Title: South Side Vacation Home Rentals : Search Top Private Vacation Homes for Rent | Expedia.ca

  

[South Side Travel Guide](https://expedia.ca/South-Side.dx553248635074842823)[Hotels in South Side](https://expedia.ca/South-Side-Hotels.d553248635074842823.Travel-Guide-Hotels)[Vacation Rentals in South Side](https://expedia.ca/South-Side-Vacation-Rentals.d553248635074842823.Travel-Guide-VacationRentals)[Flights to South Side](https://expedia.ca/Cheap-Flights-To-South-Side.d553248635074842823.Travel-Guide-Flights)[Things to do in South Side](https://expedia.ca/Things-To-Do-In-South-Side.d553248635074842823.Travel-Guide-Activities)[South Side Car Rentals](https://expedia.ca/Car-Rentals-In-South-Side.d553248635074842823.Car-Rental-Guide)[South Side Vacation Packages](https://expedia.ca/South-Side.d553248635074842823.Destination-Travel-Guides)

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# South Side Vacation Rentals

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## Check prices for these dates

Next weekend

[Oct 31 - Nov 2](https://www.expedia.ca/Hotel-Search?regionId=553248635074842823&startDate=2025-10-31&endDate=2025-11-02&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In two weeks

[Nov 7 - Nov 9](https://www.expedia.ca/Hotel-Search?regionId=553248635074842823&startDate=2025-11-07&endDate=2025-11-09&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In one month

[Nov 21 - Nov 23](https://www.expedia.ca/Hotel-Search?regionId=553248635074842823&startDate=2025-11-21&endDate=2025-11-23&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In two months

[Dec 19 - Dec 21](https://www.expedia.ca/Hotel-Search?regionId=553248635074842823&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)

## Browse Select South Side Vacation Homes

![Exterior](https://images.trvl-media.com/lodging/50000000/49100000/49092500/49092456/w953h720x163y0-0c76a558.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)

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

### A quiet stay while you are away

Oak Park

9.8/10

Exceptional

(32)

"We stayed a few nights and everything was nice and clean. Thank you!"

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

Karigan H.

CA $82

CA $270 total

includes taxes & fees

Oct 29 - Oct 30

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

![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)

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

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

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

Charles W.

CA $201

CA $281 total

includes taxes & fees

Oct 27 - Oct 28

[](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/eaaebb85.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)

### Pleasant 3-bedroom house in Sauk Village

Sauk Village

CA $95

CA $170 total

includes taxes & fees

Nov 12 - Nov 13

[](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/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)

![Interior](https://images.trvl-media.com/lodging/89000000/88180000/88178900/88178891/f64972cc.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

Oct 25 - Oct 26

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

![Beach nearby](https://images.trvl-media.com/lodging/84000000/83030000/83025900/83025813/7374e6e7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV](https://images.trvl-media.com/lodging/84000000/83030000/83025900/83025813/7ff9f215.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/84000000/83030000/83025900/83025813/327a76af.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor dining](https://images.trvl-media.com/lodging/84000000/83030000/83025900/83025813/e0894c26.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Dunes Escape - Minutes from Indiana Dunes National Park

Miller Beach

9.8/10

Exceptional

(36)

"We loved our stay and had a relaxing time in the area. Buying groceries to cook was great with a full kitchen to cook with. Rooms were super nice and also had every accommodation we could need. Definitely will be looking to stay again!"

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

Braden S.

CA $175

CA $494 total

includes taxes & fees

Nov 1 - Nov 2

[](https://www.expedia.ca/Gary-Hotels-Dunes-Escape-Minutes-From-Indiana-Dunes-National-Park.h83025813.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)

![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)

![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)

### 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 $231

CA $515 total

includes taxes & fees

Oct 28 - Oct 29

[](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/72000000/71680000/71677300/71677273/a0f5c46e.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)

![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)

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

(52)

"Perfect place for an 8 person golf trip! "

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

Griffin P.

CA $216

CA $467 total

includes taxes & fees

Oct 26 - Oct 27

[](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/112000000/111670000/111668700/111668679/a03596e1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/112000000/111670000/111668700/111668679/a531c8c8.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 $225

CA $555 total

includes taxes & fees

Oct 27 - Oct 28

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

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/90000000/89820000/89818200/89818126/d6cd217f.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/d8d4beb7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/90000000/89820000/89818200/89818126/99612662.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/a023af49.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Getaway Near ORD With Great Local Amenities

Des Plaines

8.8/10

Excellent

(3)

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

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

Stephanie G.

CA $98

CA $387 total

includes taxes & fees

Oct 28 - Oct 29

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

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

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

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

### Coziest estate home 20 minutes to downtown

Willow Springs

8.8/10

Excellent

(13)

"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 $562 total

includes taxes & fees

Oct 26 - Oct 27

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

![Beach](https://images.trvl-media.com/lodging/118000000/117470000/117462700/117462645/ff3980a0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/118000000/117470000/117462700/117462645/63707a12.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/118000000/117470000/117462700/117462645/b3ebc668.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, fireplace](https://images.trvl-media.com/lodging/118000000/117470000/117462700/117462645/f670e4e2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Cozy Family Getaway- 4 Blocks From The Beach!

Miller Beach

[](https://www.expedia.ca/Gary-Hotels-Cozy-Family-Getaway-4-Blocks-Or-A-9-Minute-Walk-To-The-Beach.h117462645.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)

![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)

![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)

![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 $156

CA $401 total

includes taxes & fees

Oct 27 - Oct 28

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

![Exterior](https://images.trvl-media.com/lodging/119000000/118260000/118254100/118254007/84ad0fdb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![WiFi](https://images.trvl-media.com/lodging/119000000/118260000/118254100/118254007/e50e827c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Living area](https://images.trvl-media.com/lodging/119000000/118260000/118254100/118254007/485e4f87.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/119000000/118260000/118254100/118254007/d01606a5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Spacious 3BR Home • Firepit and Grill

Miller Beach

10/10

Exceptional

(1)

"Lovely, relaxing and clean. Host is very responsive. "

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

Jennifer L.

CA $182

CA $528 total

includes taxes & fees

Nov 5 - Nov 6

[](https://www.expedia.ca/Gary-Hotels-Spacious-3BR-House-With-Firepit-And-Grill.h118254007.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)

![Exterior](https://images.trvl-media.com/lodging/109000000/108890000/108885800/108885786/w1200h796x0y4-555fde87.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 $318

CA $637 total

includes taxes & fees

Oct 26 - Oct 27

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

![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

(11)

"Very nice place "

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

Elliot H.

CA $208

CA $338 total

includes taxes & fees

Oct 23 - Oct 24

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

![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)

![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)

![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

(51)

"We loved how cute this house was! It was very convenient for visiting our daughter and nice to have plenty of space and amenities. Our host was very prompt communication. Would definitely stay here again!"

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

Mary

CA $238

CA $432 total

includes taxes & fees

Oct 27 - Oct 28

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

![TV, fireplace](https://images.trvl-media.com/lodging/122000000/121310000/121303900/121303866/2b52d153.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)

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

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

Forest Park

CA $175

CA $560 total

includes taxes & fees

Oct 26 - Oct 27

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

![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)

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

![3 bedrooms, desk, iron/ironing board, travel crib](https://images.trvl-media.com/lodging/85000000/84320000/84314800/84314776/w1019h683x3y0-935e50e6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

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

Lombard

9.6/10

Exceptional

(15)

"Everything was great, most of our activities were a short drive or Uber. The beds and couch was comfortable. It was a nice stay everyone had a good time!"

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

Israel M.

CA $194

CA $442 total

includes taxes & fees

Oct 27 - Oct 28

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

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

![Interior](https://images.trvl-media.com/lodging/106000000/105140000/105136600/105136524/33378924.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 $287

CA $771 total

includes taxes & fees

Nov 11 - Nov 12

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

![Smart TV](https://images.trvl-media.com/lodging/97000000/96840000/96832200/96832141/c19bf78c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Shower, hair dryer, bidet, towels](https://images.trvl-media.com/lodging/97000000/96840000/96832200/96832141/668390df.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/97000000/96840000/96832200/96832141/46c69250.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/97000000/96840000/96832200/96832141/6304a47a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Luxury Suite in Glen Ellyn, IL USA

Glen Ellyn

9.6/10

Exceptional

(10)

"We have a family of six adults, they have a huge couch where we could all sit comfortably together and watch a movie. We were in for a family wedding and it was nice to all stay together, rather than individual hotel rooms. We highly recommend this location if you need somewhere to stay in the Chicago land area."

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

Julie T.

CA $223

CA $483 total

includes taxes & fees

Oct 23 - Oct 24

[](https://www.expedia.ca/Chicago-Hotels-Luxury-Suite-In-Glen-Ellyn.h96832141.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=2025-11-05&endDate=2025-11-06&regionId=553248635074842823&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true)

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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%2FSouth-Side-Private-Vacation-Homes.d553248635074842823-aaPrivateVacationHomes.Travel-Guide-Accommodation)[Sign up, it's free](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FSouth-Side-Private-Vacation-Homes.d553248635074842823-aaPrivateVacationHomes.Travel-Guide-Accommodation)

## Top South Side Hotel Reviews

![Hyatt Place Chicago-South/University Medical Center](//images.trvl-media.com/lodging/7000000/6060000/6059100/6059069/722a9f0a_y.jpg)

### Hyatt Place Chicago-South/University Medical Center

10/10 Excellent

"Just an overnight stay for a college campus visit, but had the Hyatt recommended by numerous people and it didn't disappoint. What a great community the Hyde Park area was. Rooms were very nice, big and extremely clean. Will definitely be making that out go to for all future trips to the Chicago land area"

[](https://expedia.ca/Chicago-Hotels-Hyatt-Place-Chicago-SouthUniversity-Medical-Center.h6059069.Hotel-Information)

![Motel 6 - Chicago, IL](//images.trvl-media.com/lodging/116000000/115880000/115871700/115871645/55e03c95_y.jpg)

### Motel 6 - Chicago, IL

10/10 Excellent

"Staff was nice room was nice"

[](https://expedia.ca/Chicago-Hotels-Motel-6-Chicago.h115871645.Hotel-Information)

![Jaslin Hotel](//images.trvl-media.com/lodging/14000000/13330000/13320300/13320264/90849841_y.jpg)

### Jaslin Hotel

10/10 Excellent

"Great hotel "

[](https://expedia.ca/Chicago-Hotels-Jaslin-Hotel.h13320264.Hotel-Information)

![Chicago Marriott Midway](//images.trvl-media.com/lodging/1000000/900000/892200/892168/99523df7_y.jpg)

### Chicago Marriott Midway

10/10 Excellent

"Our stay was hassle free. The room was immaculate. The staff was helpful and courteous. "

[](https://expedia.ca/Chicago-Hotels-Chicago-Marriott-Midway.h892168.Hotel-Information)

![Sophy Hyde Park](//images.trvl-media.com/lodging/23000000/22360000/22355300/22355297/f98af4f7_y.jpg)

### Sophy Hyde Park

10/10 Excellent

"Ridiculous junk resort fee."

[](https://expedia.ca/Chicago-Hotels-Sophy-Hyde-Park.h22355297.Hotel-Information)

![Holiday Inn Express Hotel & Suites Chicago-Midway Airport by IHG](//images.trvl-media.com/lodging/1000000/210000/201300/201281/65c30d17_y.jpg)

### Holiday Inn Express Hotel & Suites Chicago-Midway Airport by IHG

10/10 Excellent

"Excellent. Booked our next stay before we left!"

[](https://expedia.ca/Chicago-Hotels-Holiday-Inn-Express-Hotel-Suites-Chicago-Midway-Airport.h201281.Hotel-Information)

![Carlton Inn Midway](//images.trvl-media.com/lodging/3000000/2950000/2949200/2949171/f9196562_y.jpg)

### Carlton Inn Midway

10/10 Excellent

"Very friendly! With airport shuttle!"

[](https://expedia.ca/Chicago-Hotels-Carlton-Inn-Midway.h2949171.Hotel-Information)

![SpringHill Suites by Marriott Chicago Chinatown](//images.trvl-media.com/lodging/65000000/64630000/64624400/64624399/575b0923_y.jpg)

### SpringHill Suites by Marriott Chicago Chinatown

10/10 Excellent

"Very friendly staff, convenient parking, our suite is very nice"

[](https://expedia.ca/Chicago-Hotels-SpringHill-Suites-By-Marriott-Chicago-Chinatown.h64624399.Hotel-Information)

![Mccormick Place Guest House](//images.trvl-media.com/lodging/23000000/22680000/22671000/22670906/b6c2dad6_y.jpg)

### Mccormick Place Guest House

10/10 Excellent

"Parking was a little confusing on the street cleaning. But everything else was amazing! I felt safe to sleep there in a whole new state!"

[](https://expedia.ca/Chicago-Hotels-Mccormick-Place-Guest-House.h22670906.Hotel-Information)

## Find out more about South Side

## South Side Vacation Homes information

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

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-   [Washington Park Hotels](https://www.expedia.ca/Washington-Park-Chicago-Hotels.0-n171466-0.Travel-Guide-Filter-Hotels)
-   [Washington Park Court Hotels](https://www.expedia.ca/Washington-Park-Court-Chicago-Hotels.0-n6132200-0.Travel-Guide-Filter-Hotels)
-   [Hotels near Washington Park](https://www.expedia.ca/Washington-Park-Hotels.0-l507383-0.Travel-Guide-Filter-Hotels)
-   [Cheap Hotels in Woodlawn](https://www.expedia.ca/Woodlawn-Chicago-Hotels-Cheap-Hotels.0-n6132422-0-tCheapHotels.Travel-Guide-Filter-Hotels)
-   [Hotels with an Indoor Pool in Woodlawn](https://www.expedia.ca/Woodlawn-Chicago-Hotels-Hotels-With-Indoor-Pool.0-n6132422-0-tHotelswithIndoorPool.Travel-Guide-Filter-Hotels)
-   [Luxury Hotels in Woodlawn](https://www.expedia.ca/Woodlawn-Chicago-Hotels-Luxury-Hotel.0-n6132422-0-tLuxuryHotel.Travel-Guide-Filter-Hotels)
-   [Woodlawn Hotels](https://www.expedia.ca/Woodlawn-Chicago-Hotels.0-n6132422-0.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)

-   [Visit Canaryville](https://www.expedia.ca/Chicago-Canaryville.dx6132307)
-   [Visit Fuller Park](https://www.expedia.ca/Chicago-Fuller-Park.dx6132374)
-   [Visit Indian Village](https://www.expedia.ca/Chicago-Indian-Village.dx553248635976382922)
-   [Chicago Museum of Science and Industry](https://www.expedia.ca/Chicago-Museum-Of-Science-And-Industry-Hyde-Park.d6064043.Vacation-Attraction)
-   [Obama's House](https://www.expedia.ca/Obamas-House-Kenwood.d553248621533116333.Vacation-Attraction)
-   [Robie House](https://www.expedia.ca/Robie-House-Hyde-Park.d6064059.Vacation-Attraction)

-   [Car rentals near Hyde Park](https://www.expedia.ca/Car-Rentals-In-Hyde-Park.d117842.Car-Rental-Guide)
-   [Hertz Rental Cars in Hyde Park](https://www.expedia.ca/Hertz-Car-Rentals-In-Hyde-Park.d117842-c40.Car-Rental-Guide-Suppliers)

-   [Book Vacation Homes in South Side on Expedia.com](https://www.expedia.com/South-Side-Private-Vacation-Homes.d553248635074842823-aaPrivateVacationHomes.Travel-Guide-Accommodation)