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.
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.
Quiet atmosphere creates a perfect ambiance for dates. The spot offers a speakeasy vibe that suits intimate evenings well. Staff consistently check on reservations for couples.
"The cocktails here are creative and perfectly balanced."
"The cocktails here are so well-made and aesthetically pleasing."
"It's a great spot for a date because it's not too loud."
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.
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.
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.
A jazzy vibe sets the tone for date nights here. Sweet drinks like My Cherie and options like King Arthur add to the experience.
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 blends Italian disco theme with a speakeasy vibe and European coastal beach bar feel. Bright, breezy interior resembles a tropical library with sleek bar and communal seating. Music features vinyl-spun jazz and 80s tunes, creating a chill atmosphere with indoor and outdoor options.
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.
Espresso martinis stand out as a favorite cocktail here. The venue suits both date nights and girls' night out with a lovely atmosphere.
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.
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.
A lounge with a cozy upstairs parlor suits impromptu date nights. It hosts speed dating events that create a pleasant atmosphere for couples.
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.
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 vibe. Comfortable seating and quiet atmosphere make it good for talking and dates.
Quiet and intimate with a fireplace and couches, the lounge creates a sophisticated atmosphere ideal for date nights. It offers a great vibe for enjoying wines and cocktails in a relaxed setting.
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.
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.
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.
Cozy downstairs seating creates a cute ambience ideal for date nights. Drinks flow smoothly, making it a solid spot for a pre-show bite or drink.
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.
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.
Classic jazz club vibe with top flight musicians performing in an intimate venue. Offers a quintessential Chicago jazz experience with a strong, traditional program.
A quaint and dazzling spot with a romantic vibe perfect for date nights. Seating offers fantastic views without needing VIP access.
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.
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 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.
Offers privacy and a setting that impresses for date nights. Works well for couples looking for a great date night experience or a spot to celebrate special occasions.
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.
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.
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.
Speakeasy vibe creates a cozy, intimate setting ideal for dates. Comfortable couches and good music set a relaxed mood, while great drinks add to the experience.
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.
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.
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.
Special occasions get extra attention with birthday celebrations and personalized touches like birthday photos. The atmosphere suits both quiet dates and lively events like watch parties.
Good to know
Happy hour on Thursdays features $6 martinis from 4-7pm.
Expect a lively atmosphere during happy hour with fashionable crowds.
The venue transitions from dining to nightlife after 9pm.
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.
A popular spot in the Viagra Triangle for date nights, known for its Jason's old fashioned cocktail. The drink often gets multiple orders per visit.
Good to know
Reservations are recommended for the best seating experience.
Pandan offers Southeast Asian inspired small plates and unique cocktails.
The outside seating area can fill up quickly.
Small, intimate jazz club with phenomenal acoustics and a speakeasy atmosphere. Live performances happen up close, creating a relaxed and welcoming vibe. Cocktails stand out as among the best, complementing the music well.
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.
Offers a cozy atmosphere with live jazz performances that set a relaxed mood. Frequented for intimate date nights and enjoyable evenings with friends or family.
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.
Small, intimate comedy club with cozy atmosphere and dim lighting creates a close connection between performers and audience. Shows feature top-tier talent delivering nonstop laughter in a friendly, chill vibe. Venue supports local comedy with engaging, interactive performances.
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.
Comedy shows create a lively and fun atmosphere for couples. The spot works well for a date night or a night out with friends, offering plenty of laughs and a great time.
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.
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.
A super swanky cocktail lounge sets the tone with a stylish vibe. It hosts book clubs, blending nightlife with a relaxed, social atmosphere.
Romantic and intimate ambiance sets a speakeasy-like vibe ideal for date nights. The space feels quaint and welcoming, making it great for cocktails or quiet conversation.
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.
Outdoor movie theater on a rooftop offers fantastic views and an elegant atmosphere with individual headphones that provide clear sound and block outside noise. Cushioned chairs and fun games create a relaxed, enjoyable vibe suited for date nights or casual outings.
Outdoor movie nights happen on a Chicago rooftop with clear signage guiding to the spot. The setup uses headsets for audio, which some find less enjoyable, but it suits a date night vibe well.
Open-air setting with a rooftop view creates a relaxed vibe for couples. Comfortable seating and a curated film selection make it a solid choice for a date night.
Good to know
Arrive early to secure good seats as there are no reserved spots.
Bring a blanket for chilly evenings, as they do not provide any.
Food and drink options are limited, with only one available during my visit.
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 rooftop lounge and an indoor lounge create two distinct spaces for nightlife. No food options exist at the lounge.
Rooftop and indoor lounges create a relaxed vibe for couples. The bar serves Zen Garden cocktails and suits both dates and small groups for a nightcap or pre-dinner drink.
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.
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 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.
Smiles greet couples right away, setting a warm tone for a romantic date night. Unique drinks like the Viva Piñata mix smoked pineapple brandy and bourbon for a memorable experience.
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.
Old-school cigar lounge with historic ambiance and rich character offers a relaxing atmosphere filled with cigar smoke and classic decor. Lounge provides a private, comfortable space for quality conversation and enjoying a wide selection of cigars and pipes.
A BYOB cigar lounge offers a relaxed vibe for enjoying cigars. A private premium lounge provides unique train views and a more exclusive setting.
A quiet spot with a pleasing tobacco aroma that even non-smokers notice. Shopping for unique pipes adds a thoughtful touch to the date experience.
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.
Restaurant combines unique decor with a warm, welcoming vibe and top-tier music including hip-hop, R&B, and afrobeats. Atmosphere feels both like a casual takeout spot and a lively club under the right circumstances. Clean environment supports a positive, chill energy throughout.
Colored lights create a club vibe that feels lively yet relaxed. The spot blends lounge atmosphere with a hidden gem appeal for those avoiding typical bars and clubs.
Service stands out with attentive staff helping choose food and drinks. It suits a casual dinner or date night, especially near the Icon Theaters on Roosevelt Street.
Good to know
Happy Hour runs until 7pm with affordable drinks for dine-in only.
Live DJ performs on Taco Tuesdays, creating a lively atmosphere.
Expect a fun vibe on Fridays when the DJ is present.
Hotel offers an industrial chic vibe with luxurious, soulful ambiance and phenomenal rooftop views. Multiple bars and a café create a lively, celebratory atmosphere. Location near transit and neighborhood shops adds convenience and local flavor.
Rooftop bars offer fantastic views and a gorgeous cocktail lounge atmosphere. The Cabana Club features a happy hour by the dip pool with drinks and eats, plus a beautiful sunset scene.
Rooftop views offer a romantic skyline backdrop with a couple of drinks served. The space suits special occasions like proposals and wedding blocks, creating memorable moments.
Good to know
The Cabana Club is open to the public from 4-6 PM for happy hour.
Happy hour features discounted drinks and appetizers at The Robey.
Story hour at the Clever Coyote takes place every Sunday.
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.
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.
Offers a romantic atmosphere ideal for special moments like proposals, with staff coordinating surprises such as playing a partner's favorite song. Serves as a reliable spot for memorable date nights and pre-event dinners.
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.
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.
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.
A beautiful and intimate cocktail bar/lounge creates a perfect setting for a date night. Exceptional meals and attentive service make it ideal for special occasions like anniversaries or birthdays.
Good to know
Parking is available right outside the venue for easy access.
Happy hour runs from 4-6 pm on Fridays with special drink promotions.
Live music occurs every Wednesday, adding to the atmosphere.
Cocktail bar with dimly lit speakeasy vibe and dance floor featuring disco ball and neon lights creates a warm, lively atmosphere. Two distinct rooms separate music and dancing from intimate drink tables, while a downstairs bar offers a change in vibe. Frequent live music and outdoor seating add variety to the experience.
A cocktail club stands out with a lively bar scene. Nearby, several bars and lounges add variety, though the music room may not always be open.
Intimate setting suits deep conversations and relaxed meals. Servers handle adjustments smoothly, even when guests are in a rush. The chicken sandwich stands out as a favored dish for date nights.
Good to know
Happy hour runs from 4-7pm with great drink deals.
Moonflower hosts live music events on weekends.
Brunch drinks are charged separately from food.
Small, contemporary space combines live jazz saxophone with beautiful decor to create an inviting atmosphere. The vibe feels intimate and soulful, drawing a crowd that appreciates well-crafted soul food and a relaxed setting.
Vibrant atmosphere fuels memorable nights with excellent food that consistently impresses. Celebrations here feel special thanks to the engaging vibe and quality offerings.
Jazz music fills the room softly, letting conversations flow easily. Dishes like the Creole Soulfood Dressing and Sweet Sriracha Southern Fried Steak offer bold flavors for sharing.
Good to know
Restaurant Week 2024 offers a $59 deal for three entrees of your choice.
The lounge does not serve liquor, but customers can BYOB with a corkage fee.
Reservations are recommended, but tables are often available without one.
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 lounge tables by the firepit create a relaxed vibe for groups and dogs. Friendly hosts add to the welcoming atmosphere that invites easy socializing.
Sunset views create many photo opportunities for dates. The rooftop offers a relaxed spot for beverages and atmosphere after dinner.
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.
Hotel offers a spacious rooftop bar with beautiful city views and heated outdoor igloos. Rooms feel spacious and elegant, though street noise can be noticeable. Fitness center provides a well-equipped gym with free weights and Peloton bikes.
Rooftop lounge offers spectacular city views and a perfect spot for drinks or food. The bar and lounge showcase an A+ view of the Chicago skyline.
Couples find a wonderful time here with a vibe that invites return visits. The setting supports a comfortable stay that encourages relaxation and connection.
Good to know
Parking costs $50 per night, with valet service only.
Breakfast is included with a variety of options.
The hotel is a 10-minute walk from the blue line station.
Italian restaurant offers a modern jazz inspired design with upstairs loft featuring live music and pool table. Atmosphere shifts from quiet and intimate dining to a lively late-night hangout with DJs and bands. Decor includes quirky records and stylish interiors creating a warm, upbeat vibe.
Upstairs offers a vintage lounge vibe with billiards, old records, and a full bar. The loft feels more open with a relaxed lounge atmosphere and live music.
Quiet and intimate atmosphere suits date nights well. It works for celebrations and casual evenings but is less ideal with small children.
Good to know
Reservations are recommended, especially for larger groups, to ensure seating.
Happy hour runs from 4-7pm on weekdays with discounted drinks and appetizers.
The loft space converts into a club after 10pm with a DJ and dancing.
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 relaxed vibe. Weekends feature a small DJ booth for music, and Tuesdays host a knitting night in the lounge.
Great spot for date nights with a relaxed vibe. The old fashioned cocktail stands out as a solid choice.
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.
Large space divides into distinct atmospheres with comfortable booths and a lively club room. Music features a DJ-driven sound system playing chill, high-energy tunes that shape a fun, unpretentious vibe. Patrons include stylish young crowds, but the atmosphere welcomes all ages for drinks and conversation.
A club vibe kicks in from Thursday to Saturday around 10 PM with lounge electronic music setting the tone. The club room's chaos stays separate from the quieter restaurant area, keeping the space balanced.
Gorgeous atmosphere sets the tone for an intimate date night. Staff offer a complimentary glass of Champagne and a traveling old fashioned menu features multiple cocktail varieties to try.
Good to know
Reservations are recommended to secure a table, especially on weekends.
Happy hour runs from 5 to 7 PM Monday to Saturday with limited menu options.
Arbella turns into a club starting around 10 PM from Thursday to Saturday.
Newly remodeled space combines Great Gatsby decor with a supper club vibe and a small stage for live jazz and ukulele performances. Atmosphere feels cozy and inviting with ample table spacing for comfortable conversation. Lively evenings feature phenomenal live music that enhances the classic old school Chicago environment.
The space has a classy supper-club vibe with a chic, remodeled interior that blends a luxury train dining car feel and a New Orleans jazz lounge atmosphere.
Ribs here are fall off the bone and easy to eat with a knife and fork. The spot suits nice dinners and works well for dates and larger groups with reservations.
Good to know
Reservations are recommended because the place fills up quickly.
Live jazz music happens on Thursday, Friday, and Saturday nights.
The free parking is convenient.