Title: West Side Vacation Rentals from CA $230: 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)

![A view of the cacti and succulent display at the Garfield Park Conservatory.

Opened to the public in 1908, the Garfield Park Conservatory, consists of a series of naturalistic landscapes under glass, a revolutionary idea at the time.

Sort of off the radar of a lot of Chicago tourists because of the more downtown-centric location of the Lincoln Park Conservatory. The Garfield Park Conservatory is a gem on the west side of Chicago.

The Garfield Park Conservatory occupies 4.5 acres of the 184 acres of Garfield Park. Both Garfield Park and its conservatory are listed on the National Register of Historic Places.

The conservatory has recovered nicely from a 2011 hailstorm that shattered over 50% of the conservatory's glass panes and damaged many plants.

#colorful](https://images.trvl-media.com/place/829/ad657303-bbed-4f45-9ba5-b7c23d3e76f3.jpg?impolicy=fcrop&w=1200&h=500&q=medium)

Photo by throwingsofas

# West Side Vacation Rentals

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## Check prices for these dates

In two weeks

[Jan 9 - Jan 11](https://www.expedia.ca/Hotel-Search?regionId=553248635976475400&startDate=2026-01-09&endDate=2026-01-11&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In two months

[Feb 20 - Feb 22](https://www.expedia.ca/Hotel-Search?regionId=553248635976475400&startDate=2026-02-20&endDate=2026-02-22&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In three months

[Mar 20 - Mar 22](https://www.expedia.ca/Hotel-Search?regionId=553248635976475400&startDate=2026-03-20&endDate=2026-03-22&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In four 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)

## Our top choices for West Side vacation rentals

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/120000000/119140000/119131900/119131874/c52efc06.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/120000000/119140000/119131900/119131874/368bd483.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/120000000/119140000/119131900/119131874/664fb229.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

(4)

"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 $86

CA $230 total

includes taxes & fees

Jan 4 - Jan 5, 2026

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

![1 bedroom, iron/ironing board, travel crib, WiFi](https://images.trvl-media.com/lodging/117000000/116800000/116793100/116793043/8c87c7e1.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)

### Stylish 1BR in West Loop

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

Downtown Chicago

10/10

Exceptional

(10)

"Great host comfortable bed close to restaurants and parks"

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

Alana C.

CA $86

CA $230 total

includes taxes & fees

Jan 1 - Jan 2, 2026

[](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)

![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)

![TV, offices](https://images.trvl-media.com/lodging/117000000/116800000/116793000/116792936/c3fddccc.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)

"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 $86

CA $230 total

includes taxes & fees

Jan 4 - Jan 5, 2026

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

![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)

"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 $86

CA $230 total

includes taxes & fees

Jan 1 - Jan 2, 2026

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

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/106000000/105560000/105552500/105552490/w1350h899x0y1-d7005b5e.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/106000000/105560000/105552500/105552490/w1350h899x0y1-beef26b6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/106000000/105560000/105552500/105552490/1dd62bdd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor dining](https://images.trvl-media.com/lodging/106000000/105560000/105552500/105552490/9aa725fc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Cozy Boho Chicago - 10 Minutes to Downtown Chicago

[](https://www.expedia.ca/Chicago-Hotels-Cozy-Boho-Chicago-10-Min-To-Chicago.h105552490.Hotel-Information)

Lawndale

10/10

Exceptional

(8)

"Very nice apartment close to downtown!"

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

Dariana

CA $78

CA $272 total

includes taxes & fees

Dec 29 - Dec 30

[](https://www.expedia.ca/Chicago-Hotels-Cozy-Boho-Chicago-10-Min-To-Chicago.h105552490.Hotel-Information)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/116000000/115430000/115420400/115420356/65522cbf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/116000000/115430000/115420400/115420356/1246de2d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/116000000/115430000/115420400/115420356/59490e9f.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)

### 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

9.4/10

Exceptional

(3)

"Clean, and was exactly how described in the booking. Host was quick to respond to any questions we had. "

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

Cyril M.

CA $102

CA $349 total

includes taxes & fees

Jan 14 - Jan 15, 2026

[](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/103000000/102350000/102347900/102347806/7a3d8d81.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/c5e68da1.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)

### Flexhome Ukrainian Village 2BR D1

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

West Town

9.6/10

Exceptional

(5)

"It was clean and ready for our arrival. A big plus is having a washer and dryer on the premises."

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

Ray R.

CA $85

CA $223 total

includes taxes & fees

Jan 1 - Jan 2, 2026

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

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/117000000/116940000/116934400/116934319/918c1b0f.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/117000000/116940000/116934400/116934319/15d13989.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/117000000/116940000/116934400/116934319/fbb710a6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/117000000/116940000/116934400/116934319/d19de994.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### 15mins DT | Wicker Park Gem | Sleeps 7 | FreePark

[](https://www.expedia.ca/Chicago-Hotels-15mins-DT-Wicker-Park-Gem-Sleeps-7-FreePark.h116934319.Hotel-Information)

East Garfield Park

CA $117

CA $372 total

includes taxes & fees

Dec 26 - Dec 27

[](https://www.expedia.ca/Chicago-Hotels-15mins-DT-Wicker-Park-Gem-Sleeps-7-FreePark.h116934319.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)

![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)

![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)

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

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

Near West Side

9.4/10

Exceptional

(10)

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

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

Ryan

CA $79

CA $440 total

includes taxes & fees

Jan 20 - Jan 21, 2026

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

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/109000000/108480000/108474000/108473931/w1350h899x0y1-bfc43cb0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/109000000/108480000/108474000/108473931/w1350h899x0y1-6c6391ec.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/109000000/108480000/108474000/108473931/w1350h899x0y1-546ed985.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/109000000/108480000/108474000/108473931/d1335f89.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### 10 Minutes to Downtown Chicago - Sleeps 12 - King Beds - Games and Arcades

[](https://www.expedia.ca/Chicago-Hotels-Large-4-Bedroom-3-King-Beds.h108473931.Hotel-Information)

Lawndale

8.0/10

Very good

(2)

"While it was a great price, you get what you pay for. "

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

Deya R.

CA $89

CA $399 total

includes taxes & fees

Jan 6 - Jan 7, 2026

[](https://www.expedia.ca/Chicago-Hotels-Large-4-Bedroom-3-King-Beds.h108473931.Hotel-Information)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/103000000/102350000/102347800/102347797/6fbbac2d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, books](https://images.trvl-media.com/lodging/103000000/102350000/102347800/102347797/7b932284.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)

![Exterior detail](https://images.trvl-media.com/lodging/103000000/102350000/102347800/102347797/d8a5de19.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

9.8/10

Exceptional

(7)

"great place! clean, comfortable, safe and in a great area! highly recommend. "

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

CJ M.

CA $130

CA $279 total

includes taxes & fees

Jan 24 - Jan 25, 2026

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

![Exterior](https://images.trvl-media.com/lodging/89000000/88910000/88902400/88902311/8e911dc4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, dishwasher](https://images.trvl-media.com/lodging/89000000/88910000/88902400/88902311/7dd83b53.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Miscellaneous](https://images.trvl-media.com/lodging/89000000/88910000/88902400/88902311/4722cf7a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Shower, hair dryer, towels](https://images.trvl-media.com/lodging/89000000/88910000/88902400/88902311/4304d627.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Cabin 203 by 747 Lofts

[](https://www.expedia.ca/Chicago-Hotels-Cabin-203-By-747-Lofts.h88902311.Hotel-Information)

West Town

8.6/10

Excellent

(7)

"Was prefect for a mother/son spring break excursion. "

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

Julie R.

CA $84

CA $210 total

includes taxes & fees

Jan 1 - Jan 2, 2026

[](https://www.expedia.ca/Chicago-Hotels-Cabin-203-By-747-Lofts.h88902311.Hotel-Information)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/111000000/110690000/110681900/110681813/e066b422.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)

![Smart TV, books, stereo](https://images.trvl-media.com/lodging/111000000/110690000/110681900/110681813/d40a2f5d.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)

"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 $85

CA $223 total

includes taxes & fees

Dec 30 - Dec 31

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

![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)

![Interior](https://images.trvl-media.com/lodging/117000000/116800000/116793000/116792993/ca2aa0d7.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)

![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)

### 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)

"Great stay by the United Center "

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

Brian H.

CA $92

CA $266 total

includes taxes & fees

Jan 4 - Jan 5, 2026

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

![Studio | Exterior](https://images.trvl-media.com/lodging/89000000/88910000/88902400/88902334/c46e5d6d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Studio | Living area](https://images.trvl-media.com/lodging/89000000/88910000/88902400/88902334/f9632e6d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Studio | View from property](https://images.trvl-media.com/lodging/89000000/88910000/88902400/88902334/da815e3f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Studio | Private kitchen](https://images.trvl-media.com/lodging/89000000/88910000/88902400/88902334/aea930d7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Chicago Third Floor Studio by 747 Lofts

[](https://www.expedia.ca/Chicago-Hotels-Walk-To-Local-Hot-Spots-Or-Public-Transit-Prime-Location-In-The-Heart-Of-The-Windy-City-747-Lofts-Cabin-301-Hotel-Room.h88902334.Hotel-Information)

West Town

9.8/10

Exceptional

(6)

"Cute little studio that was clean. There was a nice size kitchen and was close to our activities in the West loop of Chicago. There was also assistance with parking located in the lofts."

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

Jennifer

CA $85

CA $305 total

includes taxes & fees

Dec 30 - Dec 31

[](https://www.expedia.ca/Chicago-Hotels-Walk-To-Local-Hot-Spots-Or-Public-Transit-Prime-Location-In-The-Heart-Of-The-Windy-City-747-Lofts-Cabin-301-Hotel-Room.h88902334.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/119000000/118120000/118113500/118113406/73273331.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)

![TV, video games](https://images.trvl-media.com/lodging/119000000/118120000/118113500/118113406/21b7a78a.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/w1350h899x0y1-e9bc3685.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

(1)

"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 $109

CA $398 total

includes taxes & fees

Jan 13 - Jan 14, 2026

[](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/117000000/116800000/116793000/116792914/904b24c8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV](https://images.trvl-media.com/lodging/117000000/116800000/116793000/116792914/bdc8d465.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/117000000/116800000/116793000/116792914/672545d9.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

8.4/10

Very good

(10)

"Clean, Good Location easy to find. If in the area would definitely stay again. "

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

tyler

CA $101

CA $289 total

includes taxes & fees

Dec 30 - Dec 31

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

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/119000000/118310000/118306200/118306109/bb826439.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/119000000/118310000/118306200/118306109/51989ea6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/119000000/118310000/118306200/118306109/2b047812.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/119000000/118310000/118306200/118306109/445cf080.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Flexhome West Town 2BR Apt T1

[](https://www.expedia.ca/Chicago-Hotels-Flexhome-West-Town-2BR-Apt-T1.h118306109.Hotel-Information)

West Town

9.0/10

Wonderful

(2)

"Awesome location, great views and comfortable."

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

Steve L.

CA $94

CA $220 total

includes taxes & fees

Jan 21 - Jan 22, 2026

[](https://www.expedia.ca/Chicago-Hotels-Flexhome-West-Town-2BR-Apt-T1.h118306109.Hotel-Information)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/124000000/123620000/123611900/123611853/w1193h900x0y0-80444137.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, offices](https://images.trvl-media.com/lodging/124000000/123620000/123611900/123611853/7b9337fd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/124000000/123620000/123611900/123611853/0fca3011.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Iron/ironing board, travel crib, WiFi, bed sheets](https://images.trvl-media.com/lodging/124000000/123620000/123611900/123611853/6d21429b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### King Bed with Chefs Kitchen and Free Parking - Pets OK

[](https://www.expedia.ca/Chicago-Hotels-King-Bed-With-Chefs-Kitchen-And-Free-Parking-Pets-OK.h123611853.Hotel-Information)

West Town

CA $183

CA $506 total

includes taxes & fees

Dec 30 - Dec 31

[](https://www.expedia.ca/Chicago-Hotels-King-Bed-With-Chefs-Kitchen-And-Free-Parking-Pets-OK.h123611853.Hotel-Information)

![2 bedrooms, iron/ironing board, travel crib, WiFi](https://images.trvl-media.com/lodging/117000000/116800000/116792900/116792839/d6d46773.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)

![Dining](https://images.trvl-media.com/lodging/117000000/116800000/116792900/116792839/e65095fe.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)

### Urban Comfort • 2BR in West Town

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

West Town

9.8/10

Exceptional

(6)

"We had a wonderful stay! The location was perfect and was close to everything we needed. The apartment was very clean and the host was excellent with communication. The check-in and our overall experience smooth and stress-free. Would definitely recommend staying here!"

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

Jared P.

CA $92

CA $257 total

includes taxes & fees

Jan 1 - Jan 2, 2026

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

![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

"I loved the balcony the most. 10/10."

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

![Holiday Inn & Suites Chicago - Downtown by IHG](https://images.trvl-media.com/lodging/1000000/210000/201300/201274/bcc149aa_y.jpg)

### Holiday Inn & Suites Chicago - Downtown by IHG

10/10 Excellent

"Excellent "

[](https://expedia.ca/Chicago-Hotels-Holiday-Inn-Suites-Chicago-Downtown.h201274.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

"We have stayed here many times. The staff are very pleasant and accommodating and the rooms are perfect.we also enjoyed a good drink and snack in the hotel bar."

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

"Nice room"

[](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

"Great location, clean and comfortable room. Convenient access "

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

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

### The Hoxton Chicago

10/10 Excellent

"The hotel is beautiful. Room was clean and the staff was super friendly and helpful with any questions we had. The hotel bar is also amazing as well as the bartenders. Had breakfast on my last day too and it was great! A must stay in Chicago for sure and I’ll definitely be back next time I’m in Chicago. "

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

"Everything was wonderful "

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

![Hotel Chicago West Loop, SureStay Collection by Best Western](https://images.trvl-media.com/lodging/16000000/15120000/15118300/15118262/2535dbb9_y.jpg)

### Hotel Chicago West Loop, SureStay Collection by Best Western

10/10 Excellent

"Good customer service everything was good"

[](https://expedia.ca/Chicago-Hotels-Hotel-Chicago-West-Loop.h15118262.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

"Fantastic stay, staff was kind and extremely helpful. Definitely will be coming back, City views are amazing. "

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

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