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New Yorkers 1st Choice
West Town's best

Rooftops

Getting above the street level to see the neighborhood from a different perspective.

Based on 456 Opinions
+453
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Updated April 2026
01
Ignite Glass Studios image 1
Ignite Glass Studios image 2
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Colorful blown glass art creates a vibrant setting with unique artistic displays. Rooftop patios offer awesome city views and a lovely skyline backdrop perfect for cocktail hours. Interactive glassblowing demos add a creative energy that blends indoor and outdoor spaces.

Large rooftop patios offer awesome city views and a lovely skyline backdrop. The space features glass displays and suits cocktail hour well.

People are saying

"These Date Spots are so fun and hands-on, you'll learn a lot."

"The rooftop has amazing skyline views for cocktails."

"It's a super cool studio with gorgeous art."

Good to know

1

Reservations are recommended for private events and classes to ensure availability.

2

Parking is available on-site, making it convenient for guests.

3

The glassblowing demonstration is a highlight and typically occurs during special events.

02
The Robey image 1

Hotel blends industrial chic with a soulful vibe and phenomenal rooftop views of downtown Chicago. Multiple bars and a cafรฉ create a lively atmosphere perfect for celebrations. Location near transit and shops adds local flavor and convenience.

Multiple rooftops offer unique views of downtown Chicago. The rooftop bar provides a chill vibe with some of the best city views around.

People are saying

"The hotel staff were so helpful and friendly."

"The rooftop offers what might be the best view in the city."

"The rooftop lounge offers amazing nightlife with fantastic city views."

Good to know

1

The Cabana Club is open to the public from 4-6 PM for happy hour.

2

Happy hour features discounted drinks and appetizers at The Robey.

3

Story hour at the Clever Coyote takes place every Sunday.

03
The Up Room image 1

Rooftop bar shines with breathtaking views and a rooftop pool for a unique experience. Cocktails are well-crafted and the vibe stays peaceful and spacious, perfect for quiet nights or dates. Cozy Warming Shack keeps it inviting even in winter.

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.

People are saying

"The city skyline views are spectacular, day or night."

"The cocktails here are amazing with unbeatable city views."

"The rooftop views here are breathtaking and unbeatable."

Good to know

1

Reservations are recommended as the space fills quickly, especially on weekends.

2

The Up Room closes at midnight, but no new guests are allowed after 11pm.

3

Happy hour is a great time to visit on weeknights for discounted drinks.

04
Royal Palms Shuffleboard Club image 1

Indoor and rooftop spaces offer shuffleboard courts and food trucks with cabana seating. Loud music creates a laid-back club vibe for groups. Rooftop shines with sun and good vibes, plus a bright decor and rooftop view add charm.

Plenty of sun and good vibes fill the rooftop. It offers a nice space to relax alongside indoor areas.

People are saying

"It's a fun spot to hang out and play shuffleboard."

"The food trucks here are a fun way to spend an evening."

"The rooftop is a fun spot to hang out and play shuffleboarding."

Good to know

1

Shuffleboard costs $29 per lane on Sundays.

2

Reservations are recommended for busy times, especially for groups of four or more.

3

Happy hour runs all day on Sundays with great specials.

05
Professor Pizza Slice & Pie - West Town image 1

Rooftop boasts fantastic city views and a lively DJ stage on weekends. Indoors, enjoy a trendy tavern-style decor with nostalgic art and cozy vibes. Crowds are lively and spacious, perfect for music lovers and socializing.

Great rooftop offers a fantastic city view and a cool stage space for a DJ on weekends. The ambience feels beautiful and inviting for dining outdoors.

People are saying

"The pizza here is insanely delicious with fresh, flavorful toppings."

"The city views from the rooftop patio are fantastic."

"The pizza here is phenomenal and definitely worth it."

Good to know

1

Expect a 40-minute wait for a table during peak hours.

2

Only online orders for pickup are accepted; no dine-in or curbside service.

3

A QR code is required to order and pay upfront.

06
Taxim image 1
Greek restaurant

Greek restaurant shines with a gorgeous rooftop patio featuring heated seating and mood lighting. Expect a lively atmosphere with sound echoing throughout. Enjoy wood-fired lamb and a fine selection of Greek wines for a cultured dining experience.

Wide open rooftop patio features heat lamps for cool evenings and fans mounted to the canopy for hot days. Everyone dines on the rooftop, making it a lively spot for dinner.

People are saying

"The Greek food here is phenomenal, especially the duck gyros."

"I had a wonderful dinner on the comfortable, open-air rooftop."

"I loved the authentic Greek dishes with incredible freshness."

Good to know

1

A 22% gratuity is automatically added to bills for parties of 2 or more.

2

The total cost for two people can exceed $200 for a meal.

3

Parking past 10:00 p.m. on Milwaukee Avenue may result in towing.

07
Homestead On The Roof image 1
Portuguese restaurant

Cozy rooftop garden offers a private terrace with lush greenery and twinkly lights. Rustic charm blends with a lively yet relaxed vibe, perfect for quiet evenings or small weddings. Ivy walls and planters create an intimate, tucked-away atmosphere above a pizza spot.

A private rooftop terrace sits tucked above a pizza spot, creating an exclusive vibe. Twinkly lights, a lush garden, and an Ivy wall with planters add to the charming atmosphere without much noise from the street.

People are saying

"The food here was amazing and really good."

"The rooftop terrace is stunning with twinkly lights and greenery."

"The food at this Rooftop is amazing and yummy."

Good to know

1

The venue is not wheelchair or stroller accessible due to no elevator.

2

The seasonal menu changes frequently, so check for availability.

3

The menu offers a wide variety of vegetarian and gluten-free options.

08
Round Two image 1
Clothing store

Two floors split new hypebeast clothes below and vintage tees above. Outdoor terrace hosts rooftop sales, including a famous five dollar summer sale. Atmosphere mixes sophisticated and chill vibes for well-curated, fairly priced finds.

Rooftop features an outside roof deck where browsing happens during sales. Frequent rooftop sales include a notable five dollar item sale in summer.

People are saying

"I found some dope vintage items and cool streetwear pieces here."

"I found amazing sneakers at pretty fair prices here."

"I loved browsing the vintage sweaters on the rooftop."

Good to know

1

Round Two offers exclusive models not found elsewhere.

2

Expect to find unique pieces that are fairly priced and easy to browse.

3

They have a five dollar item sale on the roof during the summer.

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