Title: Southwest Side Vacation Rentals from $96: Search Short-Term Rentals | Expedia.com

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

![Chicago, IL which includes landscape views and an airport](https://images.trvl-media.com/place/5719117/853282cb-4f6d-493a-819e-c77bd49895a5.jpg?impolicy=fcrop&w=1200&h=500&q=medium)

Photo by by Midway Intl Airport

![](https://images.trvl-media.com/place/5719117/853282cb-4f6d-493a-819e-c77bd49895a5.jpg?impolicy=fcrop&w=1200&h=500&q=medium)

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## Check prices for these dates

In two weeks

[Mar 13 - Mar 15](https://www.expedia.com/Hotel-Search?regionId=553248635976475403&startDate=2026-03-13&endDate=2026-03-15&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In two months

[Apr 24 - Apr 26](https://www.expedia.com/Hotel-Search?regionId=553248635976475403&startDate=2026-04-24&endDate=2026-04-26&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In three months

[May 22 - May 24](https://www.expedia.com/Hotel-Search?regionId=553248635976475403&startDate=2026-05-22&endDate=2026-05-24&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In four months

[Jun 19 - Jun 21](https://www.expedia.com/Hotel-Search?regionId=553248635976475403&startDate=2026-06-19&endDate=2026-06-21&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

## Our top choices for Southwest Side vacation rentals

![Indoor pool](https://images.trvl-media.com/lodging/77000000/76270000/76267500/76267438/58291697.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Premium Apartment, 1 Bedroom | Private kitchen | Oven, stovetop, dishwasher, coffee/tea maker](https://images.trvl-media.com/lodging/77000000/76270000/76267500/76267438/f6d9d5c9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Premium Apartment, 2 Bedrooms | Private kitchen | Oven, stovetop, dishwasher, coffee/tea maker](https://images.trvl-media.com/lodging/77000000/76270000/76267500/76267438/83f39cf6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Premium Apartment, 2 Bedrooms | Living area | 55-inch flat-screen TV with cable channels, TV](https://images.trvl-media.com/lodging/77000000/76270000/76267500/76267438/ecc0a878.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Sentral Michigan Avenue

[](https://www.expedia.com/Chicago-Hotels-Sentral-Michigan-Avenue.h76267438.Hotel-Information)

Downtown Chicago

9.2/10

Wonderful

(1,096 reviews)

"Best full kitchen multi-room family lodging"

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

Lee

$131 nightly

$154 total

Mar 3 - Mar 4

Total with taxes and fees

[](https://www.expedia.com/Chicago-Hotels-Sentral-Michigan-Avenue.h76267438.Hotel-Information)

![Full-size fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/40000000/39810000/39805900/39805843/8c061e2a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Flat-screen TV](https://images.trvl-media.com/lodging/40000000/39810000/39805900/39805843/d03e88da.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Premium bedding, pillowtop beds, in-room safe, individually decorated](https://images.trvl-media.com/lodging/40000000/39810000/39805900/39805843/4a3a770c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Deluxe Room, 1 Twin Bed, City View | Living area | Flat-screen TV](https://images.trvl-media.com/lodging/40000000/39810000/39805900/39805843/f7ca0ea3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Level Chicago – Old Town

[](https://www.expedia.com/Chicago-Hotels-LEVEL-Furnished-Living-Chicago.h39805843.Hotel-Information)

Downtown Chicago

9.0/10

Wonderful

(435 reviews)

"Clean, nice amenities and great staff."

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

Sydnee

$213 nightly

$250 total

Mar 3 - Mar 4

Total with taxes and fees

[](https://www.expedia.com/Chicago-Hotels-LEVEL-Furnished-Living-Chicago.h39805843.Hotel-Information)

![Lounge](https://images.trvl-media.com/lodging/67000000/66430000/66425400/66425311/0480d64e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Signature Apartment, 1 King Bed with Sofa bed, Pool Access (Self Check-in with Virtual Front Desk) | Living area | 55-inch flat-screen TV with digital channels, TV](https://images.trvl-media.com/lodging/67000000/66430000/66425400/66425311/2969f0ad.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby sitting area](https://images.trvl-media.com/lodging/67000000/66430000/66425400/66425311/f7e5c565_edited_04eb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Seasonal outdoor pool, open 10:00 AM to 10:00 PM, sun loungers](https://images.trvl-media.com/lodging/67000000/66430000/66425400/66425311/88e54d1a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Kasa River North Chicago

[](https://www.expedia.com/Chicago-Hotels-Kasa-River-North-Chicago.h66425311.Hotel-Information)

Downtown Chicago

9.4/10

Exceptional

(184 reviews)

"Awesome stay "

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

Sally

$234 nightly

$275 total

Mar 8 - Mar 9

Total with taxes and fees

[](https://www.expedia.com/Chicago-Hotels-Kasa-River-North-Chicago.h66425311.Hotel-Information)

![Design Apartment, Private Bathroom (The Oak Park Loft) | 2 bedrooms](https://images.trvl-media.com/lodging/108000000/107630000/107622700/107622605/dfb80f4a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Design Apartment, Private Bathroom (The Oak Park Loft) | 2 bedrooms](https://images.trvl-media.com/lodging/108000000/107630000/107622700/107622605/515455d8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Design Apartment, Private Bathroom (The Oak Park Loft) | Exterior](https://images.trvl-media.com/lodging/108000000/107630000/107622700/107622605/733d465a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/108000000/107630000/107622700/107622605/167883c0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The Oak Park Loft

[](https://www.expedia.com/Chicago-Hotels-The-Oak-Park-Loft.h107622605.Hotel-Information)

Oak Park

10/10

Exceptional

(5 reviews)

"Good location, nice neighborhood, restaurants close"

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

Linda

$237 nightly

$271 total

Mar 2 - Mar 3

Total with taxes and fees

[](https://www.expedia.com/Chicago-Hotels-The-Oak-Park-Loft.h107622605.Hotel-Information)

![Exclusive Apartment, Private Bathroom, Garden View (1st Floor) | Lounge](https://images.trvl-media.com/lodging/89000000/88180000/88173500/88173402/8abcd27a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exclusive Apartment, Private Bathroom, Garden View (1st Floor) | Interior](https://images.trvl-media.com/lodging/89000000/88180000/88173500/88173402/7547fb3d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/89000000/88180000/88173500/88173402/a6832f09.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exclusive Apartment, Private Bathroom, Garden View (1st Floor) | Shared kitchen](https://images.trvl-media.com/lodging/89000000/88180000/88173500/88173402/cf45226f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Historic Oak Park Home

[](https://www.expedia.com/Chicago-Hotels-Historic-Oak-Park-Home.h88173402.Hotel-Information)

Oak Park

10/10

Exceptional

(5 reviews)

"The owner was awesome. Convenient parking and beautiful area! Will definitely make a reservation again."

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

Janette

$249 nightly

$285 total

Mar 2 - Mar 3

Total with taxes and fees

[](https://www.expedia.com/Chicago-Hotels-Historic-Oak-Park-Home.h88173402.Hotel-Information)

![Living area](https://images.trvl-media.com/lodging/105000000/104320000/104315700/104315648/3e1fd538.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Living area](https://images.trvl-media.com/lodging/105000000/104320000/104315700/104315648/7b407b40.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/105000000/104320000/104315700/104315648/3e6dada5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Private kitchen](https://images.trvl-media.com/lodging/105000000/104320000/104315700/104315648/6dcfa9e1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Wrigleyville Suites

[](https://www.expedia.com/Chicago-Hotels-Wrigleyville-Suites.h104315648.Hotel-Information)

Lakeview

9.2/10

Wonderful

(29 reviews)

"Nice place "

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

Barry

$99 nightly

$117 total

Mar 3 - Mar 4

Total with taxes and fees

[](https://www.expedia.com/Chicago-Hotels-Wrigleyville-Suites.h104315648.Hotel-Information)

![Breakfast, lunch, dinner served; Greek cuisine ](https://images.trvl-media.com/lodging/104000000/103470000/103465500/103465448/424c972a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/104000000/103470000/103465500/103465448/3102ad4c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Full-size fridge, microwave, stovetop, dishwasher](https://images.trvl-media.com/lodging/104000000/103470000/103465500/103465448/c54d2fb6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/104000000/103470000/103465500/103465448/9897f375.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The Gem Museum Suites

[](https://www.expedia.com/Chicago-Hotels-The-Gem-Museum-Suites.h103465448.Hotel-Information)

Downtown Evanston

9.4/10

Exceptional

(105 reviews)

"This is a fantastic hotel with super friendly staff"

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

German

$172 nightly

$197 total

Mar 8 - Mar 9

Total with taxes and fees

[](https://www.expedia.com/Chicago-Hotels-The-Gem-Museum-Suites.h103465448.Hotel-Information)

![Interior](https://images.trvl-media.com/lodging/89000000/88910000/88902400/88902334/52817ea9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Studio | Private kitchen | Fridge, oven, coffee/tea maker, toaster](https://images.trvl-media.com/lodging/89000000/88910000/88902400/88902334/e09cfe7c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/89000000/88910000/88902400/88902334/faa6dc46.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Studio | Exterior](https://images.trvl-media.com/lodging/89000000/88910000/88902400/88902334/9e27f6aa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Chicago Third Floor Studio by 747 Lofts

[](https://www.expedia.com/Chicago-Hotels-Walk-To-Local-Hot-Spots-Or-Public-Transit-Prime-Location-In-The-Heart-Of-The-Windy-City-747-Lofts-Cabin-301-Hotel-Room.h88902334.Hotel-Information)

West Town

9.8/10

Exceptional

(7 reviews)

"Clean, easy to check in, all the household items you’d expect"

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

Jason

$324 nightly

$381 total

Mar 7 - Mar 8

Total with taxes and fees

[](https://www.expedia.com/Chicago-Hotels-Walk-To-Local-Hot-Spots-Or-Public-Transit-Prime-Location-In-The-Heart-Of-The-Windy-City-747-Lofts-Cabin-301-Hotel-Room.h88902334.Hotel-Information)

![Comfort Double Room | Desk, laptop workspace, blackout drapes, free WiFi](https://images.trvl-media.com/lodging/113000000/112310000/112306500/112306435/4e4fcb6b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Front of property](https://images.trvl-media.com/lodging/113000000/112310000/112306500/112306435/81879fe3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Desk, laptop workspace, blackout drapes, free WiFi](https://images.trvl-media.com/lodging/113000000/112310000/112306500/112306435/7a3c031a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Comfort Double Room | Desk, laptop workspace, blackout drapes, free WiFi](https://images.trvl-media.com/lodging/113000000/112310000/112306500/112306435/11a11fca.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Comfort Inn Chicago Southland I-80 & I-294 Near Casino

[](https://www.expedia.com/Chicago-Hotels-Comfort-Inn-Chicago-Wind-Creek-Casino.h112306435.Hotel-Information)

Harvey

4.2/10

(73 reviews)

"Under renovations so some rooms have missing appliances, even through an app they require a deposit. Utter wise nice room and workers"

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

Destin

$85 nightly

$96 total

Mar 2 - Mar 3

Total with taxes and fees

[](https://www.expedia.com/Chicago-Hotels-Comfort-Inn-Chicago-Wind-Creek-Casino.h112306435.Hotel-Information)

![Apartment, Private Bathroom | Lounge](https://images.trvl-media.com/lodging/76000000/75610000/75609600/75609586/75db7b4b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/76000000/75610000/75609600/75609586/a3594234.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Apartment, Private Bathroom | Terrace/patio](https://images.trvl-media.com/lodging/76000000/75610000/75609600/75609586/2e2b5c00.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Apartment, Private Bathroom | 3 bedrooms](https://images.trvl-media.com/lodging/76000000/75610000/75609600/75609586/b9d0f86f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### At Home in Oak Park

[](https://www.expedia.com/Chicago-Hotels-Home-In-Oak-Park.h75609586.Hotel-Information)

Oak Park

9.4/10

Exceptional

(9 reviews)

"Great place, clean, and very accommodating! "

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

Theresa

$243 nightly

$278 total

Mar 2 - Mar 3

Total with taxes and fees

[](https://www.expedia.com/Chicago-Hotels-Home-In-Oak-Park.h75609586.Hotel-Information)

![Exclusive Room, Private Bathroom, Garden View (2nd Floor) | Exterior](https://images.trvl-media.com/lodging/95000000/94680000/94670100/94670079/9b9f65df.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exclusive Room, Private Bathroom, Garden View (2nd Floor) | 4 bedrooms](https://images.trvl-media.com/lodging/95000000/94680000/94670100/94670079/5beac5cc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exclusive Room, Private Bathroom, Garden View (2nd Floor) | Exterior](https://images.trvl-media.com/lodging/95000000/94680000/94670100/94670079/3a1a2525.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exclusive Room, Private Bathroom, Garden View (2nd Floor) | Restaurant](https://images.trvl-media.com/lodging/95000000/94680000/94670100/94670079/de6cdd22.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Historic Oak Park Residence

[](https://www.expedia.com/Chicago-Hotels-Historic-Oak-Park-Residence.h94670079.Hotel-Information)

Oak Park

9.6/10

Exceptional

(12 reviews)

"Absolutely awesome "

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

Erik

$264 nightly

$302 total

Mar 3 - Mar 4

Total with taxes and fees

[](https://www.expedia.com/Chicago-Hotels-Historic-Oak-Park-Residence.h94670079.Hotel-Information)

![Interior](https://images.trvl-media.com/lodging/89000000/88910000/88902500/88902456/52022c01.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Studio | Private kitchen | Fridge, oven, coffee/tea maker, toaster](https://images.trvl-media.com/lodging/89000000/88910000/88902500/88902456/5f82c6e7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/89000000/88910000/88902500/88902456/8ae2c510.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Studio | Exterior](https://images.trvl-media.com/lodging/89000000/88910000/88902500/88902456/71624a0d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### River West, Third Floor Chicago by 747 Lofts

[](https://www.expedia.com/Chicago-Hotels-The-Perfect-Home-Away-From-Home-For-Your-Romantic-Urban-Getaway-747-Lofts-Cabin-307-Hotel-Room.h88902456.Hotel-Information)

West Town

9.0/10

Wonderful

(17 reviews)

"Loved the space and location "

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

Caroline

$392 nightly

$460 total

Mar 13 - Mar 14

Total with taxes and fees

[](https://www.expedia.com/Chicago-Hotels-The-Perfect-Home-Away-From-Home-For-Your-Romantic-Urban-Getaway-747-Lofts-Cabin-307-Hotel-Room.h88902456.Hotel-Information)

![Interior](https://images.trvl-media.com/lodging/89000000/88870000/88870000/88869908/6aa808be.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Studio | Living area](https://images.trvl-media.com/lodging/89000000/88870000/88870000/88869908/87fc1015.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/89000000/88870000/88870000/88869908/4c7850b1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Studio | Exterior](https://images.trvl-media.com/lodging/89000000/88870000/88870000/88869908/55f1cca8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### River West, Second Floor Chicago by 747 Lofts

[](https://www.expedia.com/Chicago-Hotels-You-Cant-Beat-This-Location-For-Exploring-The-Great-Windy-City-747-Lofts-Cabin-201-Hotel-Room.h88869908.Hotel-Information)

West Town

9.6/10

Exceptional

(4 reviews)

"I need to somewhere to stay for a night in Chicago and found this place. It had a varying level of reviews but found the property more the suitable for what I paid. Easy to follow instructions to get in, clean, and convienent. They even provide ear plugs to drown out the sounds of the city."

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

Anonymous traveler

$302 nightly

$355 total

Mar 8 - Mar 9

Total with taxes and fees

[](https://www.expedia.com/Chicago-Hotels-You-Cant-Beat-This-Location-For-Exploring-The-Great-Windy-City-747-Lofts-Cabin-201-Hotel-Room.h88869908.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.com/Hotel-Search?startDate=2026-03-15&endDate=2026-03-16&regionId=553248635976475403&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true)

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## 

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## Find vacation rentals that suit your style

Aparthotels

[](https://www.expedia.com/Hotel-Search?destination=Southwest+Side%2C+Illinois%2C+United+States+of+America&regionId=553248635976475403&latLong=41.792141%2C-87.701844&adults=2&startDate=2026-05-30&d1=2026-05-30&endDate=2026-06-02&d2=2026-06-02&lodging=APART_HOTEL)

Villas

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Condos

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Private vacation homes

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Apartments

[](https://www.expedia.com/Hotel-Search?destination=Southwest+Side%2C+Illinois%2C+United+States+of+America&regionId=553248635976475403&latLong=41.792141%2C-87.701844&adults=2&startDate=2026-05-30&d1=2026-05-30&endDate=2026-06-02&d2=2026-06-02&lodging=APARTMENT)

Cottages

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Residences

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## Top Southwest Side Hotel Reviews

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

### Hilton Chicago

10/10 Excellent

"The staff was wonderful and the rooms were clean."

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

![Aloft Chicago Mag Mile](https://images.trvl-media.com/lodging/27000000/27000000/26998800/26998765/d755f57e_y.jpg)

### Aloft Chicago Mag Mile

10/10 Excellent

"good environment all around "

[](https://expedia.com/Chicago-Hotels-Aloft-Chicago-Mag-Mile.h26998765.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 location, close to everything, clean room, friendly staff, included breakfast a plus. Thank you. "

[](https://expedia.com/Chicago-Hotels-Embassy-Suites-Chicago-Downtown.h11580.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

"Tudo impecável "

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

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

### LondonHouse Chicago, Curio Collection by Hilton

10/10 Excellent

"My new Favorite Property in Chicago…loved It💙"

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

"Genial ubicación "

[](https://expedia.com/Chicago-Hotels-Hilton-ChicagoMagnificent-Mile-Suites.h18514.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

"Excellent room with amazing views. Really friendly and helpful staff. Josh at reception was extremely good to us! Excellent location centre of everything. Would definitely recommend this hotel "

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

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

### Congress Plaza Hotel

10/10 Excellent

"Staff was great. Clean rooms ,great location "

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

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

### River Hotel

10/10 Excellent

"Amazing place!"

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

## Find out more about Southwest Side

**Everything you need to know about Southwest Side vacation rentals**

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Southwest Side vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Southwest Side vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

**Southwest Side vacation rentals: An excellent choice for every season**

Whenever you want to travel, a warm welcome awaits you in Southwest Side. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Southwest Side in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $96 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

**How to find incredible deals on Southwest Side rentals**

At Expedia, we put the best Southwest Side vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Southwest Side rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Southwest Side vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Southwest Side. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

## Explore a world of travel with Expedia

- Trending destinations on Expedia.com
- All accommodation types in Southwest Side

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- [Outer Banks Vacation Rentals ](https://www.expedia.com/Outer-Banks-Vacation-Rentals.d602135.Travel-Guide-VacationRentals)
- [San Diego Vacation Rentals ](https://www.expedia.com/San-Diego-Vacation-Rentals.d3073.Travel-Guide-VacationRentals)
- [Siesta Key Vacation Rentals ](https://www.expedia.com/Siesta-Key-Vacation-Rentals.d6881.Travel-Guide-VacationRentals)
- [Galveston Vacation Rentals ](https://www.expedia.com/Galveston-Vacation-Rentals.d1341.Travel-Guide-VacationRentals)
- [Clearwater Beach Vacation Rentals ](https://www.expedia.com/Clearwater-Beach-Vacation-Rentals.d10759.Travel-Guide-VacationRentals)
- [Palm Springs Vacation Rentals ](https://www.expedia.com/Palm-Springs-Vacation-Rentals.d180676.Travel-Guide-VacationRentals)
- [Florida Keys Vacation Rentals ](https://www.expedia.com/Florida-Keys-Vacation-Rentals.d6023765.Travel-Guide-VacationRentals)
- [Lake Tahoe Vacation Rentals ](https://www.expedia.com/South-Lake-Tahoe-Vacation-Rentals.d10150.Travel-Guide-VacationRentals)
- [Lake of the Ozarks Vacation Rentals ](https://www.expedia.com/Lake-Ozark-Vacation-Rentals.d177772.Travel-Guide-VacationRentals)
- [Florida Vacation Rentals ](https://www.expedia.com/Destinations-In-Florida.d211.Vacation-Rental-Destinations)
- [Hawaii Vacation Rentals ](https://www.expedia.com/Destinations-In-Hawaii.d213.Vacation-Rental-Destinations)
- [Michigan Vacation Rentals ](https://www.expedia.com/Destinations-In-Michigan.d224.Vacation-Rental-Destinations)

- [Apartments in Southwest Side ](https://expedia.com/Southwest-Side-Apartments.d553248635976475403-aaApartments.Travel-Guide-Accommodation)
- [Vacation Homes in Southwest Side ](https://expedia.com/Southwest-Side-Private-Vacation-Homes.d553248635976475403-aaPrivateVacationHomes.Travel-Guide-Accommodation)
- [Condo Rentals in Southwest Side ](https://expedia.com/Southwest-Side-Condos.d553248635976475403-aaCondos.Travel-Guide-Accommodation)
- [Motels in Southwest Side ](https://expedia.com/Southwest-Side-Motels.d553248635976475403-aaMotels.Travel-Guide-Accommodation)
- [Aparthotels in Southwest Side ](https://expedia.com/Southwest-Side-Apart-Hotels.d553248635976475403-aaApartHotels.Travel-Guide-Accommodation)
- [Cottages in Southwest Side ](https://expedia.com/Southwest-Side-Cottages.d553248635976475403-aaCottages.Travel-Guide-Accommodation)
- [B&B in Southwest Side ](https://expedia.com/Southwest-Side-Bed-And-Breakfast.d553248635976475403-aaBedAndBreakfast.Travel-Guide-Accommodation)
- [Guest Houses in Southwest Side ](https://expedia.com/Southwest-Side-Guest-Houses.d553248635976475403-aaGuestHouses.Travel-Guide-Accommodation)
- [Hostels in Southwest Side ](https://expedia.com/Southwest-Side-Hostels.d553248635976475403-aaHostels.Travel-Guide-Accommodation)
- [Resorts in Southwest Side ](https://expedia.com/Southwest-Side-Resorts.d553248635976475403-aaResorts.Travel-Guide-Accommodation)
- [Villas in Southwest Side ](https://expedia.com/Southwest-Side-Villas.d553248635976475403-aaVillas.Travel-Guide-Accommodation)
- [Farmstay in Southwest Side ](https://expedia.com/Southwest-Side-Agritourism.d553248635976475403-aaAgritourism.Travel-Guide-Accommodation)

### Expedia's Latest Trends

Hotels

- [Millennium Park hotels](https://expedia.com/Millennium-Park-Hotels.0-l6069201-0.Travel-Guide-Filter-Hotels)
- [McCormick Place hotels](https://expedia.com/McCormick-Place-Hotels.0-l6069191-0.Travel-Guide-Filter-Hotels)
- [Wrigley Field hotels](https://expedia.com/Wrigley-Field-Hotels.0-l6034754-0.Travel-Guide-Filter-Hotels)
- [United Center hotels](https://expedia.com/United-Center-Hotels.0-l6064077-0.Travel-Guide-Filter-Hotels)
- [North Suburbs Hotels with Hot Tubs](https://expedia.com/North-Suburbs-Hotels-Hotels-With-Hot-Tubs.0-0-d6059336-tHotelsWithHotTubs.Travel-Guide-Filter-Hotels)
- [Hotels in North Suburbs](https://expedia.com/North-Suburbs-Hotels.d6059336.Travel-Guide-Hotels)
- [Soldier Field hotels](https://expedia.com/Soldier-Field-Hotels.0-l6058043-0.Travel-Guide-Filter-Hotels)
- [Motel 6 Hotels in South Side](https://expedia.com/South-Side-Hotels-Motel-6.0-0-d553248635074842823--bMotel6.Travel-Guide-Filter-Hotels)
- [North Suburbs Boutique Hotels](https://expedia.com/North-Suburbs-Hotels-Boutique-Hotel.0-0-d6059336-tBoutiqueHotel.Travel-Guide-Filter-Hotels)
- [Hotels in Central Chicago](https://expedia.com/Central-Chicago-Hotels.d553248635976475413.Travel-Guide-Hotels)
- [Far Southeast Side 5 Star Hotels](https://expedia.com/5Star-Far-Southeast-Side-Hotels.s50-0-d553248635976475411.Travel-Guide-Filter-Hotels)
- [North Suburbs Family Hotels](https://expedia.com/North-Suburbs-Hotels-Family-Hotel.0-0-d6059336-tFamilyHotel.Travel-Guide-Filter-Hotels)
- [North Suburbs Luxury Hotels](https://expedia.com/North-Suburbs-Hotels-Luxury-Hotel.0-0-d6059336-tLuxuryHotel.Travel-Guide-Filter-Hotels)
- [North Suburbs Romantic Hotels](https://expedia.com/North-Suburbs-Hotels-Romantic-Hotel.0-0-d6059336-tRomanticHotel.Travel-Guide-Filter-Hotels)
- [North Suburbs Beach Hotels](https://expedia.com/North-Suburbs-Hotels-Beach-Hotel.0-0-d6059336-tBeachHotel.Travel-Guide-Filter-Hotels)
- [South Side Cheap Hotels](https://expedia.com/South-Side-Hotels-Cheap-Hotels.0-0-d553248635074842823-tCheapHotels.Travel-Guide-Filter-Hotels)
- [North Suburbs Hotels with an Outdoor Pool](https://expedia.com/North-Suburbs-Hotels-Hotels-With-Outdoor-Pool.0-0-d6059336-tHotelswithOutdoorPool.Travel-Guide-Filter-Hotels)
- [Extended Stay Hotels in North Suburbs](https://expedia.com/North-Suburbs-Hotels-Extended-Stay-Hotels.0-0-d6059336-tExtendedStayHotels.Travel-Guide-Filter-Hotels)
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- [Michigan Avenue hotels](https://expedia.com/Michigan-Avenue-Hotels.0-l6156167-0.Travel-Guide-Filter-Hotels)
- [Hotels with Early Check-in in South Side](https://expedia.com/South-Side-Hotels-Hotel-With-Early-Check-In.0-0-d553248635074842823-thotelwithearlycheckin.Travel-Guide-Filter-Hotels)
- [Navy Pier hotels](https://expedia.com/Navy-Pier-Hotels.0-l6069215-0.Travel-Guide-Filter-Hotels)
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Cars

- [Car rentals in Central Chicago](https://expedia.com/Car-Rentals-In-Central-Chicago.d553248635976475413.Car-Rental-Guide)
- [Car rentals in North Suburbs](https://expedia.com/Car-Rentals-In-North-Suburbs.d6059336.Car-Rental-Guide)

Packages

- [Central Chicago All Inclusive Vacation Packages](https://expedia.com/lp/theme-vacations/honeymoon-vacations/553248635976475413/Central-Chicago)

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