Kayla Brock

Congratulations! You’ve decided to take your first solo trip to the lovely city of Chicago. We know solo travel can feel intimidating, and navigating a new city alone can feel unsettling, but Chicago is a city built for exploration, and solo travelers are perfectly positioned to take it all in at their own pace. We’ve drawn up some iconic things to check out, no companion required. Whether you’re craving an adrenaline rush on the water, a quiet moment in a world-class museum, or the thrill of seeing the skyline from above, Chicago has a solo activity you can experience on your own terms (or with the help of our guide). By the end of your trip, you’ll be glad you took the leap.