Chicago 5-star Hotels
Compare rates for 5-star hotels in Chicago, IL from hundreds of popular travel sites on HotelsCombined.
Chicago, United States
2 May — 3 May2
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Travel insights for hotels in Chicago
Use these up-to-date, data-driven insights about booking a hotel in Chicago including ideal times to book, pricing trends, and more.
What is the cheapest month to book a hotel in Chicago?
The cheapest month to book a hotel in Chicago is January (C$ 322). Conversely, the most expensive month to stay in Chicago is October (C$ 739).
What is the cheapest day to stay in a hotel in Chicago?
The cheapest day to stay in Chicago is Sunday (C$ 406). On the other hand, travelers can expect to pay the most on Saturday, when the average nightly price is C$ 468.
Which Chicago neighborhoods are most popular to stay in?
Those visiting Chicago tend to stay in Loop, where a hotel costs around C$ 331/night. Another popular neighborhood in Chicago is Chinatown, which is C$ 220/night on average for a hotel.
How much is a hotel in Chicago tonight?
Users have found prices for hotels in Chicago tonight starting as low as C$ 33, rising to an average cost of C$ 507, based on searches in the last 72 hours. Prices start from C$ 33 for a 4-star hotel in Chicago for tonight.
How much is a Chicago hotel room this weekend?
In the past 72 hours, we’ve seen prices for hotels in Chicago this weekend for as little as C$ 65/night. If you’re specifically looking for a 3-star hotel this weekend, our users have found prices as low as C$ 161/night. For a 4-star hotel in Chicago, the cheapest rate recently found was C$ 65/night for this weekend.
How far ahead should you book a hotel in Chicago?
Save money by booking a hotel at least 58 days before your trip to Chicago. The lowest price found when booking 58 days ahead was C$ 85 per night.
Cheapest 5-star hotels in Chicago
Discover affordable 5-star hotels in Chicago that provide a quality experience without breaking the bank. 5-star hotels in Chicago can be found for as low as C$ 572 per night. Price data was last updated on 25 April 2025
These are the lowest-priced 5-star hotels our users have recently found in Chicago. Prices may vary based on dates selected and hotel location.
Show all 11 5-star hotels
155 North Peoria Street, Chicago, IL, United States
2.1 km from city centre
Pool
Free Wi-Fi
C$ 572
Avg. per night
401 North Wabash Avenue, Chicago, IL, United States
1.5 km from city centre
Pool
Free Wi-Fi
C$ 642
Avg. per night
800 North Michigan Avenue, Chicago, IL, United States
2.3 km from city centre
Pool
Free Wi-Fi
C$ 671
Avg. per night
160 East Pearson Street at Water Tower Place, Chicago, IL, United States
2.5 km from city centre
Pool
C$ 695
Avg. per night
C$ 717
Avg. per night
330 North Wabash Avenue, Chicago, IL, United States
1.4 km from city centre
Pool
Free Wi-Fi
C$ 718
Avg. per night
108 East Superior Street, Chicago, IL, United States
2.2 km from city centre
Pool
Free Wi-Fi
C$ 813
Avg. per night
Other star-rated hotels in Chicago
Hotels that are booked the most in each class receive the “Most popular” badge. Hotels with the “Best value” have the most attractive prices based on their popularity. Price data was last updated on 25 April 2025.
Not set on a 5-star hotel? We’ve got plenty of other options for you to choose from. These are the most popular and best value properties in Chicago based on hotel class.
4 stars
521 North Rush Street, Chicago, IL, United States
C$ 445
100 West Monroe Street, Chicago, IL, United States
C$ 277
3 stars
10 East Grand Avenue, Chicago, IL, United States
C$ 187
1 South Franklin Street, Chicago, IL, United States
C$ 226
11 West 26th Street, Chicago, IL, United States
C$ 149
2 stars and under
1100 South Michigan Avenue, Chicago, IL, United States
C$ 145
125 West Ohio Street, Chicago, IL, United States
C$ 165
640 North Wabash Avenue, Chicago, IL, United States
C$ 188
616 West Arlington Place, Chicago, IL, United States
C$ 72
Other accommodations in Chicago
Find deals on places to stay in Chicago that are not hotels. These are just a few of the most popular hostels and vacation rentals in the area. Pricing information was last updated on 25 April 2025.
Looking for something less traditional for your stay? Find the perfect hostel or vacation rental for your trip in Chicago.
Show all 3,549 stays
310 South Halsted Street, Chicago, IL, United States
1.7 km from city centre
Free Wi-Fi
Air Conditioning
C$ 78
Avg. per night
24 East Ida B. Wells Drive, Chicago, IL, United States
0.1 km from city centre
Free Wi-Fi
C$ 73
Avg. per night
2699 Holmes Street, Detroit, MI, United States
7.0 km from city centre
Free Wi-Fi
Parking
Air Conditioning
C$ 143
Avg. per night
155 North Peoria Street, Chicago, IL, United States
2.1 km from city centre
Pool
Free Wi-Fi
C$ 572
Avg. per night
800 North Michigan Avenue, Chicago, IL, United States
2.3 km from city centre
Pool
Free Wi-Fi
C$ 671
Avg. per night