Chicago’s skyline is filled with rooftop bars and restaurants with amazing views, all waiting and ready to give you a beautiful dining and drinking experience that’s entirely Instagram-worthy. Whether you prefer a more casual and relaxed atmosphere, or you’re going all out for a romantic aura that’s sure to impress your date, the Windy City delivers.
Chicago offers magnificent views. On one side, you have the city — filled with glittering towers that seem to expand every single time you visit. On the other, you’ve got Lake Michigan, a gorgeously refreshing hue of blue in the summer and a frozen beauty in the winter. Wherever you turn, there’s something new to catch your eye. Thankfully, there are plenty of spots for you to take it all in.
The 360 Chicago Observation Deck provides beautiful views of the skyline, lakefront and suburbs beyond, and the drinks aren’t the only attraction you’ll find at this 94th-floor venue. Throughout the rest of the year, the deck’s 360 ChiSeries provides fun events every day of the week, to attract families, couples and other travelers. While each day offers something new, for great drinks with your view, head to 360 Chicago on Thursdays for a “Hoppy Hour” presented by Revolution Brewing and KOVAL Distillery, both Chicago-based, or plan to attend one of the monthly paint-and-pour classes hosted by Bottle & Bottega. Of course, you can always stop by at any time and enjoy a cocktail at Bar 94.
875 N. Michigan Ave., 94th Floor
The Signature Room at the 95th
From the moment the elevator zips you up to the 95th floor and you step out into the marble reception area, you’ll truly feel you’ve landed somewhere sophisticated and sublime. On the 95th floor of this Chicago institution, you’ll find a restaurant serving up scrumptious brunches and delicious dinners. The views are spectacular, showing off the best of Lake Michigan; just be sure to go on a clear day — sometimes diners are disappointed to find they’re stuck in a cloud when the weather’s not so great! Must-try specialty cocktails include the Peach Manhattan (Knob Creek bourbon, peach brandy, sweet vermouth, bitters and a maraschino cherry) and the Blackberry Collins (gin, hibiscus puree, blackberry liquer, simple syrup, lime and ginger beer). For drinks only, go up one more floor, to the lounge and bar.
875 N. Michigan Avenue, 95th Floor
The Terrace at Trump
The Trump Tower in Chicago is an unmissable piece of architecture on the River, one that looks positively radiant as night falls, and the lights begin flickering on choppy waves below. The Terrace at Trump provides great views of not only the surrounding city and river, but also the lake beyond, as well as the various bridges. The space offers intimate seating in the form of various couches and high tops. The cocktails include several martini iterations, such as The Terrace Martini (gin, citron, blue curacao, lemon) and Truffle Martini (vodka, vermouth, truffle olive garnish), but also some more inventive cocktails, like the Gin & Berries (Hendrick’s, acai spirit, cranberry, sweet and sour and Sprite) and the Mango Bubble (vodka, mango rum, mango puree and prosecco).
521 N. Rush Street
Travelle is located within The Langham, with floor-to-ceiling windows that just can’t be beat. The atmosphere is warm and inviting, while still maintaining its chic sophistication. Views include the river and surrounding properties, and the inside space is just as lovely during a winter snow squall as it is a sweltering summer day. Some of the favorite cocktails on the menu include the Beet It (vodka, beet, cinnamon and citrus) and the Trinidad James (rum, bourbon, passion fruit, almond and clove). However, you really can’t go wrong with any of the cocktails. Plus, they even have a few non-alcoholic varieties for the totalitarians in your group, like the Second Ginger City (orange juice, ginger ale and ginger beer) and the Astaire & Rogers (raspberries, mint, lemon and lime).
330 N. Wabash Avenue
So perhaps you don’t necessarily want to see all sparkly skyscrapers when you look about during your cocktail hour. If you’d rather enjoy the serene lake and nothing but, head to Lincoln Park. The boutique Hotel Lincoln boasts a rooftop bar called J. Parker, with a nice cocktail list and some good craft beers. However, the cocktails aren’t the only thing that’ll keep you coming back. The small bites are pretty great, too, with options like pinto bean hummus, a Midwestern cheese plate, fried chicken sandwiches and fried kale chips.
1816 N. Clark Street
By Holly Riddle