Proof That Iceland's Ring Road Is the World's Most Beautiful Road Trip
If you're sick of the same old Downtown rooftop scene, this happening spot 13 floors above the Hotel Lincoln offers a welcome respite as well as massive lake views unobstructed by Lincoln Park if you'd rather look at trees than buildings. With a retractable roof and an excellent burger, this always-cool option named after one of Lincoln's bodyguards has quickly become a Chicago summer essential.
It's the best bar in the Loop, not to mention one of the city's most beautiful. So yeah, by now you know all about the stunning top-floor oasis atop the Chicago Athletic Association and its most Insta-worthy view overlooking Millennium Park. But that doesn't make you want to go there any less, now does it?
If the thought of partying near a hospital doesn't get you all hot and bothered, this 18th floor oasis atop Northwestern Memorial Hospital is here to make you frisky. Sample the Irish-American cocktail menu featuring drinks inspired by Chicago history with off-duty doctors and nurses (or at least, we hope they're off-duty) while taking in the massive panoramic views.
Don't let politics get in the way of a good time at this beautiful, airy playground for the well-dressed and the well-heeled. In other words, make happy hour ... great again?
More restaurant than bar, Fountainhead makes the list by virtue of one of the most pleasant rooftops in the city. Yeah, we said pleasant. Got a problem with that? Well, let's sort it out over a few of the 150-plus whiskies or 26 beers on tap, including two hand-pulled casks. Also pleasant? Your buzz.
Like your good buddy who can always be counted on to drive you home from the bar or bail you out of jail, ZED451 can always be relied on for an all-around solid Chicago rooftop experience with everything you need in the form of drinks, a sociable crowd, and killer downtown views. Also, the watermelon sangria is what summer is all about.
Are you tired of reading articles about the best Chicago rooftop bars and always seeing Drumbar? Well too bad, because the near-unanimous accolades exist for a reason. Several, actually. Like some of the finest cocktails in the city, a sexy 18th floor vibe above the Raffaello Hotel, and a ridic outdoor lounge with primo views of the lake and downtown. Grab a seat and stay a while or, what the hell, grab a room and keep the party going.
Refreshingly less chic than your typical downtown rooftop, this affable and unpretentious space of family-style seating, turquoise banquets, and coffered ceilings is a casual hangout for ordering up the house-ground Bernie's cheeseburger paired with bourbon drinks and the mandatory "
"Weekend at Bernie’s 3" tequila cocktail.
Is it possible to attend a place called Raised An Urban Rooftop Bar without putting your arms in the air to declare your intent to “raise the roof?” If you're not a total creep, it's actually pretty easy. It's also easy to love this stunner on the third floor of the Renaissance Chicago that turned a formerly unused meeting space into a gleaming indoor/outdoor rooftop deck with urban gardens, wine on tap, and sexy VIP areas for sipping in seclusion.
Somehow slipping under the radar on the 26th floor of the Virgin Hotel, Cerise’s posh flagship terrace wraps around three sides of the building. With offbeat art and DJs spinning under twinkling lights inside, this casual chic space brings a slice of LA to the Loop, aided by pitchers of rum punch and one of the finest highballs in all of the land. Also, crab tostadas. Do it.
If you don't love the delightful rooftop patio above this equally delightful Lincoln Square sausage shop, you might not be human (or at least not from Chicago). With communal wooden tables and an abundance of greenery, this relaxing European-style spot is the perfect place to tackle plates of goulash and 40+ types of smoked sausage while seeing how many beers and wines you can ingest on a Sunday afternoon before dialing into work “sick.”
No lineup of rooftop bars in Chicago is complete without the inclusion of ROOF on theWit. It's as essential to the Chicago rooftop scene as a White Castle slider atop your Bloody Mary. In other words, not very. But still nice to have as well as having live DJs, runway shows, and a retractable roof.
Replacing the old Vertigo Sky Lounge space atop the 26th floor of the Dana Hotel is this opulent newbie, featuring stunning, innovative cocktails from local mixology kingpin Benjamin Schiller. The drinks are served in custom glassware and include unique garnishes like dehydrated starfruit and edible paper butterflies. The beautiful 1,100sq ft space also has a comfortable lawn section and firepits for the colder evenings.
Up & Up and the Cabana Club are two rooftop bars in one building, thanks to the Robey’s collaboration with its sister property, The Hollander. Up & Up is the hotel’s older 13th-floor lounge, offering expansive views of the city and Robey spire (just resist the urge to scale it after ingesting a Kid Koala cocktail, which combines vodka, egg whites, and eucalyptus bitters). Opened in May 2017, the sixth-floor Cabana Club has a shimmering pool (for hotel guests only) and a 160-seat outdoor deck where you can enjoy Latin bites and Mexican-inspired drinks.
Inspired by the ‘80s Tom Cruise classic Risky Business, this lively neighborhood spot was the first location on Milwaukee Avenue with a rooftop bar when it opened in 2016. While the Wicker Park rooftop boom has continued into more upscale territory, this casual joint from the owners of Cheesie’s Pub & Grub keeps things low-key with picnic tables, sofas, and sports on the big screens. The place is famous for its decadent “fry bar,” featuring fries and chicken tenders with dozens of seasonings and sauces. And, as the name suggests, it has a seriously stacked whiskey collection.
The third-floor Joy District might not be the tallest outdoor spot in the city, but it’s always a happening scene, with an attractive crowd intermingling in a cozy space of colorful murals, twinkling lights, and exposed brick. Grab sushi, ostrich meatball ramen, and smoked spare ribs lollipops, then order something off the Japanese-themed drink menu, like a Lucky Buddha beer or 94oz Moscow Mule. That last one will cost you $70.
This third-floor oasis at the Loews Chicago is here to relax you. The large terrace is like a Zen zone in the midst of the bustling city, with large grassy areas, giant Jenga, cozy swing chairs, and great views of the lake. Grab a spot in the afternoon and enjoy some tiki cocktails as you watch the sunset. They’re so delicious, you’ll probably end up staying much later.
Proudly calling itself the “Trainwreck Rooftop Deck,” the South Loop rock club’s upstairs area offers a delightful diversion from the stuffy Downtown outdoor scene. The anything-goes 99-person playground features eight flat screens, a pool table, a Pop-A-Shot machine, cornhole, and picnic tables for munching on the standout bar menu offerings. Stop by before a show to get appropriately loose and boozy.
The 15,000 square foot venue on the fourth floor of the Godfrey Hotel has a retractable roof, a video wall, a fire pit, and a well-dressed crowd. Down a lamb lollichop and Lagunitas, then bust a move under the massive dance floor’s trippy lights.
Chicago’s only tri-level rooftop extends in glorious fashion from the 21st to 23rd floors above the London House hotel, located in a historic Beaux Arts tower. The 23rd floor cupola is only available for private reservations, but nevertheless, it’s hard to find a better spot for mingling with Chicago’s upper crust over butternut squash risotto and lobster rolls. For drinks, you’ll find a slew of cocktails, from Old Fashioneds on tap to Moscow Mules in decanters. You can even have the bartenders make you a custom concoction -- just pick a base spirit, a flavor profile like sweet, sour, herbaceous, etc., and they’ll whip something up for you.
From its famous “Smut & Eggs” late-night porn viewing sessions to its standout whiskey and Bloody Mary collections, not to mention some of the best nachos and jalapeño poppers in the city, Twisted Spoke has a lot going for it. It seems almost unfair that everyone’s favorite biker bar also happens to have one of the finest rooftops in the city, an oasis of day drinking where you can get into just the right amount of trouble.