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New Yorkers 1st Choice
Local picks in Streeterville

Rooftops

You want to be above the street level, where the noise of the city fades into the background.

Based on 493 Opinions
+490
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Updated May 2026
01
Loews Chicago Hotel image 1
Loews Chicago Hotel image 2
Loews Chicago Hotel image 3
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Modern hotel offers spacious rooms with stunning city views and a rooftop bar that serves delicious food and drinks. Atmosphere shifts from quiet comfort to lively social gatherings, perfect for couples and groups. Amenities include a large fitness center and pool for relaxation.

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.

People are saying

"The Hotel staff were so friendly and professional."

"The views from the room were excellent, especially of the city."

"The rooftop views of the city are spectacular."

Good to know

1

Valet parking costs $78 per night, with potential double charges.

2

Expect hidden fees, including a resort fee despite no resort amenities.

3

Room service charges $9 for bottled water.

02
Navy Pier - Rooftop Terrace image 1

Rooftop Terrace shines with breathtaking city views and a four-sided bar at its heart. Food bursts with flavor, making dining here a memorable experience. Calm, romantic vibe and friendly staff create an inviting spot for drinks or meals before evening events.

Stunning views greet visitors on the rooftop, paired with exceptional food that bursts with flavor. The Rooftop Terrace offers a memorable dining experience despite a tricky entrance.

People are saying

"The city and Lake Michigan views from the terrace are great."

"The food here is delicious, especially the truffle fries."

"The Rooftop offers a breathtaking view of the city skyline."

Good to know

1

Reservations are not required for Sunday morning visits.

2

The bar accepts walk-ins, even when it appears empty.

3

Food options are somewhat limited but include multiple cuisines.

03
CloudBar at 360 CHICAGO image 1

Bar atop a skyscraper offers 360-degree city views and a rooftop lounge with ample seating. Atmosphere shifts from relaxed at sunset to lively at night, attracting both tourists and locals. Unique attractions include a thrilling tilt experience and an indoor area for socializing.

Offers a 360-degree view of the city with an incredible skyline backdrop. The rooftop includes an indoor area and plenty of seating for drinks and socializing.

People are saying

"The city views from here are amazing and totally unbeatable."

"The bartender Nathan made our bar experience fun and memorable."

"The rooftop has an incredible view of the city skyline."

Good to know

1

Entry to the bar requires a general admission ticket costing around $40.

2

Expect a 30-60 minute wait for seating during peak hours.

3

Drinks take about 15 minutes to arrive after ordering.

04
Hampton Inn Chicago Downtown/Magnificent Mile image 1

Rooms provide spacious comfort and marvelous city views while staying quiet. Lobby is lively with constant foot traffic creating a busy vibe. Rooftop boasts a seasonal pool and panoramic views, offering a unique urban oasis.

An open roof reveals a seasonal pool on the top floor. The rooftop pool offers an amazing view that stands out among hotels.

People are saying

"The breakfast here is amazing and conveniently located."

"The rooms offer a nice view of downtown Chicago."

"The rooftop pool has an amazing view of the city."

Good to know

1

Parking costs $60 or more for overnight parking.

2

The hotel charges a $100 deposit per night not mentioned at booking.

3

Only 3 out of 9 elevators work, causing long wait times.

05
DoubleTree by Hilton Hotel Chicago - Magnificent Mile image 1

Hotel features a rooftop pool with city views that delights both kids and adults. Lobby is grand and elegant, but the atmosphere is often loud and busy with construction and sirens. Rooms feel comfortable yet outdated.

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.

People are saying

"The hotel staff were all amazing and so polite."

"The scenic views from the room were pretty great."

"The rooftop pool was so much fun and amazing."

Good to know

1

Parking costs $62 per day, regardless of discounts.

2

Breakfast is not included with the room rate, despite some bookings indicating otherwise.

3

The rooftop pool is closed until mid-July, which is not disclosed on the booking site.

06
The Ivy Hotel image 1

Spacious rooms blend quiet luxury with modern comfort. Rooftop bar offers fantastic city views and a relaxed vibe, perfect for celebrations with private rentals and catering. Lobby bar doubles as front desk, adding a unique but sometimes awkward atmosphere.

Elegant rooftop terrace offers private rentals with catering, bartending, and Bluetooth speakers. The space includes a rooftop bar and opens early for exclusive access, creating a beautiful setting for celebrations.

People are saying

"The bar staff were friendly and exceeded expectations."

"The staff's attentive and personalized service made my stay feel luxurious."

"The rooftop terrace is an elegant setting for celebrations."

Good to know

1

The hotel requires a credit card for a deposit and does not accept cash or debit cards.

2

Parking is not available at the hotel, and nearby options may be expensive.

3

The rooftop patio is often reserved for private events, limiting guest access.

07
Sable at Navy Pier Chicago, Curio Collection by Hilton image 1

Rooms boast spectacular lake views and a peaceful vibe with limited pier access at night. Rooftop offers amazing views and a relaxed spot with a friendly bartender and great food. Valet parking adds convenience to the upscale experience.

Rooftop offers amazing views and a relaxed spot to enjoy a drink. The bar features a friendly bartender and the space serves great food with a nice atmosphere.

People are saying

"I loved the nice view of the lake and skyline."

"The bathroom is spacious and beautifully designed."

"The rooftop views of the lake and skyline are stunning."

Good to know

1

Fireworks occur on Wednesdays and Saturdays at 10pm, visible from many rooms.

2

Check-in is at 4 pm; early check-in incurs a $50 fee.

3

Checkout is at 12 pm; late checkout may incur additional charges.

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Streeterville, Chicago

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