Location: Downtown / The Loop
Top Things to do in Downtown / The Loop
10 Nightlife in Downtown / The Loop 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. M Bar
Overall Ratings
5.0 based on 1 reviews
2. 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.
3. 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.
4. 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!!!
5. AceBounce
Overall Ratings
4.5 based on 36 reviews
AceBounce believes that everyone needs a place to let loose. Built for play and coming together with friends, AceBounce is the perfect spot for a night of laughter and fun around a table. We offer Ping Pong, Shuffleboard, Beer Pong and Wonderball set against a stunningly designed interior by Russell Sage Studio, with food and beverage by acclaimed Chef Rick Fresh and Mixologist Peter Vestinos. Want a place guaranteed to get the phones put down, and the paddles/skewers/cocktails up? Look no further for as we like to say, the greatest moments happen around a table!
Reviewed By FunMomandDad
We were in Chicago visiting our daughter for her 30th bday. She had heard about this place so we stopped there and had a blast! It was a little later in the evening but was a great alternative to just sitting in a bar/restaurant eating & drinking. While we waited for our ping pong table we had a drink and the chicken mini tacos which were delicious We were a little nervous as we drew the "the interactive" ping pong table - this was sooo much fun, I highly recommend it! People were dancing around, ping pong balls would go on your table and we would just play them as ours. For two 30 year olds and a set of 50/60 year old parents - we absolutely had a blast! The crowd was getting a little drunk but they were happy and just having fun - if you take teens or children go earlier or not on a Saturday night - otherwise, it was great fun.
6. Stocks and Blondes Bar and Grille
7. BIG Bar
8. Cerise Rooftop
Overall Ratings
4.0 based on 51 reviews
Cocktails with a view never tasted so good. Join us for a reimagined rooftop experience complete with mouthwatering cocktails, elevated culinary options, and endless tunes to dance the night away. We’ll see you soon. Open Daily 12PM – 12AM
Reviewed By RickyRey88
Had a wonderful day at this hotel, visiting from Colorado and I see why they call it the windy city. The rooftop view sells itself. The food was amazing. A quick shout out to Chiqui who welcomed us the proper Chicago way with some Malort shots. Would definitely recommend anyone who is looking for a good mango margarita!
9. ROOF on theWit
Overall Ratings
3.5 based on 245 reviews
A glamorous escape set 27 stories above it all, ROOF has earned international praises for its stunning design, sweeping views of Chicago, private event spaces and entertainment programming. Rated one of the "Top 3 Rooftop Bars in the World" -Travel+Leisure, ROOF continues to excite guests with world-renowned DJs, acoustic music series, and live runway shows.
10. O'Neil's on Wells
Overall Ratings
3.5 based on 4 reviews
The Loop's neighborhood, a laid back bar with a Rock 'n' Roll attitude. Opened as Alcock's Inn in 1978. Changed to O'Neil's on Wells in October of 2011. Our business is family owned and operated.
