Hotels in Crestwood

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Check prices for these dates

Tonight
Aug 26 - Aug 27
Tomorrow
Aug 27 - Aug 28
This weekend
Aug 28 - Aug 30
Next weekend
Sep 4 - Sep 6

Top 5 hotels in Crestwood at a glance

  1. Holiday Inn Express Crestwood by IHG — 2.5-star hotel in Crestwood. Guest rating: 7.8/10 — Good.
  2. Hilton Vacation Club Hotel Blake Chicago — 4-star hotel in Downtown Chicago. Guest rating: 9.6/10 — Exceptional.
  3. Congress Plaza Hotel — 3.5-star hotel in Downtown Chicago. Guest rating: 8.0/10 — Very Good.
  4. Sable at Navy Pier Chicago, Curio Collection by Hilton — 4-star hotel in Downtown Chicago. Guest rating: 9.4/10 — Exceptional.
  5. Fairfield Inn & Suites Chicago Downtown / Magnificent Mile — 3-star hotel in Downtown Chicago. Guest rating: 9.0/10 — Wonderful.

Where to stay in Crestwood?

A modern lobby with a reception desk, a sofa, and large windows offering a view of the outside.
A Holiday Inn Express building with a covered entrance and a parking lot.
A modern dining area with a long table, blue chairs, and a coffee station.

Holiday Inn Express Crestwood by IHG

Holiday Inn Express Crestwood by IHG
Crestwood
$135
$151 total
includes taxes & fees
Aug 30 - Aug 31
Holiday Inn Express Crestwood by IHG
A hotel entrance with a marquee and string lights above the entrance.
A hotel entrance with a classic facade, an American flag, and a sign for Hotel Blake Chicago.
A hotel entrance with a marquee, American flag, and a person standing in front.

Hilton Vacation Club Hotel Blake Chicago

Hilton Vacation Club Hotel Blake Chicago
Downtown Chicago
$161
$191 total
includes taxes & fees
Sep 2 - Sep 3
Hilton Vacation Club Hotel Blake Chicago
A spacious lobby with a central sofa, multiple seating areas, and a decorative ceiling.
A cityscape with various buildings, including a prominent skyscraper and a classical building with arched windows.
A grand ballroom with ornate ceiling decorations, multiple chandeliers, and a central table with a white tablecloth.
Outdoor seating with yellow umbrellas labeled "Twisted Tea," wicker chairs, and tables.

Congress Plaza Hotel

Congress Plaza Hotel
Downtown Chicago
$135
$161 total
includes taxes & fees
Sep 7 - Sep 8
Congress Plaza Hotel
An outdoor seating area with tables and chairs, a planter with greenery, and a large brick structure in the background.
A view from a room with a large window overlooking a cityscape at night, featuring a river and illuminated buildings.
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.

Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
$174
$241 total
includes taxes & fees
Aug 30 - Aug 31
Sable at Navy Pier Chicago, Curio Collection by Hilton
A spacious lobby with a checkered floor, a large sofa, and multiple chairs.
A hotel room with two beds, a desk with a computer, a chair, a TV, and a large mirror.
A modern kitchen with a built-in refrigerator, a coffee maker, and a flat-screen TV on the countertop.
A modern kitchen area with a long counter, various food items, and a coffee machine.

Fairfield Inn & Suites Chicago Downtown / Magnificent Mile

Fairfield Inn & Suites Chicago Downtown / Magnificent Mile
Downtown Chicago
$127
$151 total
includes taxes & fees
Aug 30 - Aug 31
Fairfield Inn & Suites Chicago Downtown / Magnificent Mile
A cozy room with a sofa, a dining table, and a window with a view of buildings.
A lobby with two brown leather chairs, a marble table, and a large potted plant.
A hotel room with a large bed, a small dining table with chairs, a brick wall, and a window with blinds.
A cozy seating area with a round table and two chairs, a brick wall, and a window with a view of buildings.

LIVN - West Loop Chicago

LIVN - West Loop Chicago
Downtown Chicago
$155
$182 total
includes taxes & fees
Aug 31 - Sep 1
LIVN - West Loop Chicago
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 'Treats' wall and a 'Welcome to Hampton' sign.
A hotel room with a flat-screen TV, a round mirror, a wooden desk, a chair, and two beds.

Hampton Inn Majestic Chicago Theatre District

Hampton Inn Majestic Chicago Theatre District
Downtown Chicago
$162
$193 total
includes taxes & fees
Sep 7 - Sep 8
Hampton Inn Majestic Chicago Theatre District
A marble-floored lobby with double doors and elevators, each marked with a 'CQ' sign.
A hotel room with a grey sofa, a bed with a white mattress, a wooden dresser, and a large window with curtains.
A man in a suit sitting by a window with a vase of red flowers.
A conference room with a long table, chairs, and a vase.

River Hotel

River Hotel
Downtown Chicago
$145
$172 total
includes taxes & fees
Sep 7 - Sep 8
River Hotel
A multi-story building with a Starbucks Coffee on the ground floor, emergency exit signs, and a Hyatt Center sign.
An indoor swimming pool with lounge chairs and exercise equipment.
A modern workspace with two Apple iMacs, a desk with a keyboard, and a bookshelf filled with books and decorative items.
A modern hotel room with a sofa, ottoman, and a dining area with a bar.

Hyatt Centric Chicago Magnificent Mile

Hyatt Centric Chicago Magnificent Mile
Downtown Chicago
$173
$235 total
includes taxes & fees
Sep 1 - Sep 2
Hyatt Centric Chicago Magnificent Mile
A building with a sign reading "111" and "III West Adams Street" indicating a pub and restaurant.
A modern living room with a fireplace, leather sofas, and a wooden floor.
A modern lobby with leather sofas, a wooden coffee table, a TV mounted on the wall, and a bookshelf.
A person sitting on a couch with a laptop, reading a book, in a room with a large window and a framed picture on the wall.

Central Loop Hotel

Central Loop Hotel
Downtown Chicago
$133
$158 total
includes taxes & fees
Aug 30 - Aug 31
Central Loop Hotel
A cityscape at dusk with high-rise buildings, including a Hilton hotel.
A hotel room with a bed, a desk, a television, a sofa, and a large window with a city view.
A dining table set for a meal with a floral centerpiece, surrounded by chairs, in a room with a cityscape view.
A modern hotel lobby with a central seating area, a reception desk, and a cityscape mural on the wall.

Hilton Chicago/Magnificent Mile Suites

Hilton Chicago/Magnificent Mile Suites
Downtown Chicago
$145
$173 total
includes taxes & fees
Sep 1 - Sep 2
Hilton Chicago/Magnificent Mile Suites
A spacious lobby with a central coffee table, sofas, and a large mirror.
A spacious lobby with high ceilings, large arched windows, and a grand staircase.
A spacious lobby with a grand fireplace, elegant columns, and a seating area with chairs and a table.
A spacious lounge area with leather sofas, round tables, and comfortable chairs, featuring a wooden ceiling and elegant decor.

The Chicago Hotel Collection Ambassador Gold Coast

The Chicago Hotel Collection Ambassador Gold Coast
Downtown Chicago
$134
$159 total
includes taxes & fees
Aug 31 - Sep 1
The Chicago Hotel Collection Ambassador Gold Coast
A bar area with a high ceiling, bar stools, and a counter with bottles.
A modern interior with a bar area, seating, and decorative lighting.
A modern interior with wooden shelves, tables, and chairs, and a large window with the word "FOUND" on the wall.

FOUND Hotels, Chicago, Series by Marriott

FOUND Hotels, Chicago, Series by Marriott
Downtown Chicago
$139
$163 total
includes taxes & fees
Aug 30 - Aug 31
FOUND Hotels, Chicago, Series by Marriott
An indoor swimming pool with clear glass walls, a wooden ceiling, and a view of a red brick building.
A modern hotel lobby with a reception desk, seating area, and a large window providing a view of the outdoors.
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 hotel entrance with glass doors, a visible reception desk, and signage for Hilton Garden Inn and Homewood Suites.

Hilton Garden Inn Chicago Downtown South Loop

Hilton Garden Inn Chicago Downtown South Loop
Downtown Chicago
$152
$181 total
includes taxes & fees
Sep 7 - Sep 8
Hilton Garden Inn Chicago Downtown South Loop
An outdoor rooftop lounge with seating, a fire feature, and a view of the city skyline at night.
The Chicago Hotel Collection building with a glass facade, American flag, and signage for Barista Bar and Seighity events.
A modern lobby with a wooden ceiling, leather sofas, and a coffee bar.
A modern lounge area with leather sofas, wooden coffee tables, and ambient lighting.

The Chicago Hotel Collection - Magnificent Mile

The Chicago Hotel Collection - Magnificent Mile
Downtown Chicago
$143
$170 total
includes taxes & fees
Sep 1 - Sep 2
The Chicago Hotel Collection - Magnificent Mile
A hotel with a modern design, featuring a prominent curved glass facade and multiple floors.
A hotel room with two beds, a large window with a city view, a wooden wardrobe, and a bedside table with a lamp.
A modern hotel lobby with multiple dining areas, a central food station, and a high-ceiling atrium with balconies.
A hotel reception area with a black reception desk, a concierge service sign, and a tiled floor.

Embassy Suites by Hilton Chicago Downtown Magnificent Mile

Embassy Suites by Hilton Chicago Downtown Magnificent Mile
Downtown Chicago
$156
$215 total
includes taxes & fees
Sep 1 - Sep 2
Embassy Suites by Hilton Chicago Downtown Magnificent Mile
A modern kitchen with a large window, a dining area, and a view of the sea.
An indoor swimming pool with clear glass walls, a wooden ceiling, and a view of a red brick building.
A modern restaurant interior with a long counter, booths, and tables.
A modern living room with a sectional sofa, a fireplace, and a large window offering a city view.

Homewood Suites by Hilton Chicago Downtown South Loop

Homewood Suites by Hilton Chicago Downtown South Loop
Downtown Chicago
$156
$186 total
includes taxes & fees
Sep 7 - Sep 8
Homewood Suites by Hilton Chicago Downtown South Loop
A corridor with ornate black metal railings and a patterned carpet.
A dining area with tables and chairs, a hanging light fixture, and a view of the street through a window.
A bed with a pillow featuring a pineapple design and the text "Sleep with me." A window reveals a cityscape at night.
A modern hotel room with a sofa, a small table, a bench, a TV, and a cabinet.

Staypineapple, An Iconic Hotel, The Loop

Staypineapple, An Iconic Hotel, The Loop
Downtown Chicago
$155
$214 total
includes taxes & fees
Aug 30 - Aug 31
Staypineapple, An Iconic Hotel, The Loop
A modern building with large glass windows and a covered walkway.
A spacious lobby with two elevators, a reception area, and a seating area with blue and white ottomans.
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.

Holiday Inn & Suites Chicago - Downtown by IHG

Holiday Inn & Suites Chicago - Downtown by IHG
Downtown Chicago
$149
$189 total
includes taxes & fees
Sep 7 - Sep 8
Holiday Inn & Suites Chicago - Downtown by IHG
A building with a sign reading "111" and "III West Adams Street" indicating a pub and restaurant.
A modern living room with a fireplace, leather sofas, and a wooden floor.
A hotel room with a large window, a bed, and a suitcase.
A restaurant interior with brick walls, wooden tables and chairs, and a bar area.

Club Quarters Hotel, Central Loop, Chicago

Club Quarters Hotel, Central Loop, Chicago
Downtown Chicago
$133
$158 total
includes taxes & fees
Aug 30 - Aug 31
Club Quarters Hotel, Central Loop, Chicago
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Our prices for hotels in Crestwood are cheapest in December
Price trends for hotels in Crestwood
Pricing is based on two traveler single night rates
View properties in August
Typical weather for Crestwood
August
High 27°C / low 19°C. Sunny most days.
View properties in August
27°
19°
24°
16°
17°
9°
9°
2°
3°
-3°
-1°
-7°
1°
-6°
8°
0°
14°
5°
20°
11°
25°
17°
28°
19°
Monthly weather averages (˚C)

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 Lake Katherine Nature Center and Childrens Museum of Oak Lawn, 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

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

10/10 Excellent
"❤️"
Adriana 2-night trip
Posted less than an hour ago
Hotel Riu Plaza Chicago
Crowne Plaza Chicago West Loop by IHG

Crowne Plaza Chicago West Loop by IHG

8/10 Good
"Loved our stay"
Jaclyn 3-night trip
Posted 1 hour ago
Crowne Plaza Chicago West Loop by IHG
Hyatt Regency McCormick Place Chicago

Hyatt Regency McCormick Place Chicago

10/10 Excellent
"The staff was very friendly and helpful. The room and hotel was clean and comfortable."
Shenise 1-night trip
Posted 4 hours ago
Hyatt Regency McCormick Place Chicago
The Royal Sonesta Chicago Downtown

The Royal Sonesta Chicago Downtown

10/10 Excellent
"Perfect location! Very clean rooms and helpful staff. Would definitely recommend"
Tammy 3-night trip
Posted 4 hours ago
The Royal Sonesta Chicago Downtown
River Hotel

River Hotel

10/10 Excellent
"Overall a great stay location is perfect and the view was amazing. Room was basic and simple but it was clean. Everything worked so I’d recommend it for future travelers."
Jasmon 3-night trip
Posted 4 hours ago
River Hotel
Fairmont Chicago at Millennium Park

Fairmont Chicago at Millennium Park

10/10 Excellent
"Great place, friendly/helpful staff, clean/nice rooms (although not a lot of insulation between rooms), good location to parks, museums, and shopping."
Sarah 3-night trip
Posted 5 hours ago
Fairmont Chicago at Millennium Park
L7 Chicago by LOTTE

L7 Chicago by LOTTE

10/10 Excellent
"Prime location on the river. Exciting night life, good food and shopping just outside the hotel. Staff were nice, responsive, and friendly. The Korean restaurant & bar on the first floor was an amazing experience- shout out to our bartender Christopher. They have a free coffee/cappuccino bar from 6am-6pm in the lobby. Our room was very spacious, clean & comfortable. All in all, a great stay & I’ll be a returning guest."
Montique 3-night trip
Posted 6 hours ago
L7 Chicago by LOTTE

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.

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