Top 10 Best Chicago Rooftop Happy Hours You Can Find Listed On WhatElse

Published by #TeamWhatElse on

The days of scouring outdated Google results for happy hour specials are over. WhatElse is Chicago’s go-to happy hour & brunch finder that allows you to search by neighborhood, rooftop, patio, and more. Download now from the App Store or Google Play.

As another brutal winter passes by in the rear view mirror, Chicagoans are beginning to shift their happy hour prerequisites from “anywhere with heat” to “anywhere with a patio and/or rooftop”. Let’s face it, there’s nothing we love more in #SummertimeChi than drinking against a spectacular backdrop of highly Instagramable city views. That’s why we’re featuring 10 of our favorite Chicago rooftop happy hours for you to check out this spring and summer.

Joy District

Source: Joy District Facebook

Looking for an Insta-friendly rooftop? Well then Joy District is a power move. They’ve got an artsy backdrops for pictures, a space for dancing, and excellent summer cocktails, of course. It’s the perfect bar for summer day drinking in Chicago with the squad. It also features a brunch menu that slaps with colorful waffles, cereal, doughnuts, and mega mimosas.



If you’re looking for tropical rooftop vibes, look no further than the 15th floor of The Kimpton Gray Hotel. Boleo’s menu emphasizes South American small plates and exotic cocktail flavors straight out of a Peruvian street-food festival. Empanadas? Yes please.


Source: drumBar Facebook

Perched atop the 18th floor of the Raffaello Hotel, drumBar has views for days. It’s a cocktail-focused bar, but they also boast a large selection of beer and wine if that’s more your thing. That said, this is the perfect spot for you if you’re more of a whiskey/scotch type of drinker. As an FYI, it has a speakeasy vibe with no food available.

Upstairs at the Gwen

Source: The Gwen Hotel Instagram

Upstairs at the Gwen has heaters on their terrace, so you can enjoy the #views of the city regardless of the weather. The décor and atmosphere are both on point. We recommend one of their signature cocktails, pork belly sliders with kettle chips, or a bacon flatbread.



As a new kid on the block and a recent addition to the WhatElse app, Devereaux has certainly lived up to the prestige of Gold Coast. Featuring sweeping views of the bustling Rush & Division area and poolside cocktails, this is the ideal spot to kick your feet up at while sitting 18 floors up.


Source: Zed451 Instagram

If you love eating at chic steakhouses on a budget, peep Zed451 for happy hour from 4:30 PM to 6:30 PM (the perfect time for sunset). You’ll be right in the city-center, which means skyscrapers up close and personal. Enjoy cozy seating and a fun atmosphere.

Bernie’s Lunch & Supper Club

Source: Bernie’s Lunch & Supper Club Instagram

Remember that Bernie dance that went viral back in 2016? Well, you likely won’t see a whole lot of that going down on this River North rooftop but you will find a wide array of bourbon, classic American fare, and spicy margaritas. Pro tip: Swing by Tuesday’s to sink your teeth into a Bernie’s Burger on special for $10 during happy hour. WhatElse.

Apogee Lounge

Source: Apogee Instagram

Oh, you’re a sucker for bougie looking cocktails you say? Then head over to The Dana Hotel and catch the elevator up to 26. This spot features a couple drinks served in picturesque seashells and giant glass mushrooms. You’ll be able to take in a slower vibe if you go early, and feel a youthful, more club-like energy if you decide to stick around later. P.S. Get ready for some views.

Whiskey Business

Source: Whiskey Business Instagram

As one of Wicker Park’s go-to rooftop spot, you can always find a bustling crowd sipping whiskey and soaking up the sun. This spot features around 75 different types of Whiskey and delicious bar munchies.



Featuring great music, delicious apps, and cozy couches – this West Loop gem is definitely a vibe. Setting on top of the Ace Hotel, the rooftop lounge is always buzzing with popular local DJs on the one’s and two’s.

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