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New Yorkers 1st Choice
Best of Loop

Rooftop cocktails

A rooftop cocktail that offers an open-air escape without the frantic energy of a packed club.

Based on 555 Opinions
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Updated May 2026
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Restaurant

Rooftop restaurant offers stunning city views and a relaxed atmosphere with friendly staff. The space features beautiful ambiance suitable for quiet meals or lively happy hours. Cocktails and small plates complement the setting, creating a charming dining experience.

Cocktails feature bourbon blackberry and blackberry whiskey sangria styles like Running with the Bulls. Gin and vodka drinks come out impeccably crafted and refreshing with reasonable prices.

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.

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Chicago Athletic Association - The Unbound Collection by Hyatt image 1

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.

Extensive bar offerings include custom cocktails crafted with the in-house restaurant. Both rooftop and indoor bars serve delicious cocktails alongside attentive service.

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 offers an awesome view of the park."

"The cocktails here have 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.

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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.

Sushi and vodka cocktail stands out at the rooftop bar. The drink list features cocktails, draft beers, bottles, and cans with solid local options. Cocktails are also available on the first floor.

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."

"The rooftop bar cocktails were awesome and the best I've ever had."

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.

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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.

Drinks include classic cocktails and unique house creations. The bartender shows outstanding knowledge and balances speed and quality while making intricate cocktails and chatting.

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 cocktails here are perfectly balanced and packed with flavor."

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.

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Rooftop bar offers gorgeous sunset views and a cozy holiday atmosphere with blankets, heaters, and fire pits. The space features comfortable couches and a notable absinthe selection. Music varies from jazz to violin performances, creating a relaxed but sometimes uneven vibe.

Rooftop setting offers a nice backdrop for a good selection of cocktails and absinthe. Mezcal cocktails stand out as interesting and well-crafted.

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.

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Restaurant

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.

Creative cocktails come with fast service and stunning river views from the terrace. Drinks are consistently incredible and enjoyable with a beer or cocktail option.

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 rooftop views of the city are stunning."

"The cocktails here offer amazing views of the river and city."

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.

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Historic building with Art Deco design offers spacious rooms featuring city views and luxurious amenities. Lobby and rooftop lounge provide a resort-like atmosphere with music and entertainment. Downtown location brings loud street noise at all hours, affecting room quietness.

Rooftop cocktail bar offers a special setting with a standout menu. The lobby bar serves delicious cocktails, while downstairs provides a swanky vibe ideal for drinks or work.

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 rooftop bar offers breathtaking city views for evening drinks."

"Dolapo's hospitality made our cocktails truly memorable."

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.

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Canopy by Hilton Chicago Central Loop image 1

Quiet, spacious rooms with luxurious decor and modern amenities create a cozy, home-like atmosphere. Heavy carpeting and thoughtful design keep noise low despite nearby urban sounds. Facilities include a well-equipped fitness center, free water refill stations, and a rooftop restaurant open for dinner.

A Running with the Bulls cocktail offers a sangria-style drink that fits the Spanish theme. Friendly staff serve drinks in a lobby with a nice ambience for both coffee and cocktails.

A rooftop restaurant offers dinner with tasty but pricey food. Occasional events like a car show happen on the roof.

People are saying

"This hotel's decor is beautifully designed and visually appealing."

"The cocktail bar staff were super knowledgeable and friendly."

"The staff at the Rooftop made my conference presentation printing a breeze."

Good to know

1

Parking at the hotel costs $75 a day, which can be high on weekends.

2

The hotel is located just 2 blocks from Union Station, making it accessible.

3

Wi-Fi issues may occur, as some guests reported authentication problems.

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