Small venue offers live blues and jazz with local talent. Cozy, intimate atmosphere feels like classic clubs. Nightlife shines with authentic Chicago blues and a friendly, electric crowd.
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.
"You can catch authentic Chicago blues and feel the passion of the music."
"This blues bar is a true Chicago gem."
"It's a cozy dive bar with an intimate atmosphere."
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.
Spacious cigar lounge features a cozy outdoor patio and live DJs spinning old-school jams. BYOB policy lets guests bring food and drinks, adding to the relaxed vibe. Crowd is mature with a good mix of women, perfect for nightlife and socializing.
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.
Good to know
The lounge is BYOB, so bring your own drinks.
You can bring both food and beverages to enjoy.
There is a $20 entrance fee unless you buy a cigar.
English pub-style space blends wood paneling with velvet lounges for a cozy yet refined feel. Warm lighting and friendly staff make it easy to relax and chat. Upstairs lounge offers comfy couches and a knowledgeable bar staff, ideal for intimate nights. Multiple TVs show European soccer 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.
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.
Spacious seating with large windows lets fresh air in, creating a quiet and elegant vibe. Walk-in humidor offers high-end cigars, including rare finds. VIP lounge adds privacy and exclusivity for a relaxing night out.
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.
Good to know
The lounge closes early on Saturday.
Non-alcoholic drinks are available for purchase.
Prices are on par with city luxury cigar lounges.
Modern, cozy space with classic decor and two bartending rooms offers a stylish yet relaxed vibe. Expertly made martinis attract a diverse Uptown/Edgewater crowd. Eclectic music and welcoming atmosphere create a timeless lounge experience with stellar service.
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.
Social club blends temperature-controlled wine lockers with cozy mini clubs for activities like wine tastings and book clubs. Warm, inviting atmosphere encourages relaxed socializing and mingling. Manager adds a personal touch, making the vibe truly casual and welcoming.
Mini clubs offer a range of activities like wine and spirit tastings, book clubs, and theater clubs. The vibe feels casual and welcoming, with a manager who stands out as a key part of the experience.
Good to know
Wine tastings and cocktail-making classes are popular events held regularly.
Birch Road is BYOB, allowing guests to bring their own drinks.
The venue is suitable for private events and gatherings for up to 60 people.
Cocktail bar offers inventive drinks and a vinyl-spun jazz soundtrack for a chill vibe. Bright, breezy interior feels like a tropical library with indoor and outdoor seating. High-fidelity speakers and great DJs create a unique nightlife mix of listening and dancing.
A mix of listening bar and dance club creates a unique nightlife vibe with high-fidelity speakers and great DJs. The cocktail lounge offers inventive drinks and friendly bartenders, making it a chill spot for both weeknights and Fridays.
Good to know
Happy hour runs from 4-7pm on weekdays with mix and match highballs.
The venue gets very busy on weekends, so arrive early.
They operate as a cafe in the morning, offering coffee and light bites.
Cozy cocktail lounge with speakeasy vibes offers a romantic, intimate spot for nightlife. Excellent cocktails and tasteful decor create a refined atmosphere. Music ranges from a great lounge playlist to occasionally loud, balancing tranquil drinking with lively energy.
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.
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 venue offers intimate vibe and excellent sound quality for live music. Cozy space has a pillar blocking some views and no seating inside. Lively crowd enjoys a fun bar atmosphere upstairs with re-entry allowed for fresh air.
Small size creates an intimate vibe with excellent sound quality and great stage views. The venue hosts live music shows and private events, offering disabled-friendly access.
Good to know
Parking is limited; arrive early to secure a spot in the free lot.
Bottom Lounge hosts weddings and private events in their upstairs space.
The venue is wheelchair accessible, making it friendly for disabled visitors.
Small lounge features cozy seating and dim lighting for a warm vibe. Enjoy premium hookahs with smooth flavors and a solid selection that stands out in Chicago nightlife. Friendly staff and Russian tunes add a unique, relaxing touch.
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.
Private club boasts classic style interiors and a gorgeous ballroom for timeless charm. Rooftop terrace offers amazing city and lakefront views with a cozy fireplace. Full bar and good wine selection create an elegant nightlife vibe.
A private club with a full bar and good wine selection offers a classic nightlife setting. The lounge and ballroom provide elegant spaces with a stunning old Chicago vibe and impressive city views.
Good to know
The Chicago Club is a private club, so membership or guest access is required.
Reservations are recommended for events, especially during peak seasons.
Dress code is formal; black tie is expected for evening events.
Hidden underground bar glows with soft red light and a jazzy atmosphere. It blends dark disco vibes with a romantic, rustic feel, serving creative cocktails and Italian beer. Perfect for fun nights or intimate dates.
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 theme and 70’s music offers a cozy, lively vibe. Unique drinks like spicy tequila cocktails pair well with burgers and onion rings. Perfect for relaxed nightlife with a nostalgic twist.
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.
Intimate venue offers excellent sound system and great sight lines for live jazz and jam bands. Cozy atmosphere with two bar areas and well-spaced tables creates a relaxed vibe. Nightlife shines with well-made cocktails, though door management could improve.
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.
Social club offers an intimate atmosphere with live entertainment and diverse art showcases. Outdoor patio boasts breathtaking views of the city skyline and Lake Michigan. It draws a creative crowd, making it a hub for artistic nightlife.
Stunning views create a unique backdrop for socializing in this club. It attracts people interested in the arts, making it a hub for creative nightlife.
Good to know
Membership is required to access the club and its amenities.
The venue hosts events connecting groups seeking funding with various foundations.
The Cliff Dwellers has been established for over 100 years, showcasing a rich history.
Cocktail bar blends industrial art deco style with live jazz music for a cozy, inclusive vibe. Upscale yet unpretentious, it draws a diverse crowd who enjoy crafty cocktails and a jazz lounge atmosphere true to Wicker Park.
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.
Bar offers live music with an upscale cocktail lounge vibe in a cozy, low-light setting. Multiple seating areas and a patio create a relaxed yet lively atmosphere. Music volume suits both listening and conversation, blending jazz club feel with chill lounge vibes.
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.
Cozy modern lounge offers top-quality hookahs with smooth flavors and excellent ventilation. Stylish interior and comfortable seating create a relaxing vibe. On weekends, lively music and karaoke bring a friendly atmosphere perfect for nightlife.
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.
Intimate jazz club offers historic décor and excellent acoustics for a cozy vibe. Talented musicians deliver a classic jazz experience with strong, traditional sets. Dim lighting and comfortable seating create a perfect spot for relaxed nightlife.
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.
Speak-easy bar offers dim lighting and comfortable lounge seating for cozy chats. Upstairs event space features leather couches and high-top tables for mingling. Outdoor patio is dog friendly, blending indoor comfort with street vibes.
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.
Rustic eclectic lounge offers a heated outdoor tent and sports screens for a lively night out. Friendly crowd enjoys an excellent cigar selection with BYOB and no minimum purchase. Beautiful architecture and a cozy smoking area create a laid-back vibe perfect for nightlife.
A public lounge with no minimum purchase offers a relaxed spot to enjoy cigars. The space features beautiful architecture and a smoking area out back that adds to the vibe.
Good to know
Up Down Cigar is BYOB, allowing you to bring your own drinks.
The establishment has both indoor and outdoor seating options.
There is no minimum purchase requirement to use the public lounge.
Classic dive bar offers vintage interior and eclectic art for a chill vibe. Lighting suits reading or laptop work while cash-only policy keeps things simple. Nightlife stays laid-back with inexpensive drinks and a quiet crowd.
A cash-only dive bar with a super cool vibe operates throughout the day and night. The spot keeps things simple and authentic for a laid-back nightlife experience.
Good to know
Rainbo Club only accepts cash payments.
Rainbo Club does not serve food, but they have chips if asked.
The crowd at Rainbo Club is mostly artists and locals.
Small jazz club shines with phenomenal acoustics and a speakeasy atmosphere. Live shows feel close and relaxed, paired with best cocktails that enhance the vibe. Nightlife here is classic, with friendly service and top-notch music.
An intimate jazz venue with phenomenal acoustics and authentic atmosphere offers out of this world music and friendly service. The vibe recalls classic jazz rooms with great cocktails and talented acts.
Good to know
Tickets can be purchased online, with VIP seating available for $40.
Winter's Jazz Club does not serve food or snacks.
Getting to the club can be somewhat hidden and may require some effort.
Social club offers a laid-back vibe with live music and dance lessons that energize the nights. Warm, inclusive space sparks meaningful friendships through diverse social and volunteering events. Creative, engaged crowd makes every visit inspiring.
Lively events like book club, live music, and dance lessons create a dynamic atmosphere. The club fosters meaningful friendships through varied social and volunteering opportunities.
Good to know
The club hosts a variety of events weekly, including book clubs and live music.
Neighborhood tours are offered to help newcomers explore Chicago.
Cocktail classes led by professional mixologists are available for members.
Small, intimate comedy club offers a cozy atmosphere with top-tier talent delivering nonstop laughter. Nightlife here shines with diverse comedians and a friendly vibe that keeps the crowd engaged and entertained.
An intimate atmosphere hosts a diverse lineup of comedians delivering hilarious and unforgettable performances. This small, local venue guarantees a night full of pure comedy and laughter.
Good to know
Tickets are very affordable, making it accessible for most visitors.
There is a 2-item minimum requirement for each guest during shows.
Parking is easy to find and free near the venue.
Cocktail bar blends edgy decor with intimate lounge seating for a chic vibe. Live jazz and DJ sets create a warm ambiance near shops and clubs. Signature craft cocktails and unique dishes complete the specialty lounge experience.
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.
Enjoy a vibrant dance-friendly atmosphere with smooth bottle service and drink specials. Nightlife shines with a three-club tour and easy reservations. Floor tables offer excellent views, making the experience seamless and lively.
Nightlife includes a tour of three clubs with entry fees covered at each. Booking and reservations go smoothly, supporting a seamless experience throughout the night.
Good to know
Drink specials are available at the bars throughout the night.
Entry fees are included for all clubs visited during the tour.
Bottle service is a popular option for a better experience.
Mediterranean dishes shine alongside spectacular city views from the rooftop bar. Fire pits and private couches offer cozy seating for lively nights with live music. Friendly hosts and outdoor lounge tables create a welcoming spot for groups and dogs.
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 blends vintage speakeasy vibe with a cozy lounge featuring fireplace and sofas. Creative cocktails shine alongside a relaxed energy. Nightlife perks include a small DJ booth on weekends and unique knitting night on Tuesdays.
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.
Old-school cigar lounge offers historic ambiance and classic decor for a relaxing night. BYOB policy adds to the relaxed vibe while a private premium lounge gives unique train views for exclusive enjoyment.
A BYOB cigar lounge offers a relaxed vibe for enjoying cigars. A private premium lounge provides unique train views and a more exclusive setting.
Good to know
The shop is located on the second floor of a historic building, accessible via elevator.
They offer a wide selection of cigars, pipes, and smoking accessories.
The lounge is BYOB, allowing guests to bring their own beverages.