Chicago Luxury hotels

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Booking Insights
Recommended by KAYAK

Best Chicago luxury hotels

These are the best prices for 20-27 May.
Bluegreen Vacations Hotel Blake, an Ascend Collection Hotel - Chicago - Bedroom
Bluegreen Vacations Hotel Blake, an Ascend Collection Hotel
Downtown
9.1Wonderful(1719)
Free Wi-Fi
Air conditioning
R4 820+
Check availability
Riu Plaza Chicago - Chicago - Lounge
Riu Plaza Chicago
Near North Side
9.2Wonderful(2663)
Free Wi-Fi
Air conditioning
R5 576+
Check availability
Sofitel Chicago Magnificent Mile - Chicago - Building
Sofitel Chicago Magnificent Mile
Near North Side
8.9Very Good(2836)
Free Wi-Fi
Pet-friendly
Air conditioning
R7 505+
Check availability
L7 Chicago by LOTTE - Chicago - Lounge
L7 Chicago by LOTTE
Downtown
9.1Wonderful(1817)
Free Wi-Fi
Pet-friendly
Air conditioning
R7 020+
Check availability
Viceroy Chicago - Chicago - Restaurant
Viceroy Chicago
Near North Side
9.0Wonderful(1503)
Free Wi-Fi
Pool
Pet-friendly
Air conditioning
R9 814+
Check availability
Waldorf Astoria Chicago - Chicago - Balcony
Waldorf Astoria Chicago
Near North Side
9.2Wonderful(351)
Pool
Pet-friendly
Air conditioning
R15 541+
Check availability
Four Seasons Hotel Chicago - Chicago - Lobby
Four Seasons Hotel Chicago
Near North Side
8.6Very Good(356)
Free Wi-Fi
Pool
Pet-friendly
Air conditioning
R15 878+
Check availability
The Ritz-Carlton Chicago - Chicago - Lounge
The Ritz-Carlton Chicago
Near North Side
8.5Very Good(241)
Pool
Pet-friendly
Air conditioning
R14 052+
Check availability
Hotel Zachary, Chicago, a Tribute Portfolio Hotel - Chicago - Dining room
Hotel Zachary, Chicago, a Tribute Portfolio Hotel
Wrigleyville
9.0Wonderful(306)
Free Wi-Fi
Pet-friendly
Air conditioning
R11 167+
Check availability
Nobu Hotel Chicago - Chicago - Balcony
Nobu Hotel Chicago
Near West Side
9.1Wonderful(353)
Free Wi-Fi
Pool
Pet-friendly
Air conditioning
R10 750+
Check availability
Park Hyatt Chicago - Chicago - Lounge
Park Hyatt Chicago
Near North Side
9.1Wonderful(376)
Free Wi-Fi
Pool
Pet-friendly
Air conditioning
R14 373+
Check availability
Kasa Magnificent Mile Chicago - Chicago - Balcony
Kasa Magnificent Mile Chicago
Near North Side
9.0Wonderful(567)
Free Wi-Fi
Pet-friendly
Air conditioning
R5 818+
Check availability
The Gwen, a Luxury Collection Hotel, Michigan Avenue Chicago - Chicago - Bar
The Gwen, a Luxury Collection Hotel, Michigan Avenue Chicago
Near North Side
9.0Wonderful(292)
Pet-friendly
Air conditioning
R11 095+
Check availability
The Study at the University of Chicago - Chicago - Restaurant
The Study at the University of Chicago
South Side
9.1Wonderful(449)
Pet-friendly
Air conditioning
R6 215+
Check availability
The Penthouse at Grand Plaza - Chicago - Pool
The Penthouse at Grand Plaza
Near North Side
9.3Wonderful(272)
Free Wi-Fi
Pool
Air conditioning
R13 639+
Check availability
Booking Insights

KAYAK’s insights for luxury hotels in Chicago

Discover seasonal trends, ideal booking windows, and other data-driven tips to plan your stay in Chicago with confidence.

Which month has the cheapest rates for luxury hotels?

Luxury hotels in Chicago are cheapest in November, with an average rate of R5 268. On the other hand, they are at their most expensive in September, where the average price is R11 306.

Find deals

Good to know

Low season

High season

Average price (weeknight)

Average price (weekend night)

Lowest hotel price

November
September
R7 992
R11 394
R3 083
Cheapest month to stay with an average 35% drop in price.
Most expensive month to stay with an average 40% rise in price.
Average Sun - Thu price over the last 2 weeks.
Average Fri & Sat price over the last 2 weeks.
The cheapest luxury hotel room rate in the last 7 days

KAYAK's top tips for finding Chicago luxury hotel deals

  • Prices for luxury hotels in Chicago are cheaper in the low season, which is in November and January.
  • Luxury room prices can vary depending on different factors. However, generally, rooms cost less on a Sunday. The most expensive night for a stay is Friday.
  • The most expensive cost city.

FAQs about Chicago luxury hotels

Where to stay in a luxury hotel in Chicago?

Our map will help you find the perfect place to stay in Chicago by showing you the exact location of each hotel.

Everything you need to know for your stay in Chicago