Chicago Luxury Hotels

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Recommended by KAYAK
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Recommended by KAYAK

Best Chicago luxury hotels

Most recommended Chicago luxury hotels

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Viceroy Chicago - Chicago - Restaurant
Viceroy Chicago
Near North Side
9.1Wonderful(1398)
Free Wi-Fi
Pool
Pet-friendly
Air conditioning
R6 380+
Check availability
Riu Plaza Chicago - Chicago - Lounge
Riu Plaza Chicago
Near North Side
9.1Wonderful(802)
Free Wi-Fi
Air conditioning
R3 492+
Check availability
Pendry Chicago - Chicago - Balcony
Pendry Chicago
Downtown
9.0Wonderful(1349)
Free Wi-Fi
Pet-friendly
Air conditioning
R5 050+
Check availability
Kimpton Gray Hotel - Chicago - Bar
Kimpton Gray Hotel
Downtown
8.9Very Good(655)
Pet-friendly
Air conditioning
R4 858+
Check availability
Sable At Navy Pier Chicago, Curio Collection By Hilton - Chicago - Bedroom
Sable At Navy Pier Chicago, Curio Collection By Hilton
Near North Side
8.9Very Good(940)
Free Wi-Fi
Air conditioning
R4 889+
Check availability
Sofitel Chicago Magnificent Mile - Chicago - Patio
Sofitel Chicago Magnificent Mile
Near North Side
8.9Very Good(2682)
Free Wi-Fi
Pet-friendly
Air conditioning
R5 079+
Check availability
LondonHouse Chicago, Curio Collection by Hilton - Chicago - Lounge
LondonHouse Chicago, Curio Collection by Hilton
Downtown
8.9Very Good(2075)
Free Wi-Fi
Air conditioning
R4 448+
Check availability
Waldorf Astoria Chicago - Chicago - Balcony
Waldorf Astoria Chicago
Near North Side
8.8Very Good(332)
Pool
Pet-friendly
Air conditioning
R10 428+
Check availability
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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 luxury hotel rates in Chicago?

Luxury hotels are cheapest in Chicago in February, with average rates of R90 917. In comparison, July is the most expensive month, with prices at R197 865.

What is the cheapest day of the week to book a luxury hotel in Chicago?

Sunday offers the lowest rates in Chicago, with an average nightly price of R135 143. The highest prices are found on Thursday, with average rates at R215 527.

How much is a luxury hotel in Chicago for tonight?

The best deal for a 3-star luxury hotel room in Chicago found by KAYAK users in the last 3 days was R4 917, while a 4-star luxury hotel the lowest price was R3 476. The cheapest room found overall was for R3 476.

How early should you book a hotel in Chicago?

Book at least 58 days before your stay begins to get the best price for your Chicago hotel.
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Good to know

Low season

February

High season

July

Average price (weeknight)

R9 099

Average price (weekend night)

R8 981
Cheapest month to stay with an average 39% drop in price.
Most expensive month to stay with an average 32% rise in price.
Average Sun - Thu price over the last 2 weeks.
Average Fri & Sat price over the last 2 weeks.

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 February 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 Thursday.
  • The most expensive cost city.

FAQs about Chicago luxury hotels

  • How much does a room in a luxury hotel in Chicago cost?

    On average, luxury hotel rooms in Chicago cost R15 213. Depending on when you make your booking, when you book for, and other factors, it is possible to get better deals. The cheapest price booked on KAYAK in the last 3 days was R5 350.

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

Chicago Luxury Hotel Deals. Search for luxury hotels in Chicago. Find luxury hotel rooms in Chicago. KAYAK searches hundreds of travel sites to help you find luxury hotels and book the room that suits you best.

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