Chicago 5-star Hotels
Compare rates for 5-star hotels in Chicago, IL from hundreds of popular travel sites on HotelsCombined.
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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 ($168). Conversely, the most expensive month to stay in Chicago is October ($395).
What is the cheapest day to stay in a hotel in Chicago?
The cheapest day to stay in Chicago is Sunday ($222). On the other hand, travelers can expect to pay the most on Saturday, when the average nightly price is $250.
How much is a hotel in Chicago tonight?
Users have found prices for hotels in Chicago tonight starting as low as $24, rising to an average cost of $441, based on searches in the last 72 hours. Prices start from $24 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 $48/night. If you’re specifically looking for a 3-star hotel this weekend, our users have found prices as low as $101/night. For a 4-star hotel in Chicago, the cheapest rate recently found was $48/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 $61 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 little as $421 per night. Price data was last updated on 1 May 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
$421
Avg. per night
401 North Wabash Avenue, Chicago, IL, United States
1.5 km from city centre
Pool
Free Wi-Fi
$492
Avg. per night
800 North Michigan Avenue, Chicago, IL, United States
2.3 km from city centre
Pool
Free Wi-Fi
$512
Avg. per night
160 East Pearson Street at Water Tower Place, Chicago, IL, United States
2.5 km from city centre
Pool
$526
Avg. per night
330 North Wabash Avenue, Chicago, IL, United States
1.4 km from city centre
Pool
Free Wi-Fi
$548
Avg. per night
$549
Avg. per night
108 East Superior Street, Chicago, IL, United States
2.2 km from city centre
Pool
Free Wi-Fi
$619
Avg. per night
120 East Delaware Place, Chicago, IL, United States
2.6 km from city centre
Pool
Free Wi-Fi
$622
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 1 May 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
127 West Huron, at Lasalle, Chicago, IL, United States
$186
71 East Wacker Drive, Chicago, IL, United States
$235
3 stars
10 East Grand Avenue, Chicago, IL, United States
$143
110 West Huron Street, Chicago, IL, United States
$155
33 West Illinois, Chicago, IL, United States
$172
2 stars and under
65 East Harrison Street, Chicago, IL, United States
$101
1622 W Jackson Boulevard, Chicago, IL, United States
$132
1100 South Michigan Avenue, Chicago, IL, United States
$108
3514 North Sheffield Avenue, Chicago, IL, United States
$45
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 1 May 2025.
Looking for something less traditional for your stay? Find the perfect hostel or vacation rental for your trip in Chicago.
Show all 3,551 stays
310 South Halsted Street, Chicago, IL, United States
1.7 km from city centre
Free Wi-Fi
Air conditioning
$55
Avg. per night
24 East Ida B. Wells Drive, Chicago, IL, United States
0.1 km from city centre
Free Wi-Fi
$45
Avg. per night
616 West Arlington Place, Chicago, IL, United States
5.8 km from city centre
Free Wi-Fi
$52
Avg. per night
155 North Peoria Street, Chicago, IL, United States
2.1 km from city centre
Pool
Free Wi-Fi
$421
Avg. per night
800 North Michigan Avenue, Chicago, IL, United States
2.3 km from city centre
Pool
Free Wi-Fi
$512
Avg. per night