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 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.
Cozy outdoor setting features nice lighting and an area with TVs. The patio offers a comfortable spot to relax outside.
"It's a welcoming spot to smoke cigars and vibe with good people."
"The nightlife here feels like home, everyone's so welcoming."
"The outdoor seating is so welcoming, they'll even teach you how to smoke a cigar."
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.
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 place serves great drinks and even better bar bites, with a team providing excellent service.
Back patio offers a chill vibe and open-air lounge setting. Staff supports a relaxed experience in this nice summer spot.
Good to know
Karaoke happens every Sunday night at 9 PM, drawing a lively crowd.
Brunch costs around $30 for food and unlimited mimosas.
Bingo night takes place every Monday, adding to the weekly fun.
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.
Outdoor seating includes a patio that suits people watching and summer drinks. The space features communal seating and blends indoor and outdoor areas with a long bar.
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.
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.
Outdoor seating features fireplaces and a built-in firepit that create a warm, cozy atmosphere. TVs on the patio add to the relaxed vibe while lounging with friends and dogs.
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.
Neighborhood pub with eclectic decor and a laid-back vibe offers live Americana music and a well-maintained pool table. Outdoor patio provides a relaxed space often visited by a friendly cat. Atmosphere stays friendly and welcoming, attracting open-minded locals who enjoy good humor and art.
Cozy, laid-back vibe with a small outdoor patio and an upstairs art gallery. Service stays exceptional, and the spot hosts fun events and entertainment.
A back patio offers a relaxed spot with a friendly cat that often approaches visitors. The outdoor lounge area sits in a devolved neighborhood and connects to an upstairs art gallery.
Good to know
Trivia night happens every Tuesday at 8pm with a $5 entry fee.
Live music events often start in the afternoon on weekends.
Food delivery is allowed, but limited food options are available on-site.
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 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.
A spacious patio offers shaded seating perfect for groups. The outdoor area feels like a hidden oasis with a great atmosphere for enjoying drinks.
Good to know
The Devious Lounge is only a two-minute walk to Wrigley Field.
They offer a variety of great beer options and plenty of appetizers.
The brewery is dog-friendly, so feel free to bring your pet.
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.
Watching movies outdoors happens with headphones that cancel noise, letting you focus on the film with theater-quality sound. The setting feels elegant and safe, creating a unique experience under the night sky.
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.
Small patio space fills quickly, so arriving early or reserving helps secure a table outside. Outdoor seating suits casual visits, including those with vegan-friendly options.
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.
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.
Outdoor seating features a calm but ambient atmosphere with outdoor heaters and comfortable couches. The patio offers a lively vibe that complements the indoor space well.
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.
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.
A small patio offers outdoor seating with a gorgeous decor setting. Cocktails like the Manhattan can be enjoyed outside.
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.
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.
Rooftop patio offers an amazing outside view with heated igloos for comfort. Heaters keep the space warm even in cold weather.
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.
Lounge offers a cozy outdoor heated patio tent with televisions and a live band alongside a DJ playing great music. Atmosphere stays chill and friendly, attracting a mature, seasoned crowd who enjoy laid-back vibes and dancing. Space suits private parties and after-work drinks with a safe, trouble-free environment.
A lively atmosphere fills the lounge, designed exclusively for mature adults. It offers after-work drinks, a great sound system, and an outdoor patio with a TV for a relaxed night out.
A cozy and inviting patio offers a safe outdoor spot with a TV. It works well for watching games, especially with perfect weather.
Good to know
Parking can be a challenge if there is a large party.
All street parking is available, but avoid the bus lane.
The lounge is for mature adults only.
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 nice patio offers plenty of outdoor seating to enjoy sunny days. The space suits an English style sports pub vibe with wood finishes and a relaxed atmosphere.
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.
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 bar offers nice tables for outdoor seating. People sometimes leave their seats to stand outside, even when sofas and tables are available. Food orders happen indoors before heading outside.
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.
Jazz club offers intimate candlelit setting with Chicago-style Parisian bistro decor and live experimental music performances. Atmosphere feels romantic and cozy, ideal for evening jazz and drinks. Seating layout and lighting create a refreshing vibe that highlights the music and ambiance.
Dark, sexy, and romantic ambiance with candlelit tables and plush seating creates a cozy, intimate vibe. The space channels a Parisian jazz lounge feel, transporting you to a classic European jazz club experience.
A charming patio with a fireplace creates a cozy outdoor space. Live music adds to a European neighborhood vibe that enhances the atmosphere.
Good to know
There is a music fee of $15 per person for entry.
Live jazz is played on weekends until 1 am.
Brazilian Jazz performances occur on Wednesdays.
Multilevel bar and grill with live bands and a rooftop deck featuring a basketball hoop creates a punk rock vibe. Atmosphere is lively and energetic, often very loud with dark, moody lighting. Seating includes comfy balcony spots and ample bars throughout the venue.
Three bands play here, each with different music styles. The club features an awesome sound system and focuses on rock music.
Outdoor seating includes a rooftop patio with a bar and a front patio where a blues jazz soul band plays. The patio offers a great spot to enjoy food like pulled pork sandwiches and fries.
Good to know
Parking can be challenging; consider using public transport or rideshares.
The venue hosts live music events almost every weekend.
Food service ends at 10pm, so plan accordingly.
Hotel offers modern, eclectic design with vibrant colors and creative communal spaces including a bar and terrace with city views. Rooms feature smart home technology and blackout shades, providing a quiet, well-insulated environment. Gym and workstations add to the functional, trendy atmosphere.
Modern decor sets the tone with great bar and lounge areas. The rooftop and outdoor patio lounges offer spots to relax and enjoy city views, though the patio closes from midnight to 5 am.
Rooftop and patio areas offer relaxing outdoor seating. The patio provides a calm spot after walking the city.
Good to know
The hotel is located in the heart of Chicago, close to major attractions.
Parking costs around $50 a night and is located a block away from the hotel.
The gym is one of the best hotel gyms available.
Multi-leveled bar with mechanical bull and live music creates a lively, spacious environment. Atmosphere blends cool Southern vibe with rustic charm and energetic fun. Crowd enjoys games and dancing, making it feel like a vibrant country-themed club.
The venue operates more like a club than a traditional country bar, playing club music instead of country tunes. The space evolved from an old club spot into a country-themed bar but kept a club vibe.
Three floors include a patio with cabanas that easily fit groups of 25. A vintage truck on the patio adds to the theme. Indoor and outdoor seating options create a spacious, lively atmosphere.
Good to know
Happy hour menu includes tacos, quesadillas, chips & salsa, margaritas, and espresso martinis.
Food and drink specials are available during home games.
Children are welcome until 8 p.m.
Small soul food restaurant offers an intimate atmosphere with an all-black aesthetic and live music featuring jazz and saxophone. The vibe stays laid back and refreshing, suited for quiet dinners or date nights. Space is limited, creating a cozy but sometimes cramped setting.
An intimate lounge with a perfect number of tables keeps the space from feeling overcrowded. Guests enjoy live music, great service, and timely food delivery in a clean, safe setting.
Outdoor dining offers a beautiful ambience that shines after sunset. Eating outside adds to the vibe and enhances the experience.
Good to know
Reservations are necessary to secure a spot inside the restaurant.
Parking can be difficult, often requiring a walk from 1-3 blocks away.
The restaurant has a 'No Share Policy' for events like 'The Grand Tasting'.
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.
A classic cigar lounge with great ventilation and a beautiful interior. Offers a wide selection of cigars in a fancy setting.
Outside seating includes a nearly empty patio reserved for members. A $100 fee applies for non-members to sit outside and smoke cigars, but this is not clearly explained upfront.
Good to know
A $100 fee is required for outdoor seating and smoking cigars.
Only members can access the outdoor smoking area.
Non-members have limited seating options available indoors.
Intimate live music venue with top-notch acoustics and a modern design. Crowded indoor space contrasts with a large outdoor patio featuring bars and comfortable seating. Balcony offers a great view while the atmosphere stays vibey and energetic.
Huge outdoor lounge area features large basket chairs and multiple bars for relaxing. The venue has a club vibe rather than a concert feel, suited for small nightclub events but not for EDM music.
Huge outdoor lounge area features large basket chairs and bars for relaxing. Open air patio offers a neurodivergent friendly space with a high-end sound system and modern amenities.
Good to know
Entry is not permitted until after 10:45 pm for events starting at 10 pm.
Tickets must be purchased in advance via Ticketmaster; no door sales available.
Parking is available on the street, but can be difficult to find if arriving late.
Large, well-decorated space features a library-themed course and a rooftop area with notable views. Atmosphere combines jazz music with a fun, social vibe suited for couples and groups. Miniature golf includes a digital scoring system enhancing the experience.
Lounges and bars create a relaxed vibe. Clubs cater even to left-handed players.
Patio offers great views of West Loop and connects smoothly to indoor spaces. Bar sits perfectly between outdoor sliding doors and indoor golf course, creating a seamless flow. Space accommodates groups both indoors and outdoors.
Good to know
Reservations are recommended, especially for larger groups or events.
The bar is wheelchair accessible, but the golf courses are not.
Expect upscale pricing for food and drinks at the venue.
Huge patio with fire pits and live music creates a lively outdoor space. Seasonal holiday-themed pop-ups and decorations add immersive, festive vibes. Loud music fills the air, making it energetic and social.
A cool cocktail lounge vibe defines the bar, featuring an enormous patio for outdoor seating. The lounge area invites relaxation, though experiences vary across seating options.
An enormous patio creates a cool cocktail lounge vibe with art-filled walls and a dog-friendly atmosphere. The outdoor space feels like a vibe for afternoon drinks and casual hangs.
Good to know
Happy hour offers $5 drafts on Fridays from 4-7pm.
Live music occurs every Sunday, featuring DJ Gloria on 'Soulful Sunday.'
The venue hosts special pop-up events for Halloween and Christmas.
Piano bar offers live piano music with a phenomenal, engaging pianist in a small, crowded space that encourages standing and dancing. An outdoor cigar lounge provides additional seating with couches and ashtrays. The atmosphere is lively and packed, creating an intense but vibrant vibe.
A speak-easy style cigar lounge offers a cozy, calm atmosphere with attentive service. The outside deck and live music at the piano bar add to the relaxed nightlife vibe.
A hidden outdoor deck serves as a cigar-friendly lounge accessed through a secret pathway. This space offers exclusive vibes alongside live music and drinks.
Good to know
Expect large crowds on weekends, especially after 10 PM.
Reservations are recommended for special events or large groups.
Happy hour offers discounted drinks from 4 PM to 7 PM on weekdays.
Lobby offers a welcoming atmosphere with a hip vibe and space for socializing. Rooms are spacious and chic but can be affected by loud music from the bar and rooftop nightlife. Rooftop features include a cinema experience and great views, enhancing the energetic ambiance.
A great bar and rooftop nightlife create a lively atmosphere. The Rooftop Club Cinema offers mimosas and muffins for a relaxed date vibe.
Comfortable outdoor seating includes a patio perfect for breakfast and afternoon drinks. The 5th floor balconies feature a rooftop cinema with a peaceful vibe and occasional birds snacking on dropped popcorn.
Good to know
Selva rooftop bar offers happy hour bites and cocktails until 1:00 am.
Brunch is served at 10 am on Saturdays and Sundays.
Afternoon delight promotion includes coffee and pastry discounts from 1-3 pm.
Rooftop bar offers unparalleled city views including river and Gothic architecture. Atmosphere is lively with loud music, making conversation difficult. Outdoor space features igloos and fire pits, with indoor area hosting a live DJ to maintain energy.
Rooftop views stand out with both indoor bar and outdoor lounge areas. The vibe shifts to a club atmosphere when the bar fills up, often making seating scarce before last call.
Outdoor seating includes a rooftop patio with gorgeous views. The hostess offers to arrange terrace seating upon request.
Good to know
Reservations are required to secure a table at LH Rooftop due to limited space.
Expect long wait times during peak hours, especially on weekends.
Bring your ID as it is required for entry; no photos accepted.