21 Things to Do Alone in Chicago for Main-Character Energy

Whether you live here, like me, or are visiting, this guide of 21 things to do alone in Chicago is for you. I frequently travel alone, and love how it offers the ultimate flexibility and freedom to do whatever I want!

But of course, solo traveling also means all the decision making is up to you. Sometimes, that can feel like staring at a blinking cursor wondering where to even begin. So, this list of the best things to do alone in Chicago is here to inspire your next day off or weekend visit.

 21 Things to do alone in Chicago

I have spent a lot of time on solo dates around the city, so here are my ideas for you on the top 21 things to do in Chicago alone. 

1. Explore the city parks

Chicago has some awesome parks to enjoy. Whether you want to explore or simply hang out, spending time here is one of the best free things to do in the city.

Lincoln Park offers a zoo, museums, a conservatory, public art and beautiful skyline views from a distance. While Millennium Park, in the heart of the city, has The Bean, fountains, events, and lots of green space.

Other options include tranquil Milton Lee Olive Park adjacent to Ohio Street Beach; and, the 606 Trail — a 2.7 mile elevated walkway following the Bloomingdale Trail and an obsolete railway line.

I’ve spent a lot of time walking around these parks and trails to get my steps in around the city, away from the chaotic traffic sounds. In the summer, farmers markets begin to crop up making it even more fun to wander through.

2. Enjoy time on the lakefront

The 18-mile Lakefront Trail in Chicago allows you to follow the shoreline of Lake Michigan on foot, two wheels, or even roller skates or blades. Dotted along the trail are cafes, restaurants, museums, parks and beaches, of course. 

The trail also offers access to city neighborhoods including Bronzeville, Edgewater, Hyde Park, Lakeview, Lincoln Park, South Loop, and Uptown.

If you want to unwind, buy a coffee to sip as you look out over the water and skyline, and maybe even bring a journal so you can jot down your thoughts. I used to do this all the time when I lived right off the trail in Lakeview East.

Plus, it’s hard to feel truly alone along the lakefront. You can enjoy your solitude in the company of many others enjoying the pretty pathway right alongside you. I always found something comforting and communal in that. 

3. Have a beach day

Kick back on the golden sand and relax. With a cocktail in hand, if you like. Or if you prefer more active beach days you can go boating, kayaking, paddle boarding, swimming or even jet skiing.

There are around 25 options in total, including Foster Beach, Montrose Beach, North Avenue Beach, Oak Street Beach, Ohio Street Beach, and South Shore Beach – take your pick!

Going to the beach alone takes just a little extra planning but can be such a fun way to spend time with yourself. 

If you want to be practically on the beach without the hassle of sand, towels and a distant bathroom, here’s an alternative solo date idea that’s been on my list: go for a morning coffee at Shore Club Chicago.

They open at 11:00 am on weekdays and 10:00am on weekends, and if you get there early you may find it’s still quiet enough to be relaxing. 

4. Shop at a farmers market

There are so many farmers markets in Chicago, including some for all seasons and others that pop up in summer. 

Apart from the fun of walking by picturesque stalls overflowing with colorful fruits, veggies and juices or delicious baked treats, these are a great opportunity to support local, small businesses. 

Whether you grab a snack to go or set up for your own little picnic nearby, farmers market visits make for a cute solo date.

5. Go coffee shop hopping

Chicago’s coffee shop scene is buzzing – and not just because of the caffeine.

I’m in the West Loop a fair amount and in that neighborhood I like Sawada, where coffee is an art form, and the must-try is the military latte. I also like nearby La Colombe and Beatrix. 

Heritage Bikes & Coffee is another great option, but honestly there are SO many great coffee shops scattered all across the city it would be impossible for me to list them here.

Instead, look around wherever you’re staying and visit as many as sound interesting to you. This way, you’ll find your own favorites!

6. Discover Pilsen

One of the best Chicago neighborhoods to take a deeper dive into is Pilsen. This colorful part of town is rich in arts and culture, and has thriving foodie and nightlife scenes. 

My recommendation is to go spend a couple hours at the National Museum of Mexican Art. Then, grab lunch at one of the many delicious eateries nearby. 

On my recent visit, I went to Rubi’s Tacos and had the most delicious squash blossom tacos! Next on my list for food in Pilsen – QuesaBirria Jalisco Tacos.

7. Spend the day in Chinatown

Another great place to eat out is Chicago’s Chinatown.

You also can learn about local history at the Chinese-American Museum, hunt for unique items in the shops, and take colorful pictures of the gates, the Chinese-style structures, and the Nine-Dragon Wall.

I love kicking off my day in this neighborhood with a custard bun from Saint Anna bakery. From nearby Tom Ping Memorial Park, you’ll also be able to capture some incredible photos of Chicago.

8. Join a food walking tour

Food tours are an awesome way to connect with any city’s foodie scene, and there’s so much to sample here in Chicago! 

Typically you’ll try local favorites like hot dogs, deep dish pizza, donuts, brownies, popcorn, and perhaps even craft beers. 

Or you could focus on the cuisine of another part of the world by taking a food tour of Little India or Chinatown. 

If you live in Chicago, going solo on a food tour is a great way to play tourist in your own city while making new friends. 

9. Check out a local museum

The museums in Chicago are among the best in the world. Art fans will love the Art Institute and the Museum of Contemporary Art. 

Or you could learn about the past at the Chicago History Museum, dinosaurs at the Field Museum of Natural History, or human achievements at the Museum of Science and Industry. 

If you’re not sure where to go, take your pick at Museum Campus by Lake Michigan, or choose something more unique. 

Such as the Holocaust Museum and Education Center, the American Writers Museum, the Architecture Center, the Money Museum or the Museum of Ice Cream.

You can easily make a whole day of it, stopping for lunch at a museum cafe mid-exploration and then ending the day with a nice dinner or drink out.

10. Read or write at the library’s Winter Garden 

The rooftop Winter Garden at Harold Washington library is a stunning space with a domed glass roof where you can read, write, or attend a demo or workshop.

If you can peel your eyes away from the beauty of the room, you might even be able to get some work done.

11. See a theater show 

There are many theaters in Chicago and all sorts of shows to go with them. The city’s theater district can be found within The Loop, and is home to a trio of Broadway in Chicago theaters (Cadillac Palace, CIBC, and James N. Nederlander).

There’s also the not-for-profit Goodman Theater, which is the city’s oldest, too. 

Chicago also offers comedy, independent, and storefront theaters. Or you could go to the historic Auditorium Theater at Roosevelt University, or head to the Belmont or Edgewater Theater districts. 

Find a show that intrigues you, book the tickets, get dressed up and take yourself out for the evening! While going to a show alone might sound daunting if you’ve never done it before, I actually find it to be one of the easiest solo activities. 

Think about it, you spend most of the time alone in the dark all watching a show and not talking. Who’s to really know you’re alone? How much does it really matter? 

Going to a  theater show, even a movie, is a great way to get comfortable doing things alone. 

12. Fill your belly at one of the food halls

A gastronomic feast awaits at Chicago’s food halls. There are so many to visit, offering a smorgasbord of culinary delights from all over the planet. 

The best ones include the Time Out Market in West Loop, Washington Hall in The Loop, Sterling (formerly Revival),  HeungSeng Square in Chinatown, and Chicago French Market, which also offers other options like Australian pies. 

If dining out alone at a restaurant feels scary for you, food halls are a great alternative. They’re constantly buzzing, and get a lot of solo diners as well as groups.

There are communal seating areas, but you can also find your own spot somewhere off to the side if you’d rather. Food halls are a low pressure space for solo diners.

13. Indulge your sweet tooth

Did you know that Chicago has its very own gourmet donut scene? Besides that, a whole bunch of new east and west coast faves have appeared recently including Levain, Milk Bar and Voodoo.

If you’ve got a sweet tooth, there’s no shortage of treats to try in Chicago. Plus, a love of sweets is cross-cultural. Check out Tahoora on Devon Street for Indo-Pak desserts, or Kasama in Wicker Park for Filipino sweets just to name a couple. 

14. Unwind with a wellness treatment

One of the best things to do alone anywhere is to indulge yourself at a spa, where you can have a sauna or steam bath, or book a pampering treatment like a massage, a facial, or a body scrub. 

Chicago’s best spas include the Aire Ancient Baths, the Peninsula Spa & Wellness Center, Allyu Spa, Chuan Spa at The Langham, and the Waldorf Astoria Spa, but there really are so many great ones to pick from. 

Narrow in on the right one for you by considering your: budget, desired treatment type, how much time you have. 

For example, do you want a quick and affordable facial at Clean Your Dirty Face or a full day experience at Aire Ancient Baths?

15. Browse at a local bookshop

Whether you prefer well-loved used or shiny new books, Chicago has a plethora of bookstores to browse. 

Try City Lit, the Last Chapter, Myopic, Open Books, Unabridged Bookstore… or any you like the look (or name) of.

Shout out to one of my former bosses who now owns and operates Sandmeyer’s in the historic Printer’s Row neighborhood!

16. Take a look at the local shops

There are of course shops scattered throughout the city, from The Loop to all the areas surrounding downtown.

Neighborhood stores are often the best place to find something different, and can be where you find the best Chicago souvenirs or gifts.

17. Stroll around different neighborhoods

Whether it’s for shopping, dining, culture, or a more specific purpose, exploring different neighborhoods lets you get under the skin of the city while getting a feel for different vibes. 

Head to Logan Square for broad boulevards and a buzzing vibe, Uptown for jazz clubs, Hyde Park for culture and a prestigious college, Pullman for architecture and history, or Boystown for the LGBTQ+ scene.

Or check out the districts near the Lakefront trail, which include Bronzeville, Edgewater, Lakeview, Lincoln Park, and South Loop.

18. Savor a drink or mocktail with a view 

Sip a cocktail or mocktail at a rooftop bar for sweeping city views and a chilled-out vibe. Centrally located Cindy’s at the Chicago Athletic Association hotel is fantastic in terms of both views and drinks, but the balcony has limited or often no seating. 

If you want to sit with a drink and a view, consider the Jay Parker atop the Lincoln Hotel. London House is known to have some of the best views over the city. Depending on when you want to go, consider reserving in advance. 

19. Try something new by taking a class

If you really do want to sample something new, how about taking a class in Chicago?

You could try paint and sip, a cooking class at Eataly, or a workshop at Old Town School of Folk Music. The latter offers everything from dance and music to sound baths and meditation.

20. Wander along the Riverwalk 

It’s not only the Lakefront Trail that lets you wander by the water in Chicago. You can also meander along the Riverwalk in the city center, which stretches for a mile-and-a-quarter. In fact it’s often called the “Second Waterfront.”

Along the way you can discover small shops, public art, dining out options, boat tours and more. If you’re looking for a spot to rest out of the hubbub, you can simply sit on the steps and watch the boats go by for a while.

21. Sign up for a club or league

If you want to meet people while spending time in Chicago solo, you could sign up for a sports league or a club. There are options like Chicago Girls who Walk, running clubs, sports leagues, and so on.

For ideas, take a look at Meetup. Facebook groups can also be a good hunting ground for finding locally-based, like-minded friends. 

FAQ About Things to do Alone in Chicago

Whether you’re visiting or living in Chicago, here are some top considerations to keep in mind:

How to enjoy Chicago alone?

Chicago is really a great city, with plenty to do and discover. The best way to enjoy Chicago solo is to know how to enjoy your own company. Get in touch with your likes and dislikes, your favorite activities. Then, go experience those things in the city. 

Over the summer, I made myself a solo Chicago bucket list and had so much fun doing things I genuinely wanted to do without waiting for anyone to do them with.

Where to go out alone in Chicago? 

My personal recommendation, as someone in my later 30s, would be to go to a nice cocktail bar or the bar at one of the popular restaurants in the West Loop.

Additionally, consider live music lounges. There are plenty of options, so do some digging to find what best fits your desired atmosphere.

Is Chicago a good place to visit alone?

In my opinion, yes. Chicago is a good place to visit alone because it is so easy to get around the city via walking or public transportation. For the most part, people here are friendly and grounded. There is so much to see, do and eat. 

As a major tourist destination, there are plenty of tours in the city you can sign up for when being alone starts to feel old. As someone who lives here, I’m often out and about exploring the city alone so trust me – it’s great for solo wandering. 

How do adults make friends in Chicago? 

I live here, so based on my experience I’d say you’ll have the greatest success meeting people when you go to group settings of people who like the same things you do. 

Find a workout class you love, volunteer for an organization that matters to you or join a sports league. If you’re moving here, you could also make friends at work. Although, the older I get the less I recommend that… 

Final thoughts on solo things to do in Chicago

If you were looking for a little inspo on things to do alone in Chicago, I hope this guide has given you plenty of food for thought.

From local leagues or cooking classes to shopping, sweet treats, and enjoying beach or park life, I promise you’ll never be bored when living in or visiting the Windy City!