Title: West Side Vacation Rentals from CA $341: Short-Term Rentals for 2026 | Expedia.ca

[West Side Travel Guide](https://expedia.ca/West-Side.dx553248635976475400)[Hotels in West Side](https://expedia.ca/West-Side-Hotels.d553248635976475400.Travel-Guide-Hotels)[Flights to West Side](https://expedia.ca/Cheap-Flights-To-West-Side.d553248635976475400.Travel-Guide-Flights)[Things to do in West Side](https://expedia.ca/Things-To-Do-In-West-Side.d553248635976475400.Travel-Guide-Activities)[West Side Car Rentals](https://expedia.ca/Car-Rentals-In-West-Side.d553248635976475400.Car-Rental-Guide)[West Side Vacation Packages](https://expedia.ca/West-Side.d553248635976475400.Destination-Travel-Guides)

![Garfield Park Conservatory showing interior views and a park](https://images.trvl-media.com/place/6182807/509620c2-aaab-4d64-9d41-76a439dcdfa9.jpg?impolicy=fcrop&w=1200&h=500&q=medium)

![](https://images.trvl-media.com/place/6182807/509620c2-aaab-4d64-9d41-76a439dcdfa9.jpg?impolicy=fcrop&w=1200&h=500&q=medium)

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## Check prices for these dates

In two weeks

[Mar 6 - Mar 8](https://www.expedia.ca/Hotel-Search?regionId=553248635976475400&startDate=2026-03-06&endDate=2026-03-08&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In two months

[Apr 17 - Apr 19](https://www.expedia.ca/Hotel-Search?regionId=553248635976475400&startDate=2026-04-17&endDate=2026-04-19&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In three months

[May 15 - May 17](https://www.expedia.ca/Hotel-Search?regionId=553248635976475400&startDate=2026-05-15&endDate=2026-05-17&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In four months

[Jun 12 - Jun 14](https://www.expedia.ca/Hotel-Search?regionId=553248635976475400&startDate=2026-06-12&endDate=2026-06-14&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

## Our top choices for West Side vacation rentals

![TV, offices](https://images.trvl-media.com/lodging/117000000/116800000/116793000/116792936/7d7ccc69.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)

![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)

![Shower, hair dryer](https://images.trvl-media.com/lodging/117000000/116800000/116793000/116792936/c6bb5c1b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Sun-Drenched 1BR Apartment

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

Downtown Chicago

10/10

Exceptional

(2 reviews)

"Host was very friendly and informative. Place was clean and close to lots of fun. Trains loud and busy but knew that going in. "

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

Tyler B.

CA $94

CA $240 total

includes taxes & fees

Feb 22 - Feb 23

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

![1 bedroom, iron/ironing board, travel crib, WiFi](https://images.trvl-media.com/lodging/120000000/119140000/119131900/119131874/b10cb31b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, iron/ironing board, travel crib, WiFi](https://images.trvl-media.com/lodging/120000000/119140000/119131900/119131874/b56ca762.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV](https://images.trvl-media.com/lodging/120000000/119140000/119131900/119131874/b754723c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Shower, hair dryer](https://images.trvl-media.com/lodging/120000000/119140000/119131900/119131874/4fcb7f04.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### West Loop Living – Bright 1BR

[](https://www.expedia.ca/Chicago-Hotels-West-Loop-Living-Bright-1BR.h119131874.Hotel-Information)

Downtown Chicago

10/10

Exceptional

(7 reviews)

"Well-outfitted, nice apartment. Nearby (walkable) Jewel-Osco grocery, restaurants, and pay-parking. Moderate noise from nearby Chicago "L" Green Line."

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

Jeffrey

CA $94

CA $240 total

includes taxes & fees

Feb 22 - Feb 23

[](https://www.expedia.ca/Chicago-Hotels-West-Loop-Living-Bright-1BR.h119131874.Hotel-Information)

![1 bedroom, WiFi, bed sheets](https://images.trvl-media.com/lodging/120000000/119140000/119131900/119131871/e255803d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/120000000/119140000/119131900/119131871/4b4ff505.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)

![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)

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

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

Downtown Chicago

10/10

Exceptional

(1 review)

"Great experience for me and my wife I would definitely come back "

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

ShowtimeFam1

CA $120

CA $276 total

includes taxes & fees

Mar 4 - Mar 5

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

![TV, offices](https://images.trvl-media.com/lodging/117000000/116800000/116793100/116793043/afe63d9a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, offices](https://images.trvl-media.com/lodging/117000000/116800000/116793100/116793043/19144195.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/117000000/116800000/116793100/116793043/8ec83200.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, iron/ironing board, travel crib, WiFi](https://images.trvl-media.com/lodging/117000000/116800000/116793100/116793043/143f3ef1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Modern Comfort: 1BR Unit w/ Laundry

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

Downtown Chicago

9.2/10

Wonderful

(15 reviews)

"Great host comfortable bed close to restaurants and parks"

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

Alana C.

CA $94

CA $240 total

includes taxes & fees

Feb 22 - Feb 23

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

![Interior](https://images.trvl-media.com/lodging/117000000/116800000/116793000/116792993/ca2aa0d7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/117000000/116800000/116793000/116792993/e4a26e6f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/117000000/116800000/116793000/116792993/9c142ace.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Shower, hair dryer](https://images.trvl-media.com/lodging/117000000/116800000/116793000/116792993/96d438b5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Your Perfect 2BR Home

[](https://www.expedia.ca/Chicago-Hotels-Your-Perfect-2BR-Home.h116792993.Hotel-Information)

Near West Side

8.2/10

Very good

(14 reviews)

"Great location! "

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

Kourtney K.

CA $119

CA $303 total

includes taxes & fees

Feb 22 - Feb 23

[](https://www.expedia.ca/Chicago-Hotels-Your-Perfect-2BR-Home.h116792993.Hotel-Information)

![Smart TV](https://images.trvl-media.com/lodging/116000000/115430000/115420400/115420356/b4ab2028.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/116000000/115430000/115420400/115420356/46461bf5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/116000000/115430000/115420400/115420356/cf70ee87.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/116000000/115430000/115420400/115420356/d57f872f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### NEW Private West Loop 1br with Backyard near Green Line and CTA

[](https://www.expedia.ca/Chicago-Hotels-NEW-Private-West-Loop-1br-With-Backyard-Near-Green-Line-And-CTA.h115420356.Hotel-Information)

East Garfield Park

9.6/10

Exceptional

(4 reviews)

"Very cozy stay. Host was great with communication and the place has everything needed. Would definitely book here again!"

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

Eric H.

CA $53

CA $285 total

includes taxes & fees

Feb 24 - Feb 25

[](https://www.expedia.ca/Chicago-Hotels-NEW-Private-West-Loop-1br-With-Backyard-Near-Green-Line-And-CTA.h115420356.Hotel-Information)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/103000000/102350000/102347800/102347797/be907ced.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/103000000/102350000/102347800/102347797/w1277h853x0y0-b16d8c38.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior detail](https://images.trvl-media.com/lodging/103000000/102350000/102347800/102347797/d8a5de19.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/103000000/102350000/102347800/102347797/bb2ec633.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Flexhome East Village 2BR H1

[](https://www.expedia.ca/Chicago-Hotels-Flexhome-East-Village-2BR-H1.h102347797.Hotel-Information)

West Town

9.6/10

Exceptional

(8 reviews)

"Location was great for everything we were doing in Chicago. "

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

Tom W.

CA $389

CA $646 total

includes taxes & fees

Mar 14 - Mar 15

[](https://www.expedia.ca/Chicago-Hotels-Flexhome-East-Village-2BR-H1.h102347797.Hotel-Information)

![Studio | Living area](https://images.trvl-media.com/lodging/89000000/88880000/88878700/88878619/811b307f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/89000000/88880000/88878700/88878619/6a1ece15.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Studio | Private kitchen](https://images.trvl-media.com/lodging/89000000/88880000/88878700/88878619/d56c0426.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Studio | Exterior](https://images.trvl-media.com/lodging/89000000/88880000/88878700/88878619/4f7c4b77.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Chicago Second Floor Studio by 747 Lofts

[](https://www.expedia.ca/Chicago-Hotels-Full-Kitchen.h88878619.Hotel-Information)

West Town

8.8/10

Excellent

(13 reviews)

"Great location, convenient to downtown and blue line to airport. Everything necessary in unit, comfortable temperature and full kitchen with unique grocery store nearby."

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

Barbara

CA $89

CA $273 total

includes taxes & fees

Feb 22 - Feb 23

[](https://www.expedia.ca/Chicago-Hotels-Full-Kitchen.h88878619.Hotel-Information)

![Dining](https://images.trvl-media.com/lodging/111000000/110690000/110681900/110681813/d1e56d63.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/111000000/110690000/110681900/110681813/643ba988.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/111000000/110690000/110681900/110681813/2a06854a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, books, stereo](https://images.trvl-media.com/lodging/111000000/110690000/110681900/110681813/76f24ee1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Flexhome Wicker Park 2BR DV3

[](https://www.expedia.ca/Chicago-Hotels-Flexhome-Wicker-Park-2BR-DV4.h110681813.Hotel-Information)

West Town

9.6/10

Exceptional

(4 reviews)

"Great location. The apartment has everything you will need. Had a great time . Thanks"

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

Wayne M.

CA $131

CA $280 total

includes taxes & fees

Mar 15 - Mar 16

[](https://www.expedia.ca/Chicago-Hotels-Flexhome-Wicker-Park-2BR-DV4.h110681813.Hotel-Information)

![Interior](https://images.trvl-media.com/lodging/117000000/116800000/116793000/116792914/672545d9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/117000000/116800000/116793000/116792914/904b24c8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV](https://images.trvl-media.com/lodging/117000000/116800000/116793000/116792914/05d0e593.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![3 bedrooms, iron/ironing board, travel crib, WiFi](https://images.trvl-media.com/lodging/117000000/116800000/116793000/116792914/3944b711.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### 3BR Complete and Spacious Apt

[](https://www.expedia.ca/Chicago-Hotels-3BR-Complete-And-Spacious-Apt.h116792914.Hotel-Information)

West Town

8.8/10

Excellent

(12 reviews)

"This is such a steal of a price for this beautiful place! We had a great stay. Amazing location, plenty of square footage, and the hosts are incredibly helpful. You really don’t have to do much to check out like some VRBOs either! Would definitely stay again. "

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

Alec

CA $137

CA $341 total

includes taxes & fees

Feb 22 - Feb 23

[](https://www.expedia.ca/Chicago-Hotels-3BR-Complete-And-Spacious-Apt.h116792914.Hotel-Information)

![Smart TV, books](https://images.trvl-media.com/lodging/103000000/102350000/102347900/102347806/98c674ad.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/103000000/102350000/102347900/102347806/17a39e72.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, books](https://images.trvl-media.com/lodging/103000000/102350000/102347900/102347806/a1984ee1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/103000000/102350000/102347900/102347806/7a3d8d81.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Flexhome Ukrainian Village 2BR D1

[](https://www.expedia.ca/Chicago-Hotels-Flexhome-Ukrainian-Village-2BR-D1.h102347806.Hotel-Information)

West Town

8.8/10

Excellent

(8 reviews)

"Excellent place and location."

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

Josh L.

CA $136

CA $286 total

includes taxes & fees

Mar 15 - Mar 16

[](https://www.expedia.ca/Chicago-Hotels-Flexhome-Ukrainian-Village-2BR-D1.h102347806.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/103000000/102340000/102331000/102330932/7ab6d91a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![2 bedrooms, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/103000000/102340000/102331000/102330932/46cf36e4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/103000000/102340000/102331000/102330932/a2f95807.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/103000000/102340000/102331000/102330932/cdbd7000.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The Banksy-Greystone Rooftop Firepit United Center

[](https://www.expedia.ca/Chicago-Hotels-The-Banksy-Greystone-Rooftop-Firepit-United-Center.h102330932.Hotel-Information)

Near West Side

[](https://www.expedia.ca/Chicago-Hotels-The-Banksy-Greystone-Rooftop-Firepit-United-Center.h102330932.Hotel-Information)

![Dining](https://images.trvl-media.com/lodging/117000000/116800000/116792900/116792839/e65095fe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, oven, stovetop, dishwasher](https://images.trvl-media.com/lodging/117000000/116800000/116792900/116792839/b80be946.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, offices](https://images.trvl-media.com/lodging/117000000/116800000/116792900/116792839/27c09381.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/117000000/116800000/116792900/116792839/623aaf74.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Urban Comfort • 2BR in West Town

[](https://www.expedia.ca/Chicago-Hotels-Urban-Comfort-2BR-In-West-Town.h116792839.Hotel-Information)

West Town

9.6/10

Exceptional

(7 reviews)

"The place was very clean and accommodating."

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

Mark E.

CA $103

CA $272 total

includes taxes & fees

Feb 22 - Feb 23

[](https://www.expedia.ca/Chicago-Hotels-Urban-Comfort-2BR-In-West-Town.h116792839.Hotel-Information)

![TV, video games](https://images.trvl-media.com/lodging/120000000/119330000/119326000/119325950/ceb74714.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![3 bedrooms, desk, iron/ironing board, travel crib](https://images.trvl-media.com/lodging/120000000/119330000/119326000/119325950/w1350h899x0y1-0ada272d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/120000000/119330000/119326000/119325950/w1350h899x0y1-c7cb163e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Microwave, oven, stovetop, dishwasher](https://images.trvl-media.com/lodging/120000000/119330000/119326000/119325950/w1350h899x0y1-5c6706df.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Sleeps 12 - Games - 10 Min to Downtown - Arcades - Walking Distance to Train

[](https://www.expedia.ca/Chicago-Hotels-Sleeps-12-Games-10-Min-To-Downtown-Arcades-Walking-Distance-To-Train.h119325950.Hotel-Information)

Lawndale

CA $100

CA $379 total

includes taxes & fees

Feb 22 - Feb 23

[](https://www.expedia.ca/Chicago-Hotels-Sleeps-12-Games-10-Min-To-Downtown-Arcades-Walking-Distance-To-Train.h119325950.Hotel-Information)

![TV, offices](https://images.trvl-media.com/lodging/117000000/116800000/116793000/116792989/c9d83882.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/117000000/116800000/116793000/116792989/b32b2780.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/117000000/116800000/116793000/116792989/9123cfe1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/117000000/116800000/116793000/116792989/7b26c35e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Upscale 4BR Retreat: Wicker Park

[](https://www.expedia.ca/Chicago-Hotels-Upscale-4BR-Retreat-Wicker-Park.h116792989.Hotel-Information)

West Town

8.0/10

Very good

(7 reviews)

"Great place in a great area. Would definitely stay here again!"

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

John R.

CA $134

CA $497 total

includes taxes & fees

Feb 22 - Feb 23

[](https://www.expedia.ca/Chicago-Hotels-Upscale-4BR-Retreat-Wicker-Park.h116792989.Hotel-Information)

![Interior](https://images.trvl-media.com/lodging/107000000/106260000/106255700/106255669/w1350h899x0y1-8e6f7625.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, video games](https://images.trvl-media.com/lodging/107000000/106260000/106255700/106255669/b67a1eb2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/107000000/106260000/106255700/106255669/w1350h899x0y1-f8d5da1f.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/107000000/106260000/106255700/106255669/w1350h899x0y1-92b3a773.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vintage Arcade Apt with Parking

[](https://www.expedia.ca/Chicago-Hotels-Vintage-Arcade-Apt-With-Parking.h106255669.Hotel-Information)

Lawndale

6.0/10

(6 reviews)

"Very clean and private"

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

Anthony B.

CA $64

CA $234 total

includes taxes & fees

Feb 22 - Feb 23

[](https://www.expedia.ca/Chicago-Hotels-Vintage-Arcade-Apt-With-Parking.h106255669.Hotel-Information)

![Dining](https://images.trvl-media.com/lodging/119000000/118120000/118113500/118113406/w1350h899x0y1-e4f4e07a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, video games](https://images.trvl-media.com/lodging/119000000/118120000/118113500/118113406/w1350h899x0y1-a954e392.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![3 bedrooms, desk, iron/ironing board, travel crib](https://images.trvl-media.com/lodging/119000000/118120000/118113500/118113406/819688a1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Microwave, oven, stovetop, dishwasher](https://images.trvl-media.com/lodging/119000000/118120000/118113500/118113406/w1350h899x0y1-6b0d266e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### 5 Mins to Downtown CHI Sleeps 10 - Parking + Games

[](https://www.expedia.ca/Chicago-Hotels-5-Mins-To-Downtown-CHI-Sleeps-10-Parking-Games.h118113406.Hotel-Information)

Lower West Side

10/10

Exceptional

(3 reviews)

"We loved the location, the area is awesome! Great stay, highly recommend. "

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

Db D.

CA $187

CA $522 total

includes taxes & fees

Mar 18 - Mar 19

[](https://www.expedia.ca/Chicago-Hotels-5-Mins-To-Downtown-CHI-Sleeps-10-Parking-Games.h118113406.Hotel-Information)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/117000000/116800000/116793000/116792985/cad1af12.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/117000000/116800000/116793000/116792985/224306ee.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, offices](https://images.trvl-media.com/lodging/117000000/116800000/116793000/116792985/8a1a198f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/117000000/116800000/116793000/116792985/dcd79fda.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Spacious 4BR Near Wicker Park

[](https://www.expedia.ca/Chicago-Hotels-Spacious-4BR-Near-Wicker-Park.h116792985.Hotel-Information)

West Town

9.4/10

Exceptional

(8 reviews)

"Very clean very spacious very comfortable great location"

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

Maxwell H.

CA $150

CA $526 total

includes taxes & fees

Mar 3 - Mar 4

[](https://www.expedia.ca/Chicago-Hotels-Spacious-4BR-Near-Wicker-Park.h116792985.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/89000000/88910000/88902400/88902350/81e7be6e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/89000000/88910000/88902400/88902350/70ca997d_edited_1de4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, dishwasher](https://images.trvl-media.com/lodging/89000000/88910000/88902400/88902350/74abff6f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/89000000/88910000/88902400/88902350/63e319e6_edited_d25a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Cabin 208 by 747 Lofts

[](https://www.expedia.ca/Chicago-Hotels-Cabin-208-By-747-Lofts.h88902350.Hotel-Information)

West Town

9.2/10

Wonderful

(11 reviews)

"Easy access to building right outside Chicago Blue Line Station, host was easy to reach and helped out with getting luggage storage before/after check-in and check-out. Room was clean enough, a bit old and dusty in places and the heat was a bit much, but otherwise a great stay!"

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

Farah C.

CA $84

CA $255 total

includes taxes & fees

Feb 22 - Feb 23

[](https://www.expedia.ca/Chicago-Hotels-Cabin-208-By-747-Lofts.h88902350.Hotel-Information)

![Terrace/patio](https://images.trvl-media.com/lodging/123000000/122820000/122812000/122811950/411ffb8d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/123000000/122820000/122812000/122811950/704b617f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV](https://images.trvl-media.com/lodging/123000000/122820000/122812000/122811950/07286fae.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![7 bedrooms, iron/ironing board, travel crib, WiFi](https://images.trvl-media.com/lodging/123000000/122820000/122812000/122811950/d3f5429a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Sleeps 18 • 7BR • Gym • Game Room • Theater

[](https://www.expedia.ca/Chicago-Hotels-Sleeps-18-7BR-Gym-Game-Room-Theater.h122811950.Hotel-Information)

Austin

6.0/10

(1 review)

"Ok place to fit large families if no other option available. Not suitable for kids with allergies as there are some opportunities in the cleanness and maintenance of the property.The communication were ok for reserving but very limited during the stay.The floor os severely damaged as well."

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

Adrian Cesar C.

CA $185

CA $1,228 total

includes taxes & fees

Mar 3 - Mar 4

[](https://www.expedia.ca/Chicago-Hotels-Sleeps-18-7BR-Gym-Game-Room-Theater.h122811950.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.

[View all properties](https://expedia.ca/Hotel-Search?startDate=2026-03-07&endDate=2026-03-08&regionId=553248635976475400&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true)

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## 

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## Find vacation rentals that suit your style

Aparthotels

[](https://www.expedia.ca/Hotel-Search?destination=West+Side%2C+Illinois%2C+United+States+of+America&regionId=553248635976475400&latLong=41.876968%2C-87.708186&adults=2&startDate=2026-05-22&d1=2026-05-22&endDate=2026-05-25&d2=2026-05-25&lodging=APART_HOTEL)

Apartments

[](https://www.expedia.ca/Hotel-Search?destination=West+Side%2C+Illinois%2C+United+States+of+America&regionId=553248635976475400&latLong=41.876968%2C-87.708186&adults=2&startDate=2026-05-22&d1=2026-05-22&endDate=2026-05-25&d2=2026-05-25&lodging=APARTMENT)

Private vacation homes

[](https://www.expedia.ca/Hotel-Search?destination=West+Side%2C+Illinois%2C+United+States+of+America&regionId=553248635976475400&latLong=41.876968%2C-87.708186&adults=2&startDate=2026-05-22&d1=2026-05-22&endDate=2026-05-25&d2=2026-05-25&lodging=VACATION_HOME)

Condos

[](https://www.expedia.ca/Hotel-Search?destination=West+Side%2C+Illinois%2C+United+States+of+America&regionId=553248635976475400&latLong=41.876968%2C-87.708186&adults=2&startDate=2026-05-22&d1=2026-05-22&endDate=2026-05-25&d2=2026-05-25&lodging=CONDO)

Villas

[](https://www.expedia.ca/Hotel-Search?destination=West+Side%2C+Illinois%2C+United+States+of+America&regionId=553248635976475400&latLong=41.876968%2C-87.708186&adults=2&startDate=2026-05-22&d1=2026-05-22&endDate=2026-05-25&d2=2026-05-25&lodging=VILLA)

Cottages

[](https://www.expedia.ca/Hotel-Search?destination=West+Side%2C+Illinois%2C+United+States+of+America&regionId=553248635976475400&latLong=41.876968%2C-87.708186&adults=2&startDate=2026-05-22&d1=2026-05-22&endDate=2026-05-25&d2=2026-05-25&lodging=COTTAGE)

Residences

[](https://www.expedia.ca/Hotel-Search?destination=West+Side%2C+Illinois%2C+United+States+of+America&regionId=553248635976475400&latLong=41.876968%2C-87.708186&adults=2&startDate=2026-05-22&d1=2026-05-22&endDate=2026-05-25&d2=2026-05-25&lodging=RESIDENCE)

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## Top West Side Hotel Reviews

![The Hoxton Chicago](https://images.trvl-media.com/lodging/35000000/34770000/34761400/34761378/d06b01bf_y.jpg)

### The Hoxton Chicago

10/10 Excellent

"Energy, decor, kindness/accommodations and perks. Love this hotel! "

[](https://expedia.ca/Chicago-Hotels-The-Hoxton-Chicago.h34761378.Hotel-Information)

![The Robey, Chicago, a Member of Design Hotels](https://images.trvl-media.com/lodging/16000000/15760000/15758200/15758132/5b60adf7_y.jpg)

### The Robey, Chicago, a Member of Design Hotels

10/10 Excellent

"Clean room"

[](https://expedia.ca/Chicago-Hotels-The-Robey.h15758132.Hotel-Information)

![Hampton Inn & Suites Chicago Medical District UIC](https://images.trvl-media.com/lodging/103000000/102240000/102236700/102236658/03795c9c_y.jpg)

### Hampton Inn & Suites Chicago Medical District UIC

10/10 Excellent

"Be"

[](https://expedia.ca/Chicago-Hotels-Hampton-Inn-Suites-Chicago-Medical-District-Uic.h102236658.Hotel-Information)

![Hyatt Place Chicago Medical/University District](https://images.trvl-media.com/lodging/54000000/53170000/53166000/53165905/3edad5a6_y.jpg)

### Hyatt Place Chicago Medical/University District

10/10 Excellent

"Clean and beautiful"

[](https://expedia.ca/Chicago-Hotels-Hyatt-Place-Chicago-MedicalUniversity-District.h53165905.Hotel-Information)

![Hampton Inn Chicago West Loop Fulton Market Area](https://images.trvl-media.com/lodging/16000000/15850000/15849800/15849775/3ff1c0b3_y.jpg)

### Hampton Inn Chicago West Loop Fulton Market Area

10/10 Excellent

"Clean room and good beds"

[](https://expedia.ca/Chicago-Hotels-Hampton-Inn-Chicago-Downtown-West-Loop.h15849775.Hotel-Information)

![The Neighborhood Hotel-Little Italy](https://images.trvl-media.com/lodging/97000000/96300000/96299500/96299486/05d44ec7_y.jpg)

### The Neighborhood Hotel-Little Italy

10/10 Excellent

"Very clean, all the appliances are nice and new, great location, great value!! We will stay here again!!"

[](https://expedia.ca/Chicago-Hotels-The-Neighborhood-Hotel-Little-Italy.h96299486.Hotel-Information)

![Hyatt House Chicago Medical/University District](https://images.trvl-media.com/lodging/50000000/49320000/49315100/49315022/689da744_y.jpg)

### Hyatt House Chicago Medical/University District

10/10 Excellent

"It was very nice!"

[](https://expedia.ca/Chicago-Hotels-Hyatt-House-Chicago-MedicalUniversity-District.h49315022.Hotel-Information)

![Hyatt House Chicago West Loop](https://images.trvl-media.com/lodging/36000000/35840000/35834300/35834237/d1cc0289_y.jpg)

### Hyatt House Chicago West Loop

10/10 Excellent

"Friendly and helpful stagg. Good breakfast"

[](https://expedia.ca/Chicago-Hotels-Hyatt-House-Chicago-West-Loop.h35834237.Hotel-Information)

![Crowne Plaza Chicago West Loop by IHG](https://images.trvl-media.com/lodging/2000000/1300000/1293300/1293276/f9d27fb3_y.jpg)

### Crowne Plaza Chicago West Loop by IHG

10/10 Excellent

"Yes"

[](https://expedia.ca/Chicago-Hotels-Crowne-Plaza-Chicago-West-Loop.h1293276.Hotel-Information)

## Find out more about West Side

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.  
  
As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with West Side. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.   
  
It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.   

## Explore a world of travel with Expedia

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- [Apartments in West Side ](https://expedia.ca/West-Side-Apartments.d553248635976475400-aaApartments.Travel-Guide-Accommodation)
- [Vacation Homes in West Side ](https://expedia.ca/West-Side-Private-Vacation-Homes.d553248635976475400-aaPrivateVacationHomes.Travel-Guide-Accommodation)
- [Aparthotels in West Side ](https://expedia.ca/West-Side-Apart-Hotels.d553248635976475400-aaApartHotels.Travel-Guide-Accommodation)
- [Condo Rentals in West Side ](https://expedia.ca/West-Side-Condos.d553248635976475400-aaCondos.Travel-Guide-Accommodation)
- [Villas in West Side ](https://expedia.ca/West-Side-Villas.d553248635976475400-aaVillas.Travel-Guide-Accommodation)
- [B&B in West Side ](https://expedia.ca/West-Side-Bed-And-Breakfast.d553248635976475400-aaBedAndBreakfast.Travel-Guide-Accommodation)
- [Guest Houses in West Side ](https://expedia.ca/West-Side-Guest-Houses.d553248635976475400-aaGuestHouses.Travel-Guide-Accommodation)
- [Hostels in West Side ](https://expedia.ca/West-Side-Hostels.d553248635976475400-aaHostels.Travel-Guide-Accommodation)
- [Houseboats in West Side ](https://expedia.ca/West-Side-Houseboats.d553248635976475400-aaHouseboats.Travel-Guide-Accommodation)

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- [Dollar Rent A Car Car Rentals In Central Chicago](https://expedia.ca/Dollar-Rent-A-Car-Car-Rentals-In-Central-Chicago.d553248635976475413-c43.Car-Rental-Guide-Suppliers)

Packages

- [Art Institute of Chicago](https://expedia.ca/Art-Institute-Of-Chicago-Downtown-Chicago.d6064021.Vacation-Attraction)
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- [Chicago Riverwalk](https://expedia.ca/Chicago-Riverwalk-Downtown-Chicago.d553248621533116610.Vacation-Attraction)
- [Willis Tower](https://expedia.ca/Willis-Tower-Downtown-Chicago.d6064069.Vacation-Attraction)
- [Robie House](https://expedia.ca/Robie-House-Hyde-Park.d6064059.Vacation-Attraction)
- [875 North Michigan Avenue](https://expedia.ca/875-North-Michigan-Avenue-Downtown-Chicago.d6065131.Vacation-Attraction)
- [Griffin Museum of Science and Industry](https://expedia.ca/Griffin-Museum-Of-Science-And-Industry-Hyde-Park.d6064043.Vacation-Attraction)
- [Water Tower Place](https://expedia.ca/Water-Tower-Place-Downtown-Chicago.d6064087.Vacation-Attraction)
- [Millennium Park](https://expedia.ca/Millennium-Park-Downtown-Chicago.d6069201.Vacation-Attraction)
- [Wrigley Field](https://expedia.ca/Wrigley-Field-Lakeview.d6034754.Vacation-Attraction)
- [Grant Park](https://expedia.ca/Grant-Park-Downtown-Chicago.d507389.Vacation-Attraction)

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