Upstairs at the Gwen

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521 N Rush St Fl 5
Chicago, IL 60611
Discover one of Chicago’s best-kept secrets, an Art Deco-inspired rooftop retreat, offering seemingly endless skyline vistas, sunrise-to-sundown dining, and masterful mixology in a laid-back, twinkle-lit atmosphere. Sunny summer afternoons make our open-air terrace a natural choice, but Upstairs at The Gwen takes patio season well into the winter. Reimagined for colder temperatures with warm drinks and fire pits, get cozy on the terrace for curling and cocktails, a bucket-list experience unique to The Gwen.

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Reviews

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3.5163 reviews
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Shannon E.
8/25/2025

Service was an A+ Vibe was an A+++ I got the "girl dinner". Super cute and yummy. I loved the relaxed feel of the place. In the middle of the city, but so relaxing.

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Martha T.
8/12/2025

Walked in with friends, asked to sit on the outside rooftop area, was told there would be seating available in 5-6 minutes and we could wait at the bar. It was classy and very great Gatsby....

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J'aime K.
6/21/2025

Food is good half the time. Service is poor 100% of the time. Bartenders are great!

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Ashley C.
8/25/2025

This was definitely a nice light drink. Bartender was super polite. Normally when I visit spots, the flutes are so small, but not this one. I ordered a French 75 with tequila.

Photo of Jenna C.
Jenna C.
2/26/2025

This review is for their rooftop curling - my friend had made a reservation for a particularly chilly evening so we pretty much had the outside area to ourselves. They had firepits, heat lamps,...

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