Editorial
Chicago has the best skyline in America for rooftop drinking. We checked the field and cut two that have closed since the last guides ran. The eight below cluster around the Loop and the Magnificent Mile, with views of the river, Lake Michigan, or both.
The LH Rooftop crowns the LondonHouse where the river meets Michigan Avenue, three levels of it, with the Wrigley Building lit up across the water. It is the postcard Chicago rooftop and it knows it, so expect a cover and a wait for the lift after 6pm. Come for golden hour, order a cocktail and take the dome view. Worth the hassle once a summer.
Cindy's sits on top of the old Chicago Athletic Association on Michigan Avenue, looking straight across Millennium Park to the lake. The room is handsome, the brunch is the draw and the terrace fills fast on a clear weekend. Prices match the address, but the view is free with a drink. Get there before noon at the weekend, or after work midweek for a rail spot.
The J. Parker tops the Hotel Lincoln in Lincoln Park, and the trick here is the angle, looking south over the park and the lake to the skyline rather than standing under it. A retractable roof keeps it going past summer. It draws a younger Lincoln Park crowd and books up at sunset. Go for the bottomless brunch, or an early-evening drink before the queue.
The Up Room crowns the Robey, the tallest building in Wicker Park, thirteen floors up with a small pool and a wraparound view back toward the Loop. It is the neighbourhood's only public rooftop and runs more relaxed than the downtown hotel bars. Drinks are fair for the height. Best on a weeknight, when you can actually reach the rail and the pool deck.
Vu sits twenty-two storeys over the South Loop with three bars, two patios and fire pits for when the wind turns. The view takes in downtown one way and Lake Michigan the other, which not many Chicago roofs manage. It runs busy and loud at weekends. Come early evening on a clear day, claim a patio seat and let the skyline do the work.
I|O Godfrey sits four floors up at the Godfrey Hotel in River North, and its trick is the retractable roof, which makes it the city's only true year-round rooftop. The view runs south across the skyline rather than over the water. It leans party over quiet, with DJs late and a dressed-up crowd. Go early for the view, or late if you want the noise.
Raised tops the Renaissance Chicago on Wacker, a tucked-away terrace looking out over the river and the bridges of the Loop. It is smaller and calmer than the marquee roofs, which is the point, and easier to walk into on a busy night. The cocktails are solid and the view is properly central. Best at dusk when the bridges light up and the after-work crowd thins.
Z Bar sits on the sixth floor of the Peninsula on Superior Street, lower than the tower roofs but right among the Mag Mile buildings, which gives it an intimate, hemmed-in view. It is the upscale end of the scale, with a long drinks list and global small plates to match the hotel. Dress up, book ahead and treat it as a smart first drink rather than a session.
LondonHouse and Cindy's are the two essentials. Most peak between 6 and 9 PM in summer. Closed in winter for many.
Senior US Editor — drinks his way through New York and writes about which bars actually deserve their reputations.