When I think of Chicago, I think of sprawling skyscrapers, architectural feats, and great bars. (What a combo!)
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Those skyscrapers are usually top of mind when researching or writing about Chicago—they create pretty unforgettable opportunities for travelers. For example, you can rent an Airbnb in a high-rise building, giving yourself unbeatable views of the city during your downtime. Unlike cities like New York City, Chicago’s high-rises aren’t reserved for swanky businesses and the ultra-rich.
But if you’re not the biggest fan of heights, staying in a high-rise might not be for you. You might be more interested in a shorter stay above the city’s twentieth level. If that’s the case, I humbly put forth these rooftop bars in Chicago where you can sip on a cocktail, then head back down to solid ground.
Here’s where to go for a drink amongst the clouds at the tallest rooftop bars in Chicago.
10 tallest rooftop bars in Chicago
CloudBar (94th floor)
Located in 360 CHICAGO on the top floor of the John Hancock Observatory, you can purchase a cocktail at the small bar that’s inspired by local tastes as you observe the city from above. It’s the tallest rooftop bar in the city, giving you a larger-than-life view of Lake Michigan and surrounding skyscrapers.
ROOF on theWit (27th floor)
Stylish, upscale, and with sweeping views of Chicago’s impressive skyline, ROOF is a club experience not to be missed. If you prefer to avoid DJ sets, head there during the early hours to enjoy a live music set instead. You can also order small bites to eat.
LH Rooftop (22nd floor)
Want a view that’s close to the edge? You can call ahead to reserve a table at LH Rooftop (for drinks and/or food) and request a seat close to its glass-lined perimeter. The views are jaw-dropping, and the drinks are good, but know that you’ll pay for that stunning vista in the price.
VU Rooftop Bar (22nd floor)
Located on the 22nd floor of the Hilton Garden Inn McCormick Place, VU Rooftop Bar has three different spaces for you to check out. There’s a Solarium with sweeping views, a Board Room for lounging, and a Karaoke Room. You can also order food from the full menu.
Cindy’s Rooftop (13th floor)
Cindy’s is a local eatery serving up American food and cocktails. The rooftop offers lovely views of Millenium Park and the surrounding skyscrapers. Just call ahead to make a reservation (14 days in advance) with a view. Also, come hungry—this is a restaurant, not just a bar.
The Up Room (13th floor)
Located on the top floor of the famous Robey building, this swanky bar delivers on views, atmosphere, and excellent mixology. Walk-ins are welcome. Be sure to stop by before The Up Room becomes a popular favorite—according to reviews, it’s still an under-the-radar spot.
Upstairs at The Gwen (5th floor)
This Art Deco-themed rooftop takes you straight to the heart of Chicago’s architectural scene. Expect an upscale cocktail menu, along with a seasonal lunch and dinner menu. As an added perk, you can enjoy the winter-ready patio even after the warm weather ends.
Z Bar (6 1/2th floor)
Grab a bite to eat and a cocktail to drink at this rooftop terrace offering sweeping views of the city. The bar is upscale but relatively affordable, making it perfect for a nightcap or a big date. If you’re staying at The Peninsula or nearby, don’t miss out.
IO Godfrey Rooftop Lounge (4th floor)
Who says you need to be above the clouds to enjoy great views? As with RAISED, IO Godfrey Rooftop Lounge takes you right into the action. While they aren’t the tallest rooftop bars in Chicago, they offer an immersive, urban feel. You’ll feel surrounded by towering skyscrapers as you order cocktails that this swanky lounge.
RAISED (3rd floor)
No, it’s not a traditional rooftop bar—it’s located on the third floor, after all. But if you want jaw-dropping views of Chicago’s downtown, this is a great spot to order a cocktail and get lost in the lights. Just know that it’s better to visit during the warmer months so you can take advantage of the outdoor terrace.
