Title: Far Southwest Side Vacation Home Rentals from CA $202: 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

Next weekend

[Dec 19 - Dec 21](https://www.expedia.ca/Hotel-Search?regionId=553248635976475353&startDate=2025-12-19&endDate=2025-12-21&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In two weeks

[Dec 26 - Dec 28](https://www.expedia.ca/Hotel-Search?regionId=553248635976475353&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 one month

[Jan 9 - Jan 11](https://www.expedia.ca/Hotel-Search?regionId=553248635976475353&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 6 - Feb 8](https://www.expedia.ca/Hotel-Search?regionId=553248635976475353&startDate=2026-02-06&endDate=2026-02-08&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

## Our top choices for 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)

![3 bedrooms, WiFi, bed sheets](https://images.trvl-media.com/lodging/122000000/121820000/121815200/121815186/48a5d932.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)

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

### Vacation Home in Sauk Village

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

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 $127

CA $202 total

includes taxes & fees

Dec 31 - Jan 1, 2026

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

![Smart TV](https://images.trvl-media.com/lodging/109000000/108890000/108885800/108885786/b5e3f270.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)

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

![Property grounds](https://images.trvl-media.com/lodging/109000000/108890000/108885800/108885786/40af13b6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Richton Park

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

9.0/10

Wonderful

(14)

"The house was average needs some cosmetic repairs to improve the appeal to the eye. Utilities not available for more than four, we were a party of 4 so it did not matter. The master bedroom bed was rather uncomfortable."

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

Lynette H.

CA $149

CA $429 total

includes taxes & fees

Dec 15 - Dec 16

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

![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)

![Interior](https://images.trvl-media.com/lodging/89000000/88180000/88178900/88178891/f64972cc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/89000000/88180000/88178900/88178891/8063e4d0.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)

### Vacation Home in Gary

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

CA $180

CA $581 total

includes taxes & fees

Dec 14 - Dec 15

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

![Property grounds](https://images.trvl-media.com/lodging/109000000/108220000/108219500/108219403/e3fd1233.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

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

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

9.8/10

Exceptional

(15)

"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 $197

CA $275 total

includes taxes & fees

Dec 22 - Dec 23

[](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/72000000/71680000/71677300/71677273/7b6dc406.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/72000000/71680000/71677300/71677273/5569ce20.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/72000000/71680000/71677300/71677273/932d3e6c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/72000000/71680000/71677300/71677273/26045e32.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Worth

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

9.6/10

Exceptional

(54)

"Perfect place for an 8 person golf trip! "

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

Griffin P.

CA $200

CA $420 total

includes taxes & fees

Dec 15 - Dec 16

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

![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)

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

![Interior](https://images.trvl-media.com/lodging/89000000/88500000/88494900/88494875/w905h683x59y0-660799a0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Game room](https://images.trvl-media.com/lodging/89000000/88500000/88494900/88494875/bcec636a_edited_4fdb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Willow Springs

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

8.8/10

Excellent

(16)

"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 $248

CA $548 total

includes taxes & fees

Dec 15 - Dec 16

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

![Smart TV](https://images.trvl-media.com/lodging/124000000/123570000/123567200/123567128/e22610fb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Desk, iron/ironing board, travel crib, free WiFi](https://images.trvl-media.com/lodging/124000000/123570000/123567200/123567128/85a7eeca.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV](https://images.trvl-media.com/lodging/124000000/123570000/123567200/123567128/2c0997c6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/124000000/123570000/123567200/123567128/8363a80e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Avondale

[](https://www.expedia.ca/Chicago-Hotels-Modern-Apt-In-Trendy-Neighborhood-W-Free-Parking.h123567128.Hotel-Information)

CA $123

CA $255 total

includes taxes & fees

Dec 16 - Dec 17

[](https://www.expedia.ca/Chicago-Hotels-Modern-Apt-In-Trendy-Neighborhood-W-Free-Parking.h123567128.Hotel-Information)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/117000000/116480000/116470400/116470311/aad8b09b.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)

![TV, books, offices](https://images.trvl-media.com/lodging/117000000/116480000/116470400/116470311/336bd324.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/117000000/116480000/116470400/116470311/3a85b485.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Lockport

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

10/10

Exceptional

(4)

"Amazing property had everything we need! "

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

Rachel

CA $213

CA $494 total

includes taxes & fees

Dec 15 - Dec 16

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

![Smart TV](https://images.trvl-media.com/lodging/118000000/117680000/117672000/117671933/afb1f08b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/118000000/117680000/117672000/117671933/d127a41d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/118000000/117680000/117672000/117671933/d36efedf.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)

### Vacation Home in Maywood

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

8.0/10

Very good

(20)

"Very nice place "

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

Elliot H.

CA $205

CA $325 total

includes taxes & fees

Dec 19 - Dec 20

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

![Dining](https://images.trvl-media.com/lodging/123000000/122820000/122812000/122811987/951dd1c6.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/123000000/122820000/122812000/122811987/51d80cbb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV](https://images.trvl-media.com/lodging/123000000/122820000/122812000/122811987/da7804af.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV](https://images.trvl-media.com/lodging/123000000/122820000/122812000/122811987/57335499.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Belmont Cragin

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

CA $101

CA $714 total

includes taxes & fees

Jan 13 - Jan 14, 2026

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

![2 bedrooms, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/118000000/117980000/117975600/117975506/w905h683x59y0-1e5c290a.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)

![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)

### Vacation Home in La Grange Highlands

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

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 $121

CA $355 total

includes taxes & fees

Dec 15 - Dec 16

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

![Outdoor dining](https://images.trvl-media.com/lodging/77000000/76930000/76925600/76925599/e8277045.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, Netflix, Hulu, books](https://images.trvl-media.com/lodging/77000000/76930000/76925600/76925599/b02b5cf2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, Netflix, Hulu, books](https://images.trvl-media.com/lodging/77000000/76930000/76925600/76925599/08a65ad8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/77000000/76930000/76925600/76925599/ec956b24.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Lisle

[](https://www.expedia.ca/Chicago-Hotels-VERY-Close-To-Colleges.h76925599.Hotel-Information)

9.6/10

Exceptional

(19)

"Convenient location to family that lives in the area"

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

Andrea G.

CA $169

CA $408 total

includes taxes & fees

Dec 15 - Dec 16

[](https://www.expedia.ca/Chicago-Hotels-VERY-Close-To-Colleges.h76925599.Hotel-Information)

![Interior](https://images.trvl-media.com/lodging/106000000/105140000/105136600/105136524/33378924.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)

![Exterior detail](https://images.trvl-media.com/lodging/106000000/105140000/105136600/105136524/aa9396b3.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)

### Vacation Home in Oak Park

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

10/10

Exceptional

(13)

"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 $258

CA $729 total

includes taxes & fees

Dec 17 - Dec 18

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

![Beach](https://images.trvl-media.com/lodging/103000000/102520000/102515700/102515612/b52cb489.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/103000000/102520000/102515700/102515612/6b612432.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)

![Dining](https://images.trvl-media.com/lodging/103000000/102520000/102515700/102515612/1f5f8b43.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Gary

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

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 $222

CA $619 total

includes taxes & fees

Dec 18 - Dec 19

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

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/72000000/71950000/71948000/71947955/966d8367.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)

![3 bedrooms, desk, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/72000000/71950000/71948000/71947955/20532f6e.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

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

10/10

Exceptional

(17)

"Great property and great host!"

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

Darin H.

CA $247

CA $546 total

includes taxes & fees

Dec 14 - Dec 15

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

![Dining](https://images.trvl-media.com/lodging/97000000/96390000/96384200/96384152/baf1fbd0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Private kitchen](https://images.trvl-media.com/lodging/97000000/96390000/96384200/96384152/1e6ca815.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/97000000/96390000/96384200/96384152/27ecf0e1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Living area](https://images.trvl-media.com/lodging/97000000/96390000/96384200/96384152/f7e53c4b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Elmhurst

[](https://www.expedia.ca/Chicago-Hotels-LUXE-3-BR.h96384152.Hotel-Information)

8.8/10

Excellent

(38)

"A really nice house, clean and well kept. Neighborhood is older but nice and quiet. Close to highway and lots of restaurants. The owner was very responsive and great to work with. I plan on using this VRBO again in future. Backyard was fenced in and I might bring my pets next time. "

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

Scott C.

CA $205

CA $455 total

includes taxes & fees

Dec 15 - Dec 16

[](https://www.expedia.ca/Chicago-Hotels-LUXE-3-BR.h96384152.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/106000000/105790000/105783600/105783565/839ff6dd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/106000000/105790000/105783600/105783565/524cef80.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Elmhurst

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

10/10

Exceptional

(13)

"Great stay"

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

Aaron B.

CA $293

CA $684 total

includes taxes & fees

Dec 14 - Dec 15

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

![Living area](https://images.trvl-media.com/lodging/124000000/123180000/123170100/123170055/1d875630.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/124000000/123180000/123170100/123170055/c3be97de.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Private kitchen](https://images.trvl-media.com/lodging/124000000/123180000/123170100/123170055/06240ebd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Iron/ironing board, WiFi](https://images.trvl-media.com/lodging/124000000/123180000/123170100/123170055/424f49bb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Lockport

[](https://www.expedia.ca/Lockport-Hotels-Entire-Home-In-Lockport.h123170055.Hotel-Information)

CA $190

CA $498 total

includes taxes & fees

Jan 13 - Jan 14, 2026

[](https://www.expedia.ca/Lockport-Hotels-Entire-Home-In-Lockport.h123170055.Hotel-Information)

![Exterior detail](https://images.trvl-media.com/lodging/91000000/90620000/90612900/90612832/793bb6f2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/91000000/90620000/90612900/90612832/e028cf83.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)

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

### Vacation Home in Oak Park

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

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 $248

CA $706 total

includes taxes & fees

Dec 15 - Dec 16

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

![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)

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

![Exterior](https://images.trvl-media.com/lodging/112000000/111670000/111668700/111668679/02fd1c87.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV](https://images.trvl-media.com/lodging/112000000/111670000/111668700/111668679/67091c30.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Gary

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

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 $297

CA $643 total

includes taxes & fees

Dec 15 - Dec 16

[](https://www.expedia.ca/Gary-Hotels-COMFORTABLE-ALLUSION.h111668679.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 Far Southwest Side Hotel Reviews

![Hyatt Regency Chicago](https://images.trvl-media.com/lodging/1000000/10000/5000/4903/w3837h2157x3y3-c3ed4c01_y.jpg)

### Hyatt Regency Chicago

10/10 Excellent

"The room view was beautiful! The staff was super attentive and helpful. "

[](https://expedia.ca/Chicago-Hotels-Hyatt-Regency-Chicago.h4903.Hotel-Information)

![Embassy Suites by Hilton Chicago Downtown River North](https://images.trvl-media.com/lodging/1000000/20000/11600/11580/w3840h2859x0y0-5fc518eb_y.jpg)

### Embassy Suites by Hilton Chicago Downtown River North

10/10 Excellent

"Great place always. "

[](https://expedia.ca/Chicago-Hotels-Embassy-Suites-Chicago-Downtown.h11580.Hotel-Information)

![citizenM Chicago Downtown](https://images.trvl-media.com/lodging/83000000/82660000/82652400/82652306/55b627dd_y.jpg)

### citizenM Chicago Downtown

10/10 Excellent

"Amazing property with great views and a friendly staff."

[](https://expedia.ca/Chicago-Hotels-CitizenM-Chicago-Downtown.h82652306.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 location"

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

![Hilton Chicago/Magnificent Mile Suites](https://images.trvl-media.com/lodging/1000000/20000/18600/18514/f21f6764_y.jpg)

### Hilton Chicago/Magnificent Mile Suites

10/10 Excellent

"great hotel in a great city"

[](https://expedia.ca/Chicago-Hotels-Hilton-ChicagoMagnificent-Mile-Suites.h18514.Hotel-Information)

![Club Quarters Hotel Wacker at Michigan, Chicago](https://images.trvl-media.com/lodging/1000000/890000/889800/889753/f3eb640d_y.jpg)

### Club Quarters Hotel Wacker at Michigan, Chicago

10/10 Excellent

"We loved the hotel, parking was a bit of a ways off."

[](https://expedia.ca/Chicago-Hotels-Club-Quarters-Hotel.h889753.Hotel-Information)

![Palmer House a Hilton Hotel](https://images.trvl-media.com/lodging/1000000/10000/8100/8079/7f542141_y.jpg)

### Palmer House a Hilton Hotel

10/10 Excellent

"Great room with double bathroom. Executive level with private elevator."

[](https://expedia.ca/Chicago-Hotels-Palmer-House-A-Hilton-Hotel.h8079.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

"Wonderful room, great location and friendly helpful staff. The breakfast buffet is really well done."

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

![InterContinental Chicago Magnificent Mile by IHG](https://images.trvl-media.com/lodging/1000000/30000/20300/20205/35cb1bb8_y.jpg)

### InterContinental Chicago Magnificent Mile by IHG

10/10 Excellent

"This is a great place to stay if you’re visiting Chicago! Right in the heart of downtown. Within walking distance to Millennial Park and all the shops on Michigan Avenue. Only 35 minutes from O’Hare. The staff were courteous and the hotel is beautiful! I would definitely stay here again!"

[](https://expedia.ca/Chicago-Hotels-InterContinental-Chicago-Magnificent-Mile.h20205.Hotel-Information)

## Find out more about Far Southwest Side

## Far Southwest Side Vacation Homes information

| Number of reviews | 262                |
| ----------------- | ------------------ |
| Accommodation     | 326 Vacation Homes |
| Lowest Price      | CA $202            |
| Highest Price     | CA $729            |

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