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The best things to do in Chicago when flying solo

Lisa White

Sure, we love a good rowdy night out with friends, but sometimes you need a little me time in the city that you love. The next time you want to enjoy an afternoon, evening or full day flying solo in the "Second City," enjoy one of these options for a little alone time. 

Brave an open mic without having to worry about knowing a soul there. Play your fiddle, clarinet or kazoo and don’t worry about bombing in front of your friends and loved ones.

Enjoy an art museum at your own pace. And without any snobby Art History 101 commentary from your friends or out-of-town guests.

Grab a Divvy and hit the road. You don't have to own a bike to explore the city on two wheels. Check out a new neighborhood on the cheap, just make sure not to ride on the sidewalk, please! 

Hit up your favorite record shop. It’s a lot easier to flip through vinyl without your friends impatiently waiting next to you. 

Indulge in a solo glutton crawl. How many tacos can you eat alone in Pilsen? Only one way to find out.

Make like Patrick Swayze and Demi Moore and get behind the wheel at a local pottery class. Learn a new skill and get some sweet handmade swag at the same time.

Hotel bar hop. Make up a fake backstory and see how many free drinks you can get from out-of-towners visiting in business.

Take in a midnight show at Music Box or Facets. Grab some popcorn and Junior Mints and get a little thrill out of watching cult classics way past your bedtime. 

Grab a book and a few rounds at a bar you’ve always wanted to check out. Might we suggest a glass of wine at Vera, a Wisconsin Old Fashioned at Weegee’s Lounge or simply whatever is on special at your local corner bar.

Nab a new high score at one of the numerous arcade bars around town. Now you won’t feel as sad as usual when none of your friends want to play NBA Jam with you.

Visit one of the sorta shady Chinese buffets most Chicagoans have secretly always wondered about visiting. (We’re looking at you, China Buffet).

Shop until you drop. Whether on Michigan Ave or cruising Renegade, you can plan your own route, get through the crowds or take as long as you like when going at it alone.

Float away and find some inner peace visiting an isolation chamber. You only have the option of doing this one alone, hence the key term “isolation.”

Have a steam and soak or even a massage at Red Square. The traditional European bathhouse is the perfect place to escape the city and treat yo' self. You can even grab a bowl of borscht and some herring afterward in the dining area while still snuggling up in your cozy robe.

Workshop your new karaoke standard. Whether it’s with a recording or live band, you can check out if your new jam is a flop or not. We’d pick Alice’s, and the later the better if you’re really nervous.

Visit Paws and pet all the animals. Or even better, volunteer with the organization or another local rescue group and get all the feels while you help animals find their forever homes.

Staycation. It’s all we ever wanted. Avoid the hassle of airports, packing and navigating a new city by booking a room at one of the numerous chic, adorable and lovely hotels around the city. Sleep in, order room service, take a relaxing bath or head out and spend the day exploring Chicago, tourist-style. Visit one of the spots you always talk about visiting but never do, and just relax on your "vacation" without ever leaving the city limits.

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