The Palmer House The lobby
The Loop · $$$
Photo: Palmer House a Hilton Hotel
Why it made the list: The longest continuously operating hotel in the country, first built in 1871 as a wedding gift and rebuilt after the Great Chicago Fire, and home to one of the most jaw-dropping lobbies anywhere, a two-story hall of glittering chandeliers under a sprawling painted ceiling of Greek mythology. Also the birthplace of the brownie.
The Drake The Palm Court
Gold Coast · $$$
Photo: The Drake
Why it made the list: The grande dame at the top of the Magnificent Mile, opened on New Year's Eve 1920 and host to everyone from Churchill to Princess Diana. Come for afternoon tea in the Palm Court, a secluded, club-like lobby lounge with a harpist, or a martini at the wood-paneled Coq d'Or, one of the first bars to open after Prohibition.
The Chicago Athletic Association Best all-rounder
The Loop · $$$
Photo: Chicago Athletic Association - The Unbound Collection by Hyatt
Why it made the list: A former 1890s gentlemen's athletic club on Michigan Avenue, beautifully restored into a hotel with a four-story lobby, a game room with bocce and pool, the Cindy's rooftop over Millennium Park, and the tiny eight-seat Milk Room speakeasy. It's the most fun historic hotel to just hang out in, and you don't need to be a guest.
The Blackstone The 'Hotel of Presidents'
South Loop · $$$
Photo: The Blackstone, Autograph Collection
Why it made the list: A 1909 Beaux-Arts landmark that has hosted twelve U.S. presidents, and gave the language the phrase 'smoke-filled room', coined for the back-room deal that picked a presidential nominee here in 1920. The elegant lobby and the Timothy's Hutch and Art Deco details are worth a look, with a rich political history behind them.
The Chicago Motor Club Art Deco gem
The Loop · $$
Photo: Vidhya Basak
Why it made the list: A small Art Deco jewel hidden in the Loop, the former Chicago Motor Club building from 1928, now a Hampton Inn, with a beautifully restored lobby featuring a soaring mural map of 1920s American highways and a vintage Ford Model A on display. A free, quick, delightful stop most visitors walk right past.
⭐ Bonus Pick: You Don't Need a Room to Enjoy Them
The trick with all five: the lobbies, bars and public rooms are open to anyone who walks in dressed for it. A martini at the Drake's Coq d'Or, a rooftop drink at the Chicago Athletic Association, the painted ceiling at the Palmer House, each buys you a piece of the city's history for the price of a drink, or for free. Treat the great hotel lobby as the destination.
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