Crestwood Hotels from S$91

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Tonight
20 Jul - 21 Jul
Tomorrow
21 Jul - 22 Jul
Next weekend
25 Jul - 27 Jul
In two weeks
1 Aug - 3 Aug

Filter by

Guest rating
Guest rating
Property class

Top 10 trending Crestwood hotels

Holiday Inn Express Crestwood by IHG
Free buffet breakfast

Holiday Inn Express Crestwood by IHG

2.5 star property
7.8 out of 10, Good, (1005)
"Place was great breakfast was a plus and staff was really nice."
The price is S$165
includes taxes & fees
29 Jul - 30 Jul
Holiday Inn Express Crestwood by IHG
Ameristar Casino Hotel East Chicago
Lobby

Ameristar Casino Hotel East Chicago

4.0 star property
8.4 out of 10, Very good, (1011)
"Very convenient, nice staff"
The price is S$172
includes taxes & fees
22 Jul - 23 Jul
Ameristar Casino Hotel East Chicago
Sable at Navy Pier Chicago, Curio Collection by Hilton
Terrace/patio

Sable at Navy Pier Chicago, Curio Collection by Hilton

4.0 star property
9.4 out of 10, Exceptional, (2037)
"Amazing property clean comfy bedding and wonderful views"
The price is S$370
includes taxes & fees
10 Aug - 11 Aug
Sable at Navy Pier Chicago, Curio Collection by Hilton
Swissotel - Chicago
Reception

Swissotel - Chicago

4.5 star property
8.8 out of 10, Excellent, (2459)
"Amazing Stay!"
The price is S$314
includes taxes & fees
6 Aug - 7 Aug
Swissotel - Chicago
Loews Chicago Hotel
Exterior

Loews Chicago Hotel

4.5 star property
9.4 out of 10, Exceptional, (1488)
"Great location and rooms "
The price is S$341
includes taxes & fees
27 Jul - 28 Jul
Loews Chicago Hotel
Embassy Suites by Hilton Chicago Downtown Magnificent Mile
Exterior

Embassy Suites by Hilton Chicago Downtown Magnificent Mile

4.0 star property
8.2 out of 10, Very good, (2722)
"Wonderful place to stay definitely will return"
The price is S$313
includes taxes & fees
19 Aug - 20 Aug
Embassy Suites by Hilton Chicago Downtown Magnificent Mile
DoubleTree by Hilton Chicago - Magnificent Mile
Outdoor pool, pool loungers

DoubleTree by Hilton Chicago - Magnificent Mile

4.0 star property
8.8 out of 10, Excellent, (1924)
"I loved the room pool view, the restaurants & the location "
The price is S$255
includes taxes & fees
17 Aug - 18 Aug
DoubleTree by Hilton Chicago - Magnificent Mile
Radisson Blu Aqua Hotel Chicago
Indoor pool, seasonal outdoor pool, free pool cabanas, pool loungers

Radisson Blu Aqua Hotel Chicago

4.5 star property
8.4 out of 10, Very good, (1528)
"Great location and views from rooms were beautiful. "
The price is S$317
includes taxes & fees
17 Aug - 18 Aug
Radisson Blu Aqua Hotel Chicago
Fairmont Chicago at Millennium Park
Executive lounge

Fairmont Chicago at Millennium Park

4.5 star property
8.6 out of 10, Excellent, (1811)
"Great stay, great location and very polite staff "
The price is S$357
includes taxes & fees
3 Aug - 4 Aug
Fairmont Chicago at Millennium Park
Aloft Chicago Mag Mile
Meeting facility

Aloft Chicago Mag Mile

3.0 star property
8.6 out of 10, Excellent, (2767)
"Great location and friendly staff"
The price is S$243
includes taxes & fees
27 Jul - 28 Jul
Aloft Chicago Mag Mile
Ivy Boutique Hotel
Front of property

Ivy Boutique Hotel

4.5 star property
8.8 out of 10, Excellent, (1006)
"Front desk was very welcoming and hotel was beautiful"
The price is S$260
includes taxes & fees
27 Jul - 28 Jul
Ivy Boutique Hotel
Sonesta ES Suites Chicago Downtown Magnificent Mile - Medical
Lobby

Sonesta ES Suites Chicago Downtown Magnificent Mile - Medical

3.0 star property
8.4 out of 10, Very good, (1930)
"Great stay! "
The price is S$206
includes taxes & fees
10 Aug - 11 Aug
Sonesta ES Suites Chicago Downtown Magnificent Mile - Medical
Hyatt Regency Chicago
2 bars/lounges

Hyatt Regency Chicago

4.0 star property
9.2 out of 10, Wonderful, (3297)
"Great location and stay"
The price is S$389
includes taxes & fees
6 Aug - 7 Aug
Hyatt Regency Chicago
Hilton Chicago/Magnificent Mile Suites
Restaurant

Hilton Chicago/Magnificent Mile Suites

3.5 star property
8.8 out of 10, Excellent, (2493)
"Great location and accommodations! Would definitely stay here again. "
The price is S$218
includes taxes & fees
10 Aug - 11 Aug
Hilton Chicago/Magnificent Mile Suites
Millennium Knickerbocker Chicago
Lobby

Millennium Knickerbocker Chicago

4.0 star property
8.6 out of 10, Excellent, (1893)
"It was a wonderful stay"
The price is S$222
includes taxes & fees
13 Aug - 14 Aug
Millennium Knickerbocker Chicago
Hyatt Centric Chicago Magnificent Mile
Premium bedding, pillow-top beds, in-room safe, desk

Hyatt Centric Chicago Magnificent Mile

4.0 star property
9.0 out of 10, Wonderful, (1027)
"Best place we have stayed in Chicago in a long time. "
The price is S$293
includes taxes & fees
27 Jul - 28 Jul
Hyatt Centric Chicago Magnificent Mile
The Chicago Hotel Collection - Magnificent Mile
Breakfast and dinner served

The Chicago Hotel Collection - Magnificent Mile

4.0 star property
7.2 out of 10, Good, (1111)
"Great stay"
The price is S$242
includes taxes & fees
24 Jul - 25 Jul
The Chicago Hotel Collection - Magnificent Mile
Hotel Saint Clair- Magnificent Mile
Restaurant

Hotel Saint Clair- Magnificent Mile

4.0 star property
8.2 out of 10, Very good, (1673)
"I really enjoyed my stay here, the staff was very pleasant and the rooms great!"
Hotel Saint Clair- Magnificent Mile
Hotel Riu Plaza Chicago
Front of property

Hotel Riu Plaza Chicago

4.0 star property
9.4 out of 10, Exceptional, (2208)
"Great location, incredible staff, clean rooms, great breakfast."
The price is S$330
includes taxes & fees
19 Aug - 20 Aug
Hotel Riu Plaza Chicago
The Blackstone, Autograph Collection
Meeting facility

The Blackstone, Autograph Collection

4.0 star property
9.0 out of 10, Wonderful, (1003)
"Great location"
The price is S$331
includes taxes & fees
7 Aug - 8 Aug
The Blackstone, Autograph Collection
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.
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Learn more about Crestwood

Escape to romantic Crestwood! Enjoy its dining and entertainment.

See all hotels in Crestwood

Top Crestwood Hotel Reviews

River Hotel

River Hotel

10/10 Excellent
"We just stayed one night and it was very nice. Very busy because its downtown but lots of things to do."
Ger 1-night trip
Posted 18 hours ago
River Hotel

Frequently asked questions

Where is the best place for a stay in Crestwood?

Congress Plaza Hotel, located 16.2 mi (26.1 km) from the heart of Crestwood, is a top choice for your stay, based on our traveller data. Other good options for your visit to the area are InterContinental Chicago Magnificent Mile by IHG and Hilton Chicago/Magnificent Mile Suites. See all available top hotels, or vacation rentals in Crestwood.

If I need to cancel my hotel reservation in Crestwood, will I receive a refund?

Yes, you'll find most hotel reservations are fully refundable if cancelled before the accommodation's cancellation deadline, which often is within 24-48 hours of your scheduled arrival. If your reservation is non-refundable, you might be able to cancel it and get a refund within 24 hours of your booking. Filter your search by fully refundable to find flexible hotel deals in Crestwood.

What is the top LGBTQ-friendly accommodation in Crestwood?

Holiday Inn Express Crestwood by IHG is a top LGBTQ-friendly hotel that features free breakfast and free Wi-Fi. See all available hotels listed as LGBTQ-friendly in Crestwood.

What are some accommodation options with pools in Crestwood?

Holiday Inn Express Crestwood, an IHG Hotel: Features free buffet breakfast, an indoor pool and free Internet. DoubleTree by Hilton Chicago - Magnificent Mile and Loews Chicago Hotel are a couple of other choices that offer an on-site pool.

What's it like to stay in Crestwood?

Visitors to Crestwood will definitely enjoy the restaurants and shopping. Tourists can also enjoy so much more including its entertainment choices. A top sight in the area is Soldier Field. In Crestwood, there are 2 hotels and other accommodation options to choose from. Find out more about Crestwood.

What are the top places to visit in Crestwood?

A favourite place to visit is Hollywood Park. Additionally, you'll find Soldier Field in the area. Take a look at what more there is to see and do in Expedia's Crestwood guide.

What's the weather like in Crestwood?

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.