Title: Far Southwest Side Vacation Home Rentals from CA $249: Search Top Private Vacation Homes for Rent | Expedia.ca

 

[Far Southwest Side Travel Guide](https://expedia.ca/Far-Southwest-Side.dx553248635976475353)[Hotels in Far Southwest Side](https://expedia.ca/Far-Southwest-Side-Hotels.d553248635976475353.Travel-Guide-Hotels)[Vacation Rentals in Far Southwest Side](https://expedia.ca/Far-Southwest-Side-Vacation-Rentals.d553248635976475353.Travel-Guide-VacationRentals)[Flights to Far Southwest Side](https://expedia.ca/Cheap-Flights-To-Far-Southwest-Side.d553248635976475353.Travel-Guide-Flights)[Far Southwest Side Car Rentals](https://expedia.ca/Car-Rentals-In-Far-Southwest-Side.d553248635976475353.Car-Rental-Guide)[Far Southwest Side Vacation Packages](https://expedia.ca/Far-Southwest-Side.d553248635976475353.Destination-Travel-Guides)

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# Far Southwest Side Vacation Rentals

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## Check prices for these dates

In two weeks

[Dec 12 - Dec 14](https://www.expedia.ca/Hotel-Search?regionId=553248635976475353&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 two months

[Jan 23 - Jan 25](https://www.expedia.ca/Hotel-Search?regionId=553248635976475353&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)

In three months

[Feb 20 - Feb 22](https://www.expedia.ca/Hotel-Search?regionId=553248635976475353&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 four months

[Mar 20 - Mar 22](https://www.expedia.ca/Hotel-Search?regionId=553248635976475353&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)

## Browse Select Far Southwest Side Vacation Homes

![Microwave, oven, stovetop](https://images.trvl-media.com/lodging/122000000/121820000/121815200/121815186/b1ada0e0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV](https://images.trvl-media.com/lodging/122000000/121820000/121815200/121815186/d8580e49.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![3 bedrooms, WiFi, bed sheets](https://images.trvl-media.com/lodging/122000000/121820000/121815200/121815186/6a00edbd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Toilet paper](https://images.trvl-media.com/lodging/122000000/121820000/121815200/121815186/0d8c5080.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Your Home Away From Home in Sauk Village

Sauk Village

10/10

Exceptional

(1)

"My Experience Was (NOTHING) Short Of Perfect! The Place Is Nice & The Host Was Even Better! I’ll Forsure Be Booking Again! "

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

Aaron K.

CA $168

CA $249 total

includes taxes & fees

Nov 29 - Nov 30

[](https://www.expedia.ca/Sauk-Village-Hotels-Pleasant-3-Bedroom-House-In-Sauk-Village.h121815186.Hotel-Information)

![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/109000000/108890000/108885800/108885786/3c3ca737.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/109000000/108890000/108885800/108885786/w1200h796x0y4-555fde87.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 $437 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)

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

### 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 $201

CA $280 total

includes taxes & fees

Dec 1 - Dec 2

[](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/89000000/88180000/88178900/88178891/w506h639x259y44-83e61931.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/89000000/88180000/88178900/88178891/w505h683x260y0-7687ead9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV](https://images.trvl-media.com/lodging/89000000/88180000/88178900/88178891/w505h683x260y0-df8876b1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/89000000/88180000/88178900/88178891/w508h683x259y0-938c1ece.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Honeycomb Hideout w/ 2 bedrooms

Gary

CA $183

CA $590 total

includes taxes & fees

Nov 30 - Dec 1

[](https://www.expedia.ca/Gary-Hotels-Honeycomb-Hideout-W-2-Bedrooms.h88178891.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)

![Outdoor dining](https://images.trvl-media.com/lodging/72000000/71680000/71677300/71677273/1dc70e49.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)

![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)

### \*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 $464 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)

![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)

![Outdoor dining](https://images.trvl-media.com/lodging/117000000/116480000/116470400/116470311/6a1f9864.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)

### 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 $533 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)

![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)

![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 $558 total

includes taxes & fees

Dec 1 - Dec 2

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

![Dining](https://images.trvl-media.com/lodging/106000000/105140000/105136600/105136524/c4f6c687.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)

### 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)

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

![Terrace/patio](https://images.trvl-media.com/lodging/123000000/122820000/122812000/122811987/deb34291.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)

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

Belmont Cragin

CA $133

CA $771 total

includes taxes & fees

Dec 9 - Dec 10

[](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)

![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)

![Property grounds](https://images.trvl-media.com/lodging/118000000/117680000/117672000/117671933/dc90b17f.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 $340 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/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/72000000/71950000/71948000/71947955/37f6160a.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 $251

CA $552 total

includes taxes & fees

Nov 30 - Dec 1

[](https://www.expedia.ca/Chicago-Hotels-King-Bed.h71947955.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/91000000/90620000/90612900/90612832/4c4c570d.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 $232

CA $707 total

includes taxes & fees

Dec 1 - Dec 2

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

![Beach](https://images.trvl-media.com/lodging/103000000/102520000/102515700/102515612/b52cb489.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 $226

CA $627 total

includes taxes & fees

Dec 3 - Dec 4

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

![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)

### 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 $118

CA $354 total

includes taxes & fees

Dec 1 - Dec 2

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

![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)

### 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 $258

CA $642 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, oven, stovetop](https://images.trvl-media.com/lodging/112000000/111670000/111668700/111668679/a03596e1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/112000000/111670000/111668700/111668679/fcb2b3a2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV](https://images.trvl-media.com/lodging/112000000/111670000/111668700/111668679/dd9a3475.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/112000000/111670000/111668700/111668679/cd881412.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### 20mins from beach, 10guests/WIFI/1.2 baths/ping pong/pool table/treadmill

Gary

10/10

Exceptional

(4)

"Very nice property. Kids loved staying here! "

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

Sydney D.

CA $285

CA $634 total

includes taxes & fees

Dec 1 - Dec 2

[](https://www.expedia.ca/Gary-Hotels-COMFORTABLE-ALLUSION.h111668679.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)

![Exterior](https://images.trvl-media.com/lodging/85000000/84320000/84314800/84314776/323d116b.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)

![Property grounds](https://images.trvl-media.com/lodging/85000000/84320000/84314800/84314776/w1017h683x4y0-e81f9176.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### PROMO 10% MONTHLY DISCOUNT! Comfy Home w Access to Major Roads/Hwys, Huge Yard

Lombard

9.6/10

Exceptional

(16)

"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.

[](https://www.expedia.ca/Chicago-Hotels-Comfy-Home-W-Access-To-Major-RoadsHwys.h84314776.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)

![Exterior](https://images.trvl-media.com/lodging/106000000/105790000/105783600/105783565/29e8ad65.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)

### 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 $298

CA $692 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/91000000/90010000/90008300/90008221/6ff9d9ca.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![4 bedrooms, desk, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/91000000/90010000/90008300/90008221/dfe845a9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/91000000/90010000/90008300/90008221/35aa2d12.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/91000000/90010000/90008300/90008221/43970355.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Luxury House minutes away from O'Hare and Downtown Chicago

Bensenville

10/10

Exceptional

(1)

"Easily the nicest place I have ever stayed at. Wonderful neighborhood, clean house, and great amenities. I’ll stay there again anyday. "

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

Jacob F.

CA $259

CA $813 total

includes taxes & fees

Dec 1 - Dec 2

[](https://www.expedia.ca/Chicago-Hotels-Luxury-House-Minutes-Away-From-OHare-And-Downtown-Chicago.h90008221.Hotel-Information)

![Microwave, stovetop, dishwasher](https://images.trvl-media.com/lodging/118000000/117850000/117840100/117840012/e3c24e4b.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/118000000/117850000/117840100/117840012/9a52aa75.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor dining](https://images.trvl-media.com/lodging/118000000/117850000/117840100/117840012/1c5af541.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV](https://images.trvl-media.com/lodging/118000000/117850000/117840100/117840012/92fb52b1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Charming 3BR/2BA Retreat in Villa Park – Comfort, Space & Convenience!

Villa Park

10/10

Exceptional

(1)

"Great location and perfect set up for a family size Vaca!! Loved it!"

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

Robin C.

CA $265

CA $618 total

includes taxes & fees

Dec 1 - Dec 2

[](https://www.expedia.ca/Chicago-Hotels-Charming-3BR2BA-Retreat-In-Villa-Park-Comfort.h117840012.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=2025-12-12&endDate=2025-12-13&regionId=553248635976475353&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)

## 

Black Friday Sale

Limited-time deals: save up to 50% on select hotels

[Book now](https://expedia.ca/deals?rfrr=AA_BF_PROMO_553248635976475353)

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Save an average of 15% on thousands of hotels when you're signed in

[Sign in](https://expedia.ca/user/signin?ckoflag=0&uurl=e3id%3Dredr%26rurl%3D%2FFar-Southwest-Side-Private-Vacation-Homes.d553248635976475353-aaPrivateVacationHomes.Travel-Guide-Accommodation)[Sign up, it's free](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FFar-Southwest-Side-Private-Vacation-Homes.d553248635976475353-aaPrivateVacationHomes.Travel-Guide-Accommodation)

## Top Far Southwest 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

"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)

![The Whitehall Hotel, BW Premier Collection](https://images.trvl-media.com/lodging/1000000/20000/18000/17903/daaf5f2e_y.jpg)

### The Whitehall Hotel, BW Premier Collection

10/10 Excellent

"Clean room, very comfortable, staff was helpful"

[](https://expedia.ca/Chicago-Hotels-The-Whitehall-Hotel.h17903.Hotel-Information)

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

### The Royal Sonesta Chicago Downtown

10/10 Excellent

"Everything was fantastic. Staff is great! Location is great. "

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

## Find out more about Far Southwest Side

## Far Southwest Side Vacation Homes information

| Number of reviews | 216 |
| --- | --- |
| Accommodation | 326 Vacation Homes |
| Lowest Price | CA $249 |
| Highest Price | CA $813 |

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-   [Cheap Hotels in Washington Heights](https://www.expedia.ca/Washington-Heights-Chicago-Hotels-Cheap-Hotels.0-n6132290-0-tCheapHotels.Travel-Guide-Filter-Hotels)
-   [Washington Heights Hotels](https://www.expedia.ca/Washington-Heights-Chicago-Hotels.0-n6132290-0.Travel-Guide-Filter-Hotels)
-   [Cheap Hotels in West Englewood](https://www.expedia.ca/West-Englewood-Chicago-Hotels-Cheap-Hotels.0-n6132412-0-tCheapHotels.Travel-Guide-Filter-Hotels)
-   [West Englewood Hotels](https://www.expedia.ca/West-Englewood-Chicago-Hotels.0-n6132412-0.Travel-Guide-Filter-Hotels)

-   [Flights to Chicago](https://www.expedia.ca/Cheap-Flights-To-Chicago.d178248.Travel-Guide-Flights)
-   [Flights from Toronto (YYZ) to Chicago (ORD)](https://www.expedia.ca/lp/flights/yyz/ord/toronto-to-chicago)

-   [Chatham Fields Vacations](https://www.expedia.ca/Chatham-Fields.d6132323.Destination-Travel-Guides)
-   [Visit Chicago Lawn](https://www.expedia.ca/Chicago-Chicago-Lawn.dx6132188)
-   [Visit Greater Grand Crossing](https://www.expedia.ca/Chicago-Greater-Grand-Crossing.dx6132273)
-   [Visit Morgan Park](https://www.expedia.ca/Chicago-Morgan-Park.dx6132289)
-   [Visit Roseland](https://www.expedia.ca/Chicago-Roseland.dx6132287)
-   [Visit Cook County](https://www.expedia.ca/Cook-County.dx553248635083916453)

-   [Europcar Rental Cars in Cook County](https://www.expedia.ca/Europcar-Destinations-In-Cook-County.d553248635083916453-c14.Car-Rental-Destination-Suppliers)

-   [Book Vacation Homes in Far Southwest Side on Expedia.com](https://www.expedia.com/Far-Southwest-Side-Private-Vacation-Homes.d553248635976475353-aaPrivateVacationHomes.Travel-Guide-Accommodation)