Title: West Side Vacation Home Rentals : Search Top Private Vacation Homes for Rent | 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)[Vacation Rentals in West Side](https://expedia.ca/West-Side-Vacation-Rentals.d553248635976475400.Travel-Guide-VacationRentals)[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)

# West Side Vacation Rentals

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## Check prices for these dates

In two weeks

[Dec 5 - Dec 7](https://www.expedia.ca/Hotel-Search?regionId=553248635976475400&startDate=2025-12-05&endDate=2025-12-07&adults=2&lodging=VACATION_HOME&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In two months

[Jan 16 - Jan 18](https://www.expedia.ca/Hotel-Search?regionId=553248635976475400&startDate=2026-01-16&endDate=2026-01-18&adults=2&lodging=VACATION_HOME&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In three months

[Feb 13 - Feb 15](https://www.expedia.ca/Hotel-Search?regionId=553248635976475400&startDate=2026-02-13&endDate=2026-02-15&adults=2&lodging=VACATION_HOME&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In four months

[Mar 13 - Mar 15](https://www.expedia.ca/Hotel-Search?regionId=553248635976475400&startDate=2026-03-13&endDate=2026-03-15&adults=2&lodging=VACATION_HOME&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

## Browse Select West Side Vacation Homes

![Exterior detail](https://images.trvl-media.com/lodging/109000000/108220000/108219500/108219403/e79449bd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/109000000/108220000/108219500/108219403/5ccfbbbc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/109000000/108220000/108219500/108219403/dfa31946.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/109000000/108220000/108219500/108219403/da25d2c5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Robertsdale

10/10

Exceptional

(12)

"Very clean in a safe neighborhood. I would stay here again"

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

Charles W.

CA $130

CA $201 total

includes taxes & fees

Nov 24 - Nov 25

[](https://www.expedia.ca/Whiting-Hotels-Charming-3-BR-Home-On-A-Cobblestone-Street-Near-The-Lake-Michigan-Lakefront.h108219403.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/50000000/49100000/49092500/49092456/w953h720x163y0-0c76a558.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/50000000/49100000/49092500/49092456/83dc9e9a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/50000000/49100000/49092500/49092456/d1a40a0c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/50000000/49100000/49092500/49092456/ed8d4a1a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Oak Park

9.8/10

Exceptional

(32)

"great stay"

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

matt R.

CA $100

CA $294 total

includes taxes & fees

Dec 17 - Dec 18

[](https://www.expedia.ca/Chicago-Hotels-A-Quiet-Stay-While-You-Are-Away.h49092456.Hotel-Information)

![Exterior detail](https://images.trvl-media.com/lodging/49000000/48960000/48959700/48959659/591973f6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/49000000/48960000/48959700/48959659/76fecaef.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/49000000/48960000/48959700/48959659/d81d6c50.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, desk, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/49000000/48960000/48959700/48959659/61fb0165.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Riverwoods

9.8/10

Exceptional

(73)

"Perfect secluded neighborhood. Very quiet which is what we needed to just get away from everything. Shopping and restaurants are all within 10 minutes. Owner always answered my questions right away. Would stay there again for a little retreat."

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

Timothy

CA $127

CA $261 total

includes taxes & fees

Nov 23 - Nov 24

[](https://www.expedia.ca/Chicago-Hotels-Master-Qtr-Close-To-Nature-Easy-Urban-Facilities.h48959659.Hotel-Information)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/72000000/71680000/71677300/71677273/a0f5c46e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/72000000/71680000/71677300/71677273/c1640248.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor dining](https://images.trvl-media.com/lodging/72000000/71680000/71677300/71677273/1dc70e49.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, books, offices](https://images.trvl-media.com/lodging/72000000/71680000/71677300/71677273/49bef28c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Worth

9.6/10

Exceptional

(53)

"Perfect place for an 8 person golf trip! "

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

Griffin P.

CA $218

CA $465 total

includes taxes & fees

Dec 7 - Dec 8

[](https://www.expedia.ca/Chicago-Hotels-The-Comfy-King-Ranch-King-BedFast-WiFiFree-Pkg.h71677273.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/89000000/88500000/88494900/88494875/w867h654x78y17-d683a7ce.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Game room](https://images.trvl-media.com/lodging/89000000/88500000/88494900/88494875/w506h683x260y0-79a3d3f4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Living area](https://images.trvl-media.com/lodging/89000000/88500000/88494900/88494875/w904h683x60y0-33f7d28e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/89000000/88500000/88494900/88494875/9878af78.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Willow Springs

8.8/10

Excellent

(14)

"We liked the home, it had everything we needed. We loved having the pool table to play on, that was a hit! The backyard was clean and large, with lots of room! We had the privacy that we needed!"

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

Gabriela N.

CA $253

CA $563 total

includes taxes & fees

Nov 25 - Nov 26

[](https://www.expedia.ca/Chicago-Hotels-Coziest-Estate-Home-20-Minutes-To-Downtown.h88494875.Hotel-Information)

![Smart TV](https://images.trvl-media.com/lodging/90000000/89820000/89818200/89818126/24b80113.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/90000000/89820000/89818200/89818126/d13cd0b6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/90000000/89820000/89818200/89818126/df397b69.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/90000000/89820000/89818200/89818126/58bc029b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Des Plaines

9.0/10

Wonderful

(4)

"Very nice and clean place to stay at. Great communication from property manager. I would absolutely stay here again!"

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

Stephanie G.

CA $98

CA $394 total

includes taxes & fees

Nov 25 - Nov 26

[](https://www.expedia.ca/Chicago-Hotels-Getaway-Near-ORD-With-Great-Local-Amenities.h89818126.Hotel-Information)

![Exterior detail](https://images.trvl-media.com/lodging/106000000/105140000/105136600/105136524/aa9396b3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/106000000/105140000/105136600/105136524/699d0fa8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![4 bedrooms, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/106000000/105140000/105136600/105136524/3f6e4959.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/106000000/105140000/105136600/105136524/c4f6c687.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Oak Park

10/10

Exceptional

(11)

"This location was very convenient, and in close proximity to both downtown Oak Park, and the greater Chicago area."

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

Thomas P.

CA $196

CA $657 total

includes taxes & fees

Dec 2 - Dec 3

[](https://www.expedia.ca/Chicago-Hotels-Vintage-Urban-Retreat.h105136524.Hotel-Information)

![Fitness facility](https://images.trvl-media.com/lodging/123000000/122820000/122812000/122811987/c9a94206.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV](https://images.trvl-media.com/lodging/123000000/122820000/122812000/122811987/0e363a58.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![4 bedrooms, iron/ironing board, travel crib, WiFi](https://images.trvl-media.com/lodging/123000000/122820000/122812000/122811987/d9f32857.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV](https://images.trvl-media.com/lodging/123000000/122820000/122812000/122811987/0df62c23.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Belmont Cragin

CA $133

CA $772 total

includes taxes & fees

Dec 2 - Dec 3

[](https://www.expedia.ca/Chicago-Hotels-Theater-Game-Room-Gym-Firepit-4BR-Home.h122811987.Hotel-Information)

![Microwave, oven, stovetop, dishwasher](https://images.trvl-media.com/lodging/118000000/117680000/117672000/117671933/e376d974.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV](https://images.trvl-media.com/lodging/118000000/117680000/117672000/117671933/190b2201.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/118000000/117680000/117672000/117671933/08f64820.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV](https://images.trvl-media.com/lodging/118000000/117680000/117672000/117671933/b132ab29_edited_0386.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Maywood

7.8/10

Good

(13)

"Very nice place "

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

Elliot H.

CA $209

CA $342 total

includes taxes & fees

Nov 24 - Nov 25

[](https://www.expedia.ca/Chicago-Hotels-Charming-2-Bedroom-House-In-Maywood-With-WiFi.h117671933.Hotel-Information)

![Terrace/patio](https://images.trvl-media.com/lodging/91000000/90620000/90612900/90612832/7407c2cb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/91000000/90620000/90612900/90612832/c8a15818.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/91000000/90620000/90612900/90612832/0900c857.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![4 bedrooms, desk, travel crib, free WiFi](https://images.trvl-media.com/lodging/91000000/90620000/90612900/90612832/cb5bf3e3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Oak Park

10/10

Exceptional

(26)

"Great location and walkable to restaurants. "

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

Laura B.

CA $274

CA $757 total

includes taxes & fees

Dec 2 - Dec 3

[](https://www.expedia.ca/Chicago-Hotels-Modern-Victorian-Vibes-Character-Charm.h90612832.Hotel-Information)

![Private kitchen](https://images.trvl-media.com/lodging/118000000/117980000/117975600/117975506/w906h683x59y0-58db832b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![2 bedrooms, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/118000000/117980000/117975600/117975506/w905h683x59y0-89c2c9cc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Private kitchen](https://images.trvl-media.com/lodging/118000000/117980000/117975600/117975506/w905h683x60y0-e4d44463.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/118000000/117980000/117975600/117975506/w756h683x134y0-73459ea5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in La Grange Highlands

10/10

Exceptional

(2)

"Good communication from beginning to the end. Will definitely stay at this property again on my next Chicago vacation."

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

Arnie B.

CA $118

CA $356 total

includes taxes & fees

Nov 24 - Nov 25

[](https://www.expedia.ca/Chicago-Hotels-Guesthouse-Gem-2BR.h117975506.Hotel-Information)

![Game room](https://images.trvl-media.com/lodging/123000000/122820000/122812000/122811939/f4a99625.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/123000000/122820000/122812000/122811939/33949f43.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/123000000/122820000/122812000/122811939/f0d5c893.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Children's area](https://images.trvl-media.com/lodging/123000000/122820000/122812000/122811939/a1eb624c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Belmont Cragin

CA $178

CA $717 total

includes taxes & fees

Nov 23 - Nov 24

[](https://www.expedia.ca/Chicago-Hotels-Game-Room-Fire-Pit-Playground-Gym-Billiard.h122811939.Hotel-Information)

![Outdoor dining](https://images.trvl-media.com/lodging/75000000/74250000/74243100/74243056/bf01096c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![2 bedrooms, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/75000000/74250000/74243100/74243056/fd69f00b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/75000000/74250000/74243100/74243056/45b7296c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/75000000/74250000/74243100/74243056/w1096h1452x0y0-f7b35f5a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Wheaton

10/10

Exceptional

(54)

"Great place for a family visit to Wheaton! Thanks!"

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

Lisa

CA $239

CA $433 total

includes taxes & fees

Nov 24 - Nov 25

[](https://www.expedia.ca/Chicago-Hotels-Charming-Cottage-Close-To-CollegeTownStation.h74243056.Hotel-Information)

![Smart TV](https://images.trvl-media.com/lodging/106000000/105790000/105783600/105783565/71fea1d1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/106000000/105790000/105783600/105783565/340d0fb1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV](https://images.trvl-media.com/lodging/106000000/105790000/105783600/105783565/643f9b49.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/106000000/105790000/105783600/105783565/c86038f0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Elmhurst

10/10

Exceptional

(13)

"Great stay"

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

Aaron B.

CA $298

CA $693 total

includes taxes & fees

Nov 30 - Dec 1

[](https://www.expedia.ca/Chicago-Hotels-Enamored-In-Elmhurst.h105783565.Hotel-Information)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/115000000/114890000/114880900/114880853/6d36ba2e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, video games](https://images.trvl-media.com/lodging/115000000/114890000/114880900/114880853/56d1072c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/115000000/114890000/114880900/114880853/02fa0542.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Game room](https://images.trvl-media.com/lodging/115000000/114890000/114880900/114880853/ce647314.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Hazel Crest

7.4/10

Good

(10)

"Good quiet location "

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

Augusto D.

CA $233

CA $527 total

includes taxes & fees

Nov 24 - Nov 25

[](https://www.expedia.ca/Chicago-Hotels-Charming-2-Bedroom-House-With-WiFi-In-Peaceful-Hazel-Crest.h114880853.Hotel-Information)

![TV](https://images.trvl-media.com/lodging/100000000/99270000/99269700/99269654/w1179h800x21y0-c9fb8097.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/100000000/99270000/99269700/99269654/24a188f2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/100000000/99270000/99269700/99269654/45b3ad33.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV](https://images.trvl-media.com/lodging/100000000/99270000/99269700/99269654/db12f84a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Burbank

9.4/10

Exceptional

(6)

"Check in was easy and house was in safe neighborhood. It was a quick stay really a place to sleep for a few hours on our way through. "

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

Stephanie S.

CA $258

CA $649 total

includes taxes & fees

Dec 7 - Dec 8

[](https://www.expedia.ca/Chicago-Hotels-Modern-4BR-Retreat-Near-MDW-LCP-Collection.h99269654.Hotel-Information)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/72000000/71950000/71948000/71947955/696abe25.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/72000000/71950000/71948000/71947955/7bc6fa05.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/72000000/71950000/71948000/71947955/6b638712.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, books](https://images.trvl-media.com/lodging/72000000/71950000/71948000/71947955/392f7166.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Wood Dale

10/10

Exceptional

(17)

"Great property and great host!"

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

Darin H.

CA $252

CA $554 total

includes taxes & fees

Nov 24 - Nov 25

[](https://www.expedia.ca/Chicago-Hotels-King-Bed.h71947955.Hotel-Information)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/90000000/89740000/89733700/89733678/17cec5f9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/90000000/89740000/89733700/89733678/2f690fac.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/90000000/89740000/89733700/89733678/653b9107.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/90000000/89740000/89733700/89733678/f24571b0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Skokie

10/10

Exceptional

(34)

"Great!"

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

Laura N.

CA $403

CA $920 total

includes taxes & fees

Dec 2 - Dec 3

[](https://www.expedia.ca/Chicago-Hotels-Luxe-Haus-Of-LoveRenovated-1938-Cape-Cod-Heated-FLRS.h89733678.Hotel-Information)

![Interior](https://images.trvl-media.com/lodging/120000000/119230000/119224900/119224847/2908f32b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/120000000/119230000/119224900/119224847/11ec7a13.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![11 bedrooms, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/120000000/119230000/119224900/119224847/ef119c23.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/120000000/119230000/119224900/119224847/96e3e640.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Des Plaines

10/10

Exceptional

(2)

"We really enjoyed staying in this house. It was very clean and spacious. Excellent for larger groups!"

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

TheBrittinghams

CA $7,046

CA $9,345 total

includes taxes & fees

Nov 24 - Nov 25

[](https://www.expedia.ca/Chicago-Hotels-Sleeps-24-Luxury-House-Near-Chicago-12-King-Beds.h119224847.Hotel-Information)

![Dining](https://images.trvl-media.com/lodging/85000000/84320000/84314800/84314776/b84b8d49.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, books, offices](https://images.trvl-media.com/lodging/85000000/84320000/84314800/84314776/aadd6154.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/85000000/84320000/84314800/84314776/323d116b.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/85000000/84320000/84314800/84314776/w1019h683x3y0-935e50e6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Lombard

9.6/10

Exceptional

(15)

"I had a great stay over the weekend with my family it was very relaxing and peaceful "

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

Tennika W.

CA $175

CA $420 total

includes taxes & fees

Nov 25 - Nov 26

[](https://www.expedia.ca/Chicago-Hotels-Comfy-Home-W-Access-To-Major-RoadsHwys.h84314776.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=2025-12-05&endDate=2025-12-06&regionId=553248635976475400&adults=2&lodging=VACATION_HOME&sort=RECOMMENDED&openPlayBack=true)

![](https://forever.travel-assets.com/flex/flexmanager/images/2025/11/05/BEX-BF-25_CA_1_Desktop.jpg?impolicy=fcrop&w=1400&h=600&q=mediumHigh)

## 

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[Sign in](https://expedia.ca/user/signin?ckoflag=0&uurl=e3id%3Dredr%26rurl%3D%2FWest-Side-Private-Vacation-Homes.d553248635976475400-aaPrivateVacationHomes.Travel-Guide-Accommodation)[Sign up, it's free](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FWest-Side-Private-Vacation-Homes.d553248635976475400-aaPrivateVacationHomes.Travel-Guide-Accommodation)

## Top West Side Hotel Reviews

![Homewood Suites by Hilton Chicago West Loop Fulton Mkt Area](https://images.trvl-media.com/lodging/16000000/15820000/15816100/15816026/0f7d6f35_y.jpg)

### Homewood Suites by Hilton Chicago West Loop Fulton Mkt Area

10/10 Excellent

"amazing stay! "

[](https://expedia.ca/Chicago-Hotels-Homewood-Suites-By-Hilton-Chicago-Downtown-West-Loop.h15816026.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

"The room was clean, however I did find a pill on the floor which thankfully. I saw before my grandson got to it."

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

"Very nice and clean option for anyone working in the area. Very nice host! Thank you for a simple and enjoyable stay! "

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

"Clean inexpensive and convenient. "

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

"Room was very nice with a complete kitchen "

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

"My son stayed there while his baby was in Comer Hospital and said the hotel was beautiful, new, clean."

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

"Enjoyed the area and hotel very much! Easy on site parking "

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

"The room was beyond clean, staff were really nice and helpful ,plan on staying with them real soon "

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

![Hyatt Place Chicago/Wicker Park](https://images.trvl-media.com/lodging/43000000/42200000/42197500/42197417/34425b75_y.jpg)

### Hyatt Place Chicago/Wicker Park

10/10 Excellent

"The room is spotless with a comfortable bed & nice seating area. The bathroom is clean, towels are fluffy, excellent water pressure. We stay here whenever we visit my daughter in Chicago. Oh, and the rooftop bar/cafe is a big plus. It is a great hotel! "

[](https://expedia.ca/Chicago-Hotels-Hyatt-Place-ChicagoWicker-Park.h42197417.Hotel-Information)

## Find out more about West Side

## West Side Vacation Homes information

| Number of reviews | |
| --- | --- |
| Accommodation | Vacation Homes |
| Lowest Price | |
| Highest Price | |

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-   [Visit Little Village](https://www.expedia.ca/Chicago-Little-Village.dx6132436)
-   [Visit North Lawndale](https://www.expedia.ca/Chicago-North-Lawndale.dx6132403)
-   [Visit Smith Park](https://www.expedia.ca/Chicago-Smith-Park.dx553248635976473807)
-   [Visit The Loop](https://www.expedia.ca/Chicago-The-Loop.dx800024)
-   [Visit Tri-Taylor](https://www.expedia.ca/Chicago-Tri-Taylor.dx553248635976469282)
-   [Chicago Vacations](https://www.expedia.ca/Chicago.d178248.Destination-Travel-Guides)
-   [Garfield Park Conservatory](https://www.expedia.ca/Garfield-Park-Conservatory-East-Garfield-Park.d6182807.Vacation-Attraction)
-   [United Center](https://www.expedia.ca/United-Center-Near-West-Side.d6064077.Vacation-Attraction)

-   [Book Vacation Homes in West Side on Expedia.com](https://www.expedia.com/West-Side-Private-Vacation-Homes.d553248635976475400-aaPrivateVacationHomes.Travel-Guide-Accommodation)