Title: Southwest Side Vacation Home Rentals : 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)

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# Southwest Side Vacation Rentals

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## Check prices for these dates

In two weeks

[Nov 28 - Nov 30](https://www.expedia.ca/Hotel-Search?regionId=553248635976475403&startDate=2025-11-28&endDate=2025-11-30&adults=2&lodging=VACATION_HOME&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In two months

[Jan 9 - Jan 11](https://www.expedia.ca/Hotel-Search?regionId=553248635976475403&startDate=2026-01-09&endDate=2026-01-11&adults=2&lodging=VACATION_HOME&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In three months

[Feb 6 - Feb 8](https://www.expedia.ca/Hotel-Search?regionId=553248635976475403&startDate=2026-02-06&endDate=2026-02-08&adults=2&lodging=VACATION_HOME&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In four months

[Mar 6 - Mar 8](https://www.expedia.ca/Hotel-Search?regionId=553248635976475403&startDate=2026-03-06&endDate=2026-03-08&adults=2&lodging=VACATION_HOME&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

## Browse Select Southwest 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)

![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)

![Interior](https://images.trvl-media.com/lodging/109000000/108220000/108219500/108219403/dfa31946.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)

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

Whiting

10/10

Exceptional

(11)

"Beautifully done and lovely owners! Super accommodating. Will definitely return. "

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

Tim and Becky A.

CA $125

CA $195 total

includes taxes & fees

Nov 17 - Nov 18

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

![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)

![TV](https://images.trvl-media.com/lodging/122000000/121820000/121815200/121815186/d8580e49.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)

### Pleasant 3-bedroom house 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 $112

CA $188 total

includes taxes & fees

Nov 23 - Nov 24

[](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/109000000/108890000/108885800/108885786/5b7a273e.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)

"Nice property easy check in. Experience was amazing. Thank you again "

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

Marshele W.

CA $179

CA $471 total

includes taxes & fees

Nov 17 - Nov 18

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

![Interior](https://images.trvl-media.com/lodging/123000000/122820000/122812000/122811987/b275ca33.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor dining](https://images.trvl-media.com/lodging/123000000/122820000/122812000/122811987/56107faf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Room](https://images.trvl-media.com/lodging/123000000/122820000/122812000/122811987/2246e8ca.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

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

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

Belmont Cragin

CA $91

CA $711 total

includes taxes & fees

Nov 19 - Nov 20

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

![2 bedrooms, desk, iron/ironing board, travel crib](https://images.trvl-media.com/lodging/50000000/49100000/49092500/49092456/699e81d6.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)

### A quiet stay while you are away

Oak Park

9.8/10

Exceptional

(32)

"We picked Jay's house because it's located right in the middle of Oak Park where many of Frank Lloyd Wright's works are located, we had so much fun walking the beautiful neighborhood. Jay's property is great too!"

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

Yimei Z.

CA $83

CA $272 total

includes taxes & fees

Nov 24 - Nov 25

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

"The owner was amazing house was nice and clean everything was perfect we had a really great time!"

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

Krystal N.

CA $217

CA $469 total

includes taxes & fees

Nov 17 - Nov 18

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

![Interior](https://images.trvl-media.com/lodging/123000000/122820000/122812000/122811972/791de7ad.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Iron/ironing board, travel crib, WiFi, bed sheets](https://images.trvl-media.com/lodging/123000000/122820000/122812000/122811972/c025e516.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/123000000/122820000/122812000/122811972/01917498.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Hair dryer](https://images.trvl-media.com/lodging/123000000/122820000/122812000/122811972/c377ed59.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Sleeps 18 • 8BR • Game Room • Gym • Theater

Portage Park

CA $185

CA $1,202 total

includes taxes & fees

Nov 18 - Nov 19

[](https://www.expedia.ca/Chicago-Hotels-Sleeps-18-8BR-Game-Room-Gym-Theater.h122811972.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)

![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)

![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)

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

Lockport

10/10

Exceptional

(4)

"Great stay! Clean and comfortable and inviting interior. Very convenient fenced in backyard for our dog. James is a gracious, generous host. I highly recommend this property. "

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

Brian C.

CA $237

CA $527 total

includes taxes & fees

Nov 17 - Nov 18

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

![Lobby](https://images.trvl-media.com/lodging/115000000/114890000/114880900/114880853/d332f02a.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)

### Charming 2-bedroom house with WiFi in peaceful Hazel Crest

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 $143

CA $419 total

includes taxes & fees

Nov 17 - Nov 18

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

![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)

![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)

### Getaway Near ORD With Great Local Amenities

Des Plaines

9.0/10

Wonderful

(4)

"It's hard get all this for this price. It's not that quiet like other reviews said unless you get up early in the morning. Heating works perfect, it is a bit warmer on the top floor and cooler in the kitchen but nothing to worry about. Parking on the front, walking distance to the grocery stores. 5 stars from me and will come back again."

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

Dorde U.

CA $98

CA $390 total

includes taxes & fees

Nov 19 - Nov 20

[](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)

### Vintage Urban Retreat

Oak Park

10/10

Exceptional

(11)

"Loved everything about the place, as advertised in the listing. "

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

Noah H.

CA $199

CA $651 total

includes taxes & fees

Nov 17 - Nov 18

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

![Interior](https://images.trvl-media.com/lodging/89000000/88500000/88494900/88494875/ad61d9f5.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)

![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)

### Coziest estate home 20 minutes to downtown

Willow Springs

8.8/10

Excellent

(14)

"Short"

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

Brian H.

CA $252

CA $558 total

includes taxes & fees

Nov 18 - Nov 19

[](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)

![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)

![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/w905h683x60y0-e4d44463.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)

"Very quiet and private and cl9se to alot of things "

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

Kenneth W.

CA $118

CA $357 total

includes taxes & fees

Nov 17 - Nov 18

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

![Interior](https://images.trvl-media.com/lodging/75000000/74250000/74243100/74243056/w1096h1452x0y0-f7b35f5a.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)

![Exterior](https://images.trvl-media.com/lodging/75000000/74250000/74243100/74243056/45b7296c.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 $432 total

includes taxes & fees

Nov 17 - Nov 18

[](https://www.expedia.ca/Chicago-Hotels-Charming-Cottage-Close-To-CollegeTownStation.h74243056.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/91000000/90620000/90612900/90612832/0900c857.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)

### Modern Victorian Vibes ❤️ | Character & Charm

Oak Park

10/10

Exceptional

(26)

"This was my first time booking here and it was amazing. The host was quick to communicate, and everything was smooth and easy to do. Definitely will book here again the next time my family is in town. "

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

William K.

CA $292

CA $780 total

includes taxes & fees

Dec 2 - Dec 3

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

![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)

![Smart TV](https://images.trvl-media.com/lodging/118000000/117680000/117672000/117671933/190b2201.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)

"This space was perfect for our short stay in the city; plenty of parking space for our vehicles in a nice neighborhood, a quaint living room for socializing before and after our event and comfortable beds overnight. Although we didn’t take advantage, the downstairs bar would have been a cool space for a night cap. The host was very amenable, responsive and supportive. "

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

Michael M.

CA $208

CA $338 total

includes taxes & fees

Nov 17 - Nov 18

[](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/120000000/119940000/119934600/119934530/eb62ac02.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/120000000/119940000/119934600/119934530/0c7327b5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior detail](https://images.trvl-media.com/lodging/120000000/119940000/119934600/119934530/b314c133.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/120000000/119940000/119934600/119934530/97319ba1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Two Kings Chicago A unique royal environment, kingly comfort!

Villa Park

10/10

Exceptional

(1)

"Art & Milda were fantastic hosts! Very responsive to all inquiries and requests. The home was beautiful. Very comfy beds and recliners! So many perks you never knew you wanted. Will definitely stay again. Thank you Art & Milda!"

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

Lisa V.

CA $252

CA $541 total

includes taxes & fees

Nov 17 - Nov 18

[](https://www.expedia.ca/Chicago-Hotels-Your-Private-Sanctuary.h119934530.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)

![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)

![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)

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

Gary

8.4/10

Very good

(16)

"Great place, nice location and the Hosts are extremely good to work with. Highly recommend this just out of the city stay!"

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

Alyssa M.

CA $226

CA $627 total

includes taxes & fees

Nov 17 - Nov 18

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

![Outdoor dining](https://images.trvl-media.com/lodging/77000000/76930000/76925600/76925599/267c108a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/77000000/76930000/76925600/76925599/b071d2aa.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)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/77000000/76930000/76925600/76925599/3706aabf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### PROMO 15% MONTHLY DISCOUNT! Cozy House, Close to Benedictine & North Central

Lisle

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 $166

CA $407 total

includes taxes & fees

Nov 19 - Nov 20

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

(15)

"We didn’t spend a ton of time at the home, but rather used it as a home base of operations to enjoy what Chicago had to offer. It covered our sleeping needs and was located 30 minutes outside the city to provide us with space from congestion and busyness!"

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

Jeremy H.

CA $221

CA $478 total

includes taxes & fees

Nov 19 - Nov 20

[](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=2025-11-30&endDate=2025-12-01&regionId=553248635976475403&adults=2&lodging=VACATION_HOME&sort=RECOMMENDED&openPlayBack=true)

## Find vacation rentals that suit your style

Aparthotels

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Apartments

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Cottages

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Condos

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Villas

[](https://www.expedia.ca/Hotel-Search?destination=Southwest+Side%2C+Illinois%2C+United+States+of+America&regionId=553248635976475403&latLong=41.792141%2C-87.701844&adults=2&startDate=2026-02-14&d1=2026-02-14&endDate=2026-02-17&d2=2026-02-17&lodging=VILLA)

Private vacation homes

[](https://www.expedia.ca/Hotel-Search?destination=Southwest+Side%2C+Illinois%2C+United+States+of+America&regionId=553248635976475403&latLong=41.792141%2C-87.701844&adults=2&startDate=2026-02-14&d1=2026-02-14&endDate=2026-02-17&d2=2026-02-17&lodging=VACATION_HOME)

Residences

[](https://www.expedia.ca/Hotel-Search?destination=Southwest+Side%2C+Illinois%2C+United+States+of+America&regionId=553248635976475403&latLong=41.792141%2C-87.701844&adults=2&startDate=2026-02-14&d1=2026-02-14&endDate=2026-02-17&d2=2026-02-17&lodging=RESIDENCE)

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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%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

### Hotel Riu Plaza Chicago

10/10 Excellent

"Beautiful new hotel. Amazing rooms and exceptional service. Best breakfast I have had at a hotel."

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

### Freehand Chicago

10/10 Excellent

"Super friendly and helpful staff, environment felt warm and welcoming. The people who stay there are pretty cool as well! Rooms were clean and cozy. Would definitely stay there again if I’m in Chicago again."

[](https://expedia.ca/Chicago-Hotels-Freehand-Chicago.h9418281.Hotel-Information)

### Eurostars Magnificent Mile

10/10 Excellent

"The staff was so helpful and friendly!!!! "

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

### The Wade

10/10 Excellent

"Staff was welcoming! We appreciated the engineering team for stepping in and helping us out! He was kind. Would stay again! "

[](https://expedia.ca/Chicago-Hotels-W-Chicago-Lakeshore.h1346.Hotel-Information)

### Hotel Felix River North/Magnificent Mile

10/10 Excellent

"The customer service top tier!!! The rooms were extremely small but they were clean. Staff was very helpful. "

[](https://expedia.ca/Chicago-Hotels-Hotel-Felix-Chicago.h2222364.Hotel-Information)

### The Whitehall Hotel, BW Premier Collection

10/10 Excellent

"Centrally located by the Magnificent Mile. Plenty of shopping options. Access to both train and bus public transportation. Hotel is older but kept. Staff are friendly, efficient, abd aware of comings and goings. Always greeting you ss you leave snd return. Rooms and property are clean. Rooms are spacious for a large metro city. I have stayed at this location multiple times. Will always be my first choice. "

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

### Hilton Chicago

10/10 Excellent

"It was the swankiest joint I ever strayed in! I upgraded for $40 and had a room with a view of Lake Michigan! They had three restaurants/bars right in the hotel!!"

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

### Aloft Chicago Mag Mile

10/10 Excellent

"Everything was phenomenal with our stay. The staff went above and beyond to make our trip to Chicago a special one. I would recommend this hotel to ANYONE looking to visit the area. Looking forward to visiting again one day! "

[](https://expedia.ca/Chicago-Hotels-Aloft-Chicago-Mag-Mile.h26998765.Hotel-Information)

### citizenM Chicago Downtown

10/10 Excellent

"Modern, super European, petite but very "

[](https://expedia.ca/Chicago-Hotels-CitizenM-Chicago-Downtown.h82652306.Hotel-Information)

## Find out more about Southwest Side

## Southwest Side Vacation Homes information

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

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-   [Pet-Friendly Hotels in New City](https://www.expedia.ca/New-City-Chicago-Hotels-Pet-Friendly-Hotel.0-n6132388-0-tPetfriendlyHotel.Travel-Guide-Filter-Hotels)
-   [New City Hotels](https://www.expedia.ca/New-City-Chicago-Hotels.0-n6132388-0.Travel-Guide-Filter-Hotels)
-   [Hotels near Pulaski Station](https://www.expedia.ca/Pulaski-Station-Hotels.d6211019.Travel-Guide-Hotels)
-   [Condo Rentals in South Side](https://www.expedia.ca/South-Side-Condos.d553248635074842823-aaCondos.Travel-Guide-Accommodation)
-   [Motels in South Side](https://www.expedia.ca/South-Side-Motels.d553248635074842823-aaMotels.Travel-Guide-Accommodation)
-   [Resorts in South Side](https://www.expedia.ca/South-Side-Resort-Hotels.d553248635074842823-aaResortHotels.Travel-Guide-Accommodation)
-   [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)
-   [Luxury Hotels in West Lawn](https://www.expedia.ca/West-Lawn-Chicago-Hotels-Luxury-Hotel.0-n6132413-0-tLuxuryHotel.Travel-Guide-Filter-Hotels)
-   [Pet-Friendly Hotels in West Lawn](https://www.expedia.ca/West-Lawn-Chicago-Hotels-Pet-Friendly-Hotel.0-n6132413-0-tPetfriendlyHotel.Travel-Guide-Filter-Hotels)
-   [West Lawn Hotels](https://www.expedia.ca/West-Lawn-Chicago-Hotels.0-n6132413-0.Travel-Guide-Filter-Hotels)
-   [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)