Location: Chicago
Top Things to do in Chicago
10 Nightlife in Chicago That You Shouldn't Miss
The windy city is a cornucopia of modern art, fine dining, cutting edge comedy, and die-hard sports fans. Snap a photo of your reflection in the silver Cloud Gate sculpture at Millennium Park before heading to Grant Park to get hit with the refreshing spray of Buckingham Fountain. There are dozens of museums and theater companies in Chicago, so a cultural experience is never hard to find. You’re sure to laugh your head off at the Second City Theater, the professional launch pad of many famous comedians.
Restaurants in Chicago
1. Rosa's Lounge
Overall Ratings
5.0 based on 81 reviews
Rosa's Lounge operates in the hallowed tradition of Chicago blues lounges, family owned and operated by an Italian immigrant who came to Chicago three decades ago.
Reviewed By MidwestKathM - Detroit, United States
Rosa's is doing a fabulous job of bringing live music to the fans while keeping you safe in these COVID times. Temperature check and questionnaire at the front door; masks required to enter and while walking within and while talking to anyone but your immediate party. Tables are socially distanced. Even the musicians, except those singing or playing an instrument by mouth, are required to mask up! And if this is the only way to experience live music during these times, then we are happy to mask up here!! And the music was awesome...Tom Holland and the Shuffle Kings!! Thanks for a fun evening!!
2. Chicago Magic Lounge
Overall Ratings
5.0 based on 1,029 reviews
The Chicago Magic Lounge is dedicated to re-introducing you to a style of magic created in the Windy City. Bar magic began in 1915 at a little place called Schulien's. After that, over 15 Magic Bars opened up all over the city over the next 80 years. However, with the last one closing in 1999, the city has lost the true art of "Chicago-Style Magic". Now, the magic is back. In the classic Chicago style, we perform table-side, at the bar, and on the stage. Come back nightly for a fully immersive, interactive, and unique theatrical experience. Cocktails and card tricks, the way magic was meant to be seen. Magic Bar: 5:30 P.M.: Mon-Sun, No Tickets Required. Ticketed Events: Mondays at 7:30 pm: Live Music and Close-Up Magic. Tuesdays at 7:30 pm: The Showcase: New & Experimental Works. Wednesdays at 7:30 pm: our Artist-in-Residence Series. Thurs-Sun at 7:00 pm: The Signature Show. Fri-Sat at 10:00 pm: The Signature Show, Sundays at 12:00 pm: The Family Show
Reviewed By ctworthley
What an amazing experience! I was taken to the Chicago Magic Lounge for my birthday and loved every minute. From the table magicians to the main act on stage, the magic was, well, baffling - as it should be - truly entertaining and more fun than I could even have imagined. Highly recommended!
3. Drunk Shakespeare
Overall Ratings
5.0 based on 116 reviews
"The best thing to ever happen to the theater" Slate Magazine "A live action Drunk History" TimeOut Magazine "Zany, rowdy and debaucherous" New York Times. One actor has 5 shots of whiskey and then attempts to perform in a Shakespeare play. There is a hidden library at 182 N Wabash Ave with over 10,000 books. Running Time: 90 minutes. Food & drink available. 21+ only. Photo ID required.
Reviewed By 366kg - Chicago, United States
Shakespeare and Chicago Improv, I’m in heaven. Shout out to a hard working and talented cast. They have No fear. Small and intimate space. No bad seats. Easy to get to Loop location. Drinking highly encouraged.
4. Buddy Guy's Legends
Overall Ratings
4.5 based on 861 reviews
Buddy Guy's Legends include his own reputation, plus the amazing array of local and national blues performers drawn to this music hotspot.
Reviewed By Lwoodweil - Chicago, United States
Disclaimer: I have been to this joint several times. We went to celebrate our 40th Wedding Anniversary on Monday night because: a) it was our anniversary b) the Buddy Guy's Legends Monday night jam is the best music value I have seen anywhere in the US. $10 gets you in the door to see Brother John Kattke lead the Legends House Band for a 60+ minute set, followed by local musicians. This is a continuation of the Checker Board Lounge's Monday Blues Jam from back in the day. Last night was a Fat Tuesday New Orleans blues evening, but about 80 minus into it, the MC, Robert, introduces the owner of the establishment, Buddy Guy, who comes on and performs with Brother John for another 30 minutes!!! Pictures, social media posts, autographs, drinks for the house, you are damn right it was Buddy Guy! Half the audience was from South America.
5. Nightly Spirits
Overall Ratings
4.5 based on 65 reviews
Explore the spooky and historic side of Chicago on this combination ghost tour and pub crawl. Tour goers will get to enjoy delicious libations at fantastic (and haunted!) local bars, and hear all about the fascinating history of Chicago and some of its most spine-tingling tales!
6. Kingston Mines
Overall Ratings
4.5 based on 833 reviews
Kingston Mines is a blues music nightclub with 2 rooms, 2 stages and 2 bands & live music all night, 365 nights/year. We're the home of Doc's Rib Joint with ribs, wings & more right in the heart of beautiful Lincoln Park, on Chicago's North Side. Looking for a venue to host your next party or get together? Kingston Mines is the perfect venue for large or small groups alike! Ask about our party plans.
Reviewed By 866TaylorB - Chicago, United States
Truth be told, I can't tell jazz from blues from rock 'n roll from Mozart from Sousa. It's all music to me, all of it, anytime, anywhere. For blues, the place to be is Kingston Mines, the oldest and largest continuously operating blues nightclub in Chicago. Located at 2548 North Halsted Street, in the Lincoln Park neighborhood, it has been showcasing the most celebrated blues musicians since 1982...nonstop blues action seven nights a week, 365 days a year, two separate bands every night on two stages, from Delta blues to Memphis blues to Chicago blues. Over the years, it has hosted such blues legends as Koko Taylor, Otis Rush, Carl Weathersby, Magic Slim, Junior Wells, Sugar Blue, Billy Branch, Ronnie Hicks, Mike Wheeler, Peaches Staten, Eddie Shaw, Linsey Alexander and Joanna Connor. If you have a taste for some Southern-style food, you can indulge in some ribs, buffalo wings, Caribbean-style jerk wings, catfish, red beans and rice, home-made nachos, Po'boy sandwiches, shrimp, chicken, bread pudding or pecan pie at Doc's Rib Joint, located in the back of the room and open right up to the last call at 3 a.m. Sunday through Friday and 4:30 a.m. on Saturday.
7. Jazz Showcase
Overall Ratings
4.5 based on 182 reviews
Jazz Showcase is the most historic jazz club in Chicago, founded in 1947 by Joe Segal, and now owned and operated by Wayne Segal (Joe's son). Segal's national and international honors include being declared a "Master of Jazz" by the National Endowment for the Arts (NEA). "It is a great honor to be placed in the same company with so many of the wonderful artists I have presented all of these years!" Joe Segal, 88. The greatest names in jazz have played at Jazz Showcase including the likes of Count Basie, Herbie Hancock, Sun Ra, Sonny Stitt, Dizzy Gillespie, Dexter Gordon, and Art Blakey. Having changed location numerous times since its founding, the club relocated again in 2008 to Dearborn Station, in Chicago, Illinois. Today, Jazz Showcase continues to thrive and bring in top local, national, and international talent. Jazz Showcase presents live music 7 nights a week. Our famous 4 pm Sunday Matinee is geared towards families (Free admission for kids 12 and under). The 170-seat venue is available for group outings during any of our live performances and for private events during the day.
Reviewed By Koakie - Apple Valley, United States
A really great listening room for jazz - outstanding acoustics - and a really warm and friendly vibe, and a place with so much history (live jazz club since 1947!). The cover charge was reasonable, attentive service and a really fun musical experience with family!!! Can't wait to return!!!
8. Blue Chicago
Overall Ratings
4.5 based on 542 reviews
Reviewed By adamparks - Port Saint Lucie, United States
Found Blue Chicago with a group of friends that were in town for a business event. Spent a few hours at the bar listening to some great blues performances. The places gets crowded wall-to-wall, but the sound is good from anywhere in the place. The live act on stage was great and really had the crowd engaged the entire set. Impressive and really enjoyed the night there.
9. B.L.U.E.S.
Overall Ratings
4.5 based on 154 reviews
Popular Blues club located in Chicago's North Side has hosted such great musicians as Sunnyland Slim and Pinetop Perkins.
Reviewed By justnotherjoe
Small, but just what you would expect. Now, granted this isn't the Checkerboard Lounge or Wise Fools Pub of yesteryear. This North side, doing South side best as it can.
10. Second City
Overall Ratings
4.5 based on 1,631 reviews
The Second City is the world's premiere comedy theatre offering the best in Chicago-style sketch and improv comedy every night of the week and has launched the careers of Tina Fey, Bill Murray, Stephen Colbert, Steve Carell and many, many others. First, let’s define a few terms so we’re all on the same page. Sketch comedy is scripted, well-rehearsed scenes that we never, ever call “skits.” (And most of us are mighty touchy about that one. Improv is the unscripted, spontaneous, collaborative art form Second City is famous for. Stand-Up is the classic one-comic-on-stage-with-a-mic-telling-jokes routine. Think Jerry Seinfeld against a brick wall. Typically, any stand-up performances at Second City happen in the UP Comedy Club. A classic Second City revue is made up of original sketches and songs sprinkled with a healthy dose of our world-famous improv. Second City productions are fully written and rehearsed, but no two shows are ever the same.
Reviewed By nina0118 - Boston, United States
I love to laugh, and yet, I was not a big fan of improv comedy... until I visited Second City! I laughed so hard throughout the whole performance! It was hysterical, and probably one of the best nights that I had in Chicago! If you love to laugh, and you love improv, then this is the place for you! Don’t miss it!
