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Things to Do in Chicago Alone

Updated: December 18, 2023
 By Mel

Chicago is quite popular among solo travelers and we wanted to provide them with a guide on things to do alone in the Windy City.

In this post, we list some of the best activities, recommend accommodations good for solo travelers, tell you about great places to eat, and how to meet people if you want to.

As a local Chicago tour guide, I spend time doing things alone, often before or after my tours.

When writing this post, I've relied on my and my fellow guides' experiences enjoying the city on their own.

I've also used information gathered from the members of our popular Chicago Travel Tips Facebook group.

Our group of 20,000 members (and growing) is made up of locals, like our tour guides, veteran travelers to Chicago, and newbies to the Windy City.

You don't need to become a member to read the posts, comments, and recommendations.

So, check out our group once you've finished reading this post using the link at the bottom of this page.


There are endless activities to enjoy here. From world-class museums to outdoor fun, cultural activities and awesome food, there is something for everyone.

Below are seven best activities in Chicago for solo travelers. These are just a drop in the bucket!

For more ideas, check out our ultimate list of things to do in Chicago!

On a budget? Take a look at our Free Things To Do in Chicago post.

Learn About Chicago Architecture

One reason that our guides love living in Chicago so much is the architectural diversity. Historic buildings next to modern masterpieces never get old to look at.

Taking an architecture tour is one of the most popular things to do when visiting Chi-town for the first time and there are a few types of tours available.

Our pay-what-you-wish Birth of a Skyscraper Walking Tour is a budget-friendly way to gain insight into the rich architectural heritage of the city from a local.

Watch our local guides in this video to give you a preview of our tour.

There are Chicago River cruises that offer an interesting vantage point. Bus tours are another option.

See our post, Which Chicago Architecture Tour Is Best? to find out what kind of tour interests you -- whichever you take, we promise, you will love what you see!

Explore Millenium Park

If you’ve done your research on visiting Chicago you’ve likely come across pictures of a massive stainless steel bean in a park.

This iconic 110-ton sculpture, called Cloud Gate, is in Millennium Park, one of the must-visit locales in the city.

The park has pretty gardens, an outdoor concert venue, and the super cool Crown Fountain, with digital video projections of faces that spout water in the summer!

If you want to see the park and Downtown Chicago (the Loop) with other travelers and maybe make a new friend, join our pay-what-you-like Loop and Millennium Park Tour.

Or discover it on your own using our guide to Millennium Park.

Go to a World-Class Museum

We know, this one’s an obvious suggestion for a solo traveler, but we wouldn't recommend this activity if the museums in Chicago were bad.

To the contrary! There are so many fantastic museums to go to that you may have a hard time choosing!

As locals, we have the opportunity year-round to see the latest exhibits and our favorite permanent ones at our city’s great cultural institutions.

The top museums are on the city's Museum Campus, a 57-acre park within the larger Grant Park facing Lake Michigan.

Georges Seurat, A Sunday on La Grande Jatte (1884), Art Institute of Chicago.
CC0 Public Domain.

A few of Chicago's most renowned museums are the Art Institute of Chicago, the Field Museum, the Shedd Aquarium, the Adler Planetarium, and the Museum of Contemporary Art.

But there are plenty of other types of museums that you can read about from our post on 30 Museums in Chicago

You’ll be pleasantly surprised to know that some museums are always free to visit or have free days/hours.

If street art is your thing, you might like to spend some time in the hip neighborhood of Wicker Park.

Stroll Along the Riverwalk

A stroll along Chicago’s Riverwalk is a 1.25-mile long path running along the Chicago River and is open to the public from 6 am to 11 pm every day.

It’s an excellent destination for those traveling alone as you will find yourself in the company of other solo people walking, biking, sitting by the water reading, and just people-watching.

It’s free to enjoy, and we love anything budget-oriented when we are traveling solo, we can't recommend time here more highly!

You might like to explore Riveralk with us on our pay-what-you-wish Chicago Riverwalk and History Tour.

Riverwalk is also known for its interesting public art installations and occasional free performances.

Use the video above of our local guide Andy telling you about the nifty things to do and see along Riverwalk.

If you like a bit of adventure, you can join a Chicago River kayaking tour. These tours welcome kayakers of all skill levels and other solo travelers will likely be on the tour with you.

Our local tour guides recommend this activity for the warmer months, as it's one of their favorite ways to cool down in the city!

Be Dazzled by the Chicago Skyline

Chicago’s gorgeous skyline can be seen by one of two observation decks atop skyscrapers. 

One is the Skydeck at the Willis Tower (formerly the Sears Tower), the third tallest building in America. The other is the 360 Observatory on the Hancock Building.

Both offer breathtaking views! On a clear day, you can see four states: Illinois, Indiana, Wisconsin, and Michigan!

Not sure which to visit? See our post comparing Willis Tower Skydeck vs. 360 Chicago to see which one works for you.

Visiting one or both of these skyscrapers is one of the most popular activities among tourists. 

It’s no surprise that these attractions are included for free with the purchase of a tourist discount pass, a great way to save money if you plan to visit several museums and other attractions.

Read about these passes in our detailed post, Chicago CityPass vs. Go City Chicago Passes.

Head to Navy Pier

This top Chicago attraction has a lot to offer solo travelers.

Walk along the boardwalk and do some people-watching. Have a bite to eat or do some shopping.

Plus, there are special programs, free classes, concerts, and other events.

If you like amusement rides, Pier Park has a bunch of them, including the 200-foot-tall Centennial Ferris Wheel.

The views from the top are awesome!

Find out more about how you can spend a few hours at the pier with our post about things to do at the Navy Pier.  

Catch a Live Performance

No company is needed when you see a live performance! Chicago has some great venues to see theater and live music.

If you want to see a Broadway show without going to New York, Chicago’s theater scene is top-notch. See what’s playing here.

If you like live music, many of the biggest bands come through town as well. Click here to find all the concerts in the city.

Jazz music lovers are in for a treat!  The legendary Green Mill is THE place to go to see live jazz. If it was good enough for mobster Al Capone, it’s good enough for you!

For more ideas of what to do during the evening, check out our in-depth post on things to do in Chicago at night.

Go for a Bike Ride

Chicago is bike-friendly and has 26 miles of bike trails! The Lakefront Train, along Lake Michigan, is especially pretty.

It's 18.5 miles long and is ideal for a leisurely ride. Or explore other parts of the city with our self-guided bike tour of Chicago

There are also guided bike tours, like this popular Lakefront Neighborhoods Bike Tour.

Read more about tours and where to rent bikes from our post, Best Chicago Bike Rentals Companies and Tours.


Of course, your budget will be your primary consideration when choosing a hotel, but as a solo traveler you should also keep these factors in mind:

Is it close to public transportation? The less you have to walk on your own after dark, the better.

Is it in a lively neighborhood with restaurants and cafes? This ensures that there will always be people around at night.

Is it in a neighborhood that is considered safe? Our post Is Chicago Safe For Solo Travelers? details which neighborhoods are the safest for someone new to town.

Does the hotel have a common lounge or in-house cafe/bar/restaurant that is welcoming to solo travelers? If you are looking to meet other travelers, common spaces are conducive to that.

TIP: If you want some help finding a hotel or hostel you might like, join our Chicago Travel Tips Facebook Group and post asking for recommendations for solo travelers.


Hotels in Chicago cost what you would expect in a cosmopolitan city. Downtown Chicago hotel rooms average $160 a night. 

Prices will be higher during peak times of the year, but you can find deals in off-season months.

We gathered a lot of hotel recommendations from the members of our Facebook Group page and then narrowed down the list to those that are especially good for solo travelers.

Moxy Chicago Downtown: Great location, hip vibe, and common areas to socialize with other travelers.

Selina: A hybrid hotel/hostel with private and shared rooms. In-house movie theater, shared kitchen and a social events calendar.

River Hotel: Great safe location to explore the city on foot, metro, and bus lines nearby. Welcoming staff.

Willows Hotel: This small hotel offers a warm friendly environment that solo travelers will appreciate. Breakfast is free. The front desk is open 24 hours.

Aloft Chicago Mag Mile: Great location. Open lobby with live entertainment and friendly staff.


Regardless of budget, you might like staying in a hostel. You are more likely to meet other travelers who want some company as well in a hostel.

Chicago has several very good hostels with different vibes. They are centrally located as well as are very affordable and safe.

Check out our post, Best Hostels in Chicago, to see what the options are.


As a big city, Chicago is filled with people having meals on their own. You won't be the only one, so no need to feel self-conscious.

If you are concerned about being bored dining alone, bring a book, play on your phone, or simply people-watch.

Waitstaff is often friendlier to solo diners, especially if they know you are visiting the city for the first time.

Here are a few dining options based on our first-hand knowledge of the delicious foods of our city as well as recommendations from members of our Chicago Tips Facebook Group.

Food Halls

Chicago has many food halls that are a notch above the average food court! These food halls aren't just a place to grab food, but to have a culinary experience in modern spaces.

Chicago French Market

Over 20 individual fast-casual foods with grab-and-go or dine-in options for breakfast, lunch, and dinner. It is near Union Station in the West Loop, which is convenient if you are catching a train. A big plus: free WiFi.

Revival Food Hall

Fifteen fast-casual stalls with local foods in a sleek space in the Loop in Downtown Chicago. You’ll find offshoots of some of the city’s hippest (and tastiest) restaurants. The coffee house turns into a cocktail lounge at night if you fancy a glass of wine.

Aster Hall

An elegant space that will make you think you are in a Michelin-rated food hall, but the array of foods is affordable and very tasty. It’s in the 900 North Michigan Shops, a good starting spot to do some shopping along the Magnificent Mile.

Time Out Market Chicago

Eighteen eateries, a rooftop terrace, and three bars make Time Out Market a recipe for success. There’s a wide range of cuisine that you can enjoy at one of the many communal tables. Just grab a seat and sit down even if there are other people at the same table. This definitely beats the feeling of eating alone!

Eataly Market Chicago

The massive bi-level Italian marketplace and food hall has six food counters, two restaurants and bars, and a cafe. Plus you can go shopping at the grocery stalls for authentic Italian meats, cheese, and other delicacies.

Food Tours

Combine your need for food with your interest in learning about Chicago and meet people along the way by taking a Chicago Food Tour.

There are lots of food tours to choose from focusing on different areas or themes or types of food.

On several tours, like the Chicago Favorites Ultimate Food & Walking Tour, you can try classic Chicago foods like hot dogs, Chicago-style Pizza, and Italian Beef sandwiches.

Self-guided Food Tours

If you prefer to move at your own pace and sample your way through different neighborhoods, check out our self-guided food tours.


As a cosmopolitan city, you can expect lots of travelers, many of whom are visiting on their own and looking to make new connections.

Moreover, Chicago has a diverse population and is filled with people who spend time on their own enjoying what the city has to offer.

Many locals are happy to talk to solo travelers. Some may even make suggestions about what to see.

Below are some ways to meet fellow travelers should you want to.

Join A Walking Tour

Joining a walking tour or food tour is an excellent way to both learn about Chicago and meet new people on your solo trip.

We have pay-what-you-wish walking tours of Chicago of various neighborhoods as well as a specialty evening Chicago Ghost Tour which attracts quite a lot of solo travelers.

Plus, our guides are friendly and enjoy interacting with our guests. You won't feel left out on our tours!

Check this list of free Chicago walking tours to find one you’ll enjoy.

At Your Hotel or Hostel

Most have common spaces such as a lobby with seats, a coffee shop, a hotel bar or a restaurant.

These are all good places to strike up a conversation with strangers, who are also travelers.

Some may even be looking to connect with other people.

TIP: In a hotel bar, be a bit more on guard when talking to strangers.

Join a Chicago Meetup

If you are familiar with, use it as a resource for spending time with other people.

Many Chicago Meetup groups arrange all sorts of activities and often, the people who turn up don't know each other so they are in the same boat as you!

From playing board games to picnicking in the park, from going to a museum or having a meal together, there are always interesting gatherings to join. And it’s free to do so!


It’s normal to be concerned with safety when traveling alone, even more so in a large city like Chicago.

Rest assured, you will be fine if you follow some safety tips. Check our post Is Chicago Safe For Solo Travelers? where we offer tips for staying safe.

The post applies to both men and women of all ages. We know though that women traveling on their own face challenges that men solo travelers typically do not.

These two in-depth articles are tailored to women traveling alone: Solo Travel Safety Tips for Solo Female Travelers and Safety Tips for Solo Female Travelers.

We hope that all the information above helps you enjoy your time in Chicago!

Be sure to check out our comprehensive list of things to do by month in Chicago, and read our posts about the weather when you'll be visiting.

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About The Author


Mel loves to be a tourist in her own city. With a background in performing arts, tourism, and photography, giving tours and being a story-teller comes naturally to her. She loves traveling, food, and theatre. Mel splits her time between Chicago and Los Angeles (#theatrelife) and leads tours and manages both cities!
Updated: December 18th, 2023
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