Toast Chicago from a sky-high rooftop lounge that’s open all four seasons. Chilly temps and a few snowflakes are no match for determined rooftop lounge lizards. Luckily, Chicago has a number of crafty venues with retractable glass roofs that keep out the cold while letting nighttime city views shine. Here are six spots where you can ride out the winter with sizzling appetizers and cool craft cocktails.

I|O Godfrey

Interior of I|O Godfrey rooftop bar in Chicago
©I|O Godfrey

This sprawling rooftop lounge on the fourth floor of The Godfrey Hotel Chicago features a retractable roof and two-level fire pit that make it a year-round destination. Drink in the city views, along with a craft cocktail like the I|O Cosmo (Absolut Citron, fresh grapefruit and a touch of cherry). Snag a communal booth and split a shareable such as the octopus bruschetta or Kobe beef sliders.

ROOF on theWit

Roof on the Wit

This lively rooftop lounge on the 27th floor of theWit hotel keeps the party going all year round, thanks to its retractable roof. With its modern design, glittering city views and nightclub vibe courtesy of live DJs, it’s no wonder Travel + Leisure named it one of the top three rooftop bars in the world. Cozy up on a couch by the fireplace and indulge in finger foods such as the seared scallops or empanadas, paired with a house-made shot like The Lululemon Drop.

Gibsons Italia

Interior of Gibsons Italia rooftop bar in Chicago
©Gibsons Italia

Gibsons Italia is a stunning three-level Italian steakhouse that boasts sweeping views of the Chicago River. The main dining room is on the second floor, while the third floor features a lounge with a dramatic retractable roof that allows for year-round cocktails with picturesque water views that change with the season. Don’t miss the USDA-certified Gibsons Prime Angus filet mignon sided with a classic Manhattan.

The J. Parker

Interior of The J. Parker rooftop restaurant with views of Chicago
©The J. Parker

Located atop the Hotel Lincoln, this popular 13th-floor rooftop lounge features sweeping views of Lincoln Park and the lakefront from its atrium-like perch. Snack on shareables, such as the buffalo chicken lollipops or truffle frites. On a chilly winter evening, warm up with a hot cocktail like the Boss (George Dickel No. 8 whiskey, spiced chocolate, and whipped cream).


Women sitting at the bar in Cindy's rooftop restaurant in Chicago

Inspired by a Great Lakes beach house with its glowing string lights and picnic table seating, Cindy’s rooftop restaurant perched atop the Chicago Athletic Association Hotel features jaw-dropping views of Millennium Park and Lake Michigan. Share the shellfish platter (piled high with Maine lobster and king crab legs) and pair it with one of Spirit Guide Nandini Khaund’s elixirs, like the Howl at the Jun (gin, Kombucha, grapefruit, and sparkling rosé).


Located on the 15th floor of the boutique Kimpton Gray Hotel, Boleo maintains its sultry South American vibe year ‘round thanks to its retractable glass roof. Enjoy Peruvian street food favorites like ceviche mixta or yaquitas (crispy yucca fries). Then, kick back with an authentic pisco sour and listen to live DJs spin beats under the starry city sky.