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Check availability on Crestwood Luxury Hotels

Our top choices for Crestwood luxury hotels

Cocktail bar
Freehand Chicago

Freehand Chicago

Freehand Chicago
4.0 star property
Downtown Chicago
8.0 out of 10, Very good, (2649)
"The room was spotless and the staff where great!"
United States
Maria
The price is ₹5,308
₹7,829 total
includes taxes & fees
5 Jan - 6 Jan 2026
Freehand Chicago
Lobby
Ameristar Casino Hotel East Chicago

Ameristar Casino Hotel East Chicago

Ameristar Casino Hotel East Chicago
4.0 star property
East Chicago
8.6 out of 10, Excellent, (1004)
"Great stay in clean modern room."
United States
Douglas
The price is ₹9,481
₹11,705 total
includes taxes & fees
1 Jan - 2 Jan 2026
Ameristar Casino Hotel East Chicago
Front of property
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago
4.0 star property
Downtown Chicago
9.4 out of 10, Exceptional, (2988)
"Excellent stay great location and great rooms"
United States
Joseph
The price is ₹9,043
₹13,173 total
includes taxes & fees
6 Jan - 7 Jan 2026
Hotel Riu Plaza Chicago
Terrace/patio
Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton
4.0 star property
Downtown Chicago
9.4 out of 10, Exceptional, (2266)
"Great staff and restaurants!!"
United States
Abigale
The price is ₹8,407
₹12,959 total
includes taxes & fees
6 Jan - 7 Jan 2026
Sable at Navy Pier Chicago, Curio Collection by Hilton
Snack bar
Cambria Hotel Chicago Loop - Theatre District

Cambria Hotel Chicago Loop - Theatre District

Cambria Hotel Chicago Loop - Theatre District
4.0 star property
Downtown Chicago
8.8 out of 10, Excellent, (1462)
"Clean room and great staff"
United States
Leontae
The price is ₹7,938
₹9,318 total
includes taxes & fees
4 Jan - 5 Jan 2026
Cambria Hotel Chicago Loop - Theatre District
Restaurant
Hotel Saint Clair- Magnificent Mile

Hotel Saint Clair- Magnificent Mile

Hotel Saint Clair- Magnificent Mile
4.0 star property
Downtown Chicago
8.4 out of 10, Very good, (1787)
"Great stay in a great area."
United States
Giselle
Hotel Saint Clair- Magnificent Mile
Exterior
Embassy Suites by Hilton Chicago Downtown Magnificent Mile

Embassy Suites by Hilton Chicago Downtown Magnificent Mile

Embassy Suites by Hilton Chicago Downtown Magnificent Mile
4.0 star property
Downtown Chicago
8.4 out of 10, Very good, (2750)
"Excellent place to stay "
United States
Teniesha
The price is ₹7,450
₹11,417 total
includes taxes & fees
11 Jan - 12 Jan 2026
Embassy Suites by Hilton Chicago Downtown Magnificent Mile
Reception
Eurostars Magnificent Mile

Eurostars Magnificent Mile

Eurostars Magnificent Mile
4.0 star property
Downtown Chicago
9.0 out of 10, Wonderful, (3163)
"Amazing stay very clean and beautiful views "
United States
Deigo
The price is ₹8,739
₹10,258 total
includes taxes & fees
11 Jan - 12 Jan 2026
Eurostars Magnificent Mile
American cuisine, al fresco dining
The Godfrey Hotel Chicago

The Godfrey Hotel Chicago

The Godfrey Hotel Chicago
4.5 star property
Downtown Chicago
8.6 out of 10, Excellent, (1931)
"Rooftop bar was amazing rooms are nice and ataff is friendly and accommodating "
United States
Sydney
The price is ₹8,666
₹12,311 total
includes taxes & fees
12 Jan - 13 Jan 2026
The Godfrey Hotel Chicago
Reception
River Hotel

River Hotel

River Hotel
4.0 star property
Downtown Chicago
8.8 out of 10, Excellent, (4861)
"Great location, comfortable room, and nice staff."
United States
Claudia
The price is ₹7,428
₹8,720 total
includes taxes & fees
30 Dec - 31 Dec
River Hotel
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Crestwood Hotel Reviews

Crowne Plaza Chicago West Loop by IHG

Crowne Plaza Chicago West Loop by IHG

10/10 Excellent
"Friendly/Helpful staff made for a great welcome! "
Lisa 2-night trip
Posted 8 hours ago
Crowne Plaza Chicago West Loop by IHG

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Frequently asked questions

Are you searching for the perfect hotel for your luxury holiday in Crestwood?
Expedia can help you arrange a flight to Chicago Midway Airport (MDW) airport or Chicago O'Hare International Airport (ORD) airport, and then you can select from various places to stay that will deliver the luxury you'd like to find. Amenities are important when you plan a holiday, so we make it easy to get what you want to make your stay special. If you want an upscale hotel that has fine dining, a spa or several swimming pools, Expedia can assist you in finding the best luxury hotel experience that Crestwood offers. During your visit, you might want to enjoy the restaurants which Crestwood is known for.
When can I expect good weather in Crestwood?
Planning for the weather is an important factor for making your trip to Crestwood a success, especially when you're splurging. The hottest months are usually July and August, with an average temperature of 22°C, while the coldest months are January and February, with an average of -1°C. Average annual precipitation for Crestwood is 1187 mm.
What's there to see and do in Crestwood?
Take in some sights and attractions while you're in Crestwood by visiting Hollywood Park, Soldier Field and Gaelic Park. If you have a bit of extra time while you're in the area, you might want to check out Lake Katherine Nature Center and Childrens Museum of Oak Lawn.