Crestwood Holiday Rentals, Chicago: Private House Rentals

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

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Go beyond your typical stay in Crestwood

Pet friendly

Pool

Apartment

Apart hotel

Hot tub

Spa

Family friendly

Condo

Waterpark

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Our top choices for Crestwood hotels

1. Holiday Inn Express Crestwood by IHG

Crestwood

Juanita

3.390.140 ₫

3.796.279 ₫ total

includes taxes & fees

29 Sept - 30 Sept

2. Hyatt Place Chicago/Downtown - The Loop

Downtown Chicago

LISA

4.407.182 ₫

5.239.698 ₫ total

includes taxes & fees

7 Sept - 8 Sept

Room, 1 King Bed with Sofa bed, Non Smoking, Corner (Panoramic City View)

3. La Quinta Inn & Suites by Wyndham Chicago Downtown

Downtown Chicago

Shilpa

4.013.665 ₫

5.236.816 ₫ total

includes taxes & fees

7 Sept - 8 Sept

4. DoubleTree by Hilton Chicago - Magnificent Mile

Downtown Chicago

MAGALY

4.142.751 ₫

4.925.317 ₫ total

includes taxes & fees

1 Sept - 2 Sept

5. Hilton Vacation Club Hotel Blake Chicago

Downtown Chicago

Melanie

4.731.592 ₫

5.625.390 ₫ total

includes taxes & fees

1 Sept - 2 Sept

6. River Hotel

Downtown Chicago

Meri

3.588.072 ₫

4.265.839 ₫ total

includes taxes & fees

10 Sept - 11 Sept

7. L7 Chicago by LOTTE

Downtown Chicago

Girivasan

6.738.295 ₫

8.011.161 ₫ total

includes taxes & fees

20 Sept - 21 Sept

8. Embassy Suites by Hilton Chicago Downtown Magnificent Mile

Downtown Chicago

Rajiv

4.278.096 ₫

5.851.617 ₫ total

includes taxes & fees

9 Sept - 10 Sept

9. Fairfield Inn & Suites Chicago Downtown / Magnificent Mile

Downtown Chicago

Karaline

3.195.859 ₫

3.799.556 ₫ total

includes taxes & fees

7 Sept - 8 Sept

10. Hotel Riu Plaza Chicago

Downtown Chicago

Peter

4.579.643 ₫

6.187.961 ₫ total

includes taxes & fees

7 Sept - 8 Sept

11. Sonesta ES Suites Chicago Downtown Magnificent Mile - Medical

Downtown Chicago

Julia

4.089.030 ₫

4.861.448 ₫ total

includes taxes & fees

7 Sept - 8 Sept

12. Hyatt Place Chicago/River North

Downtown Chicago

Shoma

4.433.260 ₫

5.270.702 ₫ total

includes taxes & fees

7 Sept - 8 Sept

13. Hilton Garden Inn Chicago Downtown Riverwalk

Downtown Chicago

Daniel

4.255.408 ₫

5.059.254 ₫ total

includes taxes & fees

8 Sept - 9 Sept

Suite, 1 Bedroom, Corner | Private kitchen

14. Homewood Suites by Hilton Chicago Downtown South Loop

Downtown Chicago

AMBER

4.189.431 ₫

4.980.813 ₫ total

includes taxes & fees

7 Sept - 8 Sept

15. Silversmith Hotel Chicago Downtown

Downtown Chicago

Xiao

3.521.803 ₫

4.982.971 ₫ total

includes taxes & fees

7 Sept - 8 Sept

16. Aloft by Marriott Chicago Mag Mile

Downtown Chicago

Odessia

4.016.012 ₫

4.774.636 ₫ total

includes taxes & fees

7 Sept - 8 Sept

17. Hyatt Centric The Loop Chicago

Downtown Chicago

Tamika

6.232.642 ₫

8.062.796 ₫ total

includes taxes & fees

7 Sept - 8 Sept

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

Downtown Chicago

Leonela

6.019.953 ₫

8.205.172 ₫ total

includes taxes & fees

13 Sept - 14 Sept

19. Embassy Suites by Hilton Chicago Downtown River North

Downtown Chicago

Hugo

3.967.768 ₫

4.717.279 ₫ total

includes taxes & fees

7 Sept - 8 Sept

20. The Royal Sonesta Chicago River North

Downtown Chicago

Tiffany

5.528.536 ₫

7.407.761 ₫ total

includes taxes & fees

31 Aug - 1 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

River Hotel

10/10 Excellent

"Room was very clean and perfect for my needs. Check in and check out was so convenient and the staff was helpful when I needed to ask a question. The manager was so lovely and friendly, and the staff who assisted me at check in greeted me right away and was so personable, I believe his name was Pedro. Had an excellent experience overall and the location was very central to the things I wanted to do in the downtown area!"

Fairmont Chicago at Millennium Park

10/10 Excellent

"Room was clean. Staff were exceptional. Didn’t catch the breakfast or bar"

Club Quarters Hotel, Central Loop, Chicago

8/10 Good

"We had a Nespresso machine in our room, but we didn't use it because the water vessel looked molded. I think the layout of the room could have been better. There was no end table for one side of the bed. the bathroom counter was not much of a counter. The highlight of the stay was the staff, specifically Adrian at the front desk. She gave us specific instructions about parking and when to scan our pass. She was so sweet and made us feel extremely welcome and called us her babies. We love Adrian soooo much."

Travelodge by Wyndham Downtown Chicago

10/10 Excellent

"The hotel was a bit older but had an excellent stay! Spacious rooms and cold ac. I would say the water isn't super hot if you're showering after someone but that isn't a deal breaker and it wasn't uncomfortable. Stayed here for a BTS show in Soldier Field and it was in a great location. Would stay here again for sure."

InterContinental Chicago Magnificent Mile by IHG

10/10 Excellent

"Would have liked to have been informed that the pool would be closed during our stay for renovations"

Eurostars Magnificent Mile

10/10 Excellent

"An amazing view paired with the very best customer service I heve received in years made our experience top notch!"

Holiday Inn Chicago Dwtn - The Mart by IHG

8/10 Good

"Had a great stay! It was comfy and had a wonderful view."

The Wade

8/10 Good

"Great location, grew views of the lake, beds were comfortable"

Kasa Magnificent Mile Chicago

8/10 Good

"Check in can be slightly confusing however you get the hang of it quickly. It was close to many amenities, a train away or a longer walk. The loft was cleaning than most however there was still dust and some crumbs left behind. Over all we were pleased with our stay even though very pricey for 3 nights"

More cheap stays in Crestwood

Red Roof Inn PLUS+ Chicago - Willowbrook

7535 Kingery Highway Willowbrook IL

1.640.306 ₫

1.836.814 ₫ total

6 Sept - 7 Sept

includes taxes & fees

Quality Inn & Suites Orland Park - Chicago

8800 W 159th St Orland Park IL

2.173.341 ₫

2.433.707 ₫ total

27 Sept - 28 Sept

includes taxes & fees

Sleep Inn Midway Airport Bedford Park

6650 S Cicero Ave Chicago IL

2.972.501 ₫

3.492.094 ₫ total

27 Sept - 28 Sept

includes taxes & fees

8/10 Very good! (2,089 reviews)

Travelodge by Wyndham Downtown Chicago

65 E Harrison St Chicago IL

3.051.126 ₫

3.627.485 ₫ total

31 Aug - 1 Sept

includes taxes & fees

7.6/10 Good! (2,809 reviews)

Holiday Inn Chicago – Midway Airport S by IHG

7353 S Cicero Avenue Chicago IL

3.311.906 ₫

4.148.625 ₫ total

8 Sept - 9 Sept

includes taxes & fees

8.2/10 Very good! (1,012 reviews)

Hampton Inn Chicago Downtown/Magnificent Mile

160 E Huron Street Chicago IL

4.189.431 ₫

4.980.815 ₫ total

8 Sept - 9 Sept

includes taxes & fees

Hotels in Crestwood with star rating

Frequently asked questions

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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Find hotels in Crestwood, IL from 1.836.814 ₫

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Treat yourself

Be picky

Go beyond your typical stay in Crestwood

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Our top choices for Crestwood hotels

1. Holiday Inn Express Crestwood by IHG

2. Hyatt Place Chicago/Downtown - The Loop

3. La Quinta Inn & Suites by Wyndham Chicago Downtown

4. DoubleTree by Hilton Chicago - Magnificent Mile

5. Hilton Vacation Club Hotel Blake Chicago

6. River Hotel

7. L7 Chicago by LOTTE

8. Embassy Suites by Hilton Chicago Downtown Magnificent Mile

9. Fairfield Inn & Suites Chicago Downtown / Magnificent Mile

10. Hotel Riu Plaza Chicago

11. Sonesta ES Suites Chicago Downtown Magnificent Mile - Medical

12. Hyatt Place Chicago/River North

13. Hilton Garden Inn Chicago Downtown Riverwalk

14. Homewood Suites by Hilton Chicago Downtown South Loop

15. Silversmith Hotel Chicago Downtown

16. Aloft by Marriott Chicago Mag Mile

17. Hyatt Centric The Loop Chicago

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

19. Embassy Suites by Hilton Chicago Downtown River North

20. The Royal Sonesta Chicago River North

Stay near popular Crestwood attractions

Hollywood Park

Learn more about Crestwood

Top Crestwood Hotel Reviews

River Hotel

Fairmont Chicago at Millennium Park

Club Quarters Hotel, Central Loop, Chicago

Travelodge by Wyndham Downtown Chicago

InterContinental Chicago Magnificent Mile by IHG

Eurostars Magnificent Mile

Holiday Inn Chicago Dwtn - The Mart by IHG

The Wade

Kasa Magnificent Mile 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

Hotels in Crestwood with star rating

Frequently asked questions

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