Chicago, Illinois, Solo Travel, USA

28 Fun Things to do Alone in Chicago (Perfect for Solo Travelers!)

September 15, 2022

Are you looking for things to do alone in Chicago? Here are our favorite ideas for solo travelers in the windy city!

If you’re visiting Chicago by yourself, then you may be looking for things to do alone in Chicago.

It can be tricky knowing where to start, but this list should point you in the right direction! We’ve compiled all our favorite things to do alone in Chicago right here!

^ That’s me! ^

Luckily for you, this list is full of 26 great ideas for things to do alone in Chicago for solo travelers. From art museums, and selfie hotspots, to boat tours and incredible spas – this list has it all.

So let’s get started, and fill you in on all the amazing things to do alone in Chicago!


Our favorite things to do alone in Chicago…


Visit Millennium Park

Editorial credit: My_Ticklefeet / Shutterstock.com

No trip to Chicago is complete without visiting Millennium Park. So, we thought it was only right to include it on our list of things to do alone in Chicago!

You can also spend time walking around the park itself with a cup of coffee while you take in the scenery.

Whatever you choose to do here, you’re bound to agree that it’s one of the best things to do alone in Chicago.

Click here to book a self-guided tour!


Take a selfie with the Bean!

Next on our list of things to do alone in Chicago, it’s taking a selfie with the Bean!

Now, we really recommend visiting super early in the morning, before the crowds gather, as it can get super busy here!

Taking a selfie by the Bean is just an absolute must, as it’s one of the most famous sculptures in the world! This should be at the top of your list of things to do alone in Chicago!


Explore the Chicago Riverwalk

If you’re looking for relaxing things to do alone in Chicago that will lift your spirits, you’re bound to love the Chicago Riverwalk.

It’s essentially a 1.25-mile path that crosses through four separate districts – the Confluence, the Arcade, the Esplanade, and the Civic.

As you walk, you’ll pass several skyscrapers, Lake Michigan, and several local restaurants where you can grab a bite to eat. This is a great choice for things to do alone in Chicago.


Join a Chinatown food tour

Next on our list of things to do alone in Chicago, it’s a food tour of Chinatown. We’ll include a few food tours on our list of things to do alone in Chicago, because we think they’re so much fun!

Food tours are perfect for solo travelers, they’re also a great way to meet people and spend the day with lively company too!

You can book our favorite food tour of Chinatown by clicking here!


Take in a show

The next thing on our list of amazing things to do alone in Chicago? It’s seeing a show!

Chicago is known for hosting an incredible range of shows, and you can catch everything from Broadway-level musical theatre performances to straight plays.

We recommend stopping by the iconic Chicago Theater, but the James. M Nederlander Theater and the CIBC Theater also host excellent entertainment throughout the year.

Throw in a couple of interval drinks and snacks, and you’ll see why this is one of our favorite things to do alone in Chicago!


Do a donut tour!

Do you love soft, pillowy donuts? If so, then you’ll totally want to add a donut tour to your list of things to do alone in Chicago.

Chicago’s famous Underground Donut Tour remains the only official tour that’s led by a professional donut expert (yep – donut expert).

It guides you through a two-hour experience that hits the best donut stores in town, making it one of the best things to do alone in Chicago for foodies.

You can book tickets by clicking here!


Admire the Art Institute of Chicago

The Art Institute of Chicago remains one of the ultimate things to do alone in Chicago for culture lovers and art fiends. You can book tickets by clicking here!

It’s one of the best things to do alone in Chicago because you can truly dedicate time to each exhibit.

No rushing. No tutting from members of your party. Just pure enjoyment and appreciation.

It’s located right in the heart of the city, making it a fabulous place to visit for solo travelers wanting to be at the center of the action.


Take a Lake Michigan Skyline Sightseeing Cruise

Next up on our list of things to do alone in Chicago, it’s the Lake Michigan Skyline Sightseeing Cruise.

Seeing the city from the lake is simply magic, it’s a totally fresh perspective on the skyline, and a great way to admire the city’s buildings.

On a sunny day, there’s nothing like it, and it’s certainly one of the best things to do alone in Chicago.

You can book tickets to the Lake Michigan Skyline Sightseeing Cruise by clicking here.


Try Portillo’s famous chocolate cake

Portillo’s is our next suggestion for things to do alone in Chicago. Portillo’s is a bit of a Chicago legend, and it’s a favorite with locals and tourists alike.

You’ll find so much delicious food here, and it’s a kind of ‘diner-style’ with counter service. So it’s a great dining spot for solo travelers.

Anyway, they have the best chocolate cake in the world, hands down. The secret? They mix mayonnaise into the frosting of the cake. Sounds weird (we know) but once you try it, you’ll be hooked.

It’s one of the top things to do alone in Chicago, and a great place to eat.


Things to do alone in Chicago: Take a walk along Concrete Beach

Next on our list of things to do alone in Chicago, we recommend visiting Concrete Beach.

It’s one of those spots in Chicago that you simply have to check out, and it’s a bit of a local hub for joggers, walkers (and even swimmers in the summer months!).

If you’re visiting Chicago in the summertime, then Concrete Beach is a must-do, and one of the best things to do alone in Chicago.


Big Bus Hop-on Hop-off Sightseeing Tour

Editorial credit: Sorbis / Shutterstock.com

The Big Bus Hop-on Hop-off Sightseeing Tour is a classic way to see Chicago’s sights, and it’s a perfect choice for things to do alone in Chicago.

Open-top bus tours are a great way to see a city, and we think it’s always a really unrated way of exploring.

Sure, it’s touristy, but you’ll get guided commentary, and you’ll go past all of the big sights worth seeing, in a few hours.

There are also some fantastic views on offer from the Big Bus Hop-on Hop-off Sightseeing Tour, making it another great choice for things to do alone in Chicago.

You can book tickets by clicking here.


Walk through one of Chicago’s many parks

Chicago is one of the greenest cities around, and there are several parks to explore if you’re flying solo.

In addition to the famous Millennium Park, you can check out Maggie Daley Park, Humboldt Park, Grant Park, or Jackson Park to get your steps in.

It’s one of the top things to do in Chicago as it lets you stretch your legs away from the hustle and bustle of the city center.

Throw in a picnic and a fresh cup of local coffee, and you’ll have an incredible afternoon on your hands!

Read more about Chicago: 20 of the best desserts in Chicago, you have to try!


Go shopping

You may be visiting the city for a taste of culture but indulging in a spot of retail therapy is among the best things to do alone in Chicago.

You’ll be surrounded by like-minded people, be waited on hand and foot, and be able to spend as long as you want in stores without a partner hurrying you along.

Perfection.

The Magnificent Mile is a wonderful place to shop, but you can also check out Water Tower Place and Bloomingdales! It’s a great pick for things to do alone in Chicago!


Check out the Skydeck

If you’re on the hunt for things to do alone in Chicago, face your fears and head to the top of the Willis Tower.

The famous Chicago Skydeck is located on the 103rd floor of the Willis Tower and it provides truly unbeatable views over the entire city.

Brave folks should head out to the Ledge, which is essentially an all-glass balcony that lets you snap next-level Instagram shots.

Just don’t add it to your list of things to do alone in Chicago if you’re afraid of heights! Click here to book tickets!


Go on an Architecture Boat Tour

If you’d like to learn more about Chicago’s skyline while you’re in town, you should totally book an Architecture Tour. It’s one of the top things to do alone in Chicago!

The most popular tour company is Architecture Tour Chicago

It offers river tours, firework tours, and jazz/cocktail tours which allow you to experience the best of the city by day and night.

During your adventure, you’ll head along the Chicago River and learn all about the Neo-Classical, Art Deco, and Gothic buildings that characterize the city.

It’s educational and remains one of the best things to do alone in Chicago for culture lovers. You can book tickets by clicking here!


Walk along the Magnificent Mile

Editorial credit: EQRoy / Shutterstock.com

We briefly mentioned the Magnificent Mile, but we felt that this incredible district deserved a spot of its own!

Visiting this vibrant area is one of the best things to do alone in Chicago as you’ll feel surrounded by excitement.

From the luxe boutiques to the cool restaurants and neo-Gothic architecture, you can spend hours exploring this area without getting bored.

Press play on your favorite podcast, and you’ll truly be in solo traveler heaven.

Ah, we’ve got goosebumps just thinking about it, it’s a great choice for things to do alone in Chicago.

Read more about Chicago: What is the coldest month in Chicago?


Things to do alone in Chicago: Visit the French Market

Editorial credit: Sorbis / Shutterstock.com

If you’re looking for amazing things to do alone in Chicago that involve food, then you need to visit the French Market – pronto.

It’s home to tons of local vendors who sell everything from loaded salads to homemade Mac & Cheese.

Whether you want to grab a few crepes or would rather grab a few goodies to go, you’re bound to agree that meandering through the market is one of the best things to do alone in Chicago!


Take Chicago’s ‘Ultimate food tour’

Editorial credit: jamie.sue.photography / Shutterstock.com

Next up on our list of things to do alone in Chicago, it’s the ‘Ultimate Chicago food tour’. This is one of the best food tours in Chicago, featuring some of the most iconic Chicago foods!

You’ll get loads of samples on this food tour… making it a great choice for things to do alone in Chicago!

From deep dish pizza, and Chicago hot dogs, to Italian beef and sweet treats too!

You can book tickets to this amazing food tour by clicking here!


Take a self-guided walking tour

One of the best things to do alone in Chicago is to take a self-guided walking tour of the city. It allows you to see the finest attractions, hidden gems, and local haunts without paying a penny!

Sites like Free Tours by Foot and GPS My City offer excellent self-guided tours that should get you from A to B without a hitch.

This way, you can put your headphones in, block out any distractions, and explore the beauty of Chicago with a phone as your expert guide!

Don’t love being chained to a phone? Print out a guide and get walking!

Believe us when we say that a walking tour is one of the best things to do alone in Chicago – so don’t miss out!

Read more about Chicago: 13 of the top pizza restaurants in Chicago


Explore the city’s street art

Our next suggestion for things to do alone in Chicago is checking out the local street art. There is so much amazing local art to explore and admire.

The only thing tricky about checking out the city’s street art, is knowing where to look for it. So, we actually recommend taking a tour.

That way, you can meet lots of great people, get lots of amazing info and history, and also be taken to all the best places and best art. It’s such a fun choice for things to do alone in Chicago.

You can book tickets to the best street art tour by clicking here.


Visit the Navy Pier Centennial Wheel

The Navy Pier Centennial Wheel is our next suggestion for things to do alone in Chicago.

If you’re looking for a way to pass a little time in the city, and enjoy some pretty incredible views whilst you’re at it – this is a perfect activity.

It’s a classic choice for things to do alone in Chicago – we think you’ll love it.

You can book tickets by clicking here.


Visit the Garfield Park Conservatory

Editorial credit: Carlos Yudica / Shutterstock.com

Garfield Park Conservatory is among the most beautiful places in the city. So, we couldn’t write a list of the best things to do alone in Chicago!

This is the spot to visit if you need a touch of quiet contemplation. It’s brimming with botanical conservatories and relaxing places to sit. 

We’re not kidding when we say that no one will bat an eyelid if you choose to pull out a book and read here for the afternoon.

It takes about 90 minutes to cover in its entirety, but you can easily stay for longer.

If you’re searching for low-key things to do alone in Chicago that won’t cost a bomb, you should add this spot to your itinerary.


Walk around the Field Museum

Editorial credit: Sergii Figurnyi / Shutterstock.com

Next on our list of things to do alone in Chicago, it’s the Field Museum.

We’d say that the Field Museum was one of those spots in Chicago that you need to check out before leaving.

It’s an iconic tourist attraction that takes you through a whole host of natural history. So, you can expect to find artifacts, natural wonders, age-old art, and everything in between.

As it’s one of the best things to do alone in Chicago, you can take yourself through the museum at your own pace.

Just make sure to leave before the doors close for the night!


Get spooked on the Gangsters and Ghosts Walking Tour

If you’re looking for scary things to do alone in Chicago, then you should consider booking the famous Gangsters and Ghosts Walking Tour.

This tour covers the darkest side of Chicago’s history. It delves into murders of the 1920s, the underground speakeasies of the post-war era, and the many shootings that have occurred here over the years.

We don’t recommend adding this to your list of things to do alone in Chicago if you spook easily. 

But we promise it’s bundles of fun if you have the constitution for it! You can book tickets by clicking here.


Check out Myopic Books

Are you searching for low-key things to do alone in Chicago that don’t cost a dime? If you answered “YES!”, then you’ll want to check out Myopic Books while you’re in town.

It’s Chicago’s ultimate second-hand bookstore and it truly feels like walking onto the set of Harry Potter.  Seriously, we thought we’d walked into Ollivander’s when we first visited!

After you’ve finished admiring the layout, you can trawl through the rows and rows of books that line the shelves.

Although this spot specializes in historic period concerts and poetry, you’ll be able to pick up anything your heart desires.

Be still, our beating hearts – there’s a reason this is one of our all-time favorite things to do alone in Chicago. You can simply take a seat in a corner and read the day way!


Visit Aire spa

We all need a spot of TLC from time to time, which is why we’ve included a spa visit on our list of awesome things to do alone in Chicago!

If we had to choose an amazing spa to recommend, we’d say Aire Ancient Baths is the place to be.

It gives off serious ancient Roman vibes with its enormous spa baths, but you’ll get catapulted straight into the 21st century with its modern treatment menu.

Offering everything from antioxidant soaks to mammoth massages, this is one of the things to do alone in Chicago that will keep you feeling Zen.

Read more about visiting Chicago: Christmas In Chicago! 20 festive things to do in Chicago at Christmas!


Go thrifting

Whether you’re a thrifting expert or are new to the game, hitting the city’s second-hand boutiques is one of the best things to do alone in Chicago.

If you’re visiting the Dunning area, Thrift and Thrive is fabulous.

Planning to explore the Lower West Side? Knee Deep Vintage is full of incredible finds at bargain prices.

Regardless of where you choose to grab your threads, this is one of the things to do alone in Chicago that you need to add to your itinerary!


Experience some jazz music

Editorial credit: Saejun Ahn / Shutterstock.com

The final thing on our list of things to do alone in Chicago is experiencing some jazz at a local music venue.

If you’d like to catch an after-dinner favorite, you can check out Green Mill for classic tunes and a dose of history.

On the hunt for things to do alone in Chicago that will get you home a little earlier? Andy’s Jazz Club & Restaurant opens at 5:30 pm!


We hope this list of things to do alone in Chicago has given you loads of ideas!

Which of these things to do alone in Chicago will you be trying? No matter which of things to do alone in Chicago you decide to try out, we know you’ll love this city!

Read more about Chicago: 17 restaurants open on Thanksgiving in Chicago

You Might Also Like