Private club housed in a historic building with classic style interiors and a gorgeous ballroom. Rooftop terrace offers amazing city and lakefront views alongside a fireplace and party area. Atmosphere blends old school elegance with timeless charm.
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.
A newly renovated rooftop terrace offers a picturesque setting, perfect for events like wedding ceremonies. The space includes a fireplace and hosts lively party areas.
"The food here was excellent."
"The nightlife here has amazing city and lakefront views."
"The rooftop terrace is picturesque and ideal for ceremonies."
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.
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.
Multiple rooftops offer unique views of downtown Chicago. The rooftop bar provides a chill vibe with some of the best city views around.
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.
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.
Breathtaking views define the rooftop experience here, making it a standout spot for dinner and drinks. The rooftop bar offers a great atmosphere with a popular happy hour running daily from 5-7pm.
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.
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.
The rooftop offers breathtaking views and a rooftop pool near the bar. A Warming Shack keeps it cozy in winter, making it great year-round.
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.
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.
Incredible views define the rooftop experience here. The rooftop bar offers a great ambiance and attentive staff, making it a standout spot to relax.
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.
Floor-to-ceiling windows offer stunning city views and fill spaces with natural light. The atmosphere stays clean, bright, and quiet, creating a calm environment. Amenities include a rooftop pool, gym, and in-unit washer and dryer, supporting a comfortable and convenient stay.
Sky lounge offers a great indoor spot to relax with wine and nibbles. The rooftop pool adds a very relaxing vibe to the nightlife experience.
A large rooftop terrace features a pool and lounge areas with grills. The rooftop pool offers a breathtaking view and a relaxing atmosphere.
Good to know
The apartment includes a fully equipped kitchen and a washer and dryer.
The location is within walking distance to restaurants and grocery stores.
There is no onsite parking available for guests.
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 happens on a warm rooftop with clear directions to get there. The setting creates a great ambience that suits date nights or celebrations.
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.
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.
A three-level dive bar with a rooftop deck that offers a fun outdoor patio to chill, watch trains pass by, and enjoy entertainment before shows.
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.
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 and unique rooftop lounge with good views that look pretty at sunset. Offers a cute rooftop spot for drinks in a relaxed setting.
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.
Venetian-Gothic architecture shapes a stylish hotel with ornate woodwork and intricate carvings. Lively atmosphere fills public game rooms and a rooftop bar with great views of the lake and park. Athletic-themed amenities include basketball, bocce, and yoga, blending historic charm with active recreation.
A restored 19th-century athletic club offers a speakeasy room, rooftop lounge with views of the Bean, and a game room. Bars and lounges create a vibe like stepping into a time machine.
Spectacular city skyline views and a gothic all-glass roof create a unique rooftop experience. The spot works well for a pre-dinner drink with breathtaking sights of the stars and city.
Good to know
Happy hour runs daily from 4-6pm with discounted drinks.
Expect wedding crowds on weekends due to the hotel's wedding venue status.
Reservations are required weeks in advance for dinner at Cindy's Rooftop.
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.
Outdoor areas offer a relaxing vibe with a rooftop lounge perfect for drinks and city views. Live comedy shows and bands add to the entertaining atmosphere on the rooftop.
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.
Rooms offer spacious layouts with spectacular river views and maintain a quiet atmosphere despite nearby city noise. Rooftop bar provides a comfortable setting with heaters and fire pits, creating a pleasant spot to relax. Central bar stays lively, attracting a steady crowd, while the overall vibe remains luxurious and calm.
A rooftop bar on the third floor features comfortable sofas, heaters, and fire pits. It offers both outdoor and indoor seating with nice snack food and excellent libations.
Good to know
The hotel charges $80 for overnight parking.
Valet parking is available for $88 per night.
The hotel is located right off the river, providing great views.
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.
Rooftop space sits on the 3rd floor with a bar perfectly placed between indoor and outdoor areas. The rooftop terrace offers a chill vibe and a memorable view despite not being expansive.
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.
Modern hotel offers spacious rooms with fantastic city views and a stunning rooftop bar. Atmosphere ranges from quiet and comfortable to lively at the bar, attracting couples and social gatherings. Amenities include a large fitness center, pool, and welcoming common areas.
An upscale and lively bar in the lobby lounge offers great food and drinks with a relaxing vibe. The lounge and bathrooms stay clean, and For Five Coffee Roasters adds to the convenience.
Rooftop features include a bar with city views and a terrace for receptions. Food and drinks at the rooftop bar are delicious, and the service is friendly and engaging.
Good to know
Valet parking costs $78 per night, with potential double charges.
Expect hidden fees, including a resort fee despite no resort amenities.
Room service charges $9 for bottled water.
Rooftop bar offers panoramic lake and skyline views with a vibrant nightlife featuring loud music and DJs. Interior spaces feel cozy and quaint but show signs of wear and outdated decor. Amenities include a rooftop pool, sushi restaurant, and convenient coffee shop, creating a neighborhood boutique vibe.
Stunning rooftop views include downtown, the lake, and Old Town Neighborhood. The rooftop lounge offers a beautiful setting with delicious drinks and food.
The rooftop offers incredible views of the lake, park, and city. The bar serves drinks with awesome service and a cool atmosphere.
Good to know
The rooftop bar may be closed for private events, check in advance.
Expect limited access to the rooftop bar during busy times.
Complimentary happy hour drinks are available on the rooftop.
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.
Unparalleled rooftop views showcase the Chicago River, bridges, and Gothic architecture from the 22nd floor. The rooftop offers a great spot for brunch and drinks with an accommodating atmosphere and kind staff.
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.
Hotel offers great views and modern, comfortable rooms with thoughtful amenities like in-room kettles and a well-equipped gym. Rooftop bar and club create a loud atmosphere with bass noise permeating halls late into the night. Design is upscale and clean, but overall vibe is not warm or welcoming.
Rooftop club offers amazing drinks, music, and skyline views at night. The bar club atmosphere creates strong vibes with a unique cityscape backdrop.
Rooftop parties feature a rooftop bar with great views and a sweet coffee place. Staff are friendly from reception to the rooftop.
Good to know
Rooftop parties occur on weekends, featuring house music and a vibrant atmosphere.
Happy Hour offers complimentary drinks for guests from 4-5pm daily.
Reservations for special events like birthday celebrations are recommended for personalized services.
Boutique hotel blends vibey lobby with rooftop views and a speakeasy bar. Noise from nearby elevated train and thin walls affects quiet moments. Spaces include live music venues and a small rooftop pool with age restrictions.
A busy lounge area draws a grown and sexy crowd on weekends with excellent music. The hotel also offers a nice bar and restaurant for nightlife options.
Rooftop views stand out with great city sights. The rooftop pool offers a gorgeous spot to relax. The rooftop bar and restaurants create a cozy vibe.
Good to know
The pool is open to the public after 4 PM on Sundays.
The pool closes at 2 PM on Saturdays, so plan accordingly.
Expect a lively nightlife scene in the lobby on weekends.
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.
A beautiful rooftop bar offers cozy, reclining lawn chairs with built-in headrests for a stress-free hangout. Selva serves happy hour bites like tacos and Paloma cocktails, and movies sometimes play outdoors.
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.
Hotel offers lively rooftop bar with great city views and vibrant atmosphere. Rooms and common areas feature funky artwork and a comfy, eclectic design. Nighttime brings street noise and energetic crowds, especially near the club and light rail.
A nightclub on the rooftop offers a beautiful setting to party after concerts. The location provides walkable access to theaters, riverwalk, and other nightlife spots in the heart of the Loop.
A bar called ROOF sits on the top floor, offering a hip vibe. The rooftop provides great scenic views visible from the bar and many rooms.
Good to know
The rooftop bar hosts a brunch buffet on weekends.
Private events frequently close the rooftop bar, limiting access.
Valet service is recommended as there is no parking available.
Hotel offers a rooftop pool with city views and a grand, elegant lobby. Atmosphere tends to be loud and busy, with frequent noise from construction, sirens, and lively groups. Rooms feel comfortable but somewhat outdated.
Hothouse Lounge offers a gourmet experience with excellent service from staff like Jose A. The rooftop pool and lounge area add a clean, inviting vibe to the nightlife scene.
An incredible rooftop pool sits on the 5th floor, offering fun for both kids and adults. The pool area includes a lounge space and stays busy, especially in summer.
Good to know
Parking costs $62 per day, regardless of discounts.
Breakfast is not included with the room rate, despite some bookings indicating otherwise.
The rooftop pool is closed until mid-July, which is not disclosed on the booking site.
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.
Rooftop offers seating options both inside and outside. Smoking happens on the rooftop, which can affect the 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.