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Local picks

Nightlife lounges in Chicago

When the sun goes down, the only priority is finding a space that keeps the energy high and the night moving.

Based on 801 Opinions
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Updated May 2026
01
Wil’s Martini Lounge image 1
Wil’s Martini Lounge image 2
Wil’s Martini Lounge image 3
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Modern, cozy space with classic decor and two bartending rooms creates a stylish yet relaxed vibe. Expertly made martinis draw a diverse crowd, making it easy to enjoy without the usual bar crowding. Eclectic music and welcoming atmosphere add to the inviting experience.

Classic and cozy decor sets the scene for a true martini lounge experience. The spot draws a lively Uptown/Edgewater crowd and offers stellar service with martinis that stand out from other places.

Classic and cozy decor sets the scene for a timeless lounge experience with stellar service. The crowd leans Uptown/Edgewater, and the martinis stand out as better than most other spots.

People are saying

"The drinks here are strong and tasty."

"The martinis at this Night Lounge are amazing and expertly made."

"The martinis and other cocktails here are amazing."

Good to know

1

Expect a short wait during peak hours, especially on weekends.

2

The prices for martinis are among the most reasonable in Chicago.

3

The lounge is often busy, so arrive early to secure a spot.

02
The Red Room hookah lounge image 1

Small lounge offers cozy seating and dim lighting that create a warm, inviting atmosphere. Music selection includes Russian tunes, adding a unique vibe to the relaxing environment. Premium hookahs provide smooth, flavorful sessions that last long, making it a favored spot for chill and work.

Small size fits the typical Chicago lounge scene. Friendly staff create a welcoming vibe. Offers a solid hookah experience with a good variety of flavors.

Small lounge offers a friendly staff and a relaxing atmosphere for hookah. Known for a solid selection of flavors, it stands out among Chicago hookah spots.

People are saying

"The service here is amazing, truly the best I've experienced."

"This is the best hookah lounge in Chicago."

"I found the best hookah in Chicago here."

Good to know

1

Reservations are not required but recommended for larger groups.

2

The lounge allows outside food delivery, but only dessert is served on-site.

3

Credit cards and mobile payments are accepted; cash is preferred for tips.

03
The Clayton Cigar Shop and Smoking Lounge Chicago image 1

Cigar lounge offers spacious seating with large windows and high ceilings allowing fresh air through open windows. Atmosphere stays quiet and elegant, fostering friendly conversation without loud music or alcohol. Selection includes high-end cigars, some rare, in a cozy, well-kept setting open to non-members.

A sophisticated cigar lounge with a walk-in humidor offers a good selection of cigars at fair prices. The space is spacious and relaxing, featuring a VIP lounge for privacy and the option to open windows for ventilation.

A sophisticated cigar lounge offers a walk-in humidor with a good selection and plenty of seating. The VIP lounge provides privacy and exclusivity, while open windows improve ventilation for a relaxing atmosphere.

People are saying

"I found a wonderful selection of high-end cigars to buy."

"The cigar selection here is impressive and often hard to find."

"The Night Lounge has a sophisticated, impressive collection of cigars."

Good to know

1

The lounge closes early on Saturday.

2

Non-alcoholic drinks are available for purchase.

3

Prices are on par with city luxury cigar lounges.

04
Bar Sotto image 1

Hidden underground bar with soft red glow and jazzy atmosphere creates an intimate, cozy vibe. Space feels mysterious and character-rich, attracting an upbeat crowd for fun nights out or romantic dates. Creative cocktails and unique design details add to its distinct charm.

Fun, dark disco vibes fill the basement lounge beneath Italian Village. The space feels romantic and rustic, serving excellent craft cocktails alongside Italian beer and wine.

A basement lounge offers dark disco vibes with a romantic, rustic atmosphere. The space feels like a speakeasy with touches of European nightlife and serves craft cocktails, Italian beer, and wine.

People are saying

"The bar staff here feels like family and makes you feel right at home."

"The craft cocktails and shareable bites here are excellent."

"The Night Lounge's pastas were delicious and made for great leftovers."

Good to know

1

Happy hour offers discounted drinks and bites after work.

2

The bar features a rotating menu of small shareable plates and pasta.

3

Reservations are recommended for busy evenings, especially weekends.

05
Lemon image 1

Bar combines live music with an upscale cocktail lounge vibe in a cozy, low-light setting. Space includes multiple seating areas and a patio, creating a relaxed yet lively atmosphere. Music volume balances well for both listening and conversation.

Lemon blends a lively atmosphere with live music and an upscale cocktail lounge feel. It offers unique drinks with a chill lounge vibe.

A lively spot with live music and a mix of classic cocktails and unique drinks. It blends a jazz club feel with chill lounge vibes and an upscale cocktail lounge atmosphere.

People are saying

"The cocktails here are thoughtful, creative, and perfectly balanced."

"The cocktails here are inventive and expertly crafted."

"The cocktails here are unique and expertly crafted."

Good to know

1

Live music performances occur from Thursday to Saturday, featuring various bands.

2

Happy hour runs from 4-7pm with $5 shots and beers.

3

Bingo night is hosted every Wednesday at 8pm with a small entry fee.

06
The Albion Manor image 1
English restaurant

English pub-style space combines wood paneling, snugs, and velvet lounges for a mix of casual and sophisticated vibes. Warm lighting and personable staff create a comfortable atmosphere where conversation flows easily. Multiple TVs show major European soccer leagues, making it a popular spot for sports fans.

Upstairs offers an old school English lounge vibe with comfy couches and a knowledgeable bar staff. The space feels cozy and intimate, perfect for date nights or small gatherings.

Upstairs offers an old school English lounge vibe with comfy couches and a knowledgeable bar staff. The space feels cozy and intimate, perfect for date nights or small gatherings.

People are saying

"The bar's cocktails are creatively made and amazing."

"The upstairs lounge offers a cozy, intimate vibe for nightlife."

"The upstairs lounge has a classy, sexy, old-school English vibe."

Good to know

1

Happy hour offers half-price appetizers from 4-7pm on weekdays.

2

Trivia night occurs every Sunday at 7pm with a competitive atmosphere.

3

The burlesque shows are held on Saturday nights with a lively crowd.

07
Barrel cheese & wine | cocktails | Event Space image 1

Speak-easy bar with dim lighting and comfortable lounge seating creates an intimate, cozy atmosphere ideal for quiet conversation. Upstairs event space offers a mingle-friendly setup with leather couches and high-top tables. Outdoor patio is dog friendly and opens to the sidewalk, blending indoor and street vibes.

Dim lighting and velvet lounge chairs create a cozy, low key atmosphere. Comfortable seating and beautiful decor make it easy to talk and suitable for dates.

Dim lighting and velvet lounge chairs create a cozy, low key vibe. Comfortable seating and quiet atmosphere make it good for talking and dates.

People are saying

"I loved the wine selection, especially with the cheese boards."

"The dim, warm lighting and cozy lounge seating make for great nightlife."

"The Night Lounge has a warm, dim-lit atmosphere with cozy seating."

Good to know

1

Happy hour runs from 4-7pm on weekdays with discounted drinks.

2

Live music performances occur on Wednesdays and Thursdays.

3

The venue offers a spacious event space suitable for 40-50 guests.

08
Po Fred's Lounge image 1

Small lounge with a back patio and newly remodeled bar offers a chill and friendly atmosphere. Crowd leans toward older, local grown folks creating a cozy, character-filled vibe. Karaoke and adult entertainment add to the relaxed, family-like environment.

Small and cozy with a back patio and a newly remodeled bar in the back, this lounge serves skillful bartenders and good drinks. It attracts an older crowd and offers a family-like vibe with chill music.

Small and cozy with a back patio and a newly remodeled bar in the back. Drinks are pretty good and bartenders are skillful, attracting an older crowd in a family-like environment.

People are saying

"It's a cozy lounge with a grown folks vibe."

"The karaoke here was off the chain."

"The Night Lounge is a small, cozy spot with an older crowd."

Good to know

1

Parking near Po Fred's Lounge can be difficult; plan to arrive early.

2

Po Fred's Lounge does not sell food; it's catered from nearby vendors.

3

Karaoke happens regularly at Po Fred's Lounge, attracting a lively crowd.

09
Bernard’s image 1
Cocktail bar

Cozy cocktail lounge with speakeasy vibes and tasteful decor offers a romantic atmosphere and excellent cocktails. Music ranges from a great lounge playlist to occasionally loud, affecting conversation. Frequented for tranquil, refined drinking and date night rendezvous.

Cozy cocktail lounge with speakeasy vibes and a refined atmosphere. Quiet corner spot with a great music playlist and a lounge-style setting.

A cozy cocktail lounge with speakeasy vibes offers a quiet, refined spot for nightlife. The great music playlist adds to the intimate, lounge-style atmosphere.

People are saying

"The cocktails here are creative and perfectly balanced."

"The cocktails here are masterfully crafted and aesthetically pleasing."

"The cocktails here are so well-made and aesthetically pleasing."

Good to know

1

Reservations are suggested, but same-day tables are often available online.

2

Valet parking is available for guests visiting the bar.

3

Most cocktails range from $20 to $30 each.

10
The Boss Hookah Lounge image 1

Cozy modern lounge with stylish interior and excellent ventilation ensures a clean, pleasant environment. Music and karaoke create a lively vibe on weekends, while comfortable seating invites relaxation. Hookahs offer top-quality, smooth flavors that last long without bitterness.

A cozy and relaxing atmosphere sets the tone with top-quality hookahs crafted by Nursultan. Friendly and professional staff create a welcoming vibe that shifts to a lively spot with great music on weekends.

A cozy and relaxing atmosphere sets the tone with top-quality hookahs crafted by a skilled maker. Friendly staff create a welcoming vibe that shifts to a lively spot with great music on weekends.

People are saying

"The atmosphere here is so cozy and stylish."

"The staff at this Night Lounge are so friendly and welcoming."

"The nightlife here has such friendly and attentive staff."

Good to know

1

The lounge offers a wide selection of tobacco flavors.

2

Prices at the lounge are fair and reasonable.

3

The lounge is clean and well-maintained.

11
The Getaway image 1

Bar offers cozy atmosphere with dim lighting and a vintage speakeasy vibe. Seating includes a front area and back lounge with sofas and fireplace, creating a comfortable space for mingling. Cocktails are a highlight, featuring creative and well-crafted drinks alongside a relaxed, inviting energy.

A cozy back lounge features sofas, a fireplace, and a small DJ booth active on weekends. The front area offers more seating, and Tuesdays host a knitting night in the back lounge.

A cozy back lounge with sofas and a fireplace creates a relaxed vibe. Weekends feature a small DJ booth for music, and Tuesdays host a knitting night in the lounge.

People are saying

"The cocktails here are super creative and beautifully made."

"The dim lighting and fireplace make it feel so cozy."

"The Night Lounge bartenders are so engaged and make phenomenal drinks."

Good to know

1

Happy hour runs from 4-7pm on weekdays with discounted drinks.

2

Karaoke night is on Thursdays starting at 10pm with a two-drink minimum.

3

The Getaway hosts a knitting night every Tuesday in the back lounge.

12
Rosa's Lounge image 1
Live music venue

Small, intimate venue offers live blues and jazz music with local talent on stage. Atmosphere feels cozy and welcoming, reminiscent of classic blues clubs. Shared tables and a dance floor create a relaxed, friendly environment where every seat feels close to the action.

Live music here is authentic Chicago blues with a raw, soulful vibe that feels like a personal jam session. The crowd is electric and welcoming, and the staff is friendly with great drinks.

Live shows deliver authentic Chicago blues with a raw, soulful vibe that feels like a personal jam session. The crowd stays electric and welcoming, and prices remain reasonable for a genuine blues experience.

People are saying

"You can catch authentic Chicago blues and feel the passion of the music."

"This blues bar is a true Chicago gem."

"It's the best blues bar for authentic music and soul."

Good to know

1

Tickets are required to enter Rosa’s Lounge but can be purchased at the door.

2

Live blues performances occur five nights a week, featuring various artists.

3

Parking is on the street, so consider using public transport to avoid tickets.

13
Windy City Cigar Lounge image 1

Spacious cigar lounge with cozy outdoor patio and comfortable seating offers a welcoming, chill atmosphere with a mature crowd and a good mix of women. Music features live DJs playing old-school jams and games on big screens. BYOB policy allows bringing food and drinks, enhancing the relaxed vibe.

Cozy outdoor setting with nice lighting creates a welcoming vibe. The lounge offers a roomy cigar room with good DJ spins and space to relax and unwind. It is BYOB, common for cigar lounges here.

Cozy outdoor seating with nice lighting sets a relaxed tone. The lounge offers a roomy cigar room and a friendly vibe with good DJ spins and conversation.

People are saying

"It's a welcoming spot to smoke cigars and vibe with good people."

"The nightlife here feels like home, everyone's so welcoming."

"The Night Lounge here feels like a joyous family reunion."

Good to know

1

The lounge is BYOB, so bring your own drinks.

2

You can bring both food and beverages to enjoy.

3

There is a $20 entrance fee unless you buy a cigar.

14
The Welcome Back Lounge image 1

Retro garage decor and 1950s wallpaper set a unique tone, complemented by a spacious back patio with an open lounge vibe. Energetic music, often with a DJ on weekends, creates a lively atmosphere that can get loud. The place suits larger groups and hosts parties well, offering a functional bingo board as a distinctive feature.

A back open patio lounge offers a nice spot during summer. The lounge serves great drinks and even better bar bites, with a team providing excellent service.

A back open patio lounge offers a nice spot during summer. The place serves great drinks and even better bar bites, with a team providing excellent service.

People are saying

"The patio is super sick and really cute."

"The Night Lounge here is perfect for hosting parties."

"The nightlife here makes your night unforgettable."

Good to know

1

Karaoke happens every Sunday night at 9 PM, drawing a lively crowd.

2

Brunch costs around $30 for food and unlimited mimosas.

3

Bingo night takes place every Monday, adding to the weekly fun.

15
Valedor image 1
Cocktail bar

Cocktail lounge blends Japanese and Mexican fusion with a luxe, spacious design and captivating decor. Music features a live DJ that sets a chill, vibey atmosphere, though it can be loud. Small bites and creative cocktails complement the stylish, swanky vibe.

Cocktail lounge offers awesome cocktails and a small but impressive food menu. The vibe is upscale and cute, making it a spot to impress friends if you find a seat.

Upscale cocktail lounge offers awesome cocktails and a small but impressive food menu. The lounge has a cute vibe and can be a spot to impress friends if you find a seat.

People are saying

"The cocktails at Happy Hour are amazing and there's a huge variety."

"The Night Lounge's happy hour is a great deal and includes free tapas."

"The nightlife here has an amazing happy hour with free tapas."

Good to know

1

Reservations are recommended because the place is not very big.

2

Valedor offers a happy hour from 5 to 7 PM every day, including weekends.

3

Valedor advertises rotating complimentary tapas during happy hour with cocktail orders.

16
After Chicago image 1

Luxurious space with glowing circular bar and plush velvet seating creates a moody lounge atmosphere. Live music adds intimate, vibrant energy while acoustics keep conversations private. Drinks and food offer a unique, crafted experience with standout cocktails and dishes.

Moody lounge atmosphere sets a chill vibe with soft lighting and grooving music. The space offers intimate seating ideal for dates or nights out, plus unique cocktail pairings and late-night snacks.

A moody lounge atmosphere sets a chill vibe with soft lighting and grooving music. The space offers a beautiful and intimate setting ideal for cocktails and late-night snacks.

People are saying

"The food here is delicious, thoughtfully prepared, and creative."

"The Night Lounge has creative cocktails, like the "Almost Naked" that's citrusy and delicious."

"The creative cocktails here are outstanding and inventive."

Good to know

1

Parking is available right outside the venue for easy access.

2

Happy hour runs from 4-6 pm on Fridays with special drink promotions.

3

Live music occurs every Wednesday, adding to the atmosphere.

17
Pilot Project Brewing - Wrigleyville image 1

Three-story brewpub offers spacious patio, cozy basement lounge, and rooftop bar with a fun, relaxed atmosphere. Outdoor seating includes a heated tent, creating a comfortable space for gatherings. The vibe suits pre- and post-game crowds with a mix of casual and swanky areas.

A cozy downstairs cocktail lounge with a vibe like entering a high-class dungeon offers unique cocktails. The space includes a super patio area and works well for pre and post-game gatherings.

A basement cocktail lounge offers a cozy, dungeon-like vibe with unique cocktails. Multiple levels include a rooftop and large patio, making it a solid spot for pre and post-game gatherings.

People are saying

"The food here is delicious and offers great vegetarian options."

"The outdoor seating has great beer and delicious food options."

"The Devious Lounge downstairs has such a great vibe for nightlife."

Good to know

1

The Devious Lounge is only a two-minute walk to Wrigley Field.

2

They offer a variety of great beer options and plenty of appetizers.

3

The brewery is dog-friendly, so feel free to bring your pet.

18
Nine Bar image 1
Cocktail bar

Speakeasy-style cocktail bar with a hidden entrance and vaporwave aesthetic creates a unique, intimate setting. The atmosphere is lively and energetic, driven by a live DJ booth and upbeat music. Comfortable seating invites guests to relax while enjoying creative, Asian-inspired cocktails.

A speakeasy style lounge offers a Chinatown-tiki-lounge vibe with a hidden feel. Craft cocktails come with great bartenders behind the counter.

Hidden entrance creates a secret club feel. Cocktail lounge blends Chinatown-tiki vibe with a speakeasy style. Craft cocktails come with great bartenders behind the counter.

People are saying

"I thought the cocktails were amazing and unique."

"The nightlife here offers unique craft cocktails with Chinese influences."

"The Night Lounge has unique, balanced cocktails with Chinese influences."

Good to know

1

Getting there early is necessary to grab a seat at Nine Bar.

2

Parking at Chinatown Parking costs $2 for nearby businesses that validate.

3

Nine Bar does not validate parking.

19
Elements karaoke lounge image 1

Private karaoke rooms offer vibrant, comfortable spaces with good sound systems and amazing lighting. The atmosphere stays fun and energetic, though rooms can get stuffy without HVAC vents. Music plays loudly, creating an unmatched vibe for singing with friends.

Atmosphere offers an authentic KTV vibe with a fun lounge view. Service runs slow even when empty, and food options are limited.

Karaoke lounge offers an atmosphere like authentic KTV spots with a fun vibe and a great lounge view. It works well as a club or drink spot where dancing is easy.

People are saying

"I had a blast with all the fun activities here!"

"The nightlife here has an amazing atmosphere and fun vibes."

"The Night Lounge has such a beautiful atmosphere and fun vibes."

Good to know

1

Reservations for karaoke rooms are recommended to ensure availability.

2

A 20% service charge is automatically added to all drink orders.

3

Expect a $5 up-charge for premium liquor in cocktails.

20
Hookah Joint Lounge image 1

Private curtains create an intimate setting divided into two sections with different pricing. The vibe stays relaxed and low-key, with a cozy atmosphere that suits groups looking to chill. Hookahs rank well above average in quality, enhancing the overall experience.

Private curtains create an intimate setting with a low-key vibe. Service is consistently good, and the flavors stand out in this relaxed night lounge.

Low-key vibe and private curtains create an intimate setting. Service is consistently good, enhancing the relaxed atmosphere for a chill night out.

People are saying

"The service at the Night Lounge was so friendly and attentive."

"The hookah here is amazing, a real 10/10."

"The nightlife here has friendly staff who tend to your needs."

Good to know

1

Section 1 is a cheaper option for seating.

2

Section 2 offers a private booth experience at a higher price.

3

The quality of the hookahs is above average.

21
Biggs Mansion Chicago image 1

Mansion-style cigar lounge offers a vintage decor and classic sophistication with comfortable seating and excellent ventilation. Atmosphere stays relaxed and masculine, attracting cigar smokers from various places. Large walk-in humidor features a world-class cigar selection, including unique blends.

The lounge offers a fabulous cigar selection and a classic, elegant atmosphere. It stands out as a premiere cigar lounge with a beautiful and fancy interior.

A classic cigar lounge with great ventilation and a beautiful interior. Offers a wide selection of cigars in a fancy setting.

People are saying

"I loved the great cigar selection here."

"This cigar lounge is a must-visit for enthusiasts."

"I found it to be a classic, fancy cigar lounge."

Good to know

1

A $100 fee is required for outdoor seating and smoking cigars.

2

Only members can access the outdoor smoking area.

3

Non-members have limited seating options available indoors.

22
Dearly Beloved image 1
Cocktail bar

Cocktail bar showcases edgy and classy decor with amazing sculptures behind the bar, creating a warm, inviting ambiance. Lounge and bar seating offer intimate and Instagram-worthy spaces enhanced by live jazz and DJ sets. Signature craft cocktails and unique dishes complement the visually stunning, chic atmosphere.

Specialty cocktails come with careful attention to detail. Lounge seating creates an intimate vibe, and the perfect volume and space make conversations easy.

Specialty cocktail lounge offers intimate lounge seating and pays close attention to every detail. The space feels beautiful and cool, located near many shops, restaurants, and clubs.

People are saying

"The cocktails here are amazing, thanks to Genesis's great recommendations."

"The nightlife here is amazing; the servers are so attentive and friendly."

"The Night Lounge is stunningly pretty and has a dark elegance."

Good to know

1

Happy hour runs from 4-6 PM Monday through Friday, offering half off all specialties.

2

Enjoy $2 oysters and $10 martinis during happy hour every day.

3

Reservations are recommended, especially during busy hours.

23
Carbon image 1
Restaurant

Beautiful space blends lounge and club with stylish atmosphere and awesome music. Energy shifts from chill vibes during dinner to lively nightlife with DJs. Crowd enjoys top-tier service and a unique setting unlike typical venues.

Atmosphere blends upscale lounge vibes with a warm, social feel where everyone gets attention. Lounge shifts into a club with a Miami-style energy and offers bottle service options.

Vibe shifts from dinner to a lively upscale nightclub with great music and beautiful decor. Bottle service and premium cocktails add to the energetic nightlife experience.

People are saying

"The staff's friendly, attentive service makes the nightlife here unforgettable."

"Happy Hour oysters and fries are a must-try."

"The Night Lounge staff are amazing, friendly, and genuine."

Good to know

1

Happy hour on Thursdays features $6 martinis from 4-7pm.

2

Expect a lively atmosphere during happy hour with fashionable crowds.

3

The venue transitions from dining to nightlife after 9pm.

24
W. Hideaway Lounge image 1

Small lounge with modern elegance and cozy comfort hosts phenomenal DJs playing house and hip hop music. Atmosphere feels lively and energetic yet intimate, attracting a stylish crowd. Clean, Black-owned spot rooted in community offers a neighborly vibe with a well-managed security presence.

A chic and inviting atmosphere sets the tone with events like Bingo Night, Karaoke, and House Music Fridays. The lounge offers great service and a warm, authentic vibe rooted in the community.

A chic and inviting atmosphere sets the tone with house music Fridays, karaoke, and bingo nights energizing the crowd. The lounge offers great service and a warm, authentic vibe rooted in the community.

People are saying

"This bar has a chic, inviting atmosphere with good music."

"The Night Lounge has a chic, inviting, and sexy atmosphere."

"The nightlife here is professional and attentive, making you feel well taken care of."

Good to know

1

Karaoke happens every Tuesday night, with a two-drink minimum.

2

Happy hour runs from 3 to 6 PM, with drinks priced between $6 and $8.

3

The lounge does not serve food, so plan accordingly.

25
Pandan image 1
Lounge

Rooftop lounge offers incredible 18th-floor views with a chic, modern design featuring plush seating and ambient lighting. Atmosphere stays vibrant and inviting, balancing lively music and conversation without overwhelming noise. Guests enjoy thoughtful cocktails and a mix of small plates in a stylish, energetic setting.

Cozy rooftop lounge with a mid-century modern design featuring leather couches, emerald green accents, and brass hardware. Atmosphere shifts from sun-soaked to chic lounge as the evening progresses.

Cozy rooftop lounge with a mid-century modern design featuring leather couches, emerald green accents, and brass hardware. Atmosphere shifts from sun-soaked to chic lounge as the evening progresses.

People are saying

"The view from Pandan is amazing and beautiful."

"The cocktails are complex, lovely, and visually appealing."

"The views from this rooftop lounge are amazing."

Good to know

1

Reservations are recommended for the best seating experience.

2

Pandan offers Southeast Asian inspired small plates and unique cocktails.

3

The outside seating area can fill up quickly.

26
Tortoise Supper Club image 1
American restaurant

Elegant supper club blends live jazz music with a cozy, lively atmosphere featuring dark wood and colorful jazz-inspired wallpaper. Dining spaces include a private room with a bar, creating intimate vibes amid a bustling crowd. The setting combines elements of a jazz club and restaurant for a unique experience.

Live jazz music plays in the lounge, creating a cool vibe for gatherings. The space fits about 100 guests and works well for private events and welcome receptions.

Combining a jazz club, supper club, and restaurant creates a unique nightlife vibe. The space suits special events like weddings and anniversaries, offering great food and impeccable service.

People are saying

"The food at these dinner spots was spectacular and delicious."

"The staff made my birthday celebration feel so special."

"The Night Lounge staff were so accommodating and attentive."

Good to know

1

Reservations are required for private events and should be made well in advance.

2

Happy hour runs from 4-6pm on weekdays with discounted drinks and appetizers.

3

Valet parking costs $16 for three hours, making it convenient for guests.

27
Clara image 1
Cocktail bar

Cocktail bar with industrial art deco style and live jazz music creates a cozy, inclusive atmosphere where seating adjusts to the vibe. The space feels upscale but unpretentious, attracting a diverse crowd who enjoy crafty cocktails and engaging entertainment.

Upscale yet unpretentious vibe fits well with the neighborhood's character. Lounge jazz creates a smoky atmosphere reminiscent of classic spots, adding to the relaxed but refined feel.

Upscale cocktail lounge offers a jazz lounge vibe with music reminiscent of Smokey lounge. Atmosphere stays true to Wicker Park's character without feeling pretentious.

People are saying

"The spicy margarita was a highlight, truly spicy and delicious."

"The live music and cocktails at the Night Lounge were amazing."

"The live music and cocktails here are amazing."

Good to know

1

Happy hour runs from Wednesday to Sunday, between 4 and 6 PM.

2

Clara offers live music on Fridays and Saturdays.

3

Cocktails cost $15 each, with a variety of options available.

28
The Up Room image 1

Rooftop bar offers unbeatable city skyline views with both indoor and outdoor lounges. Atmosphere stays peaceful and spacious, with a vibe suited for quiet evenings rather than loud crowds. Cocktails are well-crafted and flavorful, complementing the setting for dates or nightcaps.

A small rooftop lounge sits atop a historic flatiron building now a hotel, offering both outdoor and indoor spaces. No food is served, making it a spot mainly for drinks and waiting.

A rooftop lounge and an indoor lounge create two distinct spaces for nightlife. No food options exist at the lounge.

People are saying

"The city skyline views are spectacular, day or night."

"The nightlife offers spectacular nighttime views of the city."

"The Night Lounge has spectacular nighttime city views."

Good to know

1

Reservations are recommended as the space fills quickly, especially on weekends.

2

The Up Room closes at midnight, but no new guests are allowed after 11pm.

3

Happy hour is a great time to visit on weeknights for discounted drinks.

29
Broken Shaker at Freehand Chicago image 1

Cozy, dark basement setting blends 70s funk and tiki bar vibes with a hidden, tucked-away layout. Live jazz and DJ sets create an energetic yet civilized atmosphere where people chat and relax. Seating offers ample lounging space near bars that face both street and interior areas.

A chill lounge vibe sets the mood with well balanced cocktails and signature drinks. The space feels cute and welcoming, with friendly servers adding to the relaxed atmosphere.

A chill lounge vibe sets the mood with a well balanced cocktail menu and club-level music volume. The bar feels cute and the servers bring a fun, friendly energy.

People are saying

"The cocktails here are inventive and delightfully complex."

"The cocktails here are strong, creative, and perfectly balanced."

"The Night Lounge cocktails are strong and creative."

Good to know

1

Happy hour offers $4 off cocktails, but check for specific times.

2

The bar closes an hour earlier than usual on some nights.

3

Parking can be challenging in front of the bar.

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