

One of the largest cities in the country, Chicago is set on Lake Michigan in Illinois. It’s also referred to as the “Windy City” and renowned for its skyscrapers, culture, and food. But, what stuns visitors is the number of things to do here. For instance, attractions like the John Hancock Center, Tribune Tower, Millenium Park, Willis Tower, and so much more, will keep you busy throughout your vacation here. And the city’s rooftop bars only add to Chicago’s beauty. Drinking and dining while soaking the city views is a mind-blowing feeling. So, check out some of these top rooftop bars in downtown Chicago, Illinois, on your next visit.
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1. Cindy's
One of the most beautiful rooftop bars in the city, Cindy’s overlooks the Instagram-worthy view of Millennium Park. This stylish, hip bar on the rooftop above the Chicago Athletic Association serves seasonal fare, accompanied with fine wine, your choice of cocktails, and craft beer. You can also try one of their custom cakes and various other sweet treats while here.
Cindy's
Address: 12 S Michigan Ave, Chicago, IL 60603, United States
Website: Cindy’s
Opening hours: Mon - Fri: 11am - 1am; Sat: 10am - 2am; Sun: 10am - 12am
2. Boleo

On the 15th-floor rooftop of the Kimpton Gray Hotel, Boleo is known for keeping it classy all through the year under its retractable roof. The Peruvian-inspired menu features chips, street food, and empanadas that are so tasty, it will have you coming back for more.
If you are more into the liquor, try the Boleo old-fashioned, their Maria Bonita, and Abuela. You will also find fine wine, craft beer, and various other spirits that blend perfectly with all their dishes.
Boleo
Address: 122 W Monroe St, Chicago, IL 60603, United States
Website: Boleo
Opening hours: Wed - Thu: 4:30pm - 12am; Fri: 4:30pm - 1am; Sat: 5:30pm - 1am (closed on Sun - Tue)
3. Raised

If you make your way to the Renaissance Hotel, head to the third-floor rooftop bar called Raised. Although it is doesn’t sit as high as some of the other rooftop bars on this list, as the famous saying goes, “Don’t judge a book by its cover”.
The garden-inspired rooftop bar boasts Chicago River views and the surrounding skyline with a clear view of the Michigan Avenue Bridge, Marina City, and more. Here, you can grab a seat by the curved railing and sip on cocktails inspired by botanical elements.
Raised
Address: 1 West Upper Wacker Drive, Chicago
Website: Raised
Opening hours: Mon - Thu: 4pm - 12am; Fri - Sat: 2pm - 12am (closed on Sun)
4. Z Bar

A crowd favorite in recent years, Z Bar is an internationally inspired rooftop bar, located on the 6th level of the Peninsula Chicago. If you want to try something different, head to this bar to taste their internationally curated meals, such as their Malaysian chicken and beef or steak fondue, accompanied with chilled beer, wine, or one of their craft cocktails.
There is also a live DJ spinning fun tracks to set the mood. The bar organizes a monthly spirits series called Wanderlust, where you can learn one or too many things about your favorite drinks.
Z Bar
Address: 108 E Superior St, Chicago, IL 60611, United States
Website: Z Bar
Opening hours: Sun - Thu: 5pm - 12am; Fri - Sat: 4pm - 1am
5. Fountainhead
If you could do with more food and fewer drinks, this is the bar for you. The Fountainhead is the most attractive rooftops in Illinois, Chicago. The seasonal rooftop garden space is known for serving organic bar bites and a long list of craft beer. Some of the fare you can try here are their Amish chicken, mussels, mushroom toast, burgers, cheese curds, and more.
The expansive windows and open space make it the perfect place to have great conservation with your loved ones while enjoying a meal and drinks.
Fountainhead
Address: 1970 W Montrose Ave, Chicago, IL 60613, United States
Website: Fountainhead
Opening hours: Mon - Fri: 4pm - 2am; Sat: 11am - 3am; Sun: 11am - 2am
6. The J.Parker
If your heart craves something new, something different, it must have what it wants. Bring your heart and yourself to the J. Parker, situated on the 13th floor of the Hotel Lincoln, which will give you a nice break from the ordinary. The vast views of the lake encompassed by Lincoln Park are a great sight to behold if you are into looking at nature more than buildings.
The roof is retractable and the mouthwatering delectables include burgers, nachos, fries, and more, which will have you coming back for more. This rooftop bar is named after one of the bodyguards of Abraham Lincoln, which is a pretty cool origin story.
The J.Parker
Address: 1816 N Clark St, Chicago, IL 60614, United States
Website: The J.Parker
Opening hours: Mon - Thu: 7am - 11am & 5pm - 12am; Fri: 7am - 11am & 3pm - 2am; Sat: 2pm - 2am; Sun: 2pm - 12am
7. Devereaux
Situated on the Viceroy Chicago’s 18th floor, Devereaux is a rooftop bar featuring alluring blue lighting all over, which bounces off of the pool to exude a classic summertime vibe, sure to put you in a nice mood. The Hollywood-style bar provides breathtaking views of the Gold Coast, perfect to catch some stunning sunsets.
This small, intimate bar serves excellent bar bites, including fried chicken and more, accompanied by curated cocktails.
Devereaux
Address: 1112 N State St 18th floor, Chicago, IL 60610, United States
Website: Devereaux
Opening hours: Sun - Thu: 4pm - 11pm; Fri - Sat: 4pm - 1am
8. Cerise Rooftop
Situated on the 26th floor of the Virgin Hotel, Cerise Rooftop wraps around three sides of the structure. The hip venue with unusual artwork and a DJ that spins cool tunes under the starry lights makes this place a chic space in the city.
You can try out a variety of cocktail drinks here, including their Devil to Pay, Margherita, and their Pau Hana, among others. There is also a variety of bar grub that will go perfectly hand-in-hand with their craft beer.
Cerise Rooftop
Address: 203 N Wabash Ave 26th floor, Chicago, IL 60601, United States
Website: Cerise Rooftop
Opening hours: Thu - Fri: 5pm - 12:30am; Fri: 5pm - 2:30am (closed on Sun - Wed)
9. The Up Room

An upscale 13th-floor rooftop bar, the Up Room at Robey boasts sweeping city views of the area, which is not really known for its panoramic scenery. The rooftop bar exudes a Mad Men vibe because of its stylish and dark decor, and it is open throughout the year.
Although it has limited space, the bar acts as a perfect date night spot with pleasant views of the city and a serene ambiance. Along with this, the cocktails are brilliantly curated and perfectly accompanies the tasty fare served here.
The Up Room
Address: 2018 W North Ave, Chicago, IL 60647, United States
Website: The Up Room
Opening hours: Mon - Thu: 6pm - 11pm; Fri: 6pm - 1am; Sat: 1pm - 1am; Sun: 1pm - 12am
10. Upstairs at The Gwen
Situated in the River North, 5 levels above the Gwen, Upstairs is a luxurious rooftop bar covering an area of 3,000 square feet (278 square meters) and boasting panoramic city views of some unique architectural gems. While here, you will notice some of the craft cocktails are named after the neighborhoods of Chicago, for instance, the Avondale. This swanky venue, along with offering various drink options, also serves American bar bites.
Upstairs at The Gwen
Address: 521 N Rush St 5th Flr, Chicago, IL 60611, United States
Website: Upstairs at The Gwen
Opening hours: Sun - Fri: 11am - 11pm; Sat: 11am - 12am
Enjoy some drinks with stunning Chicago city views

When it comes to the drinking and dining scene in Chicago, the city has some of the best places to offer. These rooftop bars in Chicago provide an amazing setting to enjoy the views and to relax, drink, and dine.
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