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Loved by locals

Hotels with rooftops in the Loop

Made for those who view a rooftop vantage point as a non-negotiable requirement for their lodging.

Based on 604 Opinions
+601
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Updated April 2026
01
citizenM Chicago Downtown image 1
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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.

Location stands out for being close to everything and easy to get around. Rooms offer comfortable pillows and staff provide personal touches like cards and champagne. The gym ranks among the best hotel gyms experienced.

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.

02
Renaissance Chicago Downtown Hotel image 1

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.

Centrally located by the Riverwalk and close to major attractions like Michigan Avenue shops and the lakefront path. Offers great service and modern amenities in a clean, comfortable setting.

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.

03
The St. Regis Chicago image 1

Towering skyscraper offers spacious rooms with epic city views and an elegant atmosphere. Amenities include a large indoor pool, well-equipped gym, and personalized butler service. Dining spaces provide luxurious settings with rooftop views and unique breakfast options.

Luxury defines the hotel with outstanding service and a professional, kind staff. The environment feels like a home away from home with attentive care from front desk to courtesy drivers.

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.

04
Kasa South Loop Chicago image 1

Apartment-style hotel offers spectacular city and lake views with a quiet, safe atmosphere. Spacious units include full kitchens, in-unit laundry, and private balconies, creating a comfortable, home-like feel. Amenities include a beautiful gym and rooftop deck with panoramic vistas.

Offers hotel apartments with larger living areas and full kitchens. Includes washer/dryer and costs less than nearby hotels with similar views and locations.

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."

"This hotel offers amazing value with a full kitchen and washer/dryer."

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.

05
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.

Rooms combine historic charm with modern comfort, supported by attentive staff who handle situations with care. The hotel offers a central location and a memorable stay experience.

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."

"This hotel's stunning design blends old-world charm with modern comfort."

"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.

06
Sports Illustrated Resorts Chicago image 1

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.

Rooms stay clean and nice with friendly staff providing excellent service. The hotel sits in a great location near theaters and Michigan Avenue, offering strong overall value.

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.

07
Pendry Chicago image 1

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.

Rooms include a legit wet bar. Staff greet guests warmly, creating a welcoming vibe. This hotel serves as a reliable choice for stays in the city.

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.

08
theWit Chicago, a Hilton Hotel image 1

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.

Freshly renovated rooms create a modern vibe. Staff show exceptional communication and ownership in handling issues. Location is perfectly central for easy access.

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
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.

Boutique hotel offers a beautiful setting with a great location near the Amtrak station. Features include a free water refill station on the ground floor.

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 bartenders here are amazing and so welcoming."

"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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Chicago Loop, Chicago

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