Rooftop Viewing Areas for the Chicago Air & Water Show

One of Chicago’s most beloved – and thrilling – events, The Chicago Air and Water Show, is returning to the city this weekend for its 63rd edition. The U.S. Air Force Thunderbirds, the U.S. Army Parachute Team Golden Knights and more will be flying over Chicago’s lakefront on Saturday, August 19 and Sunday, August 20 from 10 a.m. to 3 p.m., with practice flyovers beginning Friday, August 18.

Every year, millions of spectators gather along the shores of Lake Michigan to witness a display of daredevil stunts. The main viewing area stretches from Oak Street to Fullerton Avenue, with North Avenue Beach serving as center stage.

But while many spectators flock to Chicago’s beautiful beaches, rooftop bars are another popular destination, offering an enhanced viewing experience hundreds of feet off the ground. Read on for our picks of the best rooftop bars to watch the Chicago Air and Water Show 2023.

Cindy’s Rooftop

Perched on the 13th floor of the Chicago Athletic Association Hotel, Cindy’s Rooftop is a fan-favorite for locals, suburbanites and tourists alike.  And with panoramic views of the city’s skyline and Lake Michigan, it’s sure to be one of the best spots to catch The Chicago Air and Water Show. Choose a seat on the balcony that faces Lake Michigan, or enjoy the scene from inside, which is covered by a glass atrium.

In between the aerial action, guests can enjoy a roster of excellent cocktails and a menu created by Chopped Grand Champion and Cindy’s Executive Chef, Kaleena Bliss. Located in the heart of the Loop on Michigan Avenue, make sure to get there early to claim your spot.

The J. Parker

If you’ve never visited The J. Parker in Lincoln Park, The Chicago Air and Water Show may be the perfect occasion to cross this bar off your Chicago bucket list. Complete with an indoor lounge and outdoor patio, this year-round venue has a retractable glass roof and offers unobstructed views of Lake Michigan and the city’s skyline.

The J. Parker offers a nice selection of craft beer, wines and signature cocktails. Food options include light New American cuisine with popular dishes like the buffalo cauliflower and the signature J. Parker burger.


Branded as the largest rooftop venue in the nation, Navy Pier’s Offshore Rooftop & Bar features 36,000 square feet of glassed indoor space and a 20,000 square-foot terrace that has two lawns, seven fire pits and an entertainment and gaming area. All of this is surrounded by 360-views of Lake Michigan and the Chicago skyline, perfect for a day of jet-watching.

Outside of amazing views and a great time, Offshore offers small plates of seasonal and contemporary American fare, as well as a selection of classic cocktails, bubbles, wines and craft beers.

VU Rooftop

For a vantage point from the south, spend your day at VU Rooftop, a bar and restaurant located 22 stories high in the South Loop. Next door to McCormick Place, VU has two outdoor spaces from which to catch the show. Each has multiple bars, lounge seating and sweeping views of the lakefront.  And if all the action makes you hungry, VU offers a brunch menu and a locally driven beverage program, plus all-you-can-drink mimosas for $40.

CloudBar at 360

You’ll be high in the sky – and close to the action – at CloudBar at 360, which sits on the 94th floor of 875 N. Michigan Avenue (the former John Hanock Center) and offers access to the observation decks and the TILT thrill ride. The bar’s interior features a mirrored ceiling, floor-to-ceiling windows lined with ledge seating and illustrations by Chicago street artist, Lauren Asta.

CloudBar serves food and drinks from local purveyors and neighborhood restaurants such as Revolution Brewing, Kit Kat Lounge and Supper Club and more. Cocktails and mocktails like the “L” Fashioned, Gold Coast Manhattan, and the Midway are named after Chicago neighborhoods and landmarks.

Written by @properties
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