LH Rooftop

Chef Concierge of LondonHouse Chicago Shannon Boland testifies the LH Rooftop is a summer bucket list topper, offering picturesque angles of the city that you really can’t find anywhere else. “You are eye level with some of the most striking, architecturally significant buildings in Chicago,” says Boland. “No other view really compares. You can see the Wrigley Building clock tower close up or the gothic crown of the Tribune Tower.”

LH Rooftop at LondonHouse Chicago

The Up Room

Ascended on the 13th floor of The Robey Chicago, The Up Room is a Mad Men-esque cocktail lounge offering the best eastern view of the Chicago skyline. Offering a cozy imbibing respite when the sun goes down, this spot has indoor seating and an expansive terrace. Blackstone Hotel concierge Ricardo Lemus says “The view here is different from any other rooftop views.”

The Up Room

Cindy’s

Concierge Flor Sigaran of the Chicago Athletic Association Hotel will tell you “Cindy’s modern design makes you feel like you are transported to your summer house in the Hamptons.” The panoramic views of Millennium Park, The Art Institute of Chicago, and Lake Michigan alone make Cindy’s a must-visit. But when you factor in super seasonal cocktails you’ll soon see why this is is one of the Loop’s most sought-after hot spots.

Cindy’s

Drumbar

Drumbar, on the 18th-floor of the Raffaello Hotel, has a brag-worthy selection of whiskey, scotch, bourbon, and cognac and boasts equally-impressive views from their outdoor terrace. Ritz-Carlton Chicago concierge Kyle Francis provides that Drumbar is “a top cocktail destination, the cocktails are inspired by countries and states. Scotland is their version of a whisky sour and Mexico uses jalapeno infused tequila.”

Drumbar