The Haute Seeker

Explore Chicago Solo with These 5 Amazing Activities

Museum of ice cream chicago solo travel chicao

Solo traveling is a fulfilling and exciting experience where you get to make all of the decisions and don’t have to wait around for anyone else! Visiting a large metropolitan city like Chicago is a great option for solo travelers, regardless of whether it’s your first or fiftieth time traveling alone. There are a ton of things for you to do and see, and you never truly feel like you’re alone. Check out our best solo travel ideas and try some of them out on your next trip!

1. Try a Walking Tour

Traveling solo to Chicago means that you don’t have to rent a car to get around–you can just walk everywhere! You can wander around on your own or join a walking tour. This gives you an opportunity to hit up the most popular tourist sites, as well as some local favorites. The best part of walking tours is that they are almost always free and give you a local’s expertise and recommendations. Just remember to give them a little tip at the end.

2. Eat Something Delicious

One thing you should never skip out on is eating good food while on a trip. If you find yourself in River North in Chicago and are in the mood to treat yourself, visit Brindille for a high-end French cuisine experience. It’s woman-owned and fairly priced for a three-course meal. If you’re not used to doing things solo, it might seem daunting to sit and eat in a restaurant alone. Why not try a cooking class or food tour instead? 

Black woman at the Shedd Aquarium Solo Travel Chicato

3. Visit a Museum

No city trip would be complete without visiting a museum! Metropolitan cities are great travel destinations because you can easily find a museum that interests you, whether it’s history, art, sports, or science. The Field Museum in Chicago, the Art Insitute of Chicago, and the Museum of Science and Industry are world-class museums worthy of your time.

Hand holding coffee solo travel Chicago

4. Relax in a Cafe

If you need a moment to slow down during your travels, why not choose a local cafe to wind down for a bit? You can get a delicious drink and take an hour to people-watch, read, journal, or listen to music. You might even strike up a conversation with other customers! If you’re ever in the South Loop in Chicago, check out Overflow Coffee for delicious espresso, freshly baked pastries, and live music. 

5. Try Something New

One of the best ways to remember a trip is by doing something new and exciting. Make it a habit whenever you travel that you’ll try at least one new thing on your trip, whether it’s eating alone in a restaurant for the first time, going hiking, or even bungee jumping. Chicago is a massive city with thousands of activities to try–why not go for a sail out on the lake? Trying something new will make your trip even more memorable! 

Just remember–almost every travel activity can be done solo. Don’t avoid doing something just because you think you won’t be able to do it when you’re traveling alone. You might even surprise yourself and end up enjoying way more solo activities than just on this list.  


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