Chicago is looking up. Literally.
Over the last few years, at least two dozen bars, hotels, and restaurants have created their own rooftop experiences, attracting Chicagoans and visitors eager to squeeze every minute out of summer. And since that glorious summer season seems to last about five minutes in the Windy City, many of the rooftops transform into other spaces like curling rinks and all-weather beer gardens the rest of the year.
Cabana Club Two buildings were recently combined into The Robey Hotel, a single Art Deco hotel that rocks two separate rooftop spaces. This hotel is as boutique as they come — you could even stay in one of their 20 loft rooms — originally one big warehouse. The exposed surfaces and concrete floors are a constant reminder that you’re in the city. If that’s not enough, head up to the Cabana Club, which has a rooftop pool and deck overlooking Wicker Park along with the Chicago skyline. Pro tip: come for a drink, stay for the pool, which is open to the public, not just hotel guests. This deck is only open from May to September, but if you’re visiting during the rest of the year, you could drink and dine in The Up Room, which is also a rooftop area that has a terrace and an indoor spot.
LH Rooftop The LH Rooftop inside The LondonHouse Hotel is over-the-top with a triple-level roof that includes one indoor level because Chicago, yet keeps the other two levels open year round. Come early or don’t come at all — it gets packed by 8 p.m., and stay for the food (no, it’s not English food, but it’s incredible) and the craft cocktails. If you’re here during the winter months, look out for pop-up events like their outdoor ticketed dinners, where they’ll provide the heaters, coats, seasonal decor, and hot cocktails while you glance at the Magnificent Mile Lights below as if you’re a celeb.
Upstairs at The Gwen It’s a great rooftop bar in the summer . . . but the winter is when you really want to party at The Gwen Hotel on Michigan Avenue in River North, where they transform their rooftop into an ice-less curling rink. There are curling lanes, an Alpine-inspired menu, a cozy wood-paneled cabin, Adirondack chairs, and even a swing seat.
The Ritz-Carlton This hotel did a huge revitalization in 2017, and the rooftop emerged as the absolute best part. Since the Ritz is fancy, they added a Veuve Clicquot Champagne cart, and if you’re fancying that fancy experience, then this is the rooftop du jour. Pair the bubbly with Italian bites while you chill out within this modern space. They’ve got a fire pit for those chillier days, but aren’t open when it actually gets cold.
Z Bar It’s the new rooftop that overlooks Michigan Avenue from the Peninsula Chicago. This rooftop separates itself from the rest because its small bites and cocktail menus are so ridiculously good. A few of our favorites include the Sunday Spritz (magnolia aperitif wine, elderflower, chrysanthemum, strawberry, and lemon) along with the steak fondue. But we’ve tried just about everything on the menu and you really can’t go wrong. Come winter, there’s a canopy covering part of the terrace, and an outdoor fireplace to keep you warm.
I|O Godfrey The year-round rooftop lounge at the Godfrey Hote L Chicago has retractable glass so you can relax there rain, shine, or snow. They’re totally on top of the trends, serving rainbow sangria and dragon berry mojito in the summer, along with CBD options. While this rooftop bar is crowded at all times, it’s especially popular during its signature events. For example, during the annual Kentucky Derby Viewing Party, there are Bourbon 101 classes, best hat contests, and other silly games. Or head there during a blizzard (or November through March) and you can hang out on the roof in a heated igloo while you roast s’mores, drink a hot cocktail, and be merry.
Royal Palms Shuffleboard Club This is an actual shuffleboard club in Wicker Park with a rooftop open to anyone ages 21 and up. Grab a tropical drink, a meal from a food truck (there always seems to be one roaming outside, though they don’t sell food in the club), and play on one of the 11 regulation-size courts ($40 per hour, first come, first served).
Cindy’s This rooftop is perched on top of the Chicago Athletic Association. During the summer, it has the ambiance of a Great Lakes beach house: a totally relaxed, chill-out vibe. When the weather changes, they release the blankets, hot cocktails, and fire pits. You can nibble on family-style comfort food year-round.
Drumbar One of the first rooftops — opened in 2012 — this is a moody, speakeasy-style cocktail bar with an intimate indoor lounge and an outdoor terrace. Take in the views of Lake Michigan and the Hancock building while slowly sipping your whiskey, scotch, bourbon, and cognacs — many of which are limited-release, one-of-a-kind spirits.
Cerise Located on the 26th floor of the Virgin Hotel in downtown Chicago, this is the rooftop for partying. They’ve got a DJ, strong drinks, great views, Latin bites, and a moody indoor area that makes it the place to be if you want to see or be seen; to meet 20-somethings; and to let loose. Bring earplugs if you want to be able to hear the next morning.
Gene’s Sausage Shop & Delicatessen One of these things is not like the others. There’s no dress code, no fancy DJs, no craft cocktails. There’s nothing fancy about this rooftop, but it’s so Chicago. The Lincoln Square rooftop offers more than 40 types of housemade sausages that you can pair with beers that average less than $5 per pint.
Danielle Braff can be reached at firstname.lastname@example.org.