𝗧𝗢𝗣 𝟭𝟬 𝗛𝗼𝘁𝗲𝗹𝘀 𝗶𝗻 Crestwood (2026)

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 coffee station with two coffee machines and a variety of coffee pods and cups.

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

A Holiday Inn Express building with a covered entrance and a parking lot.

1. Holiday Inn Express Crestwood by IHG

Crestwood

Kandis

S$158

includes taxes & fees

1 Nov - 2 Nov

A spacious lobby with a modern design, featuring a seating area with sofas and armchairs, a staircase, and large windows providing natural light.

A modern restaurant with a mix of seating options including tables and sofas, a kitchen area, and large windows offering views of the outdoors.

A Wingate by Wyndham hotel with a symmetrical facade, large windows, and a central entrance.

A swimming pool with lounge chairs and a view of the outside.

2. Wingate by Wyndham Tinley Park

Tinley Park

Erica

S$177

includes taxes & fees

1 Nov - 2 Nov

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

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.

A residential street with a sidewalk, houses, and greenery.

3. Carleton of Oak Park

Oak Park

Brad

S$174

includes taxes & fees

13 Oct - 14 Oct

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 a large bed, a TV mounted on the wall, a desk with a chair, and a microwave.

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.

4. SureStay Plus Hotel by Best Western Chicago Lombard

Highland Hills

Blessing

S$138

includes taxes & fees

21 Oct - 22 Oct

A modern hotel lobby with a curved white sofa, two side tables with lamps, a black coffee table, and a large chandelier.

A restaurant interior with wooden tables and chairs, a carpeted floor, and framed pictures on the walls.

A marina with numerous boats docked, surrounded by a cityscape with high-rise buildings and a stadium.

A conference room with a long table, chairs, and a large screen.

5. Hilton Chicago

Downtown Chicago

Anna

S$290

includes taxes & fees

30 Oct - 31 Oct

A spacious lobby with a central sofa, multiple seating areas, and a decorative ceiling.

Outdoor seating with yellow umbrellas labeled "Twisted Tea," wicker chairs, and tables.

A grand ballroom with ornate ceiling decorations, multiple chandeliers, and a central table with a white tablecloth.

A cityscape with various buildings, including a prominent skyscraper and a classical building with arched windows.

6. Congress Plaza Hotel

Downtown Chicago

Ashya

S$177

includes taxes & fees

10 Nov - 11 Nov

A tall, modern hotel with a brick facade and numerous windows.

A modern hotel lobby with grey upholstered chairs, a wooden coffee table, and a large window offering a view of the city and an American flag.

7. Sonesta ES Suites Chicago Downtown Magnificent Mile - Medical

Downtown Chicago

Anand

S$177

includes taxes & fees

2 Nov - 3 Nov

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

A modern hotel with a prominent "Grant Park Hotel" sign and "Best Western" branding.

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

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

8. Best Western Grant Park Hotel

Downtown Chicago

Shelby Ryann

S$190

includes taxes & fees

9 Nov - 10 Nov

A bar area with a counter, bar stools, and a display of liquor bottles.

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

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

Jeanvia

S$196

includes taxes & fees

1 Nov - 2 Nov

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 hotel room with a large window offering a cityscape view, including a prominent building with a clock tower.

10. Hampton Inn Chicago Downtown/Magnificent Mile

Downtown Chicago

William

S$167

includes taxes & fees

1 Nov - 2 Nov

A modern hotel lobby with large windows, leather sofas, and a view of the cityscape.

A restaurant with booths, tables, and a green wall in the background.

A hotel room with a bed, a desk with a chair, a sofa, and a view of a building through the window.

A lobby with a checkered floor, an ATM, a potted plant, a reception desk, computers, and a staircase.

11. Travelodge by Wyndham Downtown Chicago

Downtown Chicago

Sandra

S$175

includes taxes & fees

12 Nov - 13 Nov

A hotel room with a large bed, a nightstand with a lamp, a wall clock, and a window with curtains.

A restaurant with booths and tables, a television on the wall, and a view of the street outside.

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

12. Hilton Vacation Club Hotel Blake Chicago

Downtown Chicago

Kelsey

S$262

includes taxes & fees

4 Nov - 5 Nov

A snack bar with various packaged snacks and beverages.

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

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

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

13. Cambria Hotel Chicago Loop - Theatre District

Downtown Chicago

Vansh

S$218

includes taxes & fees

1 Nov - 2 Nov

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

A bar area with a large mural, bar stools, and a variety of bottles and glasses on the counter.

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.

14. Le Méridien Essex Chicago

Downtown Chicago

Kayla Rene

S$204

includes taxes & fees

11 Nov - 12 Nov

An indoor swimming pool with a glass ceiling, wooden walls, and seating areas.

A formal dining room with a round table set for eight, surrounded by leather chairs, a chandelier, and potted plants.

A person overlooking a cityscape from a high vantage point.

A modern building with large glass windows and a covered walkway.

15. Palmer House a Hilton Hotel

Downtown Chicago

Christy

S$328

includes taxes & fees

31 Oct - 1 Nov

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

A high-rise building with a modern architectural design, featuring a prominent glass facade and a series of vertical lines.

A room with a diamond-patterned bookshelf filled with books, a wooden floor, and a lamp.

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

16. Arlo Chicago

Downtown Chicago

Pam

S$278

includes taxes & fees

1 Nov - 2 Nov

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

A cozy room with a patterned carpet, a wooden table, and a green sofa with a white throw blanket.

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.

17. DoubleTree by Hilton Chicago - Magnificent Mile

Downtown Chicago

Poua

S$211

includes taxes & fees

1 Nov - 2 Nov

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

A bar with a circular liquor display, seating with stools, and a city view through large windows.

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

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

18. Hyatt Regency Chicago

Downtown Chicago

Mercy

S$408

includes taxes & fees

31 Oct - 1 Nov

A bar area with a long counter, bar stools, and a mirrored wall.

A tall red brick building with a classic architectural style, surrounded by modern skyscrapers.

A luxurious lobby with a grand fireplace, elegant seating arrangements, and classic wood paneling.

A restaurant with wooden flooring, long tables, and chairs with patterned upholstery.

19. The Whitehall Hotel, BW Premier Collection

Downtown Chicago

KURT

S$181

includes taxes & fees

9 Nov - 10 Nov

A building with a sign reading "111" and "III West Adams Street" indicating a pub and restaurant.

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

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.

A modern living room with a fireplace, leather sofas, and a wooden floor.

20. Central Loop Hotel

Downtown Chicago

Nathan

S$183

includes taxes & fees

1 Nov - 2 Nov

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Hotels recommended for families in Crestwood

Holiday Inn Express Crestwood by IHG

Crestwood

S$158

includes taxes & fees

1 Nov - 2 Nov

Wingate by Wyndham Tinley Park

Tinley Park

S$177

includes taxes & fees

1 Nov - 2 Nov

Carleton of Oak Park

Oak Park

S$174

includes taxes & fees

13 Oct - 14 Oct

SureStay Plus Hotel by Best Western Chicago Lombard

Highland Hills

S$138

includes taxes & fees

21 Oct - 22 Oct

Hilton Chicago

Downtown Chicago

S$290

includes taxes & fees

30 Oct - 31 Oct

Sonesta ES Suites Chicago Downtown Magnificent Mile - Medical

Downtown Chicago

S$177

includes taxes & fees

2 Nov - 3 Nov

Congress Plaza Hotel

Downtown Chicago

S$177

includes taxes & fees

10 Nov - 11 Nov

Hampton Inn Chicago Downtown/Magnificent Mile

Downtown Chicago

S$167

includes taxes & fees

1 Nov - 2 Nov

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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.

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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

The Godfrey Hotel Chicago

10/10 Excellent

"Couldn’t imagine a better place to stay in Chicago."

Congress Plaza Hotel

8/10 Good

"a bit old building, non reliable internet, noisy in the rooms facing Michigan, friendly staff"

The Chicago Hotel Collection - Magnificent Mile

10/10 Excellent

"Just as always- clean and efficient. staff is always helpful and goes above and beyond. Even housekeeping is top notch. do yourself a favor and get the guest benefits pkg. treat yourself!"

More cheap stays in Crestwood

Motel 6 Bridgeview, IL

9625 S 76th Ave Bridgeview IL

S$88

25 Oct - 26 Oct

includes taxes & fees

Red Roof Inn PLUS+ Chicago - Willowbrook

7535 Kingery Highway Willowbrook IL

S$116

18 Oct - 19 Oct

includes taxes & fees

6.2/10 (1,298 reviews)

Sleep Inn Midway Airport Bedford Park

6650 S Cicero Ave Chicago IL

S$137

1 Nov - 2 Nov

includes taxes & fees

SureStay Plus Hotel by Best Western Chicago Lombard

222 E 22nd Street Lombard IL

S$138

21 Oct - 22 Oct

includes taxes & fees

Hampton Inn Chicago Downtown/Magnificent Mile

160 E Huron Street Chicago IL

S$167

1 Nov - 2 Nov

includes taxes & fees

8/10 Very good! (1,663 reviews)

Travelodge by Wyndham Downtown Chicago

65 E Harrison St Chicago IL

S$175

12 Nov - 13 Nov

includes taxes & fees

Frequently asked questions

Where is the best place for a stay in Crestwood?

River Hotel, located 17 mi (27.3 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 Congress Plaza Hotel and The Chicago Hotel Collection Ambassador Gold Coast. 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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Things to do in Countryside

Crestwood Hotels from S$88

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. Wingate by Wyndham Tinley Park

3. Carleton of Oak Park

4. SureStay Plus Hotel by Best Western Chicago Lombard

5. Hilton Chicago

6. Congress Plaza Hotel

7. Sonesta ES Suites Chicago Downtown Magnificent Mile - Medical

8. Best Western Grant Park Hotel

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

10. Hampton Inn Chicago Downtown/Magnificent Mile

11. Travelodge by Wyndham Downtown Chicago

12. Hilton Vacation Club Hotel Blake Chicago

13. Cambria Hotel Chicago Loop - Theatre District

14. Le Méridien Essex Chicago

15. Palmer House a Hilton Hotel

16. Arlo Chicago

17. DoubleTree by Hilton Chicago - Magnificent Mile

18. Hyatt Regency Chicago

19. The Whitehall Hotel, BW Premier Collection

20. Central Loop Hotel

Hotels recommended for families in Crestwood

Holiday Inn Express Crestwood by IHG

Wingate by Wyndham Tinley Park

Carleton of Oak Park

SureStay Plus Hotel by Best Western Chicago Lombard

Hilton Chicago

Sonesta ES Suites Chicago Downtown Magnificent Mile - Medical

Congress Plaza Hotel

Hampton Inn Chicago Downtown/Magnificent Mile

Stay near popular Crestwood attractions

Hollywood Park

Learn more about Crestwood

Top Crestwood Hotel Reviews

The Godfrey Hotel Chicago

Congress Plaza Hotel

The Chicago Hotel Collection - Magnificent Mile

More cheap stays in Crestwood

Motel 6 Bridgeview, IL

Red Roof Inn PLUS+ Chicago - Willowbrook

Sleep Inn Midway Airport Bedford Park

SureStay Plus Hotel by Best Western Chicago Lombard

Hampton Inn Chicago Downtown/Magnificent Mile

Travelodge by Wyndham Downtown Chicago

Frequently asked questions

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