Chicago’s Top Five Rooftops & Patios

Summer’s in Chicago are fleeting, the weather isn’t always nice, and the sun isn’t always out. When it is, the city is vibrant, Chicagoans itineraries are event-packed, and outdoor patio season is in full effect. In a city full of neighborhoods, there is no shortage of patios and rooftops to visit in any part of the city. Chicago rooftops are renowned and praised for many attributes including ambiance, crafted spirits, creative menus, nightlife, and special events. I am highlighting the top five summer hot spots that are a must-see while in Chicago.

Fried chicken with a sweet glaze and vegetables

VU Rooftop in South Loop
A rarity to the South Loop altogether, VU, pronounced “view,” is a 13,000 square foot, rooftop restaurant, and bar. It features retractable floor to ceiling glass walls that offer tantalizing skyline and lake views year-round. Boasting three bars, two patios, fire pits, a private karaoke room, and unparalleled views of Chicago, what’s not to love?

VU’s food menu is a limited selection of shareable plates. If you’re stopping in with friends, try a combination of small plates from the menu. Be sure to include an order of the buttermilk chicken thighs or if you’re visiting solo, try the VU cheeseburger.

With a spirit-driven cocktail menu, patrons choose either vodka, mezcal, gin, rum, or cognac as the base for their cocktails. Then the bartender handcrafts the cocktail by adding locally sourced ingredients for the perfect mixture. I recommend Rum #1 or Cognac #2.

VU’s easygoing atmosphere is a refreshing addition to Chicago’s rooftop bar scene. VU’s South Loop location is likely the commencement of the bustling nightlife scene destined to come to the area. If you are looking for a nightcap to end the perfect summer night in Chicago, I wouldn’t skip the view at the VU Rooftop.

Two glasses of red wine on top of a wooden table next to a fireplace.

Cabra in West Loop
Top Chef fans, Stephanie Izard strikes gold yet again, as Cabra is the newest addition to the “goat” family in Chicago’s West Loop neighborhood. It is an open-air rooftop restaurant serving Peruvian shared plates highlighting both Latin and Japanese influence. Cabra features two terraces, a pool, a full-service bar, intimate seating amongst fire pits, and an open kitchen concept with a six-person chef’s counter ceviche bar. The cocktail menu is Latin inspired featuring wines from Central and South America and signature cocktails that have Peruvian origins, like the Pisco Sour, known for its potency. Cabra’s intimate open-air concept under the stars is perfect for a date night or a night out on the town.

Bartender pouring a pink cocktail

Paradise Park in Wicker Park
“Welcome to Paradise.” At first glance, Paradise Park is alluring, captivating, and inviting. With lush green décor and an actual trailer home at the entrance of the bar, I had imagined I had just stumbled upon a tropical trailer park. While deemed a pizza haven, Paradise Park Bar is an expansive indoor/outdoor patio restaurant serving classic and creative pies, cocktails, and drinks. If you find yourself in Wicker Park with a group of friends, I suggest you start with an appetizer, preferably the goat cheese stixs, and work your way to a couple of slices of paradise.

Whiskey Business in Wicker Park
Whiskey Business is nestled within the heart of Chicago’s Wicker Park neighborhood bar scene and located on the vibrant street of North Milwaukee Ave. Whiskey Business is a bi-level bar that is often crowded due to its expansive rooftop patio. For hot summer days on the patio, I’d recommend Frozé, all day. Frozé being the bar’s take on the refreshing popular summer slushie drink that blends rose, wine, and sometimes vodka. The energetic atmosphere also offers patio events like brunch, classic movie and karaoke nights, and rooftop yoga.

Pink cocktail with an umbrella in it.

Deuce’s Major League Bar in Wrigleyville
The formally known Deuce’s &The Diamond Club is gone, but not to worry, baseball season is here and Deuce’s Major League Bar is in full swing. With its grand opening on May 31st, Deuce’s Major League Bar is stepping up to the plate as an expansive baseball pop-up bar. Its concept promises the ultimate sports bar experience. Deuce’s is still a bustling bi-level bar with an outdoor patio featuring a pool, a patio bar, and outdoor cabanas just within earshot to the historic Chicago Cubs stadium in Chicago’s Wrigleyville neighborhood. The new redesign includes wall to wall major league decor, a creative MLB themed drink menu and a Bat Throne for photo ops! Southside White Sox’s fans please don’t be angry, but I actually enjoyed myself. Open late on weekends, drop in if you’re catching the Cubs in Wrigleyville or if you are just looking for a good place to enjoy the weather.

Remember, Summer’s in Chicago are fleeting. It is best to get out and enjoy all that the city has to offer when you can. Whether you visit rooftop and patio bars and restaurants to pass the time or admire the skyline, no one can deny outdoor dining is always enjoyed while the sun’s out, you’re thirsty, and have an appetite. Start planning your Chicago summer getaway today!

Know Before You Go

  • Chicago’s nickname is “The Windy City.”
  • Make sure to visit Millennium Park so that you can see the world-famous Bean!
  • Avoid visiting in the winter if you aren’t a fan of cold weather! The weather warms up around May.
Women in a black shirt and grey slacks

This post was written by Hilton Suggests Team Member, Brianna J. Are you interested in traveling to Chicago? Let us know if we can help you with any other recommendations. Tweet us for more great local travel tips!

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