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New Yorkers 1st Choice
Best of Chicago Loop

Rooftops

Made for those who insist on being elevated above the city streets whenever they step out for a drink.

Based on 555 Opinions
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Updated May 2026
01
The Chicago Club image 1
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Private club shines with classic style interiors and a gorgeous ballroom. Rooftop terrace offers amazing city views and a cozy fireplace for events. Atmosphere blends old school elegance with timeless charm, ideal for weddings and lively parties.

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.

People are saying

"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

1

The Chicago Club is a private club, so membership or guest access is required.

2

Reservations are recommended for events, especially during peak seasons.

3

Dress code is formal; black tie is expected for evening events.

02
Kasa South Loop Chicago image 1

Apartment-style hotel boasts spectacular city and lake views and a quiet, safe atmosphere. Spacious units feature full kitchens and private balconies for a home-like feel. Rooftop offers a 24th floor lounge with panoramic cityscape vistas and thoughtful surprises.

Views from the rooftop patio offer a full cityscape that surpasses the room view. Access includes a 24th floor lounge with some thoughtful surprises.

People are saying

"I loved the beautiful city view from the window."

"The beds here are so comfortable, I slept great."

"The rooftop views of the city and lake were amazing."

Good to know

1

Parking is available in a garage next to the building, but it's an extra cost.

2

Self-check-in requires a code to enter the building and parking garage.

3

The property prohibits leaving pets unattended, which limits pet-friendliness.

03
Seville Chicago image 1
Restaurant

Rooftop dining shines with stunning city views and an outdoor seating area. Friendly staff enhance the relaxed atmosphere perfect for quiet meals or lively happy hours. Enjoy cocktails and small plates in a charming setting that suits any mood.

A 16th floor rooftop offers a stunning city view with an outdoor seating area. The space creates a memorable evening atmosphere for dining.

People are saying

"You'll love the inventive cocktails, many are sweet."

"The food here is delicious, super juicy and flavorful."

"The food on the Rooftop was delicious and flavorful."

Good to know

1

Happy hour runs from 3:30 to 5:30pm on weekdays.

2

Happy hour offers great deals on food and drinks.

3

The restaurant is located on the 16th floor of the Hilton hotel.

04
citizenM Chicago Downtown image 1

Hotel blends modern design with vibrant colors and smart rooms for comfort. Rooftop lounge offers city views and live comedy for fun nights. Gym and workstations keep the vibe trendy and functional.

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.

People are saying

"I loved staying at this hotel; I'll definitely return."

"It's the perfect location for Date Spots, with attractions and shopping within walking distance."

"The rooftop is small but stylish and artsy."

Good to know

1

The hotel is located in the heart of Chicago, close to major attractions.

2

Parking costs around $50 a night and is located a block away from the hotel.

3

The gym is one of the best hotel gyms available.

05
Renaissance Chicago Downtown Hotel image 1

Rooms boast spacious layouts and spectacular river views while staying quiet. Rooftop bar offers fire pits and cozy seating with great snacks and drinks. Central bar keeps a lively crowd amid a calm, luxurious vibe.

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.

People are saying

"The hotel staff were so kind and professional."

"The river and city skyline views from the room were spectacular."

"I loved the rooftop bar; it was the crowning glory."

Good to know

1

The hotel charges $80 for overnight parking.

2

Valet parking is available for $88 per night.

3

The hotel is located right off the river, providing great views.

06
The St. Regis Chicago image 1

Towering skyscraper boasts epic city views and spacious rooms with an elegant vibe. Guests enjoy a large indoor pool and personalized butler service. Breakfast on the 11th floor offers a spectacular rooftop view with amazing service and occasional complimentary meals.

Breakfast on the 11th floor offers a spectacular view with a welcoming atmosphere. Service from valet to rooftop staff is consistently amazing, and credits or complimentary meals are sometimes available for guests.

People are saying

"Vince at the Hotel concierge desk went all out to make everything exceptional."

"The city views from the pool and terrace are amazing."

"The rooftop views are amazing and spectacular."

Good to know

1

Every evening at 5 pm, they do Sabrage (Champagne Sabering) for guests.

2

There is a daily champagne opening ceremony with a saber starting at 5:30 p.m.

3

The hotel is located near Riverwalk, providing easy access to attractions.

07
Chicago Athletic Association - The Unbound Collection by Hyatt image 1

Venetian-Gothic style and ornate woodwork create a stylish hotel with a lively vibe. Athletic amenities like basketball courts and yoga blend history with activity. The rooftop offers gothic all-glass roof and city skyline views perfect for drinks and star gazing.

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.

People are saying

"It's a striking historical site with authentic charm and artistic details."

"The rooftop bar has an awesome view of Millennium Park."

"The rooftop offers an awesome view of the park."

Good to know

1

Happy hour runs daily from 4-6pm with discounted drinks.

2

Expect wedding crowds on weekends due to the hotel's wedding venue status.

3

Reservations are required weeks in advance for dinner at Cindy's Rooftop.

08
theWit Chicago, a Hilton Hotel image 1

Hotel features a lively rooftop bar with great city views and a vibrant atmosphere. Rooms showcase funky artwork and comfy, eclectic design. Nighttime brings street noise and energetic crowds near the club and light rail.

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.

People are saying

"The hotel's five-star service made my day better."

"The rooftop bar has a lively atmosphere and great skyline views."

"It's a stylish, modern place with a lot of personality."

Good to know

1

The rooftop bar hosts a brunch buffet on weekends.

2

Private events frequently close the rooftop bar, limiting access.

3

Valet service is recommended as there is no parking available.

09
LH Rooftop image 1
Restaurant

Rooftop bar boasts unparalleled city views including the Chicago River and Gothic architecture. Lively atmosphere with live DJ and loud music makes conversation tough. Outdoor igloos and fire pits add cozy charm while staff remain kind and accommodating.

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.

People are saying

"The rooftop city views are stunning and beautiful."

"The food here is pretty good, though just okay."

"The rooftop views of the city are stunning."

Good to know

1

Reservations are required to secure a table at LH Rooftop due to limited space.

2

Expect long wait times during peak hours, especially on weekends.

3

Bring your ID as it is required for entry; no photos accepted.

10
Sports Illustrated Resorts Chicago image 1

Hotel boasts great views from its rooftop bar and coffee spot, with friendly staff enhancing the experience. Rooms are modern and comfortable with thoughtful amenities, while the rooftop club's loud bass can disrupt quiet moments. Design feels upscale but not warm.

Rooftop parties feature a rooftop bar with great views and a sweet coffee place. Staff are friendly from reception to the rooftop.

People are saying

"The hotel staff went above and beyond to make me feel welcome."

"The rooftop has stunning city views and is a great place to unwind."

"The rooms feel modern, comfortable, and thoughtfully designed."

Good to know

1

Rooftop parties occur on weekends, featuring house music and a vibrant atmosphere.

2

Happy Hour offers complimentary drinks for guests from 4-5pm daily.

3

Reservations for special events like birthday celebrations are recommended for personalized services.

11
Chรขteau Carbide image 1

Rooftop bar shines with gorgeous sunset views and cozy couches warmed by heaters and blankets. Enjoy a notable absinthe selection alongside jazz and violin music that sets a relaxed vibe. Fire pits add warmth, making it perfect for a holiday atmosphere.

Cozy couches and heaters with blankets create a warm vibe on the rooftop. The spot offers awesome downtown views and a solid selection of cocktails and absinthe.

People are saying

"The city views from up here are really great."

"Alondra crafted the best mezcal cocktail I've ever had."

"The rooftop cocktails here are fantastic and tasty."

Good to know

1

Reservations are required for booking a hut with a fireplace.

2

A $300 food and beverage minimum applies for booking a chateau.

3

The menu is limited, with no vegetarian options except olives and popcorn.

12
Pendry Chicago image 1

Historic building boasts Art Deco design and spacious rooms with city views. Rooftop offers breathtaking views and lively music for evening drinks. Downtown location means loud street noise can affect room quietness.

Breathtaking city views dominate the rooftop, creating a perfect backdrop for evening drinks. An open lounge area features great music and entertainment, enhancing the atmosphere.

People are saying

"The hotel staff were so friendly and helpful."

"The bar has rare liquors and a delicious cocktail menu."

"The rooftop bar offers breathtaking city views for evening drinks."

Good to know

1

The Cadillac experience is available only on select days and hours.

2

Escalade service operates on Fridays and Saturdays for rides within a two-mile radius.

3

Happy hour is offered daily at the restaurant.

13
Sonder The Plymouth Apartments Loop image 1

Spacious apartments feature newly renovated contemporary style for a quiet retreat. Rooftop offers a cozy sitting room perfect for brunch gatherings. Location near public transit ensures convenience and privacy for independent travelers and groups.

An extended living room on the rooftop offers a cozy sitting room and outdoor seating. The space serves well for brunch gatherings but is smaller than photos suggest.

People are saying

"The beds were comfortable, and I slept well."

"It's surprisingly quiet, with no noise from other guests."

"I loved the rooftop; it was an unforgettable experience."

Good to know

1

The apartment is fully equipped with a kitchen, washer, and dryer.

2

Each bedroom has its own individual air conditioning unit.

3

The location is very close to public transportation, restaurants, and attractions.

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