Hotels in Crestwood

Free cancellation options if plans change

Earn rewards on every night you stay

Save more with Member Prices

Check prices for these dates

Tonight

Tomorrow

Next weekend

In two weeks

Where to stay in Crestwood?

A modern lobby with a reception desk, a sofa, and large windows offering a view of the outside.

An indoor swimming pool area with a view of the pool, a table with chairs, and a potted plant.

A modern dining area with a long table, blue chairs, and a coffee station.

A hotel room with a bed, a blue sofa, a small table, a wall-mounted lamp, and a painting.

1. Holiday Inn Express Crestwood by IHG

Crestwood

$95

$106 total

includes taxes & fees

Nov 23 - Nov 24

A brick building with a restaurant named "BARCLAYS" and a sign for "THE COTTAGE OF OAK BURTON."

A bar area with a checkered floor, wooden chairs, a bar counter, and two televisions mounted on the wall.

A lobby with two green armchairs, a glass coffee table, a chandelier, and a fireplace.

A dimly lit restaurant with booths and tables, featuring a large clock and a television screen on the wall.

2. Carleton of Oak Park

Oak Park

$122

$136 total

includes taxes & fees

Oct 28 - Oct 29

A modern hotel lobby with a long blue sofa, numbered cushions, and hanging planters.

A hotel room with two beds, a television, a desk with a lamp, and a patterned carpet.

A reception area with a desk, a seating area with a blue sofa, and a bookshelf filled with books.

A modern conference room with a wooden table, white chairs, a potted plant, and a large window with decorative plants.

3. Hilton Vacation Club Hotel Blake Chicago

Downtown Chicago

$160

$191 total

includes taxes & fees

Nov 15 - Nov 16

A swimming pool with lounge chairs and umbrellas, surrounded by tall buildings.

A modern lobby with a seating area, a bar, and a green wall.

A hotel reception area with a modern design, featuring a wooden panel wall and a marble reception desk.

Transparent igloo-like structures with seating inside, set on a wooden deck with snow on the ground, surrounded by tall buildings.

4. DoubleTree by Hilton Chicago - Magnificent Mile

Downtown Chicago

$101

$120 total

includes taxes & fees

Nov 23 - Nov 24

An outdoor seating area with tables and chairs, a planter with greenery, and a large brick structure in the background.

A spacious outdoor dining area with large windows overlooking the sea, featuring multiple tables and stools.

A modern living room with a large window overlooking a body of water, a tripod, and a sofa.

A waterfront cityscape with modern buildings, a Ferris wheel, and several cruise ships docked.

5. Sable at Navy Pier Chicago, Curio Collection by Hilton

Downtown Chicago

$131

$190 total

includes taxes & fees

Nov 23 - Nov 24

A spacious dining area with multiple tables and chairs, large windows with a view of the city, and a modern ceiling design.

A snack and beverage kiosk with various snacks and drinks.

A hotel room with two beds, a desk, a chair, and a large window.

A spacious lobby with a modern design, featuring a seating area with sofas and chairs, a coffee table, and a large flat-screen TV mounted on the wall.

6. SureStay Plus Hotel by Best Western Chicago Lombard

Highland Hills

$89

$99 total

includes taxes & fees

Oct 26 - Oct 27

A modern hotel lobby with a bar area, seating arrangements, and a television screen.

A modern hotel lobby with a large wall mural, seating area, and a digital screen displaying information.

A modern hotel lobby with a seating area, a refrigerator stocked with beverages, and a table with snacks.

A modern hotel room with a cityscape mural, a desk with a chair, a sofa, a small table, and a lamp.

7. Cambria Hotel Chicago Loop - Theatre District

Downtown Chicago

$111

$132 total

includes taxes & fees

Nov 23 - Nov 24

A modern interior with a bar area, seating, and decorative wooden panels.

A reception area with a marble counter, decorative Buddha statues, and a wall with a quote.

A hotel room with a flat-screen TV, a wooden cabinet, a round table, a blue sofa, a desk with a computer, and a large window with curtains.

A hotel room with a large bed, a flat-screen TV, a desk with a lamp, and a chair.

8. Best Western Grant Park Hotel

Downtown Chicago

$98

$117 total

includes taxes & fees

Nov 23 - Nov 24

A hotel lobby with a large seating area, a map on the wall, and a car on the mezzanine.

A spacious lobby with a bar area, seating arrangements, and a large map on the wall.

A hotel room with a large bed, a blue sofa, a desk with a TV, and a window with a city view.

9. Hampton Inn Chicago Downtown/N Loop/Michigan Ave

Downtown Chicago

$98

$117 total

includes taxes & fees

Nov 24 - Nov 25

A rooftop pool with lounge chairs and potted plants, surrounded by modern buildings.

A breakfast buffet with a variety of fruits, pastries, and beverages on a wooden table, set against a modern room with a white sofa and a wooden accent wall.

A spacious lobby with two elevators, a reception area, and a seating area with blue and white ottomans.

A modern interior with a reception desk, seating area, and a patterned carpet.

10. Holiday Inn & Suites Chicago - Downtown by IHG

Downtown Chicago

$95

$125 total

includes taxes & fees

Nov 23 - Nov 24

A modern living room with a sofa, armchairs, a coffee table, and a bookshelf.

A restaurant with outdoor seating, covered by umbrellas, and decorated with hanging planters.

A modern living room with a sofa, chairs, a coffee table, and a bookshelf.

A modern hotel room with a large bed, a desk, a chair, a lamp, and a view of the city through large windows.

11. Le Méridien Essex Chicago

Downtown Chicago

$112

$151 total

includes taxes & fees

Nov 23 - Nov 24

A hotel entrance with a glass door, a sign above the door, and two potted plants on either side.

A hotel reception area with a wall sign reading 'welcome to Hampton' and a wall-mounted sign indicating a treats section.

12. Hampton Inn Majestic Chicago Theatre District

Downtown Chicago

$114

$136 total

includes taxes & fees

Nov 22 - Nov 23

A modern lobby with a grey sofa, checkered ottomans, and a coffee table. There are black chairs, a blue sofa, and a TV on a stand.

A modern hotel room with a bed, a sofa, a coffee table with flowers, a TV, and a large window with a city view.

A modern high-rise hotel with multiple floors, large windows, and a well-lit entrance area.

A modern indoor swimming pool with blue seating and a view of the city through large windows.

13. Aloft by Marriott Chicago Mag Mile

Downtown Chicago

$102

$122 total

includes taxes & fees

Nov 22 - Nov 23

An outdoor bar area with a view of tall buildings, wicker furniture, and a covered seating area.

A hotel sign with the name 'HYATT CENTRIC The Loop'.

A modern interior with a large abstract painting on a wall, a sleek console table, and wooden flooring.

14. Hyatt Centric The Loop Chicago

Downtown Chicago

$159

$214 total

includes taxes & fees

Oct 30 - Oct 31

A bar area with a bartender, two seated customers, and a variety of liquor bottles on shelves.

A modern living room with a brick wall mural, a green sofa, leather chairs, and a wooden coffee table.

A restaurant interior with brick walls, hanging spherical light fixtures, and a visible kitchen area.

15. Arlo Chicago

Downtown Chicago

$111

$164 total

includes taxes & fees

Nov 23 - Nov 24

The Claridge House building with a sign, American and another flag, and outdoor seating with umbrellas.

A bar area with a long counter, multiple stools, and a modern chandelier.

A modern hotel room with a large bed, a chair, a small table, and a window with a view.

A spacious living room with a large window, a sofa, a black chair, and a coffee table.

16. Claridge House Chicago, Tapestry Collection by Hilton

Downtown Chicago

$93

$139 total

includes taxes & fees

Nov 22 - Nov 23

An indoor swimming pool with clear glass walls, a wooden ceiling, and a view of a red brick building.

A hot tub with a metal ladder, surrounded by white tiled walls and floor, with a large window providing a view of the cityscape.

A modern outdoor patio with tables and chairs, a glass railing, and a view of a high-rise building.

A modern hotel entrance with glass doors, a visible reception desk, and signage for Hilton Garden Inn and Homewood Suites.

17. Hilton Garden Inn Chicago Downtown South Loop

Downtown Chicago

$97

$115 total

includes taxes & fees

Nov 23 - Nov 24

A hotel room with a large window offering a city view, a bed, a desk, and a chair.

A reception area with a modern design, featuring a large window, a reception desk, and artwork on the wall.

A coffee shop interior with a display case of pastries, a coffee machine, and a menu board.

A bar area with a granite countertop, bar stools, and a variety of bottles and glasses.

18. Courtyard by Marriott Chicago Magnificent Mile

Downtown Chicago

$110

$131 total

includes taxes & fees

Nov 23 - Nov 24

A hotel room with a sofa, a small table, and a view of the cityscape through large windows.

A restaurant with multiple tables and chairs, large windows, and a view of buildings outside.

A corner market with refrigerated shelves stocked with beverages and snacks, a bench with colorful cushions, and wooden paneling.

A modern lobby with a wooden floor, a sofa with colorful cushions, a chair, and a glass door leading outside.

19. Fairfield Inn & Suites Chicago Downtown/River North

Downtown Chicago

$115

$137 total

includes taxes & fees

Nov 23 - Nov 24

An indoor swimming pool with a glass ceiling, multiple seating areas, and city views.

A restaurant with a long counter, seating area, and a kitchen visible in the background.

A self-service food area with chilled and frozen sections, a variety of snacks, and a Dippin' Dots ice cream cooler.

A bar area with multiple seating arrangements and a variety of liquor bottles.

20. Hilton Garden Inn Chicago Downtown/Magnificent Mile

Downtown Chicago

$101

$120 total

includes taxes & fees

Nov 23 - Nov 24

View all properties

Go beyond your typical stay in Crestwood

Pet friendly

Apartment

Pool

Hot tub

Apart hotel

Spa

Family friendly

Our prices for hotels in Crestwood are cheapest in December

Top landmarks in Crestwood

Hollywood Park

If thrills are what you're after, head to Hollywood Park, located 0.5 mi (0.8 km) from central Crestwood. If you have fun at Hollywood Park, you'll love Childrens Museum of Oak Lawn and Lake Katherine Nature Center, both located nearby.

See properties

Learn more about Crestwood

The region around Crestwood is home to attractions such as Hollywood Park and McCormick Place.

See all hotels in Crestwood

A serene lake with reflections of trees and a cloudy sky.

Check out reviews of Crestwood hotels guests love

The Chicago Hotel Collection Ambassador Gold Coast

10/10 Excellent

"Clean room and great location for our trip"

Hilton Chicago

10/10 Excellent

"For being a massive hotel it is not overwhelming and is very welcoming."

River Hotel

10/10 Excellent

"I had a wonderful experience at the hotel. The staff was friendly, welcoming, and professional. Everything made my stay comfortable and enjoyable. Thank you for providing such excellent service. I would definitely recommend this hotel and look forward to staying here again!"

Arlo Chicago

10/10 Excellent

"The staff was wonderful from checking in to check out, Very helpful. The room was beautiful and clean. Location of hotel is very convenient, near a lot of shops and food spots. We were able to walk everywhere we wanted to go."

The Chicago Hotel Collection - Magnificent Mile

8/10 Good

"Solo Raymond fue la única persona amable, una señora la cual no me sé su nombre fue muy grosera con nosotros, nos habló muy golpeado y no nos explicó amablemente nada. No te hace sentir bienvenido, solo Raymond lo hace. Gracias a Dios solo nos cobraron los 150 dolares del depósito, pero escuché que te pueden cobrar 50 dólares por noche y un 18% de impuestos, la verdad no sé bien en qué casos, yo me estuve manteniendo en contacto con los de expedia para todas mis dudas. Así que aconsejo reservar cuarto sin desayuno incluido. Lo bueno del lugar es que el cuarto es amplio y que la ubicación es maravillosa. Y que el precio no es tan elevado como el de los hoteles cercanos a este (no por eso es barato) No esperen algo lujoso, es más bien algo útil. Ah, y la TV nunca funcionó, no pudimos poner música de mientras. A mi no me molesta tanto eso, pero a mi novio sí y otra cosa, el internet es muy lento."

Club Quarters Hotel, Central Loop, Chicago

10/10 Excellent

"My husband and I went for 2 nights and our stay was very pleasant, staff was super friendly, I loved that they were able to hold our luggage after checking out so we can explore the city a little longer since our flight was in the evening. Theres a lot of places to ear and visit and its very walkable, I would stay here again next time."

Eurostars Magnificent Mile

10/10 Excellent

"Good experience would definitely stay here again!"

Congress Plaza Hotel

10/10 Excellent

"Pleasant stay great location"

Hotel Saint Clair- Magnificent Mile

8/10 Good

"St. Clair hotel lists the room as premium, even though the two windows in the room had no view. Both windows faced the building outter exterior brick walls from all sides. Dim lightning with no direct sunlight, very depressing to look out. The room should have been listened and offered as standard, at best, not premium."

Frequently asked questions

What accommodations do travelers like in Crestwood?

Guests like Holiday Inn Chicago – Midway Airport S by IHG.

Can I book a refundable hotel in Crestwood?

If you need the flexibility to change your plans to Crestwood, most accommodations offer refundable* bookable rates. You can find these properties by searching our site and using the "fully refundable" filter to narrow the results down.

What will the weather in Crestwood be like during my visit?

July and August are typically the warmest months in Crestwood when the average temp is 71°F. January and February are the coldest months when the average temperature is 31°F. June and May are the months with the most rain.

Why should I book my Crestwood hotel through Hotels.com?

There are lots of reasons to book your Crestwood trip with us: our free cancellations on selected hotels gives you flexibility, and with One Key™, our rewards program, you will be able to earn and use OneKeyCash™* on all eligible bookings such as hotels, car rentals, flights, vacation rentals and more on Hotels.com, Expedia and Vrbo.

Keep exploring

More ways to book

Book Hotels in Crestwood on Hotels.com

Hotels in Crestwood

Free cancellation options if plans change

Earn rewards on every night you stay

Save more with Member Prices

Check prices for these dates

Where to stay in Crestwood?

1. Holiday Inn Express Crestwood by IHG

2. Carleton of Oak Park

3. Hilton Vacation Club Hotel Blake Chicago

4. DoubleTree by Hilton Chicago - Magnificent Mile

5. Sable at Navy Pier Chicago, Curio Collection by Hilton

6. SureStay Plus Hotel by Best Western Chicago Lombard

7. Cambria Hotel Chicago Loop - Theatre District

8. Best Western Grant Park Hotel

9. Hampton Inn Chicago Downtown/N Loop/Michigan Ave

10. Holiday Inn & Suites Chicago - Downtown by IHG

11. Le Méridien Essex Chicago

12. Hampton Inn Majestic Chicago Theatre District

13. Aloft by Marriott Chicago Mag Mile

14. Hyatt Centric The Loop Chicago

15. Arlo Chicago

16. Claridge House Chicago, Tapestry Collection by Hilton

17. Hilton Garden Inn Chicago Downtown South Loop

18. Courtyard by Marriott Chicago Magnificent Mile

19. Fairfield Inn & Suites Chicago Downtown/River North

20. Hilton Garden Inn Chicago Downtown/Magnificent Mile

Go beyond your typical stay in Crestwood

Price trends for hotels in Crestwood

Typical weather for Crestwood

Top landmarks in Crestwood

Hollywood Park

Learn more about Crestwood

Check out reviews of Crestwood hotels guests love

The Chicago Hotel Collection Ambassador Gold Coast

Hilton Chicago

River Hotel

Arlo Chicago

The Chicago Hotel Collection - Magnificent Mile

Club Quarters Hotel, Central Loop, Chicago

Eurostars Magnificent Mile

Congress Plaza Hotel

Hotel Saint Clair- Magnificent Mile

Frequently asked questions

Keep exploring