If there’s one thing Chicagoans will come out in droves for, it’s sips and noshes with a fabulous view. Enter: rooftop bars. From an urban backdrop with a glitzy wow-factor to a comfy intimate oasis with romantic lighting and delicious cocktails, we’ve got you covered. Here is our list of Chicago’s best elevated al fresco hotspots — big and small, extravagant and casual — throughout the city.
There’s no shortage of places to get a drink and a view in the Windy City, however Boleo, located on the 15th floor of the Kimpton Gray Hotel, is special because it takes you on a journey to South America, with its lush greenery, Peruvian and Argentinian fare, and vivacious music. The glass roof retracts, making this a year-round classy and sophisticated space. Take it all in and stay awhile — you won’t regret the choice.
Since 2009, Fountainhead has been the neighborhood meeting spot for great food — soups, salads, shareable plates and belly-filling entrees — and a massive list of beers, including ciders and gluten-free and non-alcoholic beers. If you like Hopleaf in Andersonville, you’ll love this English-style pub — beer aficionados will geek out over all of the beer choices and staff expertise. If you have a question about an obscure global beer you’ve been searching for, it’s likely that you’ll find answers here. Check out their continuous events, full of rare beer tastings and special releases.
Homestead on the Roof
For a farm-to-table classic-comfort experience, visit the award-winning Homestead on the Roof, located above Roots Handmade Pizza in West Town. The food here is seasonal, which means it’s super fresh, and when you dine on the al fresco rooftop patio, you’ll see directly where your meal’s ingredients come from — a 3,000 square-foot organic garden, complete with two vertical hanging gardens, is in full view. You’ll see planter boxes with fruits, vegetables and herbs, and you can sit by the fireplace to warm your trotters on a cool Chicago night. Enjoy a delightful meal, created by Chef de Cuisine, Jesse Badger, and Pastry Chef, Christopher Teixeira.
Visit for lunch or dinner, or come in for a lovely weekend brunch, and experience incredible views of Chicago’s Millennium Park, Art Institute of Chicago and the lakefront at Cindy’s. Located on top of the Chicago Athletic Association Hotel (known for housing a men’s social club back in the day), this is the prime spot for enjoying yourself and the friends you came with. Select from a number of specialty cocktails and libations, including biodynamic wines, or indulge in the Apothecary Service, delivered in a celebratory manner, featuring creations like Grey Garden, Kick in the Daisy and Howl at the Jun (kombucha brewed only during specific phases of the moon).
Raised Bar, which serves up locally-sourced American bar food with a delightful twist, opened in 2016 with Executive Chef Russell Shearer and Restaurant Chef Tim Powles at the helm. The idea here is to sip and nosh with friends over shareable plates while enjoying brilliant city views — you’ll have a front row seat to the Chicago River. Plan on staying for a spell to soak in the eclectic scene, complete with fire pits, cabanas, comfy couches and, of course, an outdoor bar. Enjoy a well-curated beverage menu with craft beers on draft, signature cocktails and shareable mixed concoctions served in a decanter for the table. Arrive early to get a good seat, no reservations are taken.
You’ll need to make a reservation to ensure a table at one of Chicago’s hottest rooftop bars: Apogee. Located in the River North neighborhood, 26 floors up in the Dana Hotel & Spa, Apogee is one of The Fifty/50 restaurant group’s most prized and celebrated places to sip a cocktail. Master mixologists will create bubbling, steaming, fizzing delightful works of liquid art, made with ingredients like jalapeño infused tequila, violet sugar, raspberry powder, pipe tobacco or lemongrass-pear ice cubes. Don’t worry, you can also enjoy a glass of wine or single malt scotch if you prefer.
Waydown is located atop the glass and concrete stunner, Ace Hotel Chicago. Sip a cocktail, enjoy an appetizer, and relax on a plush couch situated on the outdoor deck. And, if you visit at the start of the work week, you can enjoy $6 Mondays for discounted drinks and menu options. You might be wondering why this lounge and bar is called Waydown when it’s positioned way up — it’s named after a song written by Illinois native John Prine. The drinks are made strong here, perfect for enjoying nightly live music and downtown Chicago city views.
If you find yourself in Streeterville, pop into Drumbar, located 18 floors up in the Raffaello Hotel. This open-air, sexy and chic space has various seating options and lots of room to roam around. You’ll find yourself breezily wandering indoors to the lounge, and outside to the terrace, sampling signature bevvies along the way. Chat with friends by the firepit, while admiring the Hancock building and Lake Michigan, at this celebrated speakeasy-inspired Chicago rooftop.
For an Instagram-worthy rooftop scene, with colorful murals and backdrops, hang out at Joy District in River North. The party atmosphere here is palpable. Order a large gumball machine, filled with various juices and mixtures and multi-colored straws, meant to be shared. Lots of inviting seating is available but honestly, you’ll probably spend your time swaying to the DJ. Joy District also has a late-night dance club, indoors, to burn off all of the calories you consumed on the deck.
The J Parker
Themed cocktails and light-filled views of Lincoln Park and the Gold Coast sets the stage of The J Parker, located on the crown of Hotel Lincoln, 13 floors up. Covered with a cool retractable glass dome, you can enjoy the panoramic city view no matter the weather — show off your city to out-of-town guests, rain or shine. The feeling here is stress-free and laid back with a trendy undercurrent. It’s easy to settle in and pat yourself on the back for spending time in Chicago.