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.
Small and cozy atmosphere creates a comfortable hideaway feel. Friendly service complements the speakeasy vibes and intimate setting on the second floor.
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.
"The cocktails here are creative and perfectly balanced."
"It's a cozy little bar with speakeasy vibes."
"The cocktails here are so well-made and aesthetically pleasing."
Good to know
Reservations are suggested, but same-day tables are often available online.
Valet parking is available for guests visiting the bar.
Most cocktails range from $20 to $30 each.
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.
A lively and intimate atmosphere fills the small space. The setting feels like a cozy dive bar with a warm, inviting vibe.
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.
Good to know
Tickets are required to enter Rosa’s Lounge but can be purchased at the door.
Live blues performances occur five nights a week, featuring various artists.
Parking is on the street, so consider using public transport to avoid tickets.
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.
An intimate spot with a cozy warm ambiance and good acoustics makes it easy to relax. The space suits quiet talks and enjoying appetizer-style food pairings alongside cocktails and wine.
Dim lighting and velvet lounge chairs create a cozy, low key vibe. Comfortable seating and quiet atmosphere make it good for talking and dates.
Good to know
Happy hour runs from 4-7pm on weekdays with discounted drinks.
Live music performances occur on Wednesdays and Thursdays.
The venue offers a spacious event space suitable for 40-50 guests.
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.
Dim lighting and comfortable seating create a cozy and inviting atmosphere. The space feels laid-back and clean, perfect for relaxing or hanging out with friends.
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.
Good to know
Reservations are not required but recommended for larger groups.
The lounge allows outside food delivery, but only dessert is served on-site.
Credit cards and mobile payments are accepted; cash is preferred for tips.
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.
Modern and classic elements combine to create a cozy atmosphere. The space feels cute and elevated, perfect for relaxing with a martini.
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.
Good to know
Expect a short wait during peak hours, especially on weekends.
The prices for martinis are among the most reasonable in Chicago.
The lounge is often busy, so arrive early to secure a spot.
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.
Red dimmed lighting and mood lighting create an intimate, cozy atmosphere. Quiet background music supports easy conversation in this speakeasy-style setting.
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.
Good to know
Happy hour offers discounted drinks and bites after work.
The bar features a rotating menu of small shareable plates and pasta.
Reservations are recommended for busy evenings, especially weekends.
Cocktail bar with a retro/vinyl records theme and 70’s music creates a nostalgic energy. Atmosphere stays cozy and intimate while maintaining a lively but chill vibe. Unique cocktails like highballs and tiki drinks complement satisfying food options such as burgers and onion rings.
Cozy atmosphere shines with comfortable seating and a down to earth vibe. Unique cocktails and great service add to the warm, inviting feel.
Cool cocktail lounge atmosphere offers unique cocktails and a relaxed vibe. The Cactus Club features spicy tequila and mezcal drinks alongside casual food like burgers and onion rings.
Good to know
Happy hour offers classic cocktails and a $10 burger with fries.
Parking is free and readily available on Sundays.
The venue has plenty of seating for both small and large groups.
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.
A cozy atmosphere blends with a speakeasy vibe and low lighting. The space feels funky and lively yet relaxed for meetups.
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.
Good to know
Live music performances occur from Thursday to Saturday, featuring various bands.
Happy hour runs from 4-7pm with $5 shots and beers.
Bingo night is hosted every Wednesday at 8pm with a small entry fee.
Intimate jazz club with historic décor and excellent acoustics creates a cozy, relaxed atmosphere. Live performances feature talented musicians playing in a setting that honors jazz legends. Dim lighting and comfortable seating offer a balanced sound experience ideal for soaking in pure jazz.
Cozy and intimate vibes fill the venue, making it a welcoming spot to relax. The historic setting adds a homie feel perfect for a quiet night out.
Classic jazz club vibe with top flight musicians performing in an intimate venue. Offers a quintessential Chicago jazz experience with a strong, traditional program.
Good to know
Admission is $20 per person for entry.
Jazz Showcase does not serve food but allows patrons to bring their own.
It is advisable to buy tickets in advance as shows often sell out.
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 features a cozy cocktail lounge with warm, welcoming vibes. The overall atmosphere feels inviting and comfortable.
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.
Good to know
Happy hour offers half-price appetizers from 4-7pm on weekdays.
Trivia night occurs every Sunday at 7pm with a competitive atmosphere.
The burlesque shows are held on Saturday nights with a lively crowd.
Intimate concert venue with excellent sound system and great sight lines puts audiences just feet from performers. Cozy atmosphere supports live jazz and jam band performances with crisp, clear audio at comfortable volume. Two bar areas and well-spaced tables create a relaxed setting for music lovers.
Intimate space with well designed layout creates a cozy and friendly vibe. The atmosphere feels chill and inviting.
Club offers great sound and sight lines with a solid format and well-made cocktails. Door management could improve to stop cold air from entering during arrival.
Good to know
Valet parking is available for $20, but street parking is cheaper if timed right.
The venue accepts only card payments; cash is not accepted.
Dinner and show experiences are available, enhancing the visit.
Cozy space with Hollywood regency decor and mood lighting creates a speakeasy vibe. Bartenders craft exceptional cocktails, including standout Old Fashioneds and martinis. Atmosphere suits jazzy date nights and sophisticated dining with white tablecloths.
Atmosphere blends swanky and cozy vibes with a clubby feel. The space feels welcoming and intimate.
An intimate supper club with a 1950s vibe offers a unique nightlife experience. The atmosphere blends old fashioned supper club charm with Hollywood nights energy.
Good to know
Reservations are recommended, especially during busy weekend nights.
The restaurant closes early at 11 pm, so plan your visit accordingly.
They often run out of popular menu items by 8 pm on weekends.
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.
The front area feels intimate and cozy. The whole space has a super cozy vibe that makes it easy to relax.
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.
Good to know
Happy hour runs from Wednesday to Sunday, between 4 and 6 PM.
Clara offers live music on Fridays and Saturdays.
Cocktails cost $15 each, with a variety of options available.
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.
Stylish interior and pleasant music create a cozy atmosphere that feels relaxing and perfect for hanging out. The vibe stays cool and atmospheric, making it easy to unwind with friends.
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.
Good to know
The lounge offers a wide selection of tobacco flavors.
Prices at the lounge are fair and reasonable.
The lounge is clean and well-maintained.
Mediterranean restaurant with a rooftop bar offering spectacular city views and multiple seating options including fire pits and private couches. Live music creates a lively atmosphere that balances well with conversation. Cocktails and food receive strong praise, contributing to an overall vibrant and welcoming vibe.
Outdoor seating offers a warm, cozy atmosphere with fireplaces that enhance the dining experience. The space feels kid friendly and intimate.
Outdoor lounge tables by the firepit create a relaxed vibe for groups and dogs. Friendly hosts add to the welcoming atmosphere that invites easy socializing.
Good to know
Happy hour is available 7 days a week from 5-7pm.
Reservations are typically required, but walk-ins may be accommodated if available.
The happy hour offers a great selection of drinks and appetizers at unbeatable prices.
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 with sofas and a fireplace creates a warm vibe. Dim lighting and a small DJ booth add to the intimate ambiance on weekends.
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.
Good to know
Happy hour runs from 4-7pm on weekdays with discounted drinks.
Karaoke night is on Thursdays starting at 10pm with a two-drink minimum.
The Getaway hosts a knitting night every Tuesday in the back lounge.
Small, vintage blues bar with an intimate, no-frills setup focused on live music. Atmosphere feels authentic and cozy, with close proximity to local talent performing on a narrow stage at the back. Venue stays lively until late, attracting an enthusiastic crowd and offering cash-only service with room to dance.
Small size and intimate seating create a cozy vibe. The bar feels like a little gem with a warm atmosphere for music, dancing, and drinks.
An intimate spot with a down and dirty blues vibe offers an authentic experience. The club has a hallowed atmosphere that captures the true spirit of blues nightlife.
Good to know
Blue Chicago is a cash-only bar, so bring cash for drinks.
There is a $15 cover charge to enter Blue Chicago.
Live performances start at 9pm, with doors opening at 8pm.
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.
A toasty fireplace creates a warm focal point, while cozy nooks offer intimate seating. The overall vibe feels relaxing and snug, perfect for escaping cold weather.
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.
Good to know
Reservations are required for private events and should be made well in advance.
Happy hour runs from 4-6pm on weekdays with discounted drinks and appetizers.
Valet parking costs $16 for three hours, making it convenient for guests.
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.
Warm, cozy seating pairs with romantic lighting to create a stylish and inviting atmosphere. Low lighting and decorative touches set a chill, intimate tone.
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.
Good to know
Happy hour runs from 4-6 PM Monday through Friday, offering half off all specialties.
Enjoy $2 oysters and $10 martinis during happy hour every day.
Reservations are recommended, especially during busy hours.
Robots deliver food and drinks, adding a modern, fun touch to the experience. Seating includes comfortable couches and leather-upholstered high chairs, creating a cozy, well-decorated interior with varied seating areas. The atmosphere stays calm and soothing, suitable for hanging out or focusing quietly.
Rooms have many charging ports and comfy couches, making them great for studying. The dining area feels relaxing and chill with a well-done, comfortable interior.
Comfortable lounge offers a relaxed spot to enjoy fresh, homemade Asian cuisine. The atmosphere feels inviting and suits a casual night out.
Good to know
The restaurant operates a self-service system where customers order at a kiosk.
Expect large portion sizes that offer good value for the price.
The bathrooms are exceptionally clean and stylish.
Two-room space blends vintage store setting with hippie decorations and comfortable seating. Atmosphere shifts from cozy, plant-filled cafe by day to lively bar with live music and karaoke at night. Inclusive vibe welcomes diverse crowds seeking relaxed or energetic experiences.
Cozy vibes come from a quiet, plant-filled interior that invites conversation. The space feels authentic and relaxed, shifting from calm mornings to a livelier scene by lunchtime.
A mini club inside offers a lively spot for nightlife. The space blends a cocktail lounge vibe with areas for social events and casual meetups.
Good to know
The cafe operates as a coffee shop during the day and a bar at night.
Karaoke nights are popular on Sundays, with a $20 fee for 30 minutes.
Expect a lively atmosphere during weekend events and karaoke nights.
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.
Cozy atmosphere blends with a spacious layout that supports easy conversation. The speakeasy vibe adds a cute, intimate feel ideal for relaxed nights or dates.
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.
Good to know
Getting there early is necessary to grab a seat at Nine Bar.
Parking at Chinatown Parking costs $2 for nearby businesses that validate.
Nine Bar does not validate parking.
Hookah bar with modern karaoke equipment and a cozy, fancy atmosphere offers a great hookah selection and pleasant, chill vibe. Music varies from just right to loud during karaoke, affecting conversation. Outdoor covered patio and plenty of parking add to the experience.
Warm lighting and plush seating create a cozy atmosphere. The lounge feels both intimate and fancy, making evenings comfortable and inviting.
Cozy atmosphere with a covered outdoor patio and plenty of parking. Renovations create a fresh vibe that feels like visiting a friend rather than a typical lounge.
Good to know
Karaoke features a wide selection of songs and a lively atmosphere.
The establishment charges a corkage fee for bringing your own drinks.
Parking is ample and convenient for guests visiting the lounge.
Bar with intimate setting and old school decor featuring bookshelves and vinyl music creates a low-key, welcoming vibe. Small tables suit quiet conversations, making it ideal for dates or casual meetups. Cocktails are thoughtfully crafted, complementing the relaxed atmosphere.
Unique ambience creates a feeling of hanging out with friends in a cozy and welcoming environment. The place features a lovely bar and warm lighting that enhance the overall cozy vibe.
A super swanky cocktail lounge sets the tone with a stylish vibe. It hosts book clubs, blending nightlife with a relaxed, social atmosphere.
Good to know
Happy hour offers $12 old fashioneds and runs from 4-7pm on weekdays.
Inkwell tests out new cocktails every weekend, providing a fresh experience.
Drink prices range from $15-20, with food priced similarly.
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.
Seating includes couches that create an intimate feel. The interior and rooftop both offer a cozy, vibey atmosphere with a beautiful setting.
A rooftop lounge and an indoor lounge create two distinct spaces for nightlife. No food options exist at the lounge.
Good to know
Reservations are recommended as the space fills quickly, especially on weekends.
The Up Room closes at midnight, but no new guests are allowed after 11pm.
Happy hour is a great time to visit on weeknights for discounted drinks.