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Staypineapple, An Iconic Hotel, The Loop ChicagovsThe Drake

Both properties are recommended by professionals. On balance, The Alise Chicago - A Staypineapple Hotel is preferred by most professionals compared to The Drake, A Hilton Hotel. The Alise Chicago - A Staypineapple Hotel scores 94 with recommendations from 17 publications like Fodor's, Not For Tourists and Zagat.

Staypineapple, An Iconic Hotel, The Loop Chicago
8/10
1 W Washington St, Chicago, IL 60602
From $100/night
  • Pet Friendly
  • Bar/Lounge
  • Free Internet
  • Room Service
  • Laundry Service
  • Concierge
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Michelin Guide Michelin Guide
"It's all very fancy, with gilded furnishings and tasseled silk canopy beds, but it's good to be king."
Frommer's Frommer's
"If you're looking to commune with Chicago history, this sophisticated small hotel delivers a one-of-a-kind experience." Full review
i
For views of both the city and lakefront, ask for a room on a high floor in the northeast corner.
Concierge Concierge
"For a historic stay with a dash of flash, the Burnham is the place."
Fodor's Fodor's
"The design aesthetic inside is pleasantly funky, with Art Deco touches and zebra and leopard prints on the rooms' terry robes." Full review
Travel + Leisure Travel + Leisure
"Perhaps no other hotel showcases Chicago’s impressive architectural history like the Burnham." Full review
i
Rest your head on down, foam, or even buckwheat ordered up from the hotel’s pillow menu.
Time Out Time Out
"This historic architectural treasure morphed from the Reliance Building into the Hotel Burnham. Yet a National Historic Landmark, the hotel isn't stuck in the 19th century." Full review
DK Eyewitness DK Eyewitness
"Set in the magnificent Daniel Burnham-designed Reliance Building, this stunning hotel is both classic and cheerfully contemporary."
BlackBook BlackBook
"A glamorous mix of historic location and modern style located in the Reliance Building, the world's first steel-frame skyscraper."
Zagat Zagat
4.5
"This “excellent” Kimpton boutique "just blocks away" from theaters and museums is a “superb restoration” of an 1895 skyscraper with “a lot of character” and “exceptional” rooms."
Condé Nast Traveler Condé Nast Traveler
82.6
"Named for Chicago architect Daniel Burnham, this steel-and-glass former office building with a terra-cotta facade in the downtown Loop receives perfect scores for its location across from Macy’s." Full review
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The Drake
8/10
140 E. Walton Place, Magnificent Mile, Chicago, IL 60611
From $101/night
  • Pet Friendly
  • Bar/Lounge
  • Hot Tub
  • Free Internet
  • Room Service
  • Laundry Service
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Fodor's Fodor's
"Built in 1920, the grande dame of Chicago hotels stands tall where Michigan Avenue and Lake Shore Drive intersect in Chicago's swanky Gold Coast." Full review
Insight Guides Insight Guides
"Opened in 1920, the Drake keeps pace with the polished neighborhood, right off the Magnificent Mile."
Lonely Planet Lonely Planet
"The grande dame commands a striking location at the north end of Michigan Ave, near Oak St Beach." Full review
Oyster Oyster
Upscale
"The 535-room Drake Hotel is a historic property on upscale Magnificent Mile and one of Chicago’s grande dames." Full review
Travel + Leisure Travel + Leisure
"The Drake is the grande dame of Chicago hotels, with a prime location, storied history, white-glove service, and of course a distinguished guest list." Full review
i
Try to score a room facing north or east for unobstructed views of the lake and Lake Michigan’s Oak Street Beach.
Rough Guide Rough Guide
"Chicago’s society hotel, just off the Magnificent Mile, has been modernized without sacrificing its sedate charms."
Time Out Time Out
"A traditional "old money" stomping ground favored by Chicago socialites and celebrities, this stately icon exudes old-school style." Full review
Star Service Star Service
"This place competes with the InterContinental and Palmer House Hilton for the honor of Chicago's most iconic historic hotel." Full review
Gayot Gayot
"With sweeping views of Lake Michigan, this handsome hotel is an historic landmark that was built in 1920."
DK Eyewitness DK Eyewitness
"The grande dame of Chicago hotels, this luxurious Michigan Avenue destination still attracts luminaries from all over the world."
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