modern design with 549 seats, focusing smaller-scale productions.

THINGS TO DO IN SOUTH LOOP

SPEND A FEW HOURS IN THE MUSEUM CAMPUS

A large area with three popular attractions.

If you didn’t know, Chicago is home to what feels like hundreds of specialty museums. While many are paid unlike Washington DC’s Smithsonian institutions, they are very much worth visiting.

You can find these museums all over the city, but there’s a Museum Campus to check out. It’s this lakefront park featuring three major tourist attractions in Chicago:

• Shedd Aquarium: one of the oldest continually operating non-governmental aquariums in the US. See various aquatic animals like penguins and sharks, along with ocean and reef exhibits. Opens at 9AM everyday. Prices vary depending on what date and time you visit.
• Field Museum: a world-renowned natural history museum with over 40 million artifacts. See the famous T. rex dinosaur SUE and the Hall of Gems, a collection of 600+ gemstones and 150 pieces of antique jewelry. Open from 9AM to 5PM daily. General admission tickets start at $30, with options for different exhibits and VR experiences.
• Alder Planetarium: America’s first planetarium. Check out some immersive sky shows, interactive exhibits and Doane Observatory, which has the largest telescope in the area. Open from 9AM to 4PM daily besides Wednesdays, on which the museum is open from 4-10PM. Tickets start around $25, with two other options for sky shows.

If you wanted, you could spend a day here and check out all three attractions. I like how each is unique, so you don’t feel like you’re repeatedly going to the same place.

LOGISTICAL TIPS FOR THE MUSEUM CAMPUS:

• Time Needed: 4.5-6 hours
• Pair With: Harold Washington Library
• Budget Tip: Buy an attraction pass like CityPASS or Go City Chicago to save money on bundled activities. Use my Attraction Comparison Tool to ensure you’re getting the best deal.
• Get Tickets & More Info:
  • Shedd Aquarium
  • Field Museum
  • Alder Planetarium

CHECK OUT THE GARDEN AT THE HAROLD WASHINGTON LIBRARY

A public Chicago library housing a stunning winter garden.

Harold Washington Library is one of 81 public library locations.

This one is special because, aside from the blend of classic and modern architecture, it features an aesthetic winter garden on the ninth floor.

This winter garden has gorgeous marble flooring and a 52-foot stained glass dome stretching across the room. It’s a great place to wind down for a bit and read a book, write in your journal, or even get some work done.

I finally went for the first time on my fifth trip to Chicago and it looked even better than in the photos. It also wasn’t too crowded, which I appreciated (there were only about seven people).

Take the elevator unless you feel like going up nine sets of escalators.

Oh, and I recommend pairing this with the Chicago Culturwl Center, which is right in the same area.

Depending on what you’re doing, you’ll need about thirty minutes to a few hours here.

A similar activity is The 3 Arts Club Cafe at the Restoration Hardware store, located in Old Town. Just know that you’ll have to make a reservation to access it.

THINGS TO DO IN STREETERVILLE

SPEND SOME TIME AT NAVY PIER

A pier on the shoreline of Lake Michigan with several fun activities.

The Navy Pier is a waterfront entertainment and recreational area with tons of touristy things to do.

Please don’t let the touristy part turn you away — travelers and locals always seem to frown upon piers, but I think they can be cool with an open mind.

Here are some things you’ll find at Navy Pier:

• Navy Pier Fireworks: lasting around 10-15 minutes, this free fireworks show runs every Wednesday at 9PM and Saturday at 10PM from Memorial Day Weekend to Labor Day Weekend. An extended show runs on the Fourth of July every year. There are several viewpoints throughout the city, but locals often cite Buckingham Fountain, the Alder Planetarium, and river cruises as the best. You can also see the fireworks from a Lake Michigan cruise, which I recently did and enjoyed. Of course, you can simply watch the show at the pier itself, but it will be crowded, so it’s better to choose a less busy spot.
• Centennial Wheel: a nearly 200-foot-tall ferris wheel giving you jaw-dropping views of Chicago’s picturesque skyline and surrounding areas. Tickets start around $20, with VIP gondola options available.
• FlyOver Chicago: a fun, interactive experience that mimics flying over Chicago’s most recognizable landmarks. Tickets start around $40 for the main nine-minute “Believe Chicago” ride. Another option, “Call of the Rockies,” takes you through the Canadian Rockies for around $35. The attraction offers $10 off every Tuesday, so keep this in mind when planning your trip. Consider booking the bundle to save 50% on both shows.
• Summer Skate: a retro-inspired indoor roller skating experience at Navy Pier. Admission costs around $20.

LOGISTICAL TIPS FOR NAVY PIER:

• Time Needed: 1-3 hours
• Admission: FREE (with paid attractions)
• Pair With: Ohio Street Beach

SUNBATHE AT OAK STREET BEACH

One of Chicago’s best beaches.

I bet you didn’t know Chicago has beaches! Oak Street Beach is one of the most popular, especially since it’s in the same area as Navy Pier.

Give yourself some time to sunbathe, read a few chapters of a good book, or dip your toes in Lake Michigan!

Alternatively, you can go to Ohio Street Beach. I went here on my most recent Chicago trip and, honestly, it might actually be better than Oak Street Beach.

There was a good number of people, but the crowds weren’t overwhelming. I can’t say the same about Oak Street Beach. Both are only a 20-minute walk from each other along the Lakefront Trail, so you can’t really go wrong with either.

LOGISTICAL TIPS FOR OAK STREET BEACH:

• Best Time to Visit: early afternoons on weekdays
• Time Needed: 30 minutes to a few hours
• Admission: FREE
• Pair With: Navy Pier

SEE THE CITY SKYLINE FROM 360 CHICAGO

A unique observation deck that tilts you 30 degrees over Chicago.

360 CHICAGO is one of the city’s two observation decks. You can find it on the 94th floor of the John Hancock Building.

This is a truly unique observation deck because not only do you get a panoramic view of Chicago’s skyline, but you can tilt outward up to thirty degrees over the city for two minutes.

As frightening as this may sound, it’s a thrilling experience that you have to try at least once. To calm your nerves, just know that TILT consistently meets safety regulations.

Starting around $45, the experience is rather costly. And unfortunately, you won’t get access to TILT with any of Chicago’s attraction passes. But like I said, you won’t find anything similar elsewhere.

Note that in order to experience TILT, you have to buy a ticket that includes it. See the options below:

• Sip, Tilt & View (from $55)
• Tilt & View (from $45)

Keep in mind Chicago has another observation deck called Skydeck. It’s closer to South Loop and, while it’s a great option if you’re in the area, I think you’ll have a better experience at 360.

I wrote a detailed comparison to further help you decide which to pick for your trip. Feel free to read it when you get a chance!

LOGISTICAL TIPS FOR 360 CHICAGO:

• Best Time to Visit: 12-2PM or late evening
• Time Needed: 45 minutes to one hour
• Pair With: Navy Pier, Ohio Street Beach
• Budget Tips:
  • Buy your ticket directly from 360 CHICAGO. You can get tickets through several third-party providers, but they’ll usually cost a bit more.
  • Visit in the morning or in the late evening. It won’t be as busy, so tickets are often cheaper by a few dollars.

CHECK OUT THE LARGEST STARBUCKS IN THE WORLD

The Starbucks Reserve Roastery is located in Chicago’s Streeterville neighborhood.

Chicago is home to the largest Starbucks in the world, the Starbucks Reserve Roastery.

At 35,000 square feet, it’s a large building with five floors each featuring special kinds of beverages. The fifth floor is a terrace with outdoor seating and a view of Chicago’s skyline.

Not only that, but the Chicago Roastery also has a fifteen-foot curved elevator, which is the first in the Midwest.

Along with the specialty drinks, baked goods and finger foods, there are different souvenirs you can buy. I found they weren’t too pricey, so that’s nice to know.

Be sure to visit early, as this place often gets wildly crowded — especially with all the summer travelers.

LOGISTICAL TIPS FOR THE STARBUCKS RESERVE ROASTERY:

• Time Needed: 45 minutes to one hour
• Cost to Visit: FREE
• Pair With: Shopping on Magnificent Mile

SHOP ON MAGNIFICENT MILE

A mile-long stretch of retail stores.

Magnificent Mile is a mile-long stretch of retail stores. You’ll find stores like Aritzia, Nike, Burberry, and the Harry Potter Store.

I must warn there aren’t many unique stores here, but if you’re looking to do some shopping on your trip, this is a decent place to fulfill that craving.

There are also two shopping malls in the area: Water Tower Palace and The Shops at North Bridge. I’ve been to and enjoyed both. Water Tower Palace is a bit older but has some decent stores like Hollister and Bath & Body Works.

Magnificent Mile is usually crowded on weekends in summer and fall, so to avoid those crowds, consider visiting early in the morning.

THINGS TO DO IN HYDE PARK

CHECK OUT THE OBAMA PRESIDENTIAL CENTER

A large cultural building for entertainment and recreation.

Stretching nearly twenty acres with an eight-story museum in Chicago’s South Side, the Obama Presidential Center is a “cultural institution that aims to inspire, empower, and connect people to bring change home.” [SOURCE]

The location is significant because, if you didn’t know, Former President Barack Obama and First Lady Michelle Obama started their public service journeys here.

There are tons of activities to indulge in at the center, like:

• Wandering through the Obama Presidential Center Museum
• Enjoying a tranquil moment at Great Lawn
• Playing basketball at Home Court
• Read a book from the public library branch

LOGISTICAL TIPS FOR THE OBAMA PRESIDENTIAL CENTER:

• Time Needed: 2-4 hours
• Cost to Visit: FREE (museum required paid, timed tickets)
• Pair With: Promontory Point, University of Chicago Campus

SPEND A FEW HOURS AT THE LARGEST SCIENCE MUSEUM IN THE U.S.

The Museum of Science and Industry is a must!

Spanning 400,000 square feet, the Museum of Science and Industry is the largest science museum in the US. Here, you’ll find several designated exhibits, tours and shows.

I went in August 2025 and had a great time. My favorite exhibit — the first one I walked through — was The Blue Paradox.

It’s this visually rich, information-heavy immersive experience that teaches you about how intense our ocean plastic problem is. I think the best part was the free five-minute presentation that educates you on different oceanic wildlife.

It’s arguably the most popular exhibit at the museum, but totally worth it. Budget around thirty minutes for the full experience of walking around, seeing the presentation and reading the information cards.

LOGISTICAL TIPS FOR THE MUSEUM OF SCIENCE AND INDUSTRY:

• Time Needed: 2-3 hours
• Admission Cost: $30
• Pair With: Promontory Point

WALK AROUND THE UNIVERSITY OF CHICAGO

A highly-ranked university with a stunning campus.

The University of Chicago (UChicago) is one of the most highly respected academic institutions in the world. While it may not exactly be an ivy league, it’s truly in a league of its own.

But obviously you’re not a high school senior looking for colleges to apply to (hehe).

UChicago is worth visiting because of its stunning campus. There’s tons of greenery throughout the 217-acre campus along with, in true Chicago fashion, jaw-dropping architecture.

You’ll also find the Smart Museum of Art here, which has a permanent collection of over 17,000 objects. Admission is free and open to the public.

Give yourself about 1.5 hours to wander around the campus and admire the art!

SIT AT PROMONTORY POINT

A calm, serene area to deflect and walk around.

Officially named the Burnham Park Promontory Point, this is a manmade peninsula on Lake Michigan.

It’s the perfect place to take in the nature and freely wander. Since most tourists don’t know about it or care to visit, it likely won’t be too busy, especially if you visit early in the morning about 8-9AM.

HONOR BLACK HISTORY AT THE DuSABLE BLACK HISTORY MUSEUM AND EDUCATION CENTER

A Black history museum for history, culture and art.

As the first and oldest independent Black history museum in America, the DuSable Black History Museum and Education Center is dedicated to the study and conservation of African-American history, culture and art.

Tickets cost around $15, with free admission for Illinois residents. The museum is open Tuesday through Sunday from 10AM to 5PM.

If you’re visiting in mid-June, consider attending the museum’s free Juneteenth Celebration, where you can enjoy live music, yoga, lectures and more.

Plan to spend around 1-2.5 hours here, and pair with forty minutes at Promontory Point.

THINGS TO DO IN LAKE VIEW

SEE A CUBS GAME AT WRIGLEY FIELD

A true Chicago local activity.

Wrigley Field is home to the Chicago Cubs, an MLB baseball team.

Even if you aren’t a big sports fan (trust me, I’m definitely not), you HAVE to attend at least one game at some point in your Chicago travels.

The locals energetically pack into the ballpark and passionately root for the team. The roars get louder and louder throughout the game, along with several songs and cheers.

Don’t forget to grab a hot dog while you’re there!

WANDER AROUND WRIGLEYVILLE

A lively area within the Lake View neighborhood.

Before or after you attend a Cubs game, spend some time wandering around Wrigleyville. There are tons of sports bars, restaurants, local shops and sights to check out while you’re in the area.

To name a few:

• Go shopping (Brown Elephant, Unabridged and Foursided are great stores to check out)
• See a movie and grab a snack at Alamo Drafthouse Cinema Wrigleyville or Music Box Theatre
• Spend some time at Graceland Cemetery
• Grab a Chicago classic sandwich at Al’s #1 Italian Beef
• Get drinks at Sluggers Bar or Murphy’s Bleachers (as a solo traveler, please drink responsibly)
• Munch on some pizza Pequod’s

BIKE OR WALK THE LAKEFRONT TRAIL

An 18.5-mile shared-use path crossing the Lake Michigan shoreline.

The Chicago Lakefront Trail (LFT) stretches over eighteen miles from Ardmore Avenue on the north end and 71st Street in the south. It has an 18-mile bike trail for cyclists and an 18.5-mile pedestrian trail for walkers.

If you want to bike or scoot the trail, consider renting an electric Divvy bike or scooter (operated by Lyft).

You can get a day pass for around $20. Just know that each ride is free for up to three hours — after that, you can return the bike and get another one for free.

Visit the Divvy website here for more information and up-to-date pricing.

THINGS TO DO IN CHINATOWN

RIDE ON THE CHICAGO WATER TAXI

Take in the views on this scenic boat ride.

The Chinatown Water Taxi is, you guessed it, a water taxi that runs between Michigan Avenue and Chinatown. This is a slightly more unique way to get to Chinatown, compared to Uber or the train.

A roundtrip costs $20, with each ride lasting about thirty to forty-five minutes. The ride costs more than other modes of transportation, but it’s more about the journey.

Please note that rides are NOT sold as roundtrips. If you want to ride the water taxi both ways, you must buy two separate one-way tickets.

Visit the Chicago Water Taxi website here for more information and up-to-date pricing.

EXPLORE CHINATOWN SQUARE

A two-story outdoor mall with tons of food and shopping options.

When you hear someone mention Chinatown, this is likely what they’re talking about. Chinatown Square is a two-story outdoor mall with tons of restaurants, boutiques, and cultural landmarks.

You can spend around two hours exploring the area. Here are some things worth checking out:

• See the “Chinese in America” mural, which includes around 100,000 pieces of glass from China and celebrates Chinese immigration and culture
• Devour some dumplings at Qing Xiang Yuan Dumplings, slurp some ramen at Daifuku Ramen, or feast on dim sum at Dolo Restaurant and Bar
• Shop at one of the several gift shops

SPEND SOME TIME AT PING TOM MEMORIAL PARK

A 17-acre public urban park in Chinatown.

Just a six-minute walk from Chinatown Square, Ping Tom Memorial Park is a public urban park that stretches seventeen acres.

There’s a pagoda-style pavilion located near the Chicago River that makes for a great spot for photos.

WALK AROUND THE CHINESE-AMERICAN MUSEUM OF CHICAGO

An history and art museum dedicated to Chinese-Americans.

Located in the same area as the previous two activities, the Chinese American Museum of Chicago aims to promote the culture and history of Chinese-Americans in the Midwest.

Admission is free, making it a great budget-friendly activity.

THINGS TO IN OTHER CHICAGO NEIGHBORHOODS

WALK AROUND THE LINCOLN PARK CONSERVATORY

A free Victorian glass house and botanical garden.

The Lincoln Park Conservatory is a Victorian glass house and botanical garden. Here, you’ll find exotic plants from around the world in four display houses: The Palm House, Orchid House, Fern Roo, and Show House.

Admission is free, but you must book a timed-entry ticket in advance. The conservatory is open Wednesday through Sunday from 10AM to 5PM.

Plan to spend around one hour here to fully experience all of the display houses and the surrounding area.

RELAX AT THE POETRY FOUNDATION

A free space for poets, poetry lovers, and creatives.

The Poetry Foundation is a culture center in River North focused on highlighting poetry and bringing like-minded poetry lovers together in one communal space.

Here, you’ll find a library, exhibition area, and performance space. The center hosts free public events like readings, lectures, and workshops.

I didn’t know about the Poetry Foundation until I was doing research for this post. I discovered it on TikTok — which, to some, might be surprising — and I knew I had to include it in this Chicago travel guide.

Just like the winter garden at Harold Washington Library, I think this is the perfect spot to deflect and connect with your inner creative. As a writer, I’d love to check it out on a future visit!

Plan to spend anywhere from thirty minutes to a few hours here.

TRY DIFFERENT RIVER CRUISES AND TOURS

Chicago has more than just architecture cruises!

I know I mentioned the architecture boat tour earlier, but that’s not the only kind of river cruise available in Chicago. There’s also dinner cruises, sunset cruises, general leisure cruises, party cruises and firework cruises!

On top of that, there are other kinds of tours like an architecture walking tour, Gangsters and Ghosts tour, and food tasting tour.

You might want to keep these in mind for future visits. Because, trust me, you’ll want to come back! Why the heck do you think I’ve been 5 times already?

BIKE OR WALK THE 606/BLOOMINGDALE TRAIL

A 2.7-mile recreational trail and park.

The 606 — officially named the Bloomingdale Trail — is a recreational trail and park that stretches 2.7 miles across Wicker Park, Bucktown, Logan Square and Humboldt Park.

It runs about twenty feet above the ground on what used to be an industrial rail line.

Block off around 1.5 hours in your itinerary to bike or walk the trail. You’ll see lots of greenery, public art installations, and more during your journey.

TRY SOME ICONIC CHICAGO DISHES

Indulge in the best dishes in the city.

Chicago is widely considered one of the best foodie cities in the world. If you’re a foodie, you’ll be in paradise!

Here are some iconic dishes to try during your trip to Chicago:

• Deep-Dish Pizza (Giordano’s and Lou Malnati’s are popular spots, while locals favor other gems like Pequod’s, Gino’s East and Pizano’s)
• Tavern Pizza (fun fact: THIS is true Chicago-style pizza)
• Brownies (they originated at the Palmer House Hotel in The Loop)
• Chicago-Style Dogs (run them “through the garden” and don’t use ketchup; Portillo’s is a popular spot)
• Italian Beef (Al’s #1 Italian Beef is a popular spot)
• Chicago Mix Popcorn (AKA the “Garrett Mix,” a mix of sweet caramel and cheddar popcorn – Garrett’s Popcorn is a great spot)

Here’s a 3-hour guided food tour if you prefer a more curated experience. I definitely think it’s worth the $85, especially if you’re visiting Chicago for the first time. You’ll try nearly all of the above dishes on the tour, along with a few more.

CHECK OUT CHICAGO’S ENTERTAINMENT SCENE

If you couldn’t tell by now, Chicago has a large, diverse entertainment scene.

It’s a huge part of the city’s nightlife, so if you’re looking for more nighttime activities, here are some things to check out:

• Jazz Clubs: Andy’s, Jazz Showcase and The Green Mill
• Speakeasies: Green Door Tavern, The Library, Sparrow, The Alderman and The Heavy Feather
• Comedy/Improv: The Second City, iO Chicago, Laugh Factory, Annoyance Theatre & Bar and Zanies Comedy Night Club
• Drag/Gay Bars: Hydrate Nightclub, Splash, Charlie’s, Fantasy Nightclub, Kit Kat Club and Roscoe’s Tavern

ATTEND AN ANNUAL CHICAGO EVENT

Chicago has numerous of annual events and happenings.

As one of the best major cities in the US, Chicago hosts tons of events throughout the year. Like, a LOT.

Here are some to check out if they align with your trip:

• Bank of America Chicago Marathon
• Chicago Air and Water Show
• Chicago Auto Show
• Arts in the Dark Parade
• Chicago Ducky Derby
• Chicago Theatre Week
• Faces of Fitness Chicago
• St. Patrick’s Day River Dyeing

SHOP AT A FARMER’S MARKET

Grab some fresh fruit and vegetables from a neighborhood farmer’s market.

If you’re visiting the city during spring or summer, consider shopping at a farmer’s market. There are several to choose from, including:

• Green City Market Lincoln Park
• Logan Square Famers Market
• The Lincoln Park Farmers Market

TOURIST TRAPS IN CHICAGO

Chicago doesn’t have that many tourist traps, which I define as an insanely popular attraction or experience that often falls short of most expectations.

That said, here are a few to look out for:

• Hop-On Hop-Off Sightseeing Tour: this is a wildly tourist activity. I’m not personally opposed to it, but Chicago is best seen on foot or the river. There’s nothing like it!
• Chain Restaurants: Chicago is known as one of the BEST foodie cities in the world. There are lots of chain restaurants in the city, especially in The Loop. Make sure you venture off into one of Chicago’s numerous neighborhoods like Logan Square or Wicker Park for better food (which, by the way, is almost guaranteed to be more affordable).
• Downtown Nightlife: Chicago has a decent nightlife scene, but you won’t find the best spots in the downtown area. Consider spending a few hours in Andersonville or Logan Square for a more authentic, lively experience.

Chicago locals and frequent visitors would argue places like the Navy Pier, Skydeck and The Bean are major tourist traps, but I’d have to disagree.

Sure, they may not be the most amazing places in the world, but they’re popular for a reason: people like going there! I think it’s smart to visit once and see how you like it.

Because you just might love it, and you likely wouldn’t have discovered that if you let others’ opinions influence your decision.

THINGS TO THINK TWICE ABOUT

SKYDECK CHICAGO

Skydeck is one of Chicago’s two observation decks. If you remember from earlier, I recommended the other one, 360 CHICAGO. I think you should prioritize that one because the experience is more unique.

Instead of just stepping on a ledge for a painfully short period of sixty seconds, you get a more thrilling experience by tilting off the John Hancock Building. And even though the tilt costs extra, I think it’s worth it.

Not saying you shouldn’t visit Skydeck though. Its main advantage is that you walk through a museum before reaching the top of Willis Tower. 360 CHICAGO doesn’t have this experience, so that’s something to consider when deciding between the two.

For your first visit, I suggest that you go to 360 CHICAGO. Save Skydeck for when you go back. Read my full comparison here for a more detailed breakdown!

THE MUSEUM OF CONTEMPORARY ART

The Museum of Contemporary Art in Chicago is one of the world’s largest contemporary art venues.

And while that sounds great on paper, it doesn’t translate too well in reality. Many visitors say that, while the collection is nice, the museum is too small relative to the $22 admission fee.

LINCOLN PARK ZOO

I understand this zoo may be compelling because it’s free and you might already be in the area, but as a responsible traveler and travel creator, I cannot and will not recommend that you go here.

I recommend numerous other free things to do in this guide, so please check that out when you can.

ANY ACTIVITY YOU CAN DO SOMEWHERE ELSE

Although Chicago is very unique in about a million different ways, there are a few things you’ll find elsewhere. And if it’s your first time visiting, I’m sure you’d want to prioritize Chicago-specific activities.

Here are some less unique Chicago activities:

• Museum of Ice Cream
• Museum of Illusions
• The Color Factory
• WNDR Museum

I’m not saying you should never visit these places, but I want you to be aware that Chicago is not the only place you’ll find them.

ANYTHING YOU FEEL PRESSURED INTO DOING

On any trip (not just Chicago), you’ll want to avoid falling into the trap of doing anything you feel pressured about.

Remember, this is YOUR trip. And you’re going alone, so you’re free to do whatever you want!

QUICK CHICAGO NEIGHBORHOOD BREAKDOWN

• Downtown:
  • The Loop: Chicago’s downtown area. It’s called The Loop because the public transit system meets in the middle of the city, creating a loop.
  • South Loop: home to the lakefront Museum Campus, you’ll find some of Chicago’s biggest museums, along with buzzing nightlife and restaurants.
  • River North: home to one of Chicago’s best nightlife scenes, River North is an ultra-stylish district of art galleries, studios, and restaurants.
  • Steeterville: located in the Near North Side community, north of the Chicago River.
• South:
  • Hyde Park: the site of the Chicago World’s Fair of 1893 and home to former President Barack Obama.
  • Chinatown: a century-old neighborhood that reminds you of Asia. Amazing shops, restaurants, and nature areas.
• North:
  • Lincoln Park: Boutiques, museums, dining, a zoo, and plenty of waterfront.
  • Lake View: known for entertainment, shopping, and its lakefront locale.
  • Wicker Park: cool boutiques, street art, and a great bar scene.
  • Andersonville: home to one of Chicago’s biggest LGBTQ+ communities.

FINAL THOUGHTS: THINGS TO DO IN CHICAGO

In this post, I shared some of the absolute BEST things to do on your first trip to Chicago as a solo traveler.

This is, by NO means, an exhaustive list of things to do and see in the city. You will very much need to visit multiple times to really get a feel of Chicago.

I’ve already been five times and still haven’t done everything, so I suggest picking just a handful of activities from this list for your first visit.

Alrighty. Now, friend, it’s YOUR turn. I’m opening the floor for you to start a conversation in the comments. Here are some discussion topics:

• If you’re planning a trip to Chicago, what activities from the list sound the most exciting?
• Have you been to Chicago before? What did you do, and if you’re returning soon, would you repeat any of those activities?
• Do you live in Chicago? Is there anything I missed that you’d like to add to this list?
• Did you like the structure of this post? I find that, when planning a trip, it’s inexplicably valuable to have things grouped by neighborhood, so I hope I was able to mimic that in this guide.

I’d love to hear your thoughts! If you feel more comfortable chatting with me directly, shoot me a DM on Instagram or email me at demarcus@thesolosolstice.com.

ABOUT DEMARCUS

DeMarcus is a Midwest-based travel content creator and the founder of the solo travel blog, The Solo Solstice. He began his solo travel journey in December 2025 and since has been creating practical, in-depth travel guides for a like-minded community of first-time solo adventurers.

Visit the About Page to learn more about DeMarcus, and visit the Ethical & Responsible Tourism Page to learn more about his efforts to promote responsible tourism.