to Do Alone in Chicago

Chicago is one of the greatest cities in the world. As the third-largest city in the U.S., it is home to about 2.7 million people — and there’s always something to do.

Chicago is a great sports town, a fun bar town, and a tremendous culinary town with tons of restaurants to visit. But those are things that most people want to enjoy with friends. 

Today we're focusing on some of the fun things you can do in Chicago when you're all on your own.

Check out this list of the five best things to do alone in Chicago, Illinois.

Rent a Divvy

Divvy is Chicago’s premier bike rental service. With rental and drop-off locations all around the city, Divvy is the perfect way to take a solo tour through any part of town.
A single ride on a Divvy costs just $1 for 30 minutes of ride time. Want to bike longer? You can pay $3 more for every additional 30 minutes you want to ride.

Do you want to get a workout in and see the whole city? An all-day pass costs just $15.

Whether you live in the city or are visiting on your own, biking through Chicago is an experience. There are tons of sights to see, and it’s a great way to explore different neighborhoods when you don’t feel like walking on foot.

And the best part is, if you don't feel like biking back, you can return your Divvy to any station when the ride is over.

Visit the Museum of Contemporary Art

The Museum of Contemporary Art is the perfect place to spend an afternoon alone. After all, it’s museum etiquette not to engage in loud conversation anyway.

Chicago has lots of incredible museums, including the Art Institute of Chicago and the Field Museum. But the Museum of Contemporary Art is one you cannot miss.

MCA Chicago has over 2,400 works of art in its permanent collection. It also hosts dozens of unique exhibits throughout the year, so there’s always something new to see. Between the paintings, sculptures, and photography collections, you can easily spend a few hours here.

Stroll the Chicago River Walk

The Chicago River offers all sorts of cruises, boat rides, and fun excursions, but you don’t have to be on the water to enjoy it. You can stay on dry land and still revel in all that the river has to offer just by strolling the Chicago River Walk.

At 1.25 miles long, the Chicago River Walk is a paved walkway that’s full of things to do. Want to relax? Sit, face the water, and people-watch or gaze at the boats and cruises traveling up and down the river.

Looking for an outdoor space to listen to your favorite podcast or read a book? Grab a shady spot amidst the trees and gardens and stretch out. 

You can see the sights of the city from any vantage point on the riverwalk, so find a place you love and sit there as long as you like!

If you’re feeling hungry or thirsty, there are lots of bars and cafes where you can grab a bite to eat, sip a beer, or relax with a glass of wine.

In the mood for something sweet?

Grab a gelato at Sweet Home Gelato. They have dozens of gelato flavors on the menu, plus more than 20 sorbet flavors, an assortment of pastries, milkshakes, and coffee drinks. There’s almost no better way to experience the Chicago River Walk than with a gelato in hand!

Taking a stroll along the Chicago River is a great way to spend a beautiful, sunny day all by yourself. And if you feel like you need a little retail therapy at the end of the day, the Magnificent Mile, Chicago’s best shopping district, is just a few blocks away.

Relax at the AIRE Ancient Baths

Solitude is an absolute treat when you experience it at the AIRE ancient baths

THE place to relax and unwind on your own, this ancient bath has a relaxed, old-world feeling that will make you forget you’re in Chicago at all. It almost feels like you’re in a different place at a different time.

At AIRE, you can take an ancient thermal bath, indulge in a wine bath, or get a massage. From deep tissue massages to holistic rituals to the Himalayan Salt Experience, a day at AIRE will rejuvenate your mind, body, and spirit. 

Take a Chicago Film Tour

So many amazing films get shot on location in Chicago! The Chicago Film Tour is a must whether you live in the city or you’re visiting for the weekend.

The Chicago Film Tour is a bus ride that begins on the 600 block of N. Clark Street. From there, a tour guide will take you on a 30-mile trek throughout the city. They'll point out locations where the filming of different movies took place and provide lots of fun facts about the city itself.

The Chicago Film Tour features over 80 different movies and even shows clips of some of those movies on the bus.

If you’re a Hitchcock fan, you’ll see filming locations from North by Northwest. Do you love Batman movies? Scenes from The Dark Knight were all filmed here. If you're a diehard Ferris Bueller fan, you're going to enjoy this tour. That's right — filming for Ferris took place all over the streets of Chicago!


There is never a lack of things to do in Chicago. The restaurants, bars, and museums alone could keep you entertained for days on end. Chicago is densely populated, so even when you experience the city on your own, you never feel like you're by yourself.

Rent a Divvy and tour the city by bike. Visit a museum. Stroll the Chicago River Walk. Get a massage at the AIRE ancient baths. Hop on a tour bus to see movie film locations all around the famous streets.

Chicago is a great place to visit, and you can make it a truly memorable experience, whether you’re with friends or hanging out on your own. 


Ryan Sundling is a Group Marketing Manager at Cardinal Group Management. He has over ten years of experience in the conventional housing industry and works with The Oliver on a daily basis to help them with their marketing efforts.