You’ve got to make Chicago your next solo travel destination! It’s so easy to find something you love from outdoorsy bike trails to award-winning museums and immersive speakeasies.
Chicago is one of the most underrated destinations with endless entertainment opportunities, especially for female solo travelers. Whether you find yourself here for work or just a quick weekend getaway, the city has something for everyone.
Check out these top experiences for solo travelers in Chicago.
Lakefront Trail
Get your bearings of the city from the back of a bike and take a ride along the 18 miles of lakefront trail. Pick up an Divvy rental bike at Navy Pier near Ohio Street Beach and ride the scenic two miles south toward the Field Museum. Along the way, you’ll be treated to unobstructed views of Lake Michigan on a relaxing stretch of road designated exclusively for bikers and runners.
Oak Street Beach
On the shores of Lake Michigan, you can sit on the sand or even swim at Oak Street Beach and enjoy the waves and stunning views of the downtown Chicago skyline. Grab lunch at the Navy Pier Food Experience Corridor and bring it over to the beach for a solo picnic. From here, it’s easy to take a post-meal walk along the Lakefront Trail to continue the adventure.
The Museum of Science and Industry
Chicago has so many museums to choose from, but one of the best for a solo traveler is the Museum of Science and Industry. With highly interactive exhibits and unique pieces like a full U-505 submarine, you could spend hours here on a solo trip. Wander through exhibits like the Science Storms tornado simulator or get tickets for a show at the Giant Dome Theater. Whatever you choose, you’ll truly be impressed.
Chicago Pizza Tours
It’s not really a solo trip to Chicago without deep dish pizza, right? Choose the tour option that best fits your schedule and mobility needs and sample some of the city’s best bites with a small group of other travelers. These 3+ hour tours will leave you feeling stuffed and satisfied with 4 to 6 full servings of pizza from iconic shops like Lou Malnatis.
Insider tip: Save on some of the city’s top slices with the Chicago Pizza Pass.
Millennium Park
A walk through Millennium Park is one of the best solo travel activities in Chicago, because there’s so much to do and see. Take the iconic photo at Cloud Gate (better known as “The Bean”), then move on to the Crown Fountain and the Lurie Garden for a moment of peace amongst the native blooms. During the summer, you might be able to catch an outdoor concert or movie on the Great Lawn. In the winter, you can skate in the shadow of The Bean at the McCormick Tribune Plaza ice rink.
Cindy’s Rooftop
This popular rooftop bar will treat you to picturesque views of Millennium Park, the lake, and the iconic Cloud Gate sculpture from high above the street. Cindy’s is known for their impressive menu of craft cocktails catering to all tastes. It can be tough to get a reservation at Cindy’s, but as a Chicago solo traveler, you’ll have better luck getting a single seat at the bar or a spot on the outdoor terrace.
Wendella Chicago River Cruise
Climb aboard this renowned tour boat and learn about the city’s beginnings and its iconic architecture as you cruise the Chicago River. Choose from a variety of departure times and tour options, including a wine and cheese cruise and a seasonal fireworks cruise on select evenings throughout the summer. Cruises run in 45-minute or 90-minute durations, offering up facts about the city but mostly letting you soak up the views.
Chinatown neighborhood
One of the most underrated neighborhoods for a Chicago solo trip is Chinatown! You can get there easily by hopping on the Water Taxi for a short cruise from downtown. Treat yourself to delicious traditional Asian dishes like hot pot, dumplings, boba tea, and more. After exploring the shops and restaurants of Chinatown, take a walk through Ping Tom Memorial Park for unique views of the city skyline, riverfront, and historic bridges.
Broadway in Chicago
As a solo traveler, you can score some incredible deals on Broadway in Chicago, which brings hit touring shows to the city’s historic downtown theatre district. Take advantage of the Day-of-Show Rush Offers at the box office, where you can score a single seat in a great section at a huge discount. With showtimes most days, you can definitely find a show to fit in your packed solo trip in Chicago.
Live sports
Chicago is home to several professional sports teams, many of which are close to downtown and have a great atmosphere for solo travelers. Check out the Chicago Bears (NFL) in the fall, Chicago Sky (WNBA) in the winter, and Chicago Fire FC (MLS) and the Chicago Cubs (MLB) in the spring and summer, and more. Wait until game day to purchase a ticket and you may get lucky with a good seat at a discount!
360 CHICAGO
If you need an adrenaline rush, visit the 360 CHICAGO observation deck and see the city from the 94th floor. Continue the thrill with a ride on the TILT experience, where you’ll get tipped forward to look downwards at the city from behind a large (and safe) glass panel. The observation deck is also home to Chicago’s highest bar in the sky, CloudBar, where you can sip on themed cocktails while enjoying the panoramic views.
Three Dots and a Dash
End your trip with a unique cocktail at this captivating tropical tiki bar speakeasy in the River North neighborhood. The cocktails are delicious, offering a variety of spirits beyond rum. There’s even some small bites on the menu including drool-worthy dishes like shrimp spring rolls, pork bites, and crab rangoon dip. This spot tends to fill up quickly so make a reservation ahead of time or plan to nab a spot at the bar.
There is truly so much to see and experience in Chicago and solo travelers will fall in love with how easy it is to navigate their bucket list across the city. From architecture cruises to Broadway to luscious gardens, you’ll never be bored on a solo trip to Chicago.
