Get all you can out of the all-too-short Chicago summer experience by dining outside as often as the weather allows. Even better? Take it up top at some of our new favorite rooftop spaces. (Be sure to check out last year’s list too for even more great spots). Lake breezes, awe-inspiring views, and even a rooftop garden or two will be your reward.
Apogee
The aptly named Apogee, at the very top of the Dana Hotel and Spa in River North, is inspired by Chicago’s evening skyline. There are both indoor and outdoor elements up here, including a grassy rooftop bar and fire pit and über-posh seating. Best of all: the Fifty/50 Restaurant Group’s beverage director, cocktail-meister Benjamin Schiller, has put together an eclectic and exciting beverage menu, every drink ready for its Instagram moment. 2 W. Erie St., 26th floor, Chicago
Cabana Club
Gaze out at the distant lights of downtown from your perch overlooking Wicker Park and Bucktown, knowing you have the option to take a dip in the rooftop pool of The Hollander, the sister property to The Robey Hotel (see Up & Up below). Food options are minimalist — crudité platter, chips and salsa, two skewers, two tostadas — but the sunny beverage options, including the OMG-toh (their take on the traditional Mojito) are really why you came. 2018 W. North Ave., 6th floor of The Hollander, Chicago
Celeste Roof Garden
Ooooh, this place is pretty, and it’s easy to forget you’re in the middle of River North. By day, this sun-filled room, lined with ivy and large potted plants and populated with comfy Victorian settees and ottomans, has a definite rosé vibe; at night, suffused with a sexy glow, it’s time for champagne or a shared group cocktail experience. The copper punchbowls aren’t the only things getting hammered here. 111 W. Hubbard St., 3rd floor, Chicago
Cindy’s
There may well be no better view downtown than from 13 floors up from Michigan Avenue, overlooking Millennium Park and Lake Michigan. The new outdoor bar, cozy fire pit, and the ability to order a pristinely fresh shellfish platter add to the cachet. 12 S. Michigan Ave., 13th floor of the Chicago Athletic Association Hotel, Chicago
Fig and Olive
Mediterranean food and wine is best enjoyed outdoors, as God intended. Escape the hustle-bustle of Oak Street luxury shopping and dine under a pergola on this south-facing terrace. Brunch here is especially glorious. 104 E. Oak St., 3rd floor, Chicago
Five and Dime
Currently the hottest place in downtown Evanston, there’s often a two-hour wait at this rooftop bar that sits atop sister restaurants Lulu’s and Taco Diablo. So get here early, and stay late to play the giant Jenga game, or hit the pinball machines. Don’t miss the Mucho Nachos! 1026 Davis St., 2nd floor, Evanston
Fountainhead
Weather permitting, this Ravenswood rooftop is a-rockin’ with craft brews, the mother of all bourbon and whiskey menus, and one of the best burgers — topped with pimento cheese, bless their hearts — in the city. 1970 W. Montrose Ave., 2nd floor, Chicago
Homestead on the Roof
This is a full-service rooftop restaurant, not just a bar, and the focus here is on the delicious seasonal fare inspired by the bounty of its 3,000 square-foot organic garden. Even the cocktails here are carefully crafted by Exec Chef Scott Shulman. 1924 W. Chicago Ave., 2nd floor, Chicago
LH Rooftop
You know it’s serious when there are three different rooftop venues: indoor lounge LH on 21, outdoor terrace LH on 22, and the Cupola. LH on 22 has the views of the Chicago River twinkling with reflected light below, and Lake Michigan to the east. The Cupola is a private space available for proposal packages, because it’s just that romantic and amazing. 85 E. Wacker Drive, 21st, 22nd and 23rd floors of London House Chicago, Chicago
Mahalo
Get your tropical fix on at this Hawaiian-centric rooftop resto, from the Big Kahuna for two (served in a whole pineapple) to five different versions of poke, Kalua Pork Fried Rice or Hawaiian-style ramen. Lots of white wood and ocean turquoise cushions add to the beachy atmosphere. Welcome to Wicker Park! 1501 N. Milwaukee Ave., 2nd floor, Chicago
Noyane
Don’t be fooled by the amazing view over Streeterville and the Gold Coast — with global celebrity chef Richard Sandoval (Latinicity, Baptiste & Bottle in Chicago) at the helm, this Zen-like “hidden roof” is more than a pretty face. First-class maki rolls and sashimi, wagyu beef, sparkly sake sangria, Japanese beers and sochu all play a part to make this a must-visit this summer. 101 E. Erie St., 21st floor of Conrad Chicago, Chicago
Shanghai Terrace
This secluded terrace, surrounded by the towering buildings of Michigan Avenue, is just the ticket for a sophisticated repast. Enjoy some of Chicago’s best Chinese food while sipping one of their Imperial Garden “Noble Flowers of China” cocktails, such as the Lychee, made with lychee and lemongrass shrub, pineapple rum, mint and lime, or the Chrysanthemum, a blend of gin, ginger shrub, orange, and Koval Chrysanthemum & Honey liqueur. 108 E. Superior St., 4th floor of Peninsula Hotel, Chicago
Streeterville Social
The amazing skyline views keep the crowds coming back to this rooftop lounge. The expansive green-space Event Terrace is available for private functions for groups of 36 or larger. The Bistro area, open daily to the public, has both comfy lounge seating and tables from which to hold court. Frozen Negroni in hand, Summer Corn Flatbread on its way, summer is here. 455 N. Park Drive, 3rd floor of Loews Hotel, Chicago
The Promontory
This Hyde Park favorite hits all the right buttons: live music, chef Andrew Graves’ inspired take on American regional cuisine, and inventive craft cocktails. The sleek outdoor patio space, all metal, wood and glass, is on two levels; both are lovely. 5311 S. Lake Park Ave. W., 2nd floor, Chicago
Up & Up
It’s not always cooler by the lake. Take, for instance, this new Wicker Park gem. Catch a breeze with a view on top of this converted office building, originally built in the late ‘20s at the six-corner intersection of Damen, Milwaukee and North avenues. It’s the tallest building for miles, giving you a spectacular perspective on our fair city. Bonus: The drinks are pretty damn good. 1600 N. Milwaukee Ave., 13th floor of the Robey Hotel, Chicago
Upstairs at The Gwen
This Art Deco rooftop sanctuary in the heart of the Gold Coast provides great views of other Chicago landmarks, namely the Wrigley Building and Marina Towers. The fire element here is compelling, with a corner fire pit for warmth and a long communal fire table for company. Graze on bites like Crispy Chorizo Fritters and Honey Chipotle Shrimp or fully commit with a serious burger or prime rib. You’ve got options. 521 N. Rush St., 5th floor of The Gwen, Chicago
Julie Chernoff, Make It Better’s dining editor since its inception in 2007, graduated from Yale University with a degree in English — which she speaks fluently — and added a professional chef’s degree from the California Culinary Academy. She has worked for Boz Scaggs, Rick Bayless and Wolfgang Puck (not all at the same time); and sits on the boards of Les Dames d’Escoffier International and Northlight Theatre. She and husband Josh are empty nesters since adult kids Adam and Leah have flown the coop. Rosie the Cockapoo relishes the extra attention.
