Search Crestwood hotels

Start date: Check-in selected.
To Date
End date: Check-out

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

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

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

Tonight
7 Dec - 8 Dec
Tomorrow
8 Dec - 9 Dec
Next weekend
12 Dec - 14 Dec
In two weeks
19 Dec - 21 Dec

Filter by

Guest rating
Guest rating
Star rating

Top hotels and accommodation in Crestwood

Free buffet breakfast
Holiday Inn Express Crestwood by IHG

Holiday Inn Express Crestwood by IHG

2.5 star property
Crestwood
7.8 out of 10, Good, (1001)
"Room was clean, bathroom was clean, linen was very clean. All surfaces wiped down. Front desk staff was welcoming and had excellent customer service. Check in was a breeze and the location was perfect for food and shopping! I plan on staying there again on my next visit to Illinois and will recommend this Holiday Inn to others!!!"
United States
Jen
The price is AU$133
includes taxes & fees
19 Dec - 20 Dec
Holiday Inn Express Crestwood by IHG
Terrace/patio
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, (2259)
"Smooth check in and beautiful hotel"
United States
Monique
The price is AU$220
includes taxes & fees
6 Jan - 7 Jan 2026
Sable at Navy Pier Chicago, Curio Collection by Hilton
Premium bedding, down duvets, pillow-top beds, in-room safe
The Wade

The Wade

4.5 star property
Downtown Chicago
8.4 out of 10, Very good, (1508)
"Great location, walkable to so many area attractions. Would definitely stay here again. "
United States
Debbie
The price is AU$179
includes taxes & fees
14 Dec - 15 Dec
The Wade
Reception
Swissotel - Chicago

Swissotel - Chicago

4.5 star property
Downtown Chicago
9.0 out of 10, Wonderful, (2998)
"Very beautiful place to stay"
United States
FaithBrenda
The price is AU$246
includes taxes & fees
2 Jan - 3 Jan 2026
Swissotel - Chicago
Exterior
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, (2746)
"Great food clean room friendly staff"
United States
MARINA
The price is AU$191
includes taxes & fees
6 Jan - 7 Jan 2026
Embassy Suites by Hilton Chicago Downtown Magnificent Mile
Terrace/patio
DoubleTree by Hilton Chicago - Magnificent Mile

DoubleTree by Hilton Chicago - Magnificent Mile

4.0 star property
Downtown Chicago
8.8 out of 10, Excellent, (2181)
"Nice Hotel"
United States
Alan
The price is AU$158
includes taxes & fees
16 Dec - 17 Dec
DoubleTree by Hilton Chicago - Magnificent Mile
Indoor pool, seasonal outdoor pool, free pool cabanas, pool loungers
Radisson Blu Aqua Hotel Chicago

Radisson Blu Aqua Hotel Chicago

4.5 star property
Downtown Chicago
8.6 out of 10, Excellent, (1785)
"Friendly staff and good location to all of the city"
United States
Mark
The price is AU$287
includes taxes & fees
21 Dec - 22 Dec
Radisson Blu Aqua Hotel Chicago
Cocktail bar
Aloft Chicago Mag Mile

Aloft Chicago Mag Mile

3.0 star property
Downtown Chicago
8.6 out of 10, Excellent, (2953)
"Great location, the staff was friendly and the room was very clean. "
United States
Breanna
The price is AU$148
includes taxes & fees
11 Dec - 12 Dec
Aloft Chicago Mag Mile
Front of property
Ivy Boutique Hotel

Ivy Boutique Hotel

4.5 star property
Downtown Chicago
8.8 out of 10, Excellent, (1035)
"Clean room, nice amenities (especially like the rain shower), very centrally located, and friendly staff. "
United States
Kathleen
The price is AU$180
includes taxes & fees
4 Jan - 5 Jan 2026
Ivy Boutique Hotel
Lobby
Sonesta ES Suites Chicago Downtown Magnificent Mile - Medical

Sonesta ES Suites Chicago Downtown Magnificent Mile - Medical

3.0 star property
Downtown Chicago
8.6 out of 10, Excellent, (2275)
"Excellent hotel. Loved staying there"
United States
cristina
The price is AU$182
includes taxes & fees
14 Dec - 15 Dec
Sonesta ES Suites Chicago Downtown Magnificent Mile - Medical
Pillow-top beds, desk, blackout curtains, iron/ironing board
Fairfield Inn & Suites Chicago Downtown / Magnificent Mile

Fairfield Inn & Suites Chicago Downtown / Magnificent Mile

2.5 star property
Downtown Chicago
9.0 out of 10, Wonderful, (1001)
"Great ubicación and great breakfast "
United States
Andrea
The price is AU$148
includes taxes & fees
21 Dec - 22 Dec
Fairfield Inn & Suites Chicago Downtown / Magnificent Mile
2 bars/lounges
Hyatt Regency Chicago

Hyatt Regency Chicago

4.0 star property
Downtown Chicago
9.4 out of 10, Exceptional, (3389)
"Everything was amazing, from the staff to the room, amenities simply perfect.!! "
United States
TERESA
The price is AU$285
includes taxes & fees
22 Dec - 23 Dec
Hyatt Regency Chicago
Ballroom
Hilton Chicago/Magnificent Mile Suites

Hilton Chicago/Magnificent Mile Suites

3.5 star property
Downtown Chicago
9.0 out of 10, Wonderful, (3446)
"Great place to stay "
United States
RaShawna
The price is AU$186
includes taxes & fees
14 Dec - 15 Dec
Hilton Chicago/Magnificent Mile Suites
Lobby
Millennium Knickerbocker Chicago

Millennium Knickerbocker Chicago

4.0 star property
Downtown Chicago
8.6 out of 10, Excellent, (2006)
"Great location, clean hotel"
United States
Andre
The price is AU$193
includes taxes & fees
4 Jan - 5 Jan 2026
Millennium Knickerbocker Chicago
Exterior
Hyatt Centric Chicago Magnificent Mile

Hyatt Centric Chicago Magnificent Mile

4.0 star property
Downtown Chicago
9.0 out of 10, Wonderful, (1047)
"Great Hotel!"
United States
Wendy
The price is AU$217
includes taxes & fees
1 Jan - 2 Jan 2026
Hyatt Centric Chicago Magnificent Mile
Breakfast and lunch served
Courtyard by Marriott Chicago Magnificent Mile

Courtyard by Marriott Chicago Magnificent Mile

3.0 star property
Downtown Chicago
8.8 out of 10, Excellent, (1583)
"Great stay!!"
United States
Adrian
The price is AU$173
includes taxes & fees
18 Dec - 19 Dec
Courtyard by Marriott Chicago Magnificent Mile
Exterior
The Chicago Hotel Collection - Magnificent Mile

The Chicago Hotel Collection - Magnificent Mile

4.0 star property
Downtown Chicago
7.6 out of 10, Good, (1179)
"The room was spacious and clean and it was a good value."
United States
Dj
The Chicago Hotel Collection - Magnificent Mile
Suite, 1 King Bed, Non Smoking, Refrigerator & Microwave | View from room
Hampton Inn Chicago Downtown/Magnificent Mile

Hampton Inn Chicago Downtown/Magnificent Mile

2.5 star property
Downtown Chicago
8.0 out of 10, Very good, (1345)
"Perfect location, spacious very clean room, great staff and wonderful breakfast!! Will definitely stay here again "
United States
Lisa
The price is AU$154
includes taxes & fees
14 Dec - 15 Dec
Hampton Inn Chicago Downtown/Magnificent Mile
Front of property
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4.0 star property
Downtown Chicago
9.4 out of 10, Exceptional, (2937)
"Excellent stay great location and great rooms"
United States
Joseph
The price is AU$217
includes taxes & fees
9 Dec - 10 Dec
Hotel Riu Plaza Chicago
Meeting facility
The Blackstone, Autograph Collection

The Blackstone, Autograph Collection

4.0 star property
Downtown Chicago
9.0 out of 10, Wonderful, (1000)
"Great staff, beds and pillows very comfortable "
United States
Marty
The price is AU$269
includes taxes & fees
21 Dec - 22 Dec
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Stay near popular Crestwood attractions

Hollywood Park

Enjoy the thrill rides with your children at Hollywood Park during your trip to Crestwood. Visit the shops in this family-friendly area or simply enjoy its restaurants.
See properties

Learn more about Crestwood

Explore the sprawling Playfield Park where locals gather for weekend softball tournaments and picnics under shady oak trees. Visit Caesar Park's splash pad in summer, then grab a slice at the family-owned Aurelio's Pizza that's been serving locals since 1959.

See all hotels in Crestwood
Reflection on Lake at Dusk at Turtlehead Lake Nature Preserve in Orland Park, IL (Suburban Chicago)

Top Crestwood Hotel Reviews

Recent Reviews in Crestwood

Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton

10/10 Excellent
"Wonderful staff. Very friendly and knowledgeable about local events and recommendations for entertainment. Property was clean at all times and walkable even during inclement weather conditions. I would definitely return."
Jeneen 1-night trip
Posted 5 hours ago
Sable at Navy Pier Chicago, Curio Collection by Hilton

More cheap accommodation in Crestwood

Best Western Grant Park Hotel

Best Western Grant Park Hotel

1100 S Michigan Ave Chicago IL
The price is AU$120 per night from 5 Jan to 6 Jan
AU$120
5 Jan - 6 Jan 2026
includes taxes & fees
8/10 Very Good! (2,634 reviews)

Frequently asked questions

Where is the best place for a stay in Crestwood?
Palmer House a Hilton Hotel, located 16.5 mi (26.5 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 Embassy Suites by Hilton Chicago Downtown River North and Hilton Chicago/Magnificent Mile Suites. See all available top hotels, or vacation rentals in Crestwood.
What are some of the best holiday rentals that Crestwood has to offer?
LakeHouse: This holiday home rental outside of Crestwood is located on the beach, and has a fireplace, a balcony and a BBQ to put you at ease in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You and your friends and family can relax into your holiday with amenities such as a selection of games. See all 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'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 4 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.

Explore a world of travel with Expedia