25 Rooftop Restaurants In Chicago That Are Dream Happy Hour Spots

Nothing celebrates our love of Summer like a bright afternoon or a warm, breezy sunset paired with a good meal outside. By far one of the best places to do that is at a stellar rooftop bar. Few locations hold the excitement and delight that comes with a rooftop view, be it 2 stories up or 26.

Chicago is home to some of the world's best rooftop bars and restaurants, each with their own distinct style and beauty, and each more enthralling than the last. Whether you're ready for a swim and a mojito or a bratwurst in a biergarten, Chi Town's rooftop scene has what you're looking for.

Here, we've rounded up 25 of the most sublime sky grazing spots around the city. From casual to ornate, with unforgettable themes that range from California beach party to Victorian garden, the only thing more impressive than these eateries' elaborate decor and creative menus is their unforgettable views!

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25 Cindy's Overlooks Millenium Park


Nestled in Chicago's Loop, Cindy's is 'the Crown Jewel' of the Chicago Athletic Association hotel. Perched cozily atop the 13th floor, the large airy indoor space has ample seating in the form of family-style long tables as well as bar seats.

The incredibly popular rooftop bar frequently has lines going out of the elevators on the ground level, and just last year the space was expanded to include an outdoor bar for those looking to feel that warm summer breeze.

The menu includes a plethora of creative cocktails for your enjoyment, but even more popular are the booze-infused popsicle and ice cream bar selections!

24 LondonHouse's Sculptural Skyline Spot


LondonHouse is a classically refined, upscale hotel on the banks of the Chicago River. Its rooftop bar is one of the most highly rated and best-reviewed spots in the city, and with good reason. The sweeping 22nd-floor terrace has incredible views of the Chicago River, Lake Michigan, and the Magnificent Mile, looking out from atop one of the "big four" skyscrapers. The menu sticks to London House's core business code, serving classic and cocktails and light bites made of incredible quality ingredients made freshly. Attracting both locals and tourists, if you're looking for a "big moment" place to have a drink, this is it!

23 Chicness Overload At Celeste


Celeste is a modern Instagram dream, featuring three floors of hospitality and charm in a renovated 1888 Louis Sullivan building. Although each floor is decorated to match a distinct theme, the rooftop is by far the best. Called their "Roof Garden," the space was recently enclosed with glass paneling and fully transformed.

Decorated with sumptuous Victorian-style furniture upholstered in tropical patterns matching the lush greenery, the space is described as an ode to an English garden.

Serving delectable and beautifully presented cocktails, this space is filled on a first-come-first-serve basis. While it is open year-round, the acoustic performances and themed parties make summer the best season to visit.

22 Raised Raises The Bar (...Literally)


Opened in 2016, Raised is one of the hottest spots in Chicago. The slick, popular space extends both inside and outside, with both areas equally packed during happy hour. The bar was inspired by its 'Main Stem' river district location to "Raise the bar" in terms of hospitality and quality. The private outdoor areas overlook the scenic Chicago River and skyline, and feature fire pits to fight the chill of a summer evening breeze. While the indoor decor is super urban, featuring graffiti murals painted directly onto the brick and a neon sign saying "A Guy Walks Into A Bar," the outdoor space feels a bit more mixed, including both tree-stump stools and rustic candle cages.

21 Fountainhead Is Cool And Casual


One of the more casual places we've featured here, Fountainhead has the vibe of a large outdoor brewery. Serving a large selection of craft brews from both local and regional distilleries, Fountainhead is a good place to watch the game or kick back with friends.

The food is surprisingly artisanal; definitely a step up from your average neighborhood pub.

The menu features creative, primarily organic options like grilled Spanish octopus and rabbit gnocchi. The classic lawn-style chairs and tables keep things low-key, while the well-stocked bar has ample ordering room and large TV's. Definitely worth an afternoon visit!

20 Waydown At The Ace Hotel


The Ace Hotel's rooftop bar Waydown was named for a song by Illinois native John Prine, and inspired by Midwestern watering holes. Serving what they call "strong, no-nonsense drinks," Waydown also offers sweeping views of the Chicago cityscape and nightly music. The six dollar Mondays are worth checking out when a number of classic cocktails and hamburgers are only $6. Although it is always centered around upscale American food, the bar's menu changes regularly according to what is available fresh locally. Open daily from 4PM-2Am, Waydown regularly features musical guests and DJs.

19 Gene's Sausage Shop And Delicatessen Is Kid-Friendly And Fun


Gene's Sausage Shop and Delicatessen is obviously the go-to place in Chi-Town for sausage, offering more than 40 varieties. But what you might not know is how great the rooftop beer & wine garden is.

Firstly, it's actually a functioning garden: you dine among flowers, grapes, tomatoes, and herbs.

The menu features a number of Polish dishes including Gene's bratwursts cooked over an open wood sausage grill. To get your afternoon glow on, they offer rotating beers on tap and wines by the glass from around the world. Open 11 am - 4 pm, this cute garden grill is definitely a top lunchtime destination!

18 Drumbar On The 18th Floor


Housed within the Rafello Hotel off of Michigan Avenue, Drumbar sits prettily on the 18th floor. Opened in 2012, the bar received some serious buzz, named “[one of the] Top Ten Bars in Chicago” by Chicago Magazine, “Best Whiskey Bar” by GQ Magazine, and “One of the Best New Bars in America” by Details Magazine. With its gorgeous high arched windows and sumptuously dark, tufted and polished decor, we can see why. The speakeasy-style bar is in Chicago's Gold Coast neighborhood and features a beautiful outdoor terrace with views of Lake Michigan and the Hancock building.

17 Cerise At The Virgin Hotel Is Eclectic And Fun


Called a 'hip hotel venue,' Cerise, atop the Virgin hotel, offers drinks and dancing until the wee hours of the evening.

The lounge-style outdoor seating is 'modern, spontaneous and playful,' and a wonderful place to sit with a cocktail and watch the sunset and the city lights come to life.

Located on the 26th floor, this rooftop's location puts you right in the middle of Chicago's skyscrapers. With regular live band performances and hours that extend until 3 am in the summer, Cerise is definitely a place to party. One of five of the hotel's restaurants, Cerise is considered the "cherry on top!"

16 Apogee In Wonderland


Part of the chic and quirky Dana Hotel and spa, the Apogee bar sits 26 stories up. Apogee, meaning "the point in orbit at which an object is furthest from the earth," features both scientifically and spiritually inspired cocktails. The plush indoor and outdoor settings have earned Apogee such accolades as one of the hottest bars in Chicago by Zagat, and one of the best rooftop bars by Condé Nast Traveler. The cocktails are seriously pretty, with many featuring live flowers, dry ice and shaved ice served up with whimsical details like paper butterflies and lychee berry toppers. If you're looking for the bar with the most 'grammable cocktail, this is it.

15 The Up Room Over Wicker Park


The Robey Hotel has a rooftop setup to rival any major city, but it's overlooking Wicker Park in the Windy City.

Visit for happy hour to sample the innovative cocktails and take in a serious sunset view, or hang out all day at the rooftop pool with a cocktail and your favorite pals.

The small size keeps the vibe even more exclusive and cool. If you're coming for evening cocktails, there could be a wait, as the boutique lounge space only seats 35, but if you do manage to snag a spot be prepared for some of the most breathtaking views in town!

14 i|O At The Godfrey Goes Morning To Night

the Godfrey

The i|O rooftop at the Godfrey hotel has the pleasure of being Chicago's largest indoor/outdoor rooftop lounge. The chic lounge space is open both day and night, year round. Featuring a retractable roof and a two-level fire pit, you'll stay warm here even on the chilliest Illinois evenings. Although it's only four stories up, the I|O features incredible views of the surrounding city skyline and unbeatable afternoon sunshine. The huge space allows for more intimate table settings, including lounge settings under luxe white tents. If you want to splurge on an unforgettable afternoon or evening with friends, this lounge and club is the place to do it!

13 Go Upstairs At The Gwen For Some Serious Style

the Gwen

"Swanky" is Upstairs at the Gwen's middle name. Open seasonally, Upstairs sits atop the luxury Gwen hotel on Michigan Avenue, offering incredible views and modern-sleek decor.

The menu's focus is on artful craft cocktails, but they also offer sharable small plates in a Tapas-style American fare twist.

Unlike many of the city's rooftop bars which seat based on availability, Upstairs at the Gwen does accept reservations. Whether you're sipping on the signature Gwen Luxe, a mix of Grey Goose, dry vermouth, raspberry, egg white, lemon, and prosecco, or splitting a pitcher of rose sangria, you'll definitely enjoy Upstairs's craft cocktail specialty.

12 Artsy And Laid Back Impact At Joy District


The Top Floor of Joy District is part urban garden, part art showcase, and all fun. The super hip space was named one of Chicago’s best and hottest rooftop bars in 2017 by Culture Trip, Eater Chicago, TimeOut Chicago, and Thrillist Chicago. Beneath high-strung interwoven patio lights stand a collection of murals by upcoming artist P. Scott, which pop against the dark wood and brick materials. The vintage floral-style upholstered sofas make up the lounge style seating, which allow guests to fully relax while sipping on easygoing frozen drinks. The venue regularly features guest DJs, and if you want to keep the party going past closing time at midnight, simply head downstairs to the Joy District club!

11 Rosé And Cornhole Mix At Streeterville Social


Named for the Streeterville neighborhood of Chi Town, the Streeterville Social rooftop bar is the perfect mix of high-end product and casual atmosphere. Sitting pretty on the top of  the Lowes Chicago Hotel, the Streeterville Social features elevated American eats & cocktails. Although the building is only 3 stories up, the views are incredible.

The public part of the S. Social is called the Bistro, which has both regular tables for dining and sofa areas for lounging, plus a collection of "all things summer," including rooftop Cornhole games.

Plus, they have $5 glasses of Rose on We-Drink-Pink-Wednesdays and boozy ice pops made fresh every day. Yum!

10 Visit The Year-Round Rooftop Of The J Parker

J Parker

Sitting on top of the trendy Hotel Lincoln on Clark Street is the chic indoor-outdoor space of the J Parker rooftop bar. The large glass enclosed section remains open for colder months, but the spacious outdoor area is lush and inviting for summertime evenings. We love the little weather indicator on their website's homepage, which informed us that today (July 6th) is "the DEFINITION of a perfect day). With some of the most spectacular views in the city, the J Parker overlooks the water with an unobstructed sightline. Between the 55 indoor and 140 outdoor seats, this is one of the largest venues on our list, but that doesn't mean it won't fill up!

9 Feel Sunny And Tropical Year-Round At Boleo


The go-to place in Chicago for Latin-American flare, Boleo serves up the dramatic flavors and sultry beats of South America. Sitting atop the Kimpton Gray Hotel, Boleo is 15 stories up.

The space is fully enclosed, meaning you can enjoy the sun-soaked skylights year round, however, the sun roof is retractable, meaning you can enjoy fresh air during the summer and a jungle-greenhouse vibe during Chicago's coldest months.

Stepping out of the elevator from the Kimpton's lobby, the savory aroma of Peruvian and Argentinian street food perfumes the air. Creative, memorable and tasty!

8 Get Tipsy At Whiskey Business


Whiskey Business is the place that you go to have fun. This rooftop location in Wicker Park serves up 80s and 90s nostalgia, regular running movie and karaoke nights. Their impressive 115 different whiskey options go well with the classic pub menu. The real reason to go to Whiskey Business is for the fun themed parties. This summer (starting on the 8th of July) they're hosting their first ever "pool party," which will have 3 pools, a giant inflatable flamingo, a sprinkler system and half priced industry drinks. Sign us up!

7 Get Glam At Gibson's Italia


Gibson's Italia serves high-end Italian food, specializing in steak and pasta. Although the upscale space spans three floors, the roof deck is the place to be. The wine list is among the most expansive in the city, matching the quality of the food, which is built on a tradition and elegance but is "relentless in the pursuit of the very best."

According to their website, the iconic Gibsons Bar & Steakhouse has been one of Chicago’s leading restaurants since 1989, and was the first restaurant group in the country to have its own USDA Certified Angus Beef Program.

If you want a refined but spectacular rooftop experience, Gibson's is for you.

6 Beach Vibes In Downtown Chi Town At Beach House Social


The Beach House Social brings the West Coast to Chicago's Wicker Park. Just opened last month, it is the rebranded elder sibling of Mahalo, the shuttered Hawaiian themed bar that previously occupied the space. Describing itself as "part surf club, part beach bar and totally laid back," the space definitely is beach-chic. The light, airy interior is matched by chic white umbrellas and pastel colored chairs outside, and the menu keeps with the theme, serving jerk carnitas tacos, tuna tostadas and double-decker burgers. Although the early reviews from the new place are mixed, we have no doubt that this space will be filled all summer!

5 The Roof On theWit Stuns At 27 Stories


theWit hotel in Chicago's Loop is a DoubleTree by Hilton hotel, and comes with serious style. Aptly named "Roof," theWit's rooftop bar has sleekness to spare. It has earned international acclaim for its expressive design, and sweeping skyline views, named "One of the Top 3 Rooftop Bars in the World" by Travel and Leisure.

The area is so popular that it doesn't even come assured to the hotel's guests: everyone is expected to make a reservation, because the waiting list is so long.

The creative cocktails and eats are simply the cherry on top; the Roof is, as they put it, "the place in Chicago to see and be seen."

4 From Breakfast Buffets To Brazilian Dinners At ZED451


Chicago's own Brazilian Steakhouse, Zed451 is the ultimate in upscale all-you-can eat experiences. The inclusion of the salad bar is the only thing this place has in common with your local Applebees; with prices set at $54 per person (not including drinks), Zed's goal is to allow every person to "create a personal culinary experience." The meat is sliced at your table, and the cocktails are to die for. Created with fresh seasonal ingredients, the menu is subject to change, but generally includes such delicacies as slow-braised short ribs, Moroccan chicken and Bacon and Pheasant Sausage. Plus, they do Brunch! Their breakfast buffet is similarly expensive, but also amazing!

3 Go Green At The Promontory


Called stylish and modern with regularity, the Promontory is a double level space with indoor and outdoor seating.

The open-hearth cooking is at the heart of the conceptual menu, in what they call "hearth to table" dining.

Based in southerly Hyde Park, the Promontory features lush greenery and warm wooden accents. The restaurant is lauded for their musical performances; it's relatively large-scale hosting capacity regularly draws hip local musicians. Doing brunch Friday through Sunday and dinner nightly, this chic green space is perfect for upscale eating without too much fuss.

2 Little Goat Is Casual And Fun


The Little Goat by Stephanie Izard is Chicago's most creative Diner. Featuring a menu composed of on gourmet twists on American classics, Little Goat is usually packed. At home in the West Loop, the restaurant fills a two-story space, including a rooftop dining area. Unfortunately, the rooftop area is quite frequently closed for private events, meaning unless you're going to book it up yourself, you have to follow along on social media to find the evenings that it's open to the public, or attend an open event! There are tons of Beer Classes and Public Parties where you can reserve a spot in advance, and enjoy the cute and comfy space for yourself.

1 Enjoy Decadent Eats At NoMI


Called the NoMI Kitchen, this indoor-outdoor space is part of the upscale Park Hyatt hotel on North Michigan Avenue. This New American style eatery is park of the Golden Mile, serving a combination of Midwest flavors with French influences, plus sushi, for good measure.

Sophisticated and chic, the space's views of Lake Michigan and the historic Water Tower Square are unparalleled.

Named a top rooftop restaurant by Food & Wine Magazine, Travel + Leisure Magazine, Crain’s Chicago Business, and The Daily Meal, this is not one to miss!

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