MostBest Chicago | Rooftop Bars

It could take you hours to decide which rooftop bars are truly the best. Don’t waste your time—MostBest knows the Top 3.

There’s nothing better than relaxing with a drink on a warm summer night—except, maybe, relaxing with a drink on a rooftop bar with incredible views on a warm summer night.


via Flickr user Ashland Thomas

via Flickr user Ashland Thomas

DrumBAR is relaxed, fun, and effortlessly cool. This spot offers a few beer and wine options, but the real stars are the unique and well-crafted cocktails. Between the OOO! What’s That? (tequila, salted beet, and ginger) and Generally Mackin’ (brandy, lime, and fajita seasoning), we’re sure that you’ll find something new and tasty to try.

Grab a drink, head up to the roof, and get ready to chill out.

We Love Their: OOO! What’s That?, Generally Mackin’

201 E Delaware Pl
(312) 933-4805



via Flickr user Bing

via Flickr user Bing

As anyone who lives in the Windy City knows, the weather here is not always ideal for relaxing outdoors. While many rooftop bars in the city are limited by the seasons, such is not the case at IO Godfrey. This amazing bar has a retractable roof, which means it can be enjoyed year-round.

Come here at sunset and sip on a Godfrey Manhattan as you drink in the scene around you—it’s one of those Chicago spots that you just can’t miss.

We Love Their: Godfrey Manhattan, Chef’s Margarita

127 W Huron St
(312) 649-2000



via Flickr user Gina Collecchia

via Flickr user Gina Collecchia

ROOF on theWit, located atop theWit Hotel, is as much a chill rooftop bar as it is a raging party spot—depending on when you go. Looking for a more relaxed atmosphere? Head there in the late afternoon. When you want to party, Saturday nights are the perfect time, with DJs spinning the hottest music and drinks flowing freely.

Don’t miss the unbeatable vibe of ROOF on theWit.

We Love Their: Blackberry Ginger Mojito, Pear Pressure

201 N State St
(312) 239-9502