Crestwood Holiday Rentals, Chicago: Private House Rentals

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

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Our top choices for Crestwood hotels

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.

A Holiday Inn Express hotel with a brick facade, a central entrance, and a parking lot.

1. Holiday Inn Express Crestwood by IHG

Crestwood

Passion

฿4,264

฿4,775 total

includes taxes & fees

27 Sept - 28 Sept

A hotel with a modern design, featuring a prominent curved glass facade and multiple floors.

A hotel reception area with a black reception desk, a concierge service sign, and a tiled floor.

A modern hotel lobby with multiple dining areas, a central food station, and a high-ceiling atrium with balconies.

An indoor swimming pool with lounge chairs and a no diving sign.

2. Embassy Suites by Hilton Chicago Downtown Magnificent Mile

Downtown Chicago

Rajiv

฿5,210

฿7,157 total

includes taxes & fees

1 Sept - 2 Sept

A large, multi-story hotel with a prominent entrance and classical architectural details.

A spacious hotel lobby with a long reception desk, multiple seating areas, and a large fireplace.

A spacious hotel lobby with a large seating area, a flat-screen TV, and a view of the ocean.

A spacious lobby with a patterned carpet, comfortable seating, a fireplace, and large windows.

3. Hilton Chicago

Downtown Chicago

Konner

฿6,002

฿8,112 total

includes taxes & fees

10 Sept - 11 Sept

A modern hotel with a glass facade, multiple floors, and a visible entrance.

A gym with cardio machines, weight benches, and a large window offering a city view.

A modern hotel room with a large window, a desk with a lamp, a sofa, and a chair.

A hotel room with a large bed, a desk with a chair, a sofa, and a TV.

4. Hyatt Place Chicago/Downtown - The Loop

Downtown Chicago

LISA

฿5,543

฿6,590 total

includes taxes & fees

7 Sept - 8 Sept

A spacious bar area with high ceilings and large windows, offering views of a cityscape.

A hotel room with a bed, a sofa with cushions, a large window with a view of a cityscape and water.

A multi-level hotel lobby with a glass elevator, a seating area, and a dining space.

A cityscape with modern high-rise buildings, a river, and a boat.

5. Hyatt Regency Chicago

Downtown Chicago

Abdulsamad

฿7,891

฿10,547 total

includes taxes & fees

7 Sept - 8 Sept

A dining area with tables set for four, large windows with a view of city buildings, and a curved ceiling structure.

A multi-story building with a prominent storefront featuring a golden sign.

A spacious lobby with a patterned carpet, wooden paneling, and modern lighting fixtures.

A hotel room with a large bed, a desk with a lamp, a bench, and a view of the cityscape through large windows.

6. Omni Chicago Hotel

Downtown Chicago

Yoel

฿7,813

฿10,377 total

includes taxes & fees

1 Sept - 2 Sept

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

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

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

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

7. DoubleTree by Hilton Chicago - Magnificent Mile

Downtown Chicago

MAGALY

฿5,099

฿6,063 total

includes taxes & fees

30 Aug - 31 Aug

The Riu Plaza Chicago Hotel facade with a grand entrance, large windows, and a modern architectural design.

A couple dining at a table with a city view, surrounded by chairs and a variety of dishes.

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

A modern hotel lobby with a central seating area, a reception desk, and a decorative wall with a unique design.

8. Hotel Riu Plaza Chicago

Downtown Chicago

Peter

฿5,884

฿7,931 total

includes taxes & fees

1 Sept - 2 Sept

A modern hotel lobby with a curved seating area, large windows offering city views, and a chandelier.

An indoor swimming pool with clear water, surrounded by lounge chairs and a glass wall.

A modern lobby with a stone wall, a flat-screen TV, and a fireplace.

A spacious lobby with a modern reception desk, comfortable seating area, and large windows offering city views.

9. Homewood Suites by Hilton Chicago-Downtown

Downtown Chicago

Matthew

฿6,085

฿7,234 total

includes taxes & fees

7 Sept - 8 Sept

A modern kitchen with a large window, a dining area, and a view of the sea.

A modern restaurant interior with a long counter, booths, and tables.

A modern bar area with a long counter, multiple bar stools, and a mix of seating options including a high table and chairs.

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

10. Homewood Suites by Hilton Chicago Downtown South Loop

Downtown Chicago

AMBER

฿5,269

฿6,264 total

includes taxes & fees

7 Sept - 8 Sept

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.

11. Hilton Vacation Club Hotel Blake Chicago

Downtown Chicago

Melanie

฿5,931

฿7,051 total

includes taxes & fees

7 Sept - 8 Sept

A multi-level atrium with a central spiral staircase, multiple seating areas, and a pool.

A multi-level indoor area with a central water feature, surrounded by seating areas and greenery.

A spacious lobby with a central staircase, multiple floors, a reception desk, and seating areas.

A multi-story hotel with a prominent 'Embassy Suites' sign, a Starbucks Coffee shop, and a well-lit street at night.

12. Embassy Suites by Hilton Chicago Downtown River North

Downtown Chicago

Hugo

฿4,973

฿5,913 total

includes taxes & fees

7 Sept - 8 Sept

A cityscape at dusk with high-rise buildings, including a Hilton hotel.

A hotel room with a sofa, armchair, a flat-screen TV, a bed, and a view of the city and ocean.

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

A modern hotel lobby with a central seating area, a reception desk, and a cityscape mural on the wall.

13. Hilton Chicago/Magnificent Mile Suites

Downtown Chicago

Terrie

฿5,346

฿6,356 total

includes taxes & fees

1 Sept - 2 Sept

A multi-story hotel with a prominent 'La Quinta' sign, featuring a modern architectural design with large windows and a flat facade.

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

A hotel lobby with a reception desk, seating area, and a mural of a city skyline.

A modern bar area with a central counter, multiple seating tables, and a large window offering a view.

14. La Quinta Inn & Suites by Wyndham Chicago Downtown

Downtown Chicago

Shilpa

฿4,103

฿5,463 total

includes taxes & fees

30 Aug - 31 Aug

A person relaxing on a sofa with a laptop, a glass of red wine, and a small table with a vase of flowers and a telephone.

A room with a bed against a window overlooking a cityscape. There is a small table with a book, a vase with flowers, and a cup.

A modern hotel lobby with leather sofas, a coffee table, and a floor lamp.

A bar area with a long counter, multiple shelves of bottles, and four bar stools.

15. L7 Chicago by LOTTE

Downtown Chicago

Girivasan

฿8,446

฿10,042 total

includes taxes & fees

9 Sept - 10 Sept

A rooftop terrace with outdoor seating, a view of the city skyline, and a river.

A modern room with a view of a river and high-rise buildings.

A historic building with a classical facade, large windows, and a prominent dome.

A modern interior with seating areas, a bar, and large windows offering a city view.

16. LondonHouse Chicago, Curio Collection by Hilton

Downtown Chicago

Luis

฿7,242

฿9,572 total

includes taxes & fees

30 Aug - 31 Aug

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

17. Aloft by Marriott Chicago Mag Mile

Downtown Chicago

Odessia

฿5,034

฿5,985 total

includes taxes & fees

7 Sept - 8 Sept

A restaurant with wooden tables and chairs, large windows, and a green vine-covered ceiling.

A modern living room with a large window, a potted plant, and a variety of seating options including a sofa, armchairs, and ottoman.

A vending machine with various beverages and snacks.

A multi-story hotel with a modern glass facade, located in an urban setting with a parking lot and street views.

18. Hyatt Place Chicago/River North

Downtown Chicago

Shoma

฿5,557

฿6,607 total

includes taxes & fees

7 Sept - 8 Sept

A hotel with a modern glass facade, a prominent Hampton Inn sign, and a Homewood Suites by Hilton sign.

A modern hotel lobby with a long reception desk, seating area, and large windows offering city views.

A hotel room with a large window offering a city view, a sofa, a chair, a small table, and a desk with a chair.

A gym with treadmills, a stationary bike, and a rowing machine, with a city view through large windows.

19. Hampton Inn Chicago Downtown/Magnificent Mile

Downtown Chicago

Kimberly

฿4,835

฿5,748 total

includes taxes & fees

7 Sept - 8 Sept

A person sitting by a window with a cityscape view.

The Intercontinental hotel facade with a large American flag and a floral display.

A large indoor swimming pool with clear lanes, a sunlit ceiling with geometric patterns, and a seating area with chairs and tables on one side.

A grand lobby with a central staircase, a decorative fountain, and a high ceiling.

20. InterContinental Chicago Magnificent Mile by IHG

Downtown Chicago

Alireza

฿7,878

฿10,510 total

includes taxes & fees

8 Sept - 9 Sept

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Stay near popular Crestwood attractions

Hollywood Park

This family entertainment centre offers go-karts, mini-golf, bumper cars, and a multi-floor arcade all in one vibrant location. Enjoy chef-crafted meals between activities for a complete day of fun.

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

Top Crestwood Hotel Reviews

Eurostars Magnificent Mile

8/10 Good

"good location. two levels: one off the street and another one floor up so had to take 2 elevators to get to your room"

River Hotel

10/10 Excellent

"Clean room. Helpful staff."

Hyatt Regency McCormick Place Chicago

10/10 Excellent

"We loved our stay, we will come back and stay every time we’re in Chicago."

The Chicago Hotel Collection Ambassador Gold Coast

8/10 Good

"The rooftop had an amazing view of Chicago. The rooms could use a little refresh though."

Club Quarters Hotel, Central Loop, Chicago

10/10 Excellent

"Located conveniently to Millenium park and other nearby attractions. Staff was friendly and housekeeping was excellent."

Hotel Riu Plaza Chicago

10/10 Excellent

"Fantastic breakfast, great location, great room. The rooftop terrace was amazing, but we wishes we had known to make a reservation to be able to enjoy a drink there."

More cheap stays in Crestwood

Red Roof Inn PLUS+ Chicago - Willowbrook

7535 Kingery Highway Willowbrook IL

฿2,056

฿2,302 total

2 Sept - 3 Sept

includes taxes & fees

6.4/10 (1,249 reviews)

Quality Inn & Suites Orland Park - Chicago

8800 W 159th St Orland Park IL

฿2,923

฿3,273 total

20 Sept - 21 Sept

includes taxes & fees

Sleep Inn Midway Airport Bedford Park

6650 S Cicero Ave Chicago IL

฿3,772

฿4,432 total

22 Sept - 23 Sept

includes taxes & fees

8/10 Very good! (2,074 reviews)

Travelodge by Wyndham Downtown Chicago

65 E Harrison St Chicago IL

฿3,766

฿4,477 total

30 Aug - 31 Aug

includes taxes & fees

7.6/10 Good! (2,790 reviews)

Holiday Inn Chicago – Midway Airport S by IHG

7353 S Cicero Avenue Chicago IL

฿3,726

฿4,701 total

8 Sept - 9 Sept

includes taxes & fees

8.2/10 Very good! (1,005 reviews)

Hampton Inn Chicago Downtown/Magnificent Mile

160 E Huron Street Chicago IL

฿4,835

฿5,748 total

7 Sept - 8 Sept

includes taxes & fees

8/10 Very good! (1,539 reviews)

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 The Chicago Hotel Collection Ambassador Gold Coast and Kasa Magnificent Mile Chicago. 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'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.

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Book Hotels in Crestwood on Expedia.com

Find hotels in Crestwood, IL from ฿2,302

Change your mind

Treat yourself

Be picky

Go beyond your typical stay in Crestwood

Check prices for these dates

Filter by

Star rating

Guest rating

Our top choices for Crestwood hotels

1. Holiday Inn Express Crestwood by IHG

2. Embassy Suites by Hilton Chicago Downtown Magnificent Mile

3. Hilton Chicago

4. Hyatt Place Chicago/Downtown - The Loop

5. Hyatt Regency Chicago

6. Omni Chicago Hotel

7. DoubleTree by Hilton Chicago - Magnificent Mile

8. Hotel Riu Plaza Chicago

9. Homewood Suites by Hilton Chicago-Downtown

10. Homewood Suites by Hilton Chicago Downtown South Loop

11. Hilton Vacation Club Hotel Blake Chicago

12. Embassy Suites by Hilton Chicago Downtown River North

13. Hilton Chicago/Magnificent Mile Suites

14. La Quinta Inn & Suites by Wyndham Chicago Downtown

15. L7 Chicago by LOTTE

16. LondonHouse Chicago, Curio Collection by Hilton

17. Aloft by Marriott Chicago Mag Mile

18. Hyatt Place Chicago/River North

19. Hampton Inn Chicago Downtown/Magnificent Mile

20. InterContinental Chicago Magnificent Mile by IHG

Stay near popular Crestwood attractions

Hollywood Park

Learn more about Crestwood

Top Crestwood Hotel Reviews

Eurostars Magnificent Mile

River Hotel

Hyatt Regency McCormick Place Chicago

The Chicago Hotel Collection Ambassador Gold Coast

Club Quarters Hotel, Central Loop, Chicago

Hotel Riu Plaza Chicago

More cheap stays in Crestwood

Red Roof Inn PLUS+ Chicago - Willowbrook

Quality Inn & Suites Orland Park - Chicago

Sleep Inn Midway Airport Bedford Park

Travelodge by Wyndham Downtown Chicago

Holiday Inn Chicago – Midway Airport S by IHG

Hampton Inn Chicago Downtown/Magnificent Mile

Frequently asked questions

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