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Chicago 5-star Hotels

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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 ($164). Conversely, the most expensive month to stay in Chicago is July ($376).

What is the cheapest day to stay in a hotel in Chicago?

The cheapest day to stay in Chicago is Sunday ($185). On the other hand, travelers can expect to pay the most on Tuesday, when the average nightly price is $208.

How much is a hotel in Chicago tonight?

Users have found prices for hotels in Chicago tonight starting as low as $3, rising to an average cost of $279, based on searches in the last 72 hours. Prices start from $3 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 $8/night. If you’re specifically looking for a 3-star hotel this weekend, our users have found prices as low as $8/night. For a 4-star hotel in Chicago, the cheapest rate recently found was $4/night for this weekend.

How far ahead should you book a hotel in Chicago?

Save money by booking a hotel at least 77 days before your trip to Chicago. The lowest price found when booking 77 days ahead was $96 per night.

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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 $276 per night. Price data was last updated on 19 December 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.
Trump International Hotel & Tower Chicago
Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

401 North Wabash Avenue, Chicago, IL, United States
1.5 km from city centre
Pool
Free Wi-Fi
$276
Avg. per night
View Deal
Nobu Hotel Chicago
Nobu Hotel Chicago

Nobu Hotel Chicago

155 North Peoria Street, Chicago, IL, United States
2.1 km from city centre
Pool
Free Wi-Fi
$312
Avg. per night
View Deal
Park Hyatt Chicago
Park Hyatt Chicago

Park Hyatt Chicago

800 North Michigan Avenue, Chicago, IL, United States
2.4 km from city centre
Pool
Free Wi-Fi
$383
Avg. per night
View Deal
Waldorf Astoria Chicago
Waldorf Astoria Chicago

Waldorf Astoria Chicago

11 East Walton Street, Chicago, IL, United States
2.7 km from city centre
Pool
$400
Avg. per night
View Deal
The Ritz-Carlton Chicago
The Ritz-Carlton Chicago

The Ritz-Carlton Chicago

160 East Pearson Street at Water Tower Place, Chicago, IL, United States
2.5 km from city centre
Pool
$406
Avg. per night
View Deal
The Langham Chicago
The Langham Chicago

The Langham Chicago

330 North Wabash Avenue, Chicago, IL, United States
1.4 km from city centre
Pool
Free Wi-Fi
$416
Avg. per night
View Deal
Four Seasons Hotel Chicago
Four Seasons Hotel Chicago

Four Seasons Hotel Chicago

120 East Delaware Place, Chicago, IL, United States
2.6 km from city centre
Pool
Free Wi-Fi
$418
Avg. per night
View Deal
The Peninsula Chicago
The Peninsula Chicago

The Peninsula Chicago

108 East Superior Street, Chicago, IL, United States
2.2 km from city centre
Pool
Free Wi-Fi
$478
Avg. per night
View Deal

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 19 December 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
Omni Chicago Hotel
Omni Chicago Hotel

Omni Chicago Hotel

676 North Michigan Avenue, Chicago, IL, United States
$180
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Hilton Chicago
Hilton Chicago

Hilton Chicago

720 South Michigan Avenue, Chicago, IL, United States
$130
View Deal
Hotel Chicago Downtown, Autograph Collection
Hotel Chicago Downtown, Autograph Collection

Hotel Chicago Downtown, Autograph Collection

333 North Dearborn Street, (Driveway entrance on 350 N. State Street), Chicago, IL, United States
$146
View Deal
Hyatt Centric Chicago Magnificent Mile
Hyatt Centric Chicago Magnificent Mile

Hyatt Centric Chicago Magnificent Mile

633 North Saint Clair Street, Chicago, IL, United States
$126
View Deal
The Chicago Hotel Collection Ambassador Gold Coast
The Chicago Hotel Collection Ambassador Gold Coast

The Chicago Hotel Collection Ambassador Gold Coast

1301 North State Parkway, Chicago, IL, United States
$13
View Deal
3 stars
Hampton Inn & Suites Chicago-Downtown
Hampton Inn & Suites Chicago-Downtown

Hampton Inn & Suites Chicago-Downtown

33 West Illinois, Chicago, IL, United States
$101
View Deal
Hilton Garden Inn Chicago Downtown Magnificent Mile
Hilton Garden Inn Chicago Downtown Magnificent Mile

Hilton Garden Inn Chicago Downtown Magnificent Mile

10 East Grand Avenue, Chicago, IL, United States
$90
View Deal
Hampton Inn Chicago Downtown/Magnificent Mile
Hampton Inn Chicago Downtown/Magnificent Mile

Hampton Inn Chicago Downtown/Magnificent Mile

160 East Huron Street, Chicago, IL, United States
$93
View Deal
La Quinta Inn & Suites by Wyndham Chicago Downtown
La Quinta Inn & Suites by Wyndham Chicago Downtown

La Quinta Inn & Suites by Wyndham Chicago Downtown

1 South Franklin St, Chicago, IL, United States
$106
View Deal
Chicago South Loop Hotel
Chicago South Loop Hotel

Chicago South Loop Hotel

11 West 26th Street, Chicago, IL, United States
$64
View Deal
2 stars and under
Wrigley Hostel - Chicago
Wrigley Hostel - Chicago

Wrigley Hostel - Chicago

3514 North Sheffield Avenue, Chicago, IL, United States
$59
View Deal
Travelodge by Wyndham Downtown Chicago
Travelodge by Wyndham Downtown Chicago

Travelodge by Wyndham Downtown Chicago

65 East Harrison Street, Chicago, IL, United States
$69
View Deal
Chicago Getaway Hostel
Chicago Getaway Hostel

Chicago Getaway Hostel

616 West Arlington Place, Chicago, IL, United States
$195
View Deal
Hotel Chicago West Loop, SureStay Collection by Best Western
Hotel Chicago West Loop, SureStay Collection by Best Western

Hotel Chicago West Loop, SureStay Collection by Best Western

1622 W Jackson Boulevard, Chicago, IL, United States
$88
View Deal
Chicago Parthenon Hostel
Chicago Parthenon Hostel

Chicago Parthenon Hostel

310 South Halsted Street, Chicago, IL, United States
$54
View Deal

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 19 December 2025.
Looking for something less traditional for your stay? Find the perfect hostel or vacation rental for your trip in Chicago.
Courtyard by Marriott Chicago Downtown/River North
Courtyard by Marriott Chicago Downtown/River North

Courtyard by Marriott Chicago Downtown/River North

30 East Hubbard Street, Chicago, IL, United States
1.6 km from city centre
Pool
Free Wi-Fi
$124
Avg. per night
View Deal
L7 Chicago by LOTTE
L7 Chicago by LOTTE

L7 Chicago by LOTTE

225 North Wabash Avenue, Chicago, IL, United States
1.2 km from city centre
Free Wi-Fi
$140
Avg. per night
View Deal
Park Hyatt Chicago
Park Hyatt Chicago

Park Hyatt Chicago

800 North Michigan Avenue, Chicago, IL, United States
2.4 km from city centre
Pool
Free Wi-Fi
$383
Avg. per night
View Deal
Just Minutes from Downtown Chicago
Just Minutes from Downtown Chicago

Just Minutes from Downtown Chicago

Chicago, IL, United States
7.2 km from city centre
Air conditioning
$189
Avg. per night
View Deal

Where to stay in Chicago

Explore different areas within Chicago to find the perfect location for your stay. Map data was last updated on 19 December 2025.
The map below shows all 5-star hotels in Chicago. Zoom in to find popular attractions and click on a nearby hotel for more information about the property.

Facts about 5-star hotels in Chicago

Find useful tips and insights about 5-star hotels in Chicago to help you make the most of your experience. FAQs were last updated on 19 December 2025.

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

    For a 5-star hotel in Chicago, expect to pay around $507 per night on average, with some starting as low as $484.

  • What is the cheapest 5-star hotel in Chicago?

    Cozy 1 Bedroom Close To Downtown Chicago is the cheapest 5-star hotel in Chicago, where prices start as low as $266 per night.

  • What is the best 5-star hotel in Chicago?

    With a user review rating of 9.4, The Peninsula Chicago is one of the best 5-star hotels in Chicago. You can book a room at The Peninsula Chicago for around $660/night on average.

  • What month is cheapest to stay in a 5-star hotel in Chicago?

    If you're looking to save on accommodations in Chicago, March is the least expensive month for 5-star hotels, with an average nightly price of $213.

See more FAQs

Stay elsewhere in Chicago

Consider these popular 3-star hotels in Chicago

Stay at one of these Chicago 3-star hotels that users have found on HotelsCombined.
Hampton Inn & Suites Chicago-Downtown
Hilton Garden Inn Chicago Downtown Magnificent Mile
La Quinta Inn & Suites by Wyndham Chicago Downtown
Hampton Inn Chicago Downtown/Magnificent Mile
Congress Plaza Hotel
The Whitehall Hotel, BW Premier Collection
Hilton Chicago/Magnificent Mile Suites
Chicago South Loop Hotel
Home2 Suites by Hilton Chicago River North
Crowne Plaza Chicago West Loop By IHG
Hilton Garden Inn Chicago Downtown Riverwalk
ACME Hotel Company Chicago
Homewood Suites by Hilton Chicago - Downtown
Hilton Garden Inn Chicago Downtown South Loop
Sonesta ES Suites Chicago Downtown Magnificent Mile - Medical
Hotel Versey Chicago Lincoln Park
Hyatt Place Chicago Downtown/The Loop
Courtyard by Marriott Chicago Downtown/Magnificent Mile
Homewood Suites by Hilton Chicago Downtown/Magnificent Mile
The Willows Hotel