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

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

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

1. Holiday Inn Express Crestwood by IHG

Crestwood

Passion

S$185

includes taxes & fees

27 Sept - 28 Sept

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

A hotel room with a flat-screen TV, a round mirror, a wooden desk, a chair, and two beds.

A hotel reception area with a 'Treats' wall and a 'Welcome to Hampton' sign.

2. Hampton Inn Majestic Chicago Theatre District

Downtown Chicago

Richard

S$226

includes taxes & fees

8 Sept - 9 Sept

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 room with a checkered floor, two round tables, two armchairs, and a large window with a view of the outside.

A modern kitchen with a built-in refrigerator, a coffee maker, and a flat-screen TV on the countertop.

3. Fairfield Inn & Suites Chicago Downtown / Magnificent Mile

Downtown Chicago

Karaline

S$185

includes taxes & fees

7 Sept - 8 Sept

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.

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

A spacious bar area with a central bar, multiple seating options including bar stools and tables, and a well-lit ceiling with recessed lighting.

4. Congress Plaza Hotel

Downtown Chicago

Mia

S$160

includes taxes & fees

8 Sept - 9 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.

5. Hilton Vacation Club Hotel Blake Chicago

Downtown Chicago

Melanie

S$274

includes taxes & fees

1 Sept - 2 Sept

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

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

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

Downtown Chicago

Ashraf

S$299

includes taxes & fees

30 Aug - 31 Aug

A hotel lobby with a bar area, seating, and a large mirror.

A modern hotel lobby with seating areas, large windows, and a unique ceiling light fixture.

A modern hotel lobby with a staircase, seating area, and a shop.

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

7. Hilton Garden Inn Chicago Central Loop

Downtown Chicago

Theresa

S$236

includes taxes & fees

7 Sept - 8 Sept

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 living room with a sectional sofa, a fireplace, and a large window offering a city view.

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

8. Homewood Suites by Hilton Chicago Downtown South Loop

Downtown Chicago

AMBER

S$243

includes taxes & fees

7 Sept - 8 Sept

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

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.

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

9. Central Loop Hotel

Downtown Chicago

Yiyang

S$184

includes taxes & fees

30 Aug - 31 Aug

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

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

10. DoubleTree by Hilton Chicago - Magnificent Mile

Downtown Chicago

MAGALY

S$235

includes taxes & fees

30 Aug - 31 Aug

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

A modern bar area with seating and a bar counter.

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

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

11. La Quinta Inn & Suites by Wyndham Chicago Downtown

Downtown Chicago

Shilpa

S$212

includes taxes & fees

30 Aug - 31 Aug

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 cozy seating area with a round table and two chairs, a brick wall, and a window with a view of buildings.

A modern hotel lobby with a dark wood console, a large mirror, and a view of the city through large windows.

12. LIVN - West Loop Chicago

Downtown Chicago

Courtney

S$192

includes taxes & fees

30 Aug - 31 Aug

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 reception area with two desks, a large abstract wall art, and a view of the city through large windows.

A rooftop pool area with lounge chairs and a view of surrounding buildings.

13. Holiday Inn & Suites Chicago - Downtown by IHG

Downtown Chicago

Julenny

S$240

includes taxes & fees

7 Sept - 8 Sept

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 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.

14. Best Western Grant Park Hotel

Downtown Chicago

Diego

S$211

includes taxes & fees

1 Sept - 2 Sept

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

A dining table set for a meal with a floral centerpiece, surrounded by chairs, in a room with a cityscape view.

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.

15. Hilton Chicago/Magnificent Mile Suites

Downtown Chicago

susie

S$240

includes taxes & fees

1 Sept - 2 Sept

A multi-story building with a Starbucks Coffee on the ground floor, emergency exit signs, and a Hyatt Center sign.

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.

A bar area with a modern design, featuring a long counter and multiple seating options.

16. Hyatt Centric Chicago Magnificent Mile

Downtown Chicago

Sara

S$307

includes taxes & fees

7 Sept - 8 Sept

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.

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

17. Embassy Suites by Hilton Chicago Downtown Magnificent Mile

Downtown Chicago

Rajiv

S$277

includes taxes & fees

1 Sept - 2 Sept

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

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

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.

18. Hampton Inn Chicago Downtown/Magnificent Mile

Downtown Chicago

Kimberly

S$224

includes taxes & fees

7 Sept - 8 Sept

A restaurant interior with brick walls, wooden tables and chairs, and a bar area.

A bar with a brick archway, wooden bar counter, and stools.

19. Club Quarters Hotel, Central Loop, Chicago

Downtown Chicago

Youssef

S$200

includes taxes & fees

30 Aug - 31 Aug

A hotel room with a red sofa, a small table, and a view of city buildings through large windows.

A corner market with refrigerated display cases and shelves stocked with snacks and beverages.

A Marriott Fairfield Inn & Suites building facade with large windows and a prominent signage.

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

20. Fairfield Inn & Suites Chicago Downtown/River North

Downtown Chicago

Cindy

S$234

includes taxes & fees

7 Sept - 8 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.

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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

Fairmont Chicago at Millennium Park

10/10 Excellent

"They were so accommodating. I thoroughly enjoyed the stay."

L7 Chicago by LOTTE

10/10 Excellent

"clean and new"

The Chicago Hotel Collection - Magnificent Mile

10/10 Excellent

"Solid"

River Hotel

10/10 Excellent

"Convenient location near the CTA redline"

The Chicago Hotel Collection Ambassador Gold Coast

10/10 Excellent

"😁"

Holiday Inn Chicago Dwtn - The Mart by IHG

10/10 Excellent

"This was one of my favorite stays in Chicago. The rooms are clean, they have a coffee shop and full bar available and the staff was super helpful and friendly. The pool was okay. I would’ve wished for it to be outdoors but my little one loved it no matter what. Breakfast, great. Couldn’t have asked for anything more."

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 Wade

10/10 Excellent

"Good stay, great location"

More cheap stays in Crestwood

Red Roof Inn PLUS+ Chicago - Willowbrook

7535 Kingery Highway Willowbrook IL

S$90

9 Sept - 10 Sept

includes taxes & fees

6.4/10 (1,250 reviews)

Quality Inn & Suites Orland Park - Chicago

8800 W 159th St Orland Park IL

S$120

20 Sept - 21 Sept

includes taxes & fees

Sleep Inn Midway Airport Bedford Park

6650 S Cicero Ave Chicago IL

S$172

22 Sept - 23 Sept

includes taxes & fees

Travelodge by Wyndham Downtown Chicago

65 E Harrison St Chicago IL

S$175

30 Aug - 31 Aug

includes taxes & fees

7.6/10 Good! (2,795 reviews)

Holiday Inn Chicago – Midway Airport S by IHG

7353 S Cicero Avenue Chicago IL

S$183

9 Sept - 10 Sept

includes taxes & fees

Hampton Inn Chicago Downtown/Magnificent Mile

160 E Huron Street Chicago IL

S$224

7 Sept - 8 Sept

includes taxes & fees

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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Things to do in Countryside

Crestwood Hotels from S$90

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. Hampton Inn Majestic Chicago Theatre District

3. Fairfield Inn & Suites Chicago Downtown / Magnificent Mile

4. Congress Plaza Hotel

5. Hilton Vacation Club Hotel Blake Chicago

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

7. Hilton Garden Inn Chicago Central Loop

8. Homewood Suites by Hilton Chicago Downtown South Loop

9. Central Loop Hotel

10. DoubleTree by Hilton Chicago - Magnificent Mile

11. La Quinta Inn & Suites by Wyndham Chicago Downtown

12. LIVN - West Loop Chicago

13. Holiday Inn & Suites Chicago - Downtown by IHG

14. Best Western Grant Park Hotel

15. Hilton Chicago/Magnificent Mile Suites

16. Hyatt Centric Chicago Magnificent Mile

17. Embassy Suites by Hilton Chicago Downtown Magnificent Mile

18. Hampton Inn Chicago Downtown/Magnificent Mile

19. Club Quarters Hotel, Central Loop, Chicago

20. Fairfield Inn & Suites Chicago Downtown/River North

Stay near popular Crestwood attractions

Hollywood Park

Learn more about Crestwood

Top Crestwood Hotel Reviews

Fairmont Chicago at Millennium Park

L7 Chicago by LOTTE

The Chicago Hotel Collection - Magnificent Mile

River Hotel

The Chicago Hotel Collection Ambassador Gold Coast

Holiday Inn Chicago Dwtn - The Mart by IHG

Hyatt Regency McCormick Place Chicago

The Wade

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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