Crestwood Holiday Rentals, Chicago: Private House Rentals

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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 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

Kandis

฿3,688

฿4,130 total

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 hotel room with a bed, a desk, a chair, a sofa, and a television.

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

2. Wingate by Wyndham Tinley Park

Tinley Park

Erica

฿4,104

฿4,637 total

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

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

3. Hyatt Regency Chicago

Downtown Chicago

Mercy

฿7,980

฿10,684 total

includes taxes & fees

31 Oct - 1 Nov

A dining table set for six with a cityscape view through large windows.

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

A modern hotel room with a large window offering a city skyline view, a round table with four chairs, and a ceiling with recessed lighting.

A modern hotel room with a large window offering a cityscape view, a green sofa, two armchairs, and a coffee table with flowers.

4. Swissotel - Chicago

Downtown Chicago

Hilary

฿7,092

฿9,612 total

includes taxes & fees

31 Oct - 1 Nov

A person relaxing on a sofa with a window view of a building, a table with a glass of wine, and a vase with flowers.

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.

A modern restaurant with high ceilings, wooden flooring, and a central chandelier. Tables are set with wine glasses and red cushions.

5. L7 Chicago by LOTTE

Downtown Chicago

Jeffrey Thomas

฿6,165

฿7,330 total

includes taxes & fees

11 Nov - 12 Nov

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

A vending machine with various beverages and snacks.

A hotel room with a large bed, two bedside lamps, and a city view through a large window.

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

6. Hyatt Place Chicago/River North

Downtown Chicago

Iminique

฿5,700

฿6,777 total

includes taxes & fees

1 Nov - 2 Nov

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 modern hotel room with a large bed, a desk, a sofa, and a view of the city.

A modern living room with a sofa, coffee table, and ottoman, a fireplace, and a large window with a city view.

7. LondonHouse Chicago, Curio Collection by Hilton

Downtown Chicago

Keeven

฿7,695

฿10,146 total

includes taxes & fees

1 Nov - 2 Nov

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

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

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

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

Kevin

฿5,888

฿7,956 total

includes taxes & fees

11 Nov - 12 Nov

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

A person sitting by a window with a cityscape view.

A swimming pool area with a glass-bottomed pool, a high ceiling with hanging lights, and a staircase with people sitting on it.

A bar area with a high bar counter, multiple stools, and a seating area with booths and tables.

9. InterContinental Chicago Magnificent Mile by IHG

Downtown Chicago

Reginald

฿7,108

฿9,625 total

includes taxes & fees

31 Oct - 1 Nov

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

A swimming pool with a glass wall, a seating area with sofas, and an exit sign.

10. Embassy Suites by Hilton Chicago Downtown River North

Downtown Chicago

Eliana

฿5,672

฿6,743 total

includes taxes & fees

1 Nov - 2 Nov

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

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

Downtown Chicago

Jeanvia

฿4,310

฿5,124 total

includes taxes & fees

1 Nov - 2 Nov

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

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

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

A modern hotel room with a sofa, armchairs, a coffee table, a flat-screen TV, and a patterned wall.

12. Hilton Vacation Club Hotel Blake Chicago

Downtown Chicago

Kelsey

฿5,762

฿6,851 total

includes taxes & fees

4 Nov - 5 Nov

A modern dining area with a long wooden table, colorful chairs, and red curtains.

A modern hotel room with a large window offering a city view, a contemporary light fixture, and a clean, minimalist design.

A modern bar area with a checkered floor, wooden ceiling, and various bar equipment.

A modern high-rise building with a glass facade, surrounded by other tall buildings.

13. citizenM Chicago Downtown

Downtown Chicago

Katarina

฿5,700

฿6,777 total

includes taxes & fees

1 Nov - 2 Nov

A dining area with a table set for four, large windows offering a cityscape view at dusk.

A modern interior with a central fireplace, seating area, and wall-mounted lighting.

A high-rise hotel room with large windows offering a city view, round tables set for dining, and elegant decor with flowers and candles.

A breakfast table with croissants, a bowl of berries, a glass of orange juice, and a smoothie, set against a cityscape view through a window.

14. The Royal Sonesta Chicago Downtown

Downtown Chicago

Jordyn

฿7,008

฿9,405 total

includes taxes & fees

9 Nov - 10 Nov

A modern kitchen with a marble island, fruit bowls, and a city view.

A modern lounge area with a central bar, seating arrangements, and a decorative chandelier.

A modern bar area with a central bar, seating, and a distinctive ceiling design.

A modern hotel room with a city view, a seating area with two sofas and a coffee table, and a dining area with a table and chairs.

15. Fairmont Chicago at Millennium Park

Downtown Chicago

Ruby

฿8,521

฿11,327 total

includes taxes & fees

12 Nov - 13 Nov

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

A reception area with a modern design, including a reception desk, a decorative wall, and a display case with snacks.

16. Hyatt Place Chicago/Downtown - The Loop

Downtown Chicago

Cordula

฿7,108

฿8,451 total

includes taxes & fees

25 Oct - 26 Oct

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

A hotel room with two beds, a TV, a desk, and a window with a view.

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

A conference room with a long table, chairs, water bottles, and a large window.

17. Fairfield Inn & Suites Chicago Downtown/River North

Downtown Chicago

Cindy

฿5,532

฿6,578 total

includes taxes & fees

1 Nov - 2 Nov

An outdoor seating area with modern furniture and potted plants.

A corridor with a brick wall, hanging wicker light fixture, and potted plants.

A modern interior with a staircase, glass railings, and a visible restaurant area.

A modern hotel with a rooftop pool, surrounded by high-rise buildings and a clear view of the city skyline.

18. Radisson Blu Aqua Hotel Chicago

Downtown Chicago

Shannon

฿7,937

฿10,473 total

includes taxes & fees

31 Oct - 1 Nov

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

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.

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

19. Carleton of Oak Park

Oak Park

Brad

฿4,104

฿4,555 total

includes taxes & fees

13 Oct - 14 Oct

A modern building with a black facade and multiple windows. There is a sign for Hilton Garden Inn and a flagpole with flags.

A hotel room with two beds, a desk, a chair, a lamp, a TV, and a window with curtains.

A room with a red armchair, a window with a city view, and a wall-mounted air conditioner.

A bar area with a long counter, yellow bar stools, and a wine rack.

20. Hilton Garden Inn Chicago Downtown Riverwalk

Downtown Chicago

Brittney

฿5,471

฿6,505 total

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.

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

The Godfrey Hotel Chicago

10/10 Excellent

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

The Wade

10/10 Excellent

"Will definitely book again"

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

฿2,065

฿2,313 total

25 Oct - 26 Oct

includes taxes & fees

Red Roof Inn PLUS+ Chicago - Willowbrook

7535 Kingery Highway Willowbrook IL

฿2,707

฿3,032 total

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

฿3,052

฿3,586 total

1 Nov - 2 Nov

includes taxes & fees

SureStay Plus Hotel by Best Western Chicago Lombard

222 E 22nd Street Lombard IL

฿3,245

฿3,602 total

21 Oct - 22 Oct

includes taxes & fees

Hampton Inn Chicago Downtown/Magnificent Mile

160 E Huron Street Chicago IL

฿3,677

฿4,371 total

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

฿3,863

฿4,592 total

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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Book Hotels in Crestwood on Expedia.com

Find hotels in Crestwood, IL from ฿2,313

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. Hyatt Regency Chicago

4. Swissotel - Chicago

5. L7 Chicago by LOTTE

6. Hyatt Place Chicago/River North

7. LondonHouse Chicago, Curio Collection by Hilton

8. Hotel Riu Plaza Chicago

9. InterContinental Chicago Magnificent Mile by IHG

10. Embassy Suites by Hilton Chicago Downtown River North

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

12. Hilton Vacation Club Hotel Blake Chicago

13. citizenM Chicago Downtown

14. The Royal Sonesta Chicago Downtown

15. Fairmont Chicago at Millennium Park

16. Hyatt Place Chicago/Downtown - The Loop

17. Fairfield Inn & Suites Chicago Downtown/River North

18. Radisson Blu Aqua Hotel Chicago

19. Carleton of Oak Park

20. Hilton Garden Inn Chicago Downtown Riverwalk

Stay near popular Crestwood attractions

Hollywood Park

Learn more about Crestwood

Top Crestwood Hotel Reviews

The Godfrey Hotel Chicago

The Wade

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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