Upstairs at The Gwen

Located on the fifth floor of The Gwen Hotel, Upstairs at The Gwen has design flourishes reminiscent of the Art Deco age, while retaining a modern sensibility that offers a bit of respite from the chaotic bustle of nearby Rush Street locales. It’s just a short elevator ride up to this new Chicago rooftop. Here’s a brief guide to what you might find when you stop by for a drink or for a more elaborate dining experience.

The Gwen Lobby

Cocktails To Start

After giving the lobby the once over, you can slide over to the bar or pick out a few seats for you and your associates that will enable the appropriate level of people watching (it’s good here, by the way). Upstairs at The Gwen has a beverage program that includes new takes on some favorites from the 1930s, including the French 75, Tom Collins, Sidecar, and a refreshing Blackberry Gin Fizz.

You might also choose to pair these items with a few of their lovely small plates on the menu, which include Roasted Beets, Tuna Poke, and a elegantly Grilled Pork Belly.


Stay a While, Get Serious

Some of you might now be ready to head off to the Red Head Piano Bar or any other notable nearby entertainment enclave. But wait, wait, wait: there are large plates to be had.

Suitable for sharing, I’d give my nod to the Roasted Salmon with crispy rice cake and bok choy or the decadent Lux Burger, which features beef from the Slagel Family Farm, along with taleggio cheese, truffle aioli, and red onion jam all on a potato bun. Okay, so it’s hard to share a burger, but it’ll still be fun to attempt it, right?

Also, make sure and see if Chef Oscar Hernandez has one of his stellar tasting menus available. Block out some quality time and be prepared to see what’s going through his creative mind. On one recent visit, one of the highlights was a Pork Tamale, inspired by his mother’s cooking. A reverent and delicious familial tribute, indeed.

Gwen Food

A Host of Desserts

You might be full right about now, but I’m sure you can spare but a few more minutes for dessert. While there are always sweet treats that rotate in and out of the menu, some of the reliable favorites here include the Vanilla Bean Creme Brûlée, Chocolate and Peanut Crunch, and a variety of sorbets.


The Essentials

Upstairs at The Gwen
The Gwen Hotel Chicago
521 N. Rush Street, 5th Floor

  • Open daily; weather permitting
  • Reservations accepted on OpenTable


Image credits: Samantha Tofanelli