Chicago Nightlife Guide: Experience The Best With These Tips

A woman in red lace lingerie lays on a grey fur rug after enjoying chicago nightlife

As you get older and settle into a routine, it can be easy to forget about scheduling time for fun. While neglecting your social life is never a great idea, it becomes especially tragic when you’re living in a city like Chicago. We have unlimited incredible spaces that will provide you with everything from an artisan cocktail to quality entertainment. If you’re looking for the perfect way to shake up your week, I would love to tell you all about the best places to go for the Chicago nightlife!

Enjoy A Fun Night Out With These 6 Options From The Thriving Chicago Nightlife

Lips Chicago

2229 S. Michigan Ave

Chicago, Illinois 60616

Lips Chicago offers you a fabulous dinner with one of the best nightlife drag shows around! The bar features drag performers who dance, sing songs, and lead one-of-a-kind events. Watch live performances with The Divas, or laugh along as you play Bitchy Bingo. The club requires reservations for most of their events, so make sure you call ahead! 

The Redhead Piano Bar

16 W Ontario Street

Chicago 60654

The Redhead Piano Bar is an iconic spot with live music every night of the week. The Chicago bar features specialty cocktails alongside an unbelievably huge cigar selection for a unique nightlife experience. The club has a rotating list of performers and hosts a Ladies Night every Tuesday. Grab some cocktails and sing along to some favorite tunes performed by talented musicians. 

A woman in floral lingerie sits in an oversized wicker chair in a studio

Blue Chicago

536 N Clark St

Chicago, Illinois 60654

Blue Chicago is a blues club that has been offering energetic performances since 1985. Over the years, the stage has seen blues staples such as Bonnie Lee, Johnny B. Moore, Eddie Clearwater, and Karen Carroll. Whether you’re a major blues fan or just want to try something new, this club will deliver an experience unlike any other.

The Second City

230 W North Ave

Chicago, Illinois 60614

When it comes to legendary Chicago nightlife institutions, it doesn’t get any better than The Second City Comedy Club. For years, Second City has been helping stars like Jason Sudeikis, John Belushi, Amy Poehler, and Chris Farley get discovered. The club has a restaurant and bar so you can eat as you enjoy a show. They also offer classes so you can learn comedy from the best in the business. 

A woman in blue lingerie sits on the floor leaning against a couch in a studio after enjoying chicago nightlife

Kit Kat Lounge & Supper Club

3700 N. Halsted St. 

Chicago, Illinois 60613

The Kit Kat Lounge & Supper Club is the original Chicago drag brunch and drag dinner location. Leave your expectations at the door because the queens will make sure you have a night that you’ll never forget! Their eclectic dinner menu offers burgers, pastas, and appetizers. You’ll have a fantastic atmosphere, delicious drinks, and one of the most entertaining shows in the city!

Chicago Magic Lounge

5050 North Clark Street

Chicago, Illinois 60640

The Chicago Magic Lounge is a nightlife speakeasy that makes your dinner a little more magical. The club provides premium cocktails, small plates, and magic shows you’ll have to see to believe. To get into the club, you’ll step through a secret entrance, making it feel like you’re opening the door to the 1920s. 

Chicago Nightlife

Break up your routine tonight and take advantage of this amazing city! I can guarantee that these Chicago nightlife establishments will leave you with fantastic memories. 

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