Chicago 5-Star Hotels

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Best Chicago 5 star hotels

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5 stars

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£163 - £257£257 - £352£352 - £445£445 - £540£540+ per night

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Free cancellationFree breakfastFree parkingFree internet

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(2121)
Free Wi-Fi
Pool
Pet-friendly
Air conditioning
£418+
Check availability
The Langham Chicago - Chicago - Lounge
The Langham Chicago
Near North Side
9.4Wonderful(932)
Free Wi-Fi
Pool
Pet-friendly
Air conditioning
£627+
Check availability
Waldorf Astoria Chicago - Chicago - Balcony
Waldorf Astoria Chicago
Near North Side
9.0Wonderful(339)
Pool
Pet-friendly
Air conditioning
£680+
Check availability
The Peninsula Chicago - Chicago - Lobby
The Peninsula Chicago
Near North Side
9.4Wonderful(572)
Free Wi-Fi
Pool
Pet-friendly
Air conditioning
£689+
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.

How much does a 5-star hotel room in Chicago cost?

The average price for a 5-star hotel in Chicago is £349 but this can vary depending on the season and when you’ve booked. In the last 7 days, the cheapest price found on KAYAK was £316 at Trump International Hotel & Tower Chicago.

Which month has the cheapest rates for 5 star hotels?

5 star hotels in Chicago are cheapest in September, with an average rate of £135. On the other hand, they are at their most expensive in June, where the average price is £611.

Which neighbourhood do KAYAK users most love to book their 5-star hotel in Chicago?

The most popular neighbourhood in Chicago among KAYAK users to search for a 5-star hotel is Near North Side, with an average price of £512. Warwick Allerton Chicago, Eurostars Magnificent Mile, and Hotel Felix rank among the highest-rated hotels in Near North Side.
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Good to know

Low season

High season

Average price (weeknight)

Average price (weekend night)

Lowest hotel price

September
June
£309
£388
£163
Cheapest month to stay with an average 58% drop in price.
Most expensive month to stay with an average 91% 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 September and January.
  • 5-star room prices can vary depending on different factors. However, generally, rooms cost less on a Friday. The most expensive night for a stay is Saturday.
  • The cheapest 5-star hotel room in Chicago found on KAYAK in the last 2 weeks was £185. The most expensive cost £185.

FAQs about Chicago 5 star hotels

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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