Title: Crestwood Vacation Rentals from CA $134: Short-Term Rentals for 2025 | Expedia.ca

  

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# Crestwood Vacation Rentals

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## Check prices for these dates

Tonight

[Oct 19 - Oct 20](https://www.expedia.ca/Hotel-Search?regionId=6960&startDate=2025-10-19&endDate=2025-10-20&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

Tomorrow

[Oct 20 - Oct 21](https://www.expedia.ca/Hotel-Search?regionId=6960&startDate=2025-10-20&endDate=2025-10-21&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

Next weekend

[Oct 24 - Oct 26](https://www.expedia.ca/Hotel-Search?regionId=6960&startDate=2025-10-24&endDate=2025-10-26&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In two weeks

[Oct 31 - Nov 2](https://www.expedia.ca/Hotel-Search?regionId=6960&startDate=2025-10-31&endDate=2025-11-02&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

## Vacation Rentals in Crestwood

![Indoor pool](https://images.trvl-media.com/lodging/77000000/76270000/76267500/76267438/a9b3121a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lounge](https://images.trvl-media.com/lodging/77000000/76270000/76267500/76267438/eacd6d88.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Garden](https://images.trvl-media.com/lodging/77000000/76270000/76267500/76267438/ccaab668.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Studio, 1 Queen Bed (Studio Apartment) | Private kitchen](https://images.trvl-media.com/lodging/77000000/76270000/76267500/76267438/1bf06d5d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Sentral Michigan Avenue

Downtown Chicago

9.2/10

Wonderful

(961)

"Loved my stay! Staff was amazing and the apartment had everything to make you feel like home. "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Nicole

CA $189

CA $264 total

includes taxes & fees

Nov 10 - Nov 11

[](https://www.expedia.ca/Chicago-Hotels-Sentral-Michigan-Avenue.h76267438.Hotel-Information)

![Front of property - evening/night](https://images.trvl-media.com/lodging/40000000/39810000/39805900/39805843/8a983359.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/40000000/39810000/39805900/39805843/a7a120b4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Deluxe Room, 1 Single Bed, City View | Living area](https://images.trvl-media.com/lodging/40000000/39810000/39805900/39805843/f7ca0ea3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Seasonal outdoor pool, open 7:00 AM to 10:00 PM, pool umbrellas](https://images.trvl-media.com/lodging/40000000/39810000/39805900/39805843/cb208a99.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Level Chicago – Old Town

Downtown Chicago

9.0/10

Wonderful

(368)

"Friendly staff and great amenities "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Bryan

CA $216

CA $284 total

includes taxes & fees

Nov 3 - Nov 4

[](https://www.expedia.ca/Chicago-Hotels-LEVEL-Furnished-Living-Chicago.h39805843.Hotel-Information)

![Lobby](https://images.trvl-media.com/lodging/99000000/98590000/98589700/98589620/038aeb00.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![2 bedrooms, premium bedding, individually decorated](https://images.trvl-media.com/lodging/99000000/98590000/98589700/98589620/d277fc7f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![50-inch flat-screen TV with digital channels, streaming services](https://images.trvl-media.com/lodging/99000000/98590000/98589700/98589620/3c77060f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![2 bedrooms, premium bedding, individually decorated](https://images.trvl-media.com/lodging/99000000/98590000/98589700/98589620/a33c4e00.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Sonder by Marriott Bonvoy The Burnham Apartments Loop

Downtown Chicago

8.8/10

Excellent

(241)

"Great stay. "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Teresa

CA $189

CA $222 total

includes taxes & fees

Nov 2 - Nov 3

[](https://www.expedia.ca/Chicago-Hotels-Sonder-The-Burnham.h98589620.Hotel-Information)

![1 bedroom, individually decorated, individually furnished, desk](https://images.trvl-media.com/lodging/92000000/91690000/91683200/91683158/e3b8d058.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby lounge](https://images.trvl-media.com/lodging/92000000/91690000/91683200/91683158/593f3c13.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![50-inch flat-screen TV with digital channels, TV, streaming services](https://images.trvl-media.com/lodging/92000000/91690000/91683200/91683158/a9095b05.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Full-size fridge, electric kettle, cookware/dishes/utensils](https://images.trvl-media.com/lodging/92000000/91690000/91683200/91683158/a5314f63.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Sonder by Marriott Bonvoy Market Hall Apartments West Loop

Downtown Chicago

8.0/10

Very good

(385)

"Great stay!"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Joe

CA $154

CA $180 total

includes taxes & fees

Nov 2 - Nov 3

[](https://www.expedia.ca/Sonder-Market-Hall.h91683158.Hotel-Information)

![50-inch flat-screen TV with digital channels, TV](https://images.trvl-media.com/lodging/65000000/64880000/64871100/64871080/d10a452f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![2 bedrooms, individually decorated, individually furnished](https://images.trvl-media.com/lodging/65000000/64880000/64871100/64871080/e0b5e4c8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![50-inch flat-screen TV with digital channels, TV](https://images.trvl-media.com/lodging/65000000/64880000/64871100/64871080/851ef6de.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![2 bedrooms, individually decorated, individually furnished](https://images.trvl-media.com/lodging/65000000/64880000/64871100/64871080/dac97393.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Sonder by Marriott Bonvoy Jewelers Row Apartments Millenium Park

Downtown Chicago

8.2/10

Very good

(184)

"Place was amazing! Very centralized, all sorts of restaurants nearby, and right next to the CTA Trains which is AWESOME!"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Alexander

CA $166

CA $194 total

includes taxes & fees

Nov 2 - Nov 3

[](https://www.expedia.ca/Chicago-Hotels-Sonder-At-Jewelers-Row.h64871080.Hotel-Information)

![Business centre](https://images.trvl-media.com/lodging/67000000/66430000/66425400/66425311/825d44e9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lounge](https://images.trvl-media.com/lodging/67000000/66430000/66425400/66425311/0480d64e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Cafe](https://images.trvl-media.com/lodging/67000000/66430000/66425400/66425311/715d8399.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby sitting area](https://images.trvl-media.com/lodging/67000000/66430000/66425400/66425311/f7e5c565_edited_04eb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Kasa River North Chicago

Downtown Chicago

9.6/10

Exceptional

(171)

"This place has everything for a multi-night stay."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Dane

CA $223

CA $394 total

includes taxes & fees

Oct 27 - Oct 28

[](https://www.expedia.ca/Chicago-Hotels-Kasa-River-North-Chicago.h66425311.Hotel-Information)

![1 bedroom, individually furnished, desk, iron/ironing board](https://images.trvl-media.com/lodging/84000000/83700000/83695900/83695822/112ab7b7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, individually furnished, desk, iron/ironing board](https://images.trvl-media.com/lodging/84000000/83700000/83695900/83695822/de34b3e9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, individually furnished, desk, iron/ironing board](https://images.trvl-media.com/lodging/84000000/83700000/83695900/83695822/5077246b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![View from property](https://images.trvl-media.com/lodging/84000000/83700000/83695900/83695822/83373d31.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Sonder by Marriott Bonvoy The Opal Apartments River North

Downtown Chicago

8.4/10

Very good

(53)

"Place was in a great location close to good restaurants "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Charles

CA $178

CA $208 total

includes taxes & fees

Nov 16 - Nov 17

[](https://www.expedia.ca/Chicago-Hotels-Sonder-The-Opal.h83695822.Hotel-Information)

![Apartment, 1 Bedroom | Living room](https://images.trvl-media.com/lodging/42000000/41970000/41963600/41963526/1687c774.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property amenity](https://images.trvl-media.com/lodging/42000000/41970000/41963600/41963526/3e40aa77.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Full-size fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/42000000/41970000/41963600/41963526/26c37847.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Apartment, 3 Bedrooms](https://images.trvl-media.com/lodging/42000000/41970000/41963600/41963526/4dde9143.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Sonder by Marriott Bonvoy Greektown Apartments

Downtown Chicago

8.6/10

Excellent

(65)

"The kitchen had everything we needed, great space overall, safe location, clean, near everything we needed, access to bus and rail very close, we really enjoyed our stay. "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Samuel

CA $189

CA $222 total

includes taxes & fees

Nov 2 - Nov 3

[](https://www.expedia.ca/Chicago-Hotels-Sonder-Greektown-Suites.h41963526.Hotel-Information)

![Interior](https://images.trvl-media.com/lodging/117000000/116800000/116793200/116793104/e4126779.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, offices](https://images.trvl-media.com/lodging/117000000/116800000/116793200/116793104/964f82ea.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![2 bedrooms, iron/ironing board, travel crib, WiFi](https://images.trvl-media.com/lodging/117000000/116800000/116793200/116793104/53fb8853.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Shower, hair dryer, towels](https://images.trvl-media.com/lodging/117000000/116800000/116793200/116793104/61009377.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Twice as Nice: Chic 2BR Stay with Style & Space

Downtown Chicago

9.4/10

Exceptional

(9)

"Had a very nice time in Chicago!"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Valerie S.

CA $137

CA $315 total

includes taxes & fees

Oct 20 - Oct 21

[](https://www.expedia.ca/Chicago-Hotels-Twice-As-Nice-Chic-2BR-Stay-With-Style-Space.h116793104.Hotel-Information)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/117000000/116800000/116793200/116793110/50bbce16.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, desk, iron/ironing board, travel crib](https://images.trvl-media.com/lodging/117000000/116800000/116793200/116793110/640a9e62.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Shower, hair dryer, towels](https://images.trvl-media.com/lodging/117000000/116800000/116793200/116793110/31d1cbc1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/117000000/116800000/116793200/116793110/3815ff36.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The One: A 1BR Stay That Feels Like Home

Downtown Chicago

9.0/10

Wonderful

(2)

"Very nice condo in a quiet neighborhood"

![Canada](https://a.travel-assets.com/egds/marks/flags/ca.svg)

Patrick

CA $129

CA $284 total

includes taxes & fees

Oct 23 - Oct 24

[](https://www.expedia.ca/Chicago-Hotels-All-Set-Up-Furnished-1BR-Unit.h116793110.Hotel-Information)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/118000000/117720000/117712600/117712527/2d716375.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior detail](https://images.trvl-media.com/lodging/118000000/117720000/117712600/117712527/c67cddf3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, offices](https://images.trvl-media.com/lodging/118000000/117720000/117712600/117712527/d2dd93c1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/118000000/117720000/117712600/117712527/4b557c1b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### River North Rooftop With In and Out Parking 1

Downtown Chicago

10/10

Exceptional

(1)

"Awesome location, great place would definitely recommend will hopefully return"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

lucas c.

CA $143

CA $438 total

includes taxes & fees

Nov 19 - Nov 20

[](https://www.expedia.ca/Chicago-Hotels-River-North-Rooftop-With-In-Out-Parking-1.h117712527.Hotel-Information)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/117000000/116800000/116793100/116793043/3cc0a9a4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Shower, hair dryer, towels](https://images.trvl-media.com/lodging/117000000/116800000/116793100/116793043/89a0d93e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV](https://images.trvl-media.com/lodging/117000000/116800000/116793100/116793043/9b704ea8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/117000000/116800000/116793100/116793043/f642030c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Stylish 1BR in West Loop

Downtown Chicago

10/10

Exceptional

(6)

"We stayed for 4th of July weekend and had a wonderful time. Property is close to coffee shops, book stores, and within walking distance of nice restaurants. Easy paid parking nearby. The apartment was clean and everything we needed"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Jacob D.

CA $129

CA $284 total

includes taxes & fees

Oct 26 - Oct 27

[](https://www.expedia.ca/Chicago-Hotels-Stylish-1BR-In-West-Loop.h116793043.Hotel-Information)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/117000000/116800000/116793000/116792936/a49da56a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, offices](https://images.trvl-media.com/lodging/117000000/116800000/116793000/116792936/c3fddccc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Shower, hair dryer](https://images.trvl-media.com/lodging/117000000/116800000/116793000/116792936/6b9648de.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/117000000/116800000/116793000/116792936/93c17f93.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Sun-Drenched 1BR Apartment

Downtown Chicago

10/10

Exceptional

(1)

"The location was fantastic. We were just a couple blocks from the Green and Pink line on Clinton. There was a code to get into the building so it felt safe. The code to the door was great because there was no key to worry about since I had to work and my hubby was in and out of the apartment all day. There were a couple small things, the bed squeaks a lot. Also, it is very clear in the listing that the train is close. It is about 30ft straight out from the window. I'm not a light sleeper so I...

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Jennifer A.

CA $129

CA $284 total

includes taxes & fees

Oct 20 - Oct 21

[](https://www.expedia.ca/Chicago-Hotels-Sun-Drenched-1BR-Apartment.h116792936.Hotel-Information)

![Interior](https://images.trvl-media.com/lodging/96000000/95660000/95650200/95650151/71dd56c1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![2 bedrooms, desk, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/96000000/95660000/95650200/95650151/a2bfe582.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/96000000/95660000/95650200/95650151/786103ef.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/96000000/95660000/95650200/95650151/f52d9a12.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Your Chicago get Away

Downtown Chicago

8.4/10

Very good

(6)

"Clean, fun space and responsive host! Loved the views from our room!"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Tyler C.

CA $318

CA $637 total

includes taxes & fees

Oct 23 - Oct 24

[](https://www.expedia.ca/Chicago-Hotels-Your-Chicago-Get-Away.h95650151.Hotel-Information)

![Studio | Private kitchen](https://images.trvl-media.com/lodging/89000000/88910000/88902500/88902456/42e169d8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Studio | Interior](https://images.trvl-media.com/lodging/89000000/88910000/88902500/88902456/caa9b8f8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/89000000/88910000/88902500/88902456/352bc027.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Studio | Private kitchen](https://images.trvl-media.com/lodging/89000000/88910000/88902500/88902456/5b7f8474.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### River West, Third Floor Chicago by 747 Lofts

West Town

9.0/10

Wonderful

(17)

"Overall solid property, I will return."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Fletcher

CA $124

CA $243 total

includes taxes & fees

Oct 23 - Oct 24

[](https://www.expedia.ca/Chicago-Hotels-The-Perfect-Home-Away-From-Home-For-Your-Romantic-Urban-Getaway-747-Lofts-Cabin-307-Hotel-Room.h88902456.Hotel-Information)

![Private kitchen](https://images.trvl-media.com/lodging/117000000/116030000/116024600/116024537/4dadbd09.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/117000000/116030000/116024600/116024537/acc0487e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![3 bedrooms, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/117000000/116030000/116024600/116024537/fe7fd7f8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Shower, hair dryer, towels, soap](https://images.trvl-media.com/lodging/117000000/116030000/116024600/116024537/92ec7bf2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Spacious 3-bedroom apartment near downtown, FREE PARKING

Near West Side

9.4/10

Exceptional

(8)

"Nice place to stay. Good communication with the owner."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Ryan

CA $81

CA $467 total

includes taxes & fees

Oct 20 - Oct 21

[](https://www.expedia.ca/Chicago-Hotels-Spacious-3-Bedroom-Apartment-Near-Downtown.h116024537.Hotel-Information)

![Interior](https://images.trvl-media.com/lodging/118000000/117720000/117712600/117712513/13a40e63.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Shower, hair dryer, towels](https://images.trvl-media.com/lodging/118000000/117720000/117712600/117712513/ae9157a8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/118000000/117720000/117712600/117712513/d85cd592.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![2 bedrooms, desk, iron/ironing board, travel crib](https://images.trvl-media.com/lodging/118000000/117720000/117712600/117712513/290cff2c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### South Loop Rooftop With In & Out Parking 1

Downtown Chicago

9.0/10

Wonderful

(2)

"We loved the property! It was well kept, clean, with a seamless check in and check out process! I wish the parking garage would have been closer but otherwise everything was great! Shout out to the host for his promptness with all my questions! I would recommend this place if they are looking for a place to stay! "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Bridney K.

CA $210

CA $527 total

includes taxes & fees

Oct 26 - Oct 27

[](https://www.expedia.ca/Chicago-Hotels-South-Loop-Rooftop-With-In-Out-Parking.h117712513.Hotel-Information)

![Desk, iron/ironing board, travel crib, WiFi](https://images.trvl-media.com/lodging/121000000/120510000/120508900/120508888/bdb082e7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, offices](https://images.trvl-media.com/lodging/121000000/120510000/120508900/120508888/f72f6088.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Microwave, oven, stovetop, coffee/tea maker](https://images.trvl-media.com/lodging/121000000/120510000/120508900/120508888/eab5965a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Microwave, oven, stovetop, coffee/tea maker](https://images.trvl-media.com/lodging/121000000/120510000/120508900/120508888/8c33e770.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Cozy Gold Coast Studio Stay

Downtown Chicago

10/10

Exceptional

(1)

"The communication was really effective and made for a smooth check in and check out process. Host was friendly and made great recommendations, 10/10 would stay again!"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Seynabou

CA $129

CA $270 total

includes taxes & fees

Oct 26 - Oct 27

[](https://www.expedia.ca/Chicago-Hotels-Cozy-Gold-Coast-Studio-Stay.h120508888.Hotel-Information)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/118000000/117720000/117712600/117712536/73f1c663.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![2 bedrooms, desk, iron/ironing board, WiFi](https://images.trvl-media.com/lodging/118000000/117720000/117712600/117712536/5da8154a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/118000000/117720000/117712600/117712536/bd271405.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/118000000/117720000/117712600/117712536/360842b7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### River North Rooftop With In and Out Parking 5

Downtown Chicago

10/10

Exceptional

(2)

"Everything was amazing, property was even better than expected"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Jacob

CA $186

CA $487 total

includes taxes & fees

Oct 29 - Oct 30

[](https://www.expedia.ca/Chicago-Hotels-River-North-Rooftop-With-In-Out-Parking-5.h117712536.Hotel-Information)

![1 bedroom, WiFi, bed sheets](https://images.trvl-media.com/lodging/120000000/119140000/119131900/119131871/adbf623a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/120000000/119140000/119131900/119131871/2e28ea21.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV](https://images.trvl-media.com/lodging/120000000/119140000/119131900/119131871/96789a75.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Shower, hair dryer, towels](https://images.trvl-media.com/lodging/120000000/119140000/119131900/119131871/fe11ac9c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### 1BR Modern Luxe Apt with In-Unit Laundry

Downtown Chicago

CA $129

CA $284 total

includes taxes & fees

Oct 21 - Oct 22

[](https://www.expedia.ca/Chicago-Hotels-1BR-Modern-Luxe-Apt-With-In-Unit-Laundry.h119131871.Hotel-Information)

Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

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## Top Crestwood Hotel Reviews

![Congress Plaza Hotel](//images.trvl-media.com/lodging/1000000/10000/6500/6452/a9ee91b7_y.jpg)

### Congress Plaza Hotel

10/10 Excellent

"Everything was great."

[](https://expedia.ca/Chicago-Hotels-Congress-Plaza-Hotel.h6452.Hotel-Information)

![Hilton Chicago/Magnificent Mile Suites](//images.trvl-media.com/lodging/1000000/20000/18600/18514/f21f6764_y.jpg)

### Hilton Chicago/Magnificent Mile Suites

10/10 Excellent

"Every think was wonderful except the heater wasn’t working and the toilet was loose."

[](https://expedia.ca/Chicago-Hotels-Hilton-ChicagoMagnificent-Mile-Suites.h18514.Hotel-Information)

![Embassy Suites by Hilton Chicago Downtown River North](//images.trvl-media.com/lodging/1000000/20000/11600/11580/w3840h2859x0y0-5fc518eb_y.jpg)

### Embassy Suites by Hilton Chicago Downtown River North

10/10 Excellent

"Friendly staff and very accommodating. "

[](https://expedia.ca/Chicago-Hotels-Embassy-Suites-Chicago-Downtown.h11580.Hotel-Information)

![Hilton Chicago](//images.trvl-media.com/lodging/1000000/20000/12600/12570/274f52b9_y.jpg)

### Hilton Chicago

10/10 Excellent

"."

[](https://expedia.ca/Chicago-Hotels-Hilton-Chicago.h12570.Hotel-Information)

![Sonesta ES Suites Chicago Downtown Magnificent Mile - Medical](//images.trvl-media.com/lodging/1000000/30000/26000/25929/4e2c019f_y.jpg)

### Sonesta ES Suites Chicago Downtown Magnificent Mile - Medical

10/10 Excellent

"Love this hotel! Love that they come with a kitche, its like a mini apt, would def stay there again "

[](https://expedia.ca/Chicago-Hotels-Sonesta-ES-Suites-Chicago-Downtown.h25929.Hotel-Information)

![Warwick Allerton - Chicago](//images.trvl-media.com/lodging/1000000/30000/25500/25452/w1261h711x0y1-96bd53d1_y.jpg)

### Warwick Allerton - Chicago

10/10 Excellent

"The area was amazing "

[](https://expedia.ca/Chicago-Hotels-Warwick-Allerton-Chicago.h25452.Hotel-Information)

![The Allegro Royal Sonesta Hotel Chicago Loop](//images.trvl-media.com/lodging/1000000/40000/34500/34496/69c2e798_y.jpg)

### The Allegro Royal Sonesta Hotel Chicago Loop

10/10 Excellent

"Great room with unique character and very helpful friendly staff"

[](https://expedia.ca/Chicago-Hotels-The-Allegro-Royal-Sonesta-Hotel.h34496.Hotel-Information)

![Sable at Navy Pier Chicago, Curio Collection by Hilton](//images.trvl-media.com/lodging/58000000/57660000/57651200/57651125/6c1738b5_y.jpg)

### Sable at Navy Pier Chicago, Curio Collection by Hilton

10/10 Excellent

"Beautiful view of the city and Lake Michigan. The room was clean and modern. Staff was personable and made sure the stay was welcoming and inviting."

[](https://expedia.ca/Chicago-Hotels-Sable-At-Navy-Pier-Chicago.h57651125.Hotel-Information)

![The Royal Sonesta Chicago Downtown](//images.trvl-media.com/lodging/1000000/20000/17600/17543/696a55e6_y.jpg)

### The Royal Sonesta Chicago Downtown

10/10 Excellent

"Great location. Walkable to many popular attractions. "

[](https://expedia.ca/Chicago-Hotels-Royal-Sonesta-Chicago-Downtown.h17543.Hotel-Information)

## Find out more about Crestwood

**Everything you need to know about** **Crestwood** **vacation rentals**

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Crestwood vacation rental for you. At Expedia, you can take your pick from [private vacation homes](https://www.expedia.ca/aa/PrivateVacationHomes), [apartments](https://www.expedia.ca/aa/Apartments), cottages, [cabins](https://www.expedia.ca/aa/Cabins), villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Crestwood vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

**Crestwood vacation rentals: An excellent choice for every season**

Whenever you want to travel, a warm welcome awaits you in Crestwood. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Crestwood vacation rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Crestwood vacation rentals we have selected for you start as low as CA $134 per night. Entering your travel dates in the search wizard you might find even better deals!

**How to find incredible deals on Crestwood rentals**

At Expedia, we put the best Crestwood vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Crestwood rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Crestwood vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Crestwood. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

## Explore a world of travel with Expedia

-   Trending destinations on Expedia.ca
-   All accommodation types in Crestwood

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-   [Québec Vacation Rentals](https://www.expedia.ca/Quebec-Vacation-Rentals.d180017.Travel-Guide-VacationRentals)

-   [Apartments in Crestwood](https://expedia.ca/Crestwood-Apartments.d6960-aaApartments.Travel-Guide-Accommodation)
-   [Vacation Homes in Crestwood](https://expedia.ca/Crestwood-Private-Vacation-Homes.d6960-aaPrivateVacationHomes.Travel-Guide-Accommodation)
-   [Condo Rentals in Crestwood](https://expedia.ca/Crestwood-Condos.d6960-aaCondos.Travel-Guide-Accommodation)
-   [Aparthotels in Crestwood](https://expedia.ca/Crestwood-Apart-Hotels.d6960-aaApartHotels.Travel-Guide-Accommodation)
-   [Motels in Crestwood](https://expedia.ca/Crestwood-Motels.d6960-aaMotels.Travel-Guide-Accommodation)
-   [B&B in Crestwood](https://expedia.ca/Crestwood-Bed-And-Breakfast.d6960-aaBedAndBreakfast.Travel-Guide-Accommodation)
-   [Cottages in Crestwood](https://expedia.ca/Crestwood-Cottages.d6960-aaCottages.Travel-Guide-Accommodation)
-   [Guest Houses in Crestwood](https://expedia.ca/Crestwood-Guest-Houses.d6960-aaGuestHouses.Travel-Guide-Accommodation)
-   [Villas in Crestwood](https://expedia.ca/Crestwood-Villas.d6960-aaVillas.Travel-Guide-Accommodation)
-   [Hostels in Crestwood](https://expedia.ca/Crestwood-Hostels.d6960-aaHostels.Travel-Guide-Accommodation)
-   [Cabin Rentals in Crestwood](https://expedia.ca/Crestwood-Cabins.d6960-aaCabins.Travel-Guide-Accommodation)
-   [Resorts in Crestwood](https://expedia.ca/Crestwood-Resort-Hotels.d6960-aaResortHotels.Travel-Guide-Accommodation)
-   [Houseboats in Crestwood](https://expedia.ca/Crestwood-Houseboats.d6960-aaHouseboats.Travel-Guide-Accommodation)

## Frequently asked questions

### Can I find a vacation rental in Crestwood?

> Yes, there are vacation rentals in Crestwood close to Hollywood Park, or you can go with a more remote option if you're looking for a relaxing stay. The shops and restaurants are several reasons why visitors like Crestwood. Make sure you have time to check out the entertainment choices while you're in the area.

### What are some of the best vacation home rentals in Crestwood?

> [Charming 2-bedroom house in Maywood with WiFi, AC full basement with sofa bed](https://www.expedia.ca/Chicago-Hotels-Charming-2-Bedroom-House-In-Maywood-With-WiFi.h117671933.Hotel-Information): Visitors like this Crestwood vacation home rental. It offers a patio, a barbecue grill, and air-conditioning to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a dishwasher, a stovetop, and a microwave.

### What can I see and do in Crestwood?

> While exploring the area, visit family-friendly sights like Hollywood Park, or get outside and enjoy nature at Lake Katherine Nature Center. In the larger area, you’ll find Soldier Field and Trinity Christian College.

### What are vacation rentals like in Crestwood?

> Vacation rentals are private accommodations you can reserve for a few days or a quick weekend in Crestwood. Vacation rentals offer amenities like laundry facilities and kitchens so you'll be comfy for your stay. If you're concerned about a sanitized environment, vacation rentals can provide a sense of seclusion away from shared hotel elevators and lobbies bustling with people while still allowing you the enjoyment of travel. You'll also find more space in a vacation rental than in a traditional hotel, which makes a vacation rental a great option for a family trip or a small group gathering.

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General

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Save on select hotels and earn double points when you book on the app. Our app deals help you to save on trips so you can travel more and manage it all on the go.

Scan the QR code with your device camera and download our app

![QR code to download the app](data:image/png;base64,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)