The 12 best activities for solo travelers in Chicago

Stretching for 18 miles along Lake Michigan, the Lakefront Trail is one of the best urban biking routes in the country. Rent an e-bike or road bike from 3rd Coast Cycles and cruise between beaches, parks and skyline viewpoints. Pro tip: Keep a lookout for commuters, runners and others taking a stroll along the popular path. The benefit of biking solo? You can stop whenever and wherever you want.

Price: Starts at $35

Chicago is the birthplace of some of comedy’s biggest names, from Tina Fey to Stephen Colbert. At The Second City, you can slip into a seat for a late-night improv show with the oldest improvisational theater troupe and laugh in a room full of strangers. Open seven days a week, it’s a surprisingly great solo outing because everyone is focused on the fun, not you. Grab a drink and settle in for a good time.

Price: Varies depending on show

One of the most unique ways to see Chicago is from the water, so why not rent a kayak and paddle through some of the city’s most famous architecture? Try Kayak Chicago, where you can take a guided tour with experts who will share stories about the city, or go it alone in a single-person kayak for a tranquil moment all to yourself. It’s a surprisingly peaceful solo activity—even in the middle of downtown.

Price: Starts at $30

If you only do one classic tourist activity in Chicago, make it an architecture boat tour along the Chicago River. Volunteers walk you through how Chicago rebuilt and reimagined itself after the Great Chicago Fire, turning disaster into an opportunity for bold architectural innovation. You can simply sit back, listen and take it all in—equal parts educational and scenic.

Price: Starts at $57

Coffee shops are ideal for solo travelers—there’s a quiet comfort in being surrounded by others doing their own thing without the pressure to socialize. Settle in with a matcha at Postcard and take it slow. If you time it right, the space transforms into a vinyl listening bar as daylight ends and evening sets in.

Price: Drinks start at $4.25

Wakeboarding is a relatively low-impact water sport that’s surprisingly easy to pick up, even for beginners. With guided lessons and specialized boats from Wakesurf Chicago, you can glide past skyscrapers and see Chicago from a completely different perspective. It’s perfect for a solo activity to take advantage of a one-on-one lesson. Don’t worry if you haven’t found your sea legs yet; you’ll stand up in no time.

Price: Starts at $350

Standing 1,353 feet above the city, the Skydeck at Willis Tower offers one of the best views in the Midwest. Step out onto “The Ledge,” a glass box extending from the building, and look straight down to the streets below. It’s an activity that feels surprisingly daring, even for seasoned travelers. Make sure to take a photo at the top that you can look back at again and again.

Price: $32 for adults

Few visitors realize that Lake Michigan has shipwrecks beneath its surface. Certified divers can explore underwater sites and reefs along the lake’s coastline with Underwater Safaris Chicago and safely explore these sites without needing to organize a group. This is an adventure for those who want to try something truly unique.

Price: Starts at $399

Located in downtown Chicago, the Maggie Daley Park Climbing Wall is one of the largest outdoor climbing structures in the country. With routes for both beginners and experienced climbers, it’s a great place to challenge yourself and it’s especially well-suited for solo travelers. Staff are on-site to manage safety and belaying, so you don’t have to coordinate with anyone else to participate. And between climbs, you’re rewarded with sweeping skyline views.

Price: Starts at $15

The 606 Trail is ideal for solo exploration. This once-abandoned rail line stretches 2.7 miles through diverse neighborhoods filled with public art, murals and unexpected skyline views. Walking alone allows you to stop whenever something catches your eye—no rushing, no compromises. It’s a creative, self-guided photographic experience where you can follow your curiosity.

Price: Free