Best Night Entertainment in Chicago

Chicago, the Windy City, is renowned for its stunning architecture, vibrant arts scene, and, perhaps most notably, its electrifying nightlife. When the sun dips below the horizon, Chicago truly comes alive, offering a kaleidoscope of entertainment options to suit every mood and preference. Whether you're a jazz aficionado, a comedy connoisseur, a dance floor enthusiast, or simply seeking a unique evening adventure, the best night entertainment in Chicago awaits.

But with so many choices, how do you navigate the city's after-dark offerings to find exactly what you're looking for? This comprehensive guide will illuminate Chicago's diverse nightlife, ensuring your evenings are as unforgettable as your days.

Experience Chicago's Legendary Live Music Scene

Chicago's musical roots run deep, particularly in blues and jazz, genres that have shaped the city's cultural identity. From historic venues to modern concert halls, the live music scene here is second to none.

Jazz and Blues Clubs: A Trip Back in Time

Step into a bygone era at one of Chicago's iconic jazz and blues clubs. These intimate settings offer a chance to witness world-class musicians up close, often in venues steeped in history.

• The Green Mill Cocktail Lounge: A legendary jazz club that dates back to 1907, The Green Mill was a favorite haunt of Al Capone during Prohibition. Today, it continues to transport patrons to the 1930s and 40s with its authentic ambiance and live jazz music.
• Kingston Mines & B.L.U.E.S.: Located across the street from each other in Lincoln Park, these two blues powerhouses offer live music seven nights a week. You can even visit both in one night for a full immersion into Chicago blues.
• Buddy Guy's Legends: Owned by the blues legend himself, this club is a must-visit for any blues fan, often featuring performances by Buddy Guy when he's in town.
• Winter's Jazz Club: A more contemporary addition, offering a refined jazz experience.

Concert Venues: Rock, Indie, and Beyond

Beyond jazz and blues, Chicago boasts an impressive array of venues hosting everything from rock and indie to pop and electronic music.

• The Salt Shed: One of Chicago's newer concert venues, located in the former Morton Salt building, offering both indoor and outdoor concert spaces with the Chicago skyline as a backdrop during summer.
• Aragon Ballroom: A historic venue that has hosted a diverse range of artists, from big bands to punk legends like Nirvana and Green Day.
• City Winery Chicago: Pairs local wines and creative cuisine with intimate live music and comedy shows.
• Thalia Hall: A Pilsen landmark known for its indie music offerings and vibrant atmosphere.
• Bottom Lounge & Empty Bottle: Popular spots for rock and alternative music, offering a more intimate setting for emerging and established bands.

Laugh Out Loud at Chicago's Comedy Clubs

Chicago is the birthplace of improvisational comedy and has launched the careers of countless comedic stars, including Tina Fey, Steve Carell, and John Belushi. A night at a Chicago comedy club promises side-splitting laughter and often, a chance to see the next big thing.

• The Second City: The world's premier comedy club and school of improvisation, offering live sketch and improv shows nightly. It's an iconic institution where audience suggestions often inspire the performances.
• iO Theater: Known for its long-form improv shows and for being an alma mater to many famous comedians.
• Zanies Comedy Club: A Chicago staple for almost 50 years, Zanies is an intimate venue that attracts both up-and-coming talent and big names in stand-up comedy.
• The Laugh Factory: This historic venue, originally a movie house, now hosts an impressive roster of stand-up comedians.
• The Comedy Clubhouse & The Lincoln Lodge: These venues offer diverse shows, including stand-up and group improv, often in more intimate settings.
• The Comedy Bar: Features stand-up shows, an outdoor rooftop patio, and even serves Gino's East deep-dish pizza.

Unwind at Chicago's Best Bars and Nightclubs

From hidden speakeasies to vibrant dance clubs and breathtaking rooftop bars, Chicago's bar scene is as varied as its neighborhoods.

Rooftop Bars: Sip and See the Skyline

For unparalleled views of the city lights, head to one of Chicago's many stunning rooftop bars.

• LH Rooftop (LondonHouse Chicago): Offers sweeping vistas of the Chicago River and Michigan Avenue from its tri-level perch on the 22nd floor. It's known for signature cocktails and a lively atmosphere.
• Cindy's (Chicago Athletic Association Hotel): Perched on the 13th floor, Cindy's provides expansive views of Millennium Park and Lake Michigan, along with excellent cocktails.
• ROOF on theWit: Located 27 stories high, this internationally acclaimed rooftop offers expressive design, sweeping skyline views, and unique handcrafted cocktails.
• Raised | An Urban Rooftop Bar: Offers impressive views of the Chicago River, with an industrial, eclectic vibe and seasonal menus.
• VU Rooftop Bar: At 22 stories high, it features city vistas, multiple bars, patios, and fire pits.

Speakeasies: Discover Hidden Gems

For a taste of Prohibition-era charm and expertly crafted cocktails, seek out Chicago's hidden speakeasies.

• The Drifter: Tucked beneath the Green Door Tavern, this authentic 1920s-era speakeasy offers over 100 craft cocktails presented on Tarot cards, along with sporadic live performances.
• The Violet Hour: A classic speakeasy known for its high-end cocktails and intimate, elegant atmosphere.
• Blind Barber: A unique fusion of a barbershop by day and a vibrant speakeasy by night, offering a cozy, dark ambiance.
• Three Dots and a Dash: A speakeasy-style tiki bar offering a unique blend of island charm and tropical cocktails.
• The Office: Located below The Aviary, this is a pricier but highly acclaimed option for exceptional cocktails.
• Chicago Magic Lounge: Combines a speakeasy entrance with magic shows and a bar, offering a truly unique experience.

Nightclubs: Dance the Night Away

If you're looking to dance, Chicago's nightclubs offer pulsating beats and vibrant atmospheres, from house music to EDM and techno.

• Smartbar: A basement nightclub featuring well-known DJs spinning a wide array of dance music, including house, EDM, and techno, known for its state-of-the-art sound system.
• Prysm: An upscale nightclub with two dance floors, three cocktail bars, and high-tech lighting.
• Joy District: A multilevel venue featuring a nightclub, restaurant, and rooftop patio, often hosting top Chicago DJs and sometimes celebrity performances.
• The Underground: An exclusive subterranean experience with top DJs, private tables, and VIP service.
• Beauty Bar: A unique nightclub featuring a retro salon theme, martinis, and DJs spinning Y2K classics.

Unique Evening Experiences Beyond Bars

Chicago's nightlife isn't just about drinks and dancing. The city offers a variety of unique attractions and activities that come alive after dark.

• Night Tours & Cruises: See the illuminated skyline from a different perspective with a night boat tour on Lake Michigan or the Chicago River, or delve into the city's past with a ghost or mob history tour.
• Observation Decks: Ascend to the Skydeck at Willis Tower or 360 Chicago at the Hancock Tower for breathtaking panoramic views of the twinkling city lights.
• Navy Pier & Centennial Wheel: Stroll along Navy Pier and take a ride on the iconic Centennial Wheel for spectacular views of the skyline and waterfront, especially during summer fireworks displays on Wednesday and Saturday nights.
• Late-Night Museum Events: Several Chicago museums, including the Art Institute of Chicago, Shedd Aquarium, and Museum of Science & Industry, host occasional "After Hours" or "Happy Hour" events for adults. Even Lincoln Park Zoo sometimes has late-night adult events.
• Drunk Shakespeare: An interactive show where five actors perform a Shakespeare play, and one of them takes five shots of whiskey before the performance.

Satisfy Your Late-Night Cravings

After a night of entertainment, you're bound to get hungry. Chicago's late-night dining scene has you covered, from classic comfort food to elevated diner fare.

• Au Cheval: A diner-style bar and restaurant known for its elevated traditional diner fare, including its famous cheeseburger, open late.
• Maxwell Street Depot & Red Hot Ranch: For classic Chicago street food like Polish sausages and hot dogs, these no-frills spots are popular late-night choices.
• Dimo's Pizza: A go-to for late-night pizza in Wicker Park.
• Rose Mary: Offers late-night reservations for those looking to extend their dining experience.
• Golden Apple Grille & Breakfast House: A diner offering breakfast and grille items late into the night.

Conclusion

Chicago truly offers an unparalleled array of night entertainment, ensuring that every evening can be a unique adventure. From the soulful sounds of jazz and blues clubs to the uproarious laughter of improv shows, the breathtaking views from rooftop bars, and the hidden allure of speakeasies, the city caters to every taste. Don't forget to fuel your adventures with some of Chicago's famous late-night eats!

What's your ideal night out in Chicago? Share your favorite spots and experiences in the comments below!

Frequently Asked Questions (FAQ)

Q1: What are the best areas for nightlife in Chicago?

A1: Popular neighborhoods for nightlife in Chicago include River North, Lincoln Park, Wrigleyville, Logan Square, and the West Loop, each offering a distinct vibe and a concentration of bars, clubs, and venues.

Q2: Are there any unique, non-bar related things to do at night in Chicago?

A2: Absolutely! Beyond bars, you can enjoy night boat tours (including architecture or ghost tours), visit observation decks like Skydeck Chicago or 360 Chicago, explore Navy Pier, attend late-night events at museums or the Lincoln Park Zoo, or catch a unique show like "Drunk Shakespeare" or a magic show at Chicago Magic Lounge.

Q3: What kind of music scene does Chicago have at night?

A3: Chicago is famous for its diverse music scene, particularly its deep roots in jazz and blues. You'll find legendary venues dedicated to these genres. Additionally, the city has a vibrant rock, indie, electronic (especially house music, which originated here), and general live music scene with numerous concert halls and intimate clubs.

Q4: Are Chicago's comedy clubs good for tourists?

A4: Yes, Chicago's comedy clubs are excellent for tourists! Many, like The Second City, iO Theater, and Zanies, are world-renowned and offer a quintessential Chicago experience, showcasing top-tier improv and stand-up talent.