Title: Southwest Side Vacation Home Rentals from CA $279: Search Top Private Vacation Homes for Rent | Expedia.ca

 

[Southwest Side Travel Guide](https://expedia.ca/Southwest-Side.dx553248635976475403)[Hotels in Southwest Side](https://expedia.ca/Southwest-Side-Hotels.d553248635976475403.Travel-Guide-Hotels)[Vacation Rentals in Southwest Side](https://expedia.ca/Southwest-Side-Vacation-Rentals.d553248635976475403.Travel-Guide-VacationRentals)[Flights to Southwest Side](https://expedia.ca/Cheap-Flights-To-Southwest-Side.d553248635976475403.Travel-Guide-Flights)[Southwest Side Car Rentals](https://expedia.ca/Car-Rentals-In-Southwest-Side.d553248635976475403.Car-Rental-Guide)[Southwest Side Vacation Packages](https://expedia.ca/Southwest-Side.d553248635976475403.Destination-Travel-Guides)

![Chicago, IL showing interior views, heritage elements and an airport](https://images.trvl-media.com/place/5719117/ef1b962b-07e6-469b-abf5-73ab99ceb6ee.jpg?impolicy=fcrop&w=1200&h=500&q=medium)

Photo by by Midway Intl Airport

# Southwest Side Vacation Rentals

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## Check prices for these dates

Next weekend

[Dec 5 - Dec 7](https://www.expedia.ca/Hotel-Search?regionId=553248635976475403&startDate=2025-12-05&endDate=2025-12-07&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In two weeks

[Dec 12 - Dec 14](https://www.expedia.ca/Hotel-Search?regionId=553248635976475403&startDate=2025-12-12&endDate=2025-12-14&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In one month

[Dec 26 - Dec 28](https://www.expedia.ca/Hotel-Search?regionId=553248635976475403&startDate=2025-12-26&endDate=2025-12-28&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In two months

[Jan 23 - Jan 25](https://www.expedia.ca/Hotel-Search?regionId=553248635976475403&startDate=2026-01-23&endDate=2026-01-25&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

## Browse Select Southwest Side Vacation Homes

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/109000000/108890000/108885800/108885786/9d278ba1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV](https://images.trvl-media.com/lodging/109000000/108890000/108885800/108885786/5b7a273e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV](https://images.trvl-media.com/lodging/109000000/108890000/108885800/108885786/3c3ca737.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/109000000/108890000/108885800/108885786/138bf941.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Spacious 3br home near Chicago, fenced yard for pets

Richton Park

9.0/10

Wonderful

(13)

"Awesome stay!"

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

Patrick J.

CA $151

CA $435 total

includes taxes & fees

Nov 30 - Dec 1

[](https://www.expedia.ca/Richton-Park-Hotels-Spacious-3br-Home-Near-Chicago.h108885786.Hotel-Information)

![Exterior detail](https://images.trvl-media.com/lodging/109000000/108220000/108219500/108219403/e79449bd.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)

![Terrace/patio](https://images.trvl-media.com/lodging/109000000/108220000/108219500/108219403/f18fcae4.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)

### Charming 3-BR home on a cobblestone street near the Lake Michigan lakefront.

Robertsdale

10/10

Exceptional

(13)

"Wonderful property and nice owners. I definitely recommend and will stay again if I'm ever in the area."

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

Karen D.

CA $200

CA $279 total

includes taxes & fees

Dec 4 - Dec 5

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

![3 bedrooms, desk, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/72000000/71680000/71677300/71677273/2941b332.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)

![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)

### \*The Comfy King Ranch\*King Bed Suite\*Fast Wi-Fi

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 $217

CA $463 total

includes taxes & fees

Nov 30 - Dec 1

[](https://www.expedia.ca/Chicago-Hotels-The-Comfy-King-Ranch-King-BedFast-WiFiFree-Pkg.h71677273.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/106000000/105140000/105136600/105136524/33378924.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)

### Vintage Urban Retreat

Oak Park

10/10

Exceptional

(12)

"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 $192

CA $655 total

includes taxes & fees

Dec 1 - Dec 2

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

![2 bedrooms, desk, iron/ironing board, travel crib](https://images.trvl-media.com/lodging/90000000/89820000/89818200/89818126/f6aa2476.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Getaway Near ORD With Great Local Amenities

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 $97

CA $389 total

includes taxes & fees

Nov 30 - Dec 1

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

![Interior](https://images.trvl-media.com/lodging/117000000/116480000/116470400/116470311/48e46ac8.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/117000000/116480000/116470400/116470311/9a820eca.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/117000000/116480000/116470400/116470311/31d65898.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor dining](https://images.trvl-media.com/lodging/117000000/116480000/116470400/116470311/6a1f9864.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Lockport Haven/3 King Beds/Wi-fi/Near Downtown!

Lockport

10/10

Exceptional

(4)

"Amazing property had everything we need! "

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

Rachel

CA $245

CA $531 total

includes taxes & fees

Dec 1 - Dec 2

[](https://www.expedia.ca/Lockport-Hotels-Lockport-Haven3-King-BedsWi-FiNear-Downtown.h116470311.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)

![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)

![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)

![Interior](https://images.trvl-media.com/lodging/89000000/88500000/88494900/88494875/ad61d9f5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Coziest estate home 20 minutes to downtown

Willow Springs

8.8/10

Excellent

(15)

"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 $252

CA $556 total

includes taxes & fees

Dec 4 - Dec 5

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

![Hair dryer, towels, soap, toilet paper](https://images.trvl-media.com/lodging/118000000/117980000/117975600/117975506/w507h683x258y0-bb141c02.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)

![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)

### Guesthouse Gem 2BR, Smart TVs, W/D, & Parking

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 $117

CA $353 total

includes taxes & fees

Nov 30 - Dec 1

[](https://www.expedia.ca/Chicago-Hotels-Guesthouse-Gem-2BR.h117975506.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/123000000/122820000/122812000/122811987/0df62c23.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)

### Theater • Game Room • Gym • Firepit • 4BR Home

Belmont Cragin

CA $133

CA $769 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)

![Property grounds](https://images.trvl-media.com/lodging/118000000/117680000/117672000/117671933/dc90b17f.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)

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

### Charming 2-bedroom house in Maywood with WiFi, AC full basement with sofa bed

Maywood

7.8/10

Good

(13)

"Very nice place "

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

Elliot H.

CA $208

CA $339 total

includes taxes & fees

Nov 30 - Dec 1

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

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/103000000/102520000/102515700/102515612/010eed58.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/103000000/102520000/102515700/102515612/7448b12a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace, video games, foosball](https://images.trvl-media.com/lodging/103000000/102520000/102515700/102515612/56333a9c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Children's area](https://images.trvl-media.com/lodging/103000000/102520000/102515700/102515612/w912h683x56y0-90e9213c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### 15 mins to beach/Renew+Relax/Clean/ Nat’l Park!/Theater/Game Room/Pet Friendly

Gary

8.6/10

Excellent

(17)

"i had a good time here. the house was great. thank you"

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

Alvaro C.

CA $225

CA $625 total

includes taxes & fees

Dec 2 - Dec 3

[](https://www.expedia.ca/Gary-Hotels-Theater-RMKG-BdFam-Friendly-Home-NR-DunesBeach.h102515612.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)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/75000000/74250000/74243100/74243056/5e34eeff.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)

### ✽ Charming Cottage ✽ close to College/Town/Station

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 $238

CA $431 total

includes taxes & fees

Dec 1 - Dec 2

[](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)

![Terrace/patio](https://images.trvl-media.com/lodging/106000000/105790000/105783600/105783565/c86038f0.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)

![Exterior](https://images.trvl-media.com/lodging/106000000/105790000/105783600/105783565/29e8ad65.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Enamored in Elmhurst

Elmhurst

10/10

Exceptional

(13)

"Great stay"

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

Aaron B.

CA $297

CA $689 total

includes taxes & fees

Nov 30 - Dec 1

[](https://www.expedia.ca/Chicago-Hotels-Enamored-In-Elmhurst.h105783565.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/91000000/90620000/90612900/90612832/4c4c570d.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)

### Modern Victorian Vibes ❤️ | Character & Charm

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 $231

CA $701 total

includes taxes & fees

Dec 2 - Dec 3

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

![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)

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

### Wonderful in Wood Dale, right by O’Hare airport!

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 $250

CA $550 total

includes taxes & fees

Nov 30 - Dec 1

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

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/123000000/122660000/122655500/122655441/443df914.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Game room](https://images.trvl-media.com/lodging/123000000/122660000/122655500/122655441/6d5ce3ed.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/123000000/122660000/122655500/122655441/074afb4c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV](https://images.trvl-media.com/lodging/123000000/122660000/122655500/122655441/d8cc6f64.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Modern Stylish Comfort Near Casino and Hwy

Homewood

CA $205

CA $570 total

includes taxes & fees

Dec 2 - Dec 3

[](https://www.expedia.ca/Chicago-Hotels-Modern-Stylish-Comfort-Near-Casino-And-Hwy.h122655441.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)

![TV](https://images.trvl-media.com/lodging/100000000/99270000/99269700/99269654/db12f84a.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/100000000/99270000/99269700/99269654/d8187eff.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)

### Modern 4BR Retreat Near MDW | LCP Collection

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 $257

CA $640 total

includes taxes & fees

Nov 30 - Dec 1

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

![Fridge, microwave, stovetop, dishwasher](https://images.trvl-media.com/lodging/122000000/121310000/121303900/121303866/1b5edb97.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/122000000/121310000/121303900/121303866/d229b52f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor dining](https://images.trvl-media.com/lodging/122000000/121310000/121303900/121303866/9defe80f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/122000000/121310000/121303900/121303866/13270436.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Classic Forest Park Foursquare < 1 Mi to Blue Line

Forest Park

CA $197

CA $572 total

includes taxes & fees

Dec 2 - Dec 3

[](https://www.expedia.ca/Chicago-Hotels-Classic-Forest-Park-Foursquare-1-Mi-To-Blue-Line.h121303866.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)

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

![Smart TV, fireplace, books, video library](https://images.trvl-media.com/lodging/90000000/89740000/89733700/89733678/e7f5fdcf.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)

### Luxe Haus of Love—Renovated 1938 Cape Cod —Heated FLRS

Skokie

10/10

Exceptional

(34)

"Great place to congregate with family and a pet. Lots of room to gather."

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

Leone W.

CA $401

CA $915 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)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/119000000/118760000/118756100/118756057/w507h683x259y0-fd391321.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/119000000/118760000/118756100/118756057/4e0b5bd8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/119000000/118760000/118756100/118756057/w507h683x260y0-447e4031.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, foosball, books](https://images.trvl-media.com/lodging/119000000/118760000/118756100/118756057/w508h683x259y0-9b6c1832.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Cozy Home by O'Hare + EV Plug

Des Plaines

9.0/10

Wonderful

(4)

"Charming property in a quiet neighborhood. Host were exceptionally accommodating and replied promptly with questions. Would happily stay in this home again."

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

Michael H.

CA $226

CA $475 total

includes taxes & fees

Dec 10 - Dec 11

[](https://www.expedia.ca/Houston-Hotels-Cozy-Home-By-OHare-EV-Plug.h118756057.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=2025-12-13&endDate=2025-12-14&regionId=553248635976475403&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&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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Limited-time deals: save up to 50% on select hotels

[Book now](https://expedia.ca/deals?rfrr=AA_BF_PROMO_553248635976475403)

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[Sign in](https://expedia.ca/user/signin?ckoflag=0&uurl=e3id%3Dredr%26rurl%3D%2FSouthwest-Side-Private-Vacation-Homes.d553248635976475403-aaPrivateVacationHomes.Travel-Guide-Accommodation)[Sign up, it's free](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FSouthwest-Side-Private-Vacation-Homes.d553248635976475403-aaPrivateVacationHomes.Travel-Guide-Accommodation)

## Top Southwest Side Hotel Reviews

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

### Congress Plaza Hotel

10/10 Excellent

"Nice staff & clean room"

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

![LondonHouse Chicago, Curio Collection by Hilton](https://images.trvl-media.com/lodging/13000000/12790000/12786700/12786616/74c2f40d_y.jpg)

### LondonHouse Chicago, Curio Collection by Hilton

10/10 Excellent

"I had a river view room and it was a lovely view! The hotel was decorated beautifully with Christmas decor. The hotel food was absolutely delicious. Beds were very comfortable and the hotel was only a 7-8 minute walk to my daughter’s dorm building. Great place to stay! "

[](https://expedia.ca/Chicago-Hotels-LondonHouse-Chicago.h12786616.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

"Great"

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

![Hotel Riu Plaza Chicago](https://images.trvl-media.com/lodging/103000000/102630000/102622800/102622712/3e21593f_y.jpg)

### Hotel Riu Plaza Chicago

10/10 Excellent

"Very Nice clean New Center"

[](https://expedia.ca/Chicago-Hotels-Hotel-Riu-Plaza-Chicago.h102622712.Hotel-Information)

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

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

10/10 Excellent

"Everything was perfect "

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

![Eurostars Magnificent Mile](https://images.trvl-media.com/lodging/2000000/1890000/1880400/1880320/08bbf982_y.jpg)

### Eurostars Magnificent Mile

10/10 Excellent

"I love this Hotel!!! I stayed here at least 10 times. Room clean, friendly staff and very convenient location. "

[](https://expedia.ca/Chicago-Hotels-Eurostars-Magnificent-Mile.h1880320.Hotel-Information)

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

### The Allegro Royal Sonesta Hotel Chicago Loop

10/10 Excellent

"Fantastic hotel, great location. Highly recommended "

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

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

### Hilton Chicago

10/10 Excellent

"No toiletries in the bathroom past shampoo and conditioner! Beautiful grounds and clean! Great location to downtown and stadiums"

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

![River Hotel](https://images.trvl-media.com/lodging/3000000/2680000/2675400/2675313/9a897fc5_y.jpg)

### River Hotel

10/10 Excellent

"Excellent. Clean, courteous staff, and great location."

[](https://expedia.ca/Chicago-Hotels-River-Hotel.h2675313.Hotel-Information)

## Find out more about Southwest Side

## Southwest Side Vacation Homes information

| Number of reviews | 290 |
| --- | --- |
| Accommodation | 344 Vacation Homes |
| Lowest Price | CA $279 |
| Highest Price | CA $915 |

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-   [Hotels near Zhou B Art Center](https://www.expedia.ca/Zhou-B-Art-Center-Hotels.0-l553248621533116323-0.Travel-Guide-Filter-Hotels)

-   [Flights to Chicago](https://www.expedia.ca/Cheap-Flights-To-Chicago.d178248.Travel-Guide-Flights)
-   [Flights from Midway Intl.](https://www.expedia.ca/lp/airports/mdw/flights-from-midway-intl-airport)
-   [Porter Airlines Toronto (YTZ) to Chicago (MDW) flights](https://www.expedia.ca/lp/flight-routes/porter-airlines-from-billy-bishop-toronto-city-to-midway-intl/pd/ytz/mdw)
-   [Flights from Detroit (DTW) to Chicago (MDW)](https://www.expedia.ca/lp/flights/dtw/mdw/detroit-to-chicago)
-   [Flights from Toronto (YTZ) to Chicago (MDW)](https://www.expedia.ca/lp/flights/ytz/mdw/toronto-to-chicago)
-   [Flights from Winnipeg (YWG) to Chicago (MDW)](https://www.expedia.ca/lp/flights/ywg/mdw/winnipeg-to-chicago)
-   [Flights from Toronto (YYZ) to Chicago (MDW)](https://www.expedia.ca/lp/flights/yyz/mdw/toronto-to-chicago)
-   [Flights from Toronto (YYZ) to Chicago (ORD)](https://www.expedia.ca/lp/flights/yyz/ord/toronto-to-chicago)

-   [Visit Back of the Yards](https://www.expedia.ca/Chicago-Back-Of-The-Yards.dx553248635976382392)
-   [Visit Brighton Park](https://www.expedia.ca/Chicago-Brighton-Park.dx6132396)
-   [Visit Canaryville](https://www.expedia.ca/Chicago-Canaryville.dx6132307)
-   [Visit Chicago Lawn](https://www.expedia.ca/Chicago-Chicago-Lawn.dx6132188)
-   [Visit Englewood](https://www.expedia.ca/Chicago-Englewood.dx101911)
-   [Visit Fuller Park](https://www.expedia.ca/Chicago-Fuller-Park.dx6132374)
-   [Visit Gage Park](https://www.expedia.ca/Chicago-Gage-Park.dx6132375)

-   [Car rentals near McKinley Park](https://www.expedia.ca/Car-Rentals-In-McKinley-Park.d6132389.Car-Rental-Guide)
-   [Rental cars Midway Intl. airport](https://www.expedia.ca/Car-Rentals-In-Midway-Intl.d5719117.Car-Rental-Guide)

-   [Book Vacation Homes in Southwest Side on Expedia.com](https://www.expedia.com/Southwest-Side-Private-Vacation-Homes.d553248635976475403-aaPrivateVacationHomes.Travel-Guide-Accommodation)