Chicago 5-Star Hotels

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Booking Insights
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Best Chicago 5 star hotels

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5 stars

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C$ 373 - C$ 518C$ 518 - C$ 661C$ 661 - C$ 806C$ 806 - C$ 949C$ 949+ per night

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Most recommended Chicago 5 star hotels

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Trump International Hotel & Tower Chicago - Chicago - Building
Trump International Hotel & Tower Chicago
Near North Side
9.1Wonderful(2135)
Free Wi-Fi
Pool
Pet friendly
Spa
C$ 747+
Check availability
The Langham Chicago - Chicago - Lounge
The Langham Chicago
Near North Side
9.4Wonderful(930)
Free Wi-Fi
Pool
Pet friendly
Spa
C$ 1,120+
Check availability
Waldorf Astoria Chicago - Chicago - Balcony
Waldorf Astoria Chicago
Near North Side
9.0Wonderful(342)
Pool
Pet friendly
Spa
C$ 1,169+
Check availability
The Peninsula Chicago - Chicago - Lobby
The Peninsula Chicago
Near North Side
9.4Wonderful(574)
Free Wi-Fi
Pool
Pet friendly
Spa
C$ 1,298+
Check availability
Booking Insights

KAYAK’s insights for 5 star 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 5 star hotels?

5 star hotels in Chicago are cheapest in January, with an average rate of C$ 293. On the other hand, they are at their most expensive in August, where the average price is C$ 1,318.

What is the cheapest day of the week to book a 5 star hotel in Chicago?

The lowest prices can usually be found on Saturday, where the average nightly price is C$ 749. The most expensive night is generally Sunday, where the average price is C$ 1,047.
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Good to know

Low season

High season

Average price (weeknight)

Average price (weekend night)

Lowest hotel price

January
August
C$ 958
C$ 877
C$ 373
Cheapest month to stay with an average 68% drop in price.
Most expensive month to stay with an average 46% rise in price.
Average Sun - Thu price over the last 2 weeks.
Average Fri & Sat price over the last 2 weeks.
The cheapest 5 star hotel room rate in the last 7 days

KAYAK's top tips for finding Chicago 5 star hotel deals

  • Prices for 5-star hotels in Chicago are cheaper in the low season, which is in January and December.
  • 5-star room prices can vary depending on different factors. However, generally, rooms cost less on a Saturday. The most expensive night for a stay is Sunday.
  • The cheapest 5-star hotel room in Chicago found on KAYAK in the last 2 weeks was C$ 246. The most expensive cost C$ 2,875.

FAQs about Chicago 5 star hotels

  • How many 5 star hotels are there in Chicago?

    Currently, there are around 12 5-star hotels on KAYAK available for you to book.

  • What are the most popular 5 star hotels in Chicago?

    The most popular 5 star hotels among KAYAK users in the last 3 months are The Ritz-Carlton Chicago, Four Seasons Hotel Chicago and Waldorf Astoria Chicago.

  • What are the advantages of booking a 5-star hotel in Chicago?

    A 5-star hotel in Chicago typically includes a wide range of services and facilities, such as 24/7 concierge, gourmet dining, wellness areas like spas and fully equipped gyms, and business centres with meeting rooms. Rooms are usually larger and better appointed, often featuring premium bedding, luxury toiletries, high-end coffee machines, and smart climate controls. For travellers seeking more comfort, privacy, and on-site convenience, a 5-star hotel can be a significant upgrade over more basic accommodation types in Chicago.

Where to stay in a 5 star 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

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