Title: Southwest Side Vacation Rentals from $106: 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

[Apr 3 - Apr 5](https://www.expedia.com/Hotel-Search?regionId=553248635976475403&startDate=2026-04-03&endDate=2026-04-05&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In two months

[May 15 - May 17](https://www.expedia.com/Hotel-Search?regionId=553248635976475403&startDate=2026-05-15&endDate=2026-05-17&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In three months

[Jun 12 - Jun 14](https://www.expedia.com/Hotel-Search?regionId=553248635976475403&startDate=2026-06-12&endDate=2026-06-14&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In four months

[Jul 10 - Jul 12](https://www.expedia.com/Hotel-Search?regionId=553248635976475403&startDate=2026-07-10&endDate=2026-07-12&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

![TV](https://images.trvl-media.com/lodging/104000000/103330000/103320500/103320435/w1350h899x0y1-cb7026b8.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/104000000/103330000/103320500/103320435/w1349h899x1y1-0f9df4ef.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/104000000/103330000/103320500/103320435/w1349h899x1y1-2ba00151.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/104000000/103330000/103320500/103320435/w1349h899x1y1-aea79261.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Spacious 3 Bedroom Apartment - 10 Minutes to Downtown - Sleeps up to 10

[](https://www.expedia.com/Chicago-Hotels-Spacious-3-Bedroom-Apartment-10-Minutes-To-Downtown-Sleeps-Up-To-10.h103320435.Hotel-Information)

Brighton Park

10/10

Exceptional

(1 review)

"Family-friendly, quiet, perfect for a family or friends vacationing in Chicago. The apartment is very clean and the host was always available and responded quickly. The next time I come to Chicago, i will definitely stay at the apartment \[if available\]. "

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

Fabian H.

$230 nightly

$258 total

Mar 24 - Mar 25

Total with taxes and fees

[](https://www.expedia.com/Chicago-Hotels-Spacious-3-Bedroom-Apartment-10-Minutes-To-Downtown-Sleeps-Up-To-10.h103320435.Hotel-Information)

![Smart TV, video games](https://images.trvl-media.com/lodging/92000000/91090000/91086500/91086437/w1350h899x0y1-166f73c9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/92000000/91090000/91086500/91086437/2b5be5e9.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/92000000/91090000/91086500/91086437/w1350h899x0y1-43718ff8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/92000000/91090000/91086500/91086437/w1278h1921x2y2-bce03282.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Sunflower Apt 10 Min from Downtown Chicago - Sleeps up to 6

[](https://www.expedia.com/Chicago-Hotels-Sunflower-Apt-10-Min-From-Downtown-Chicago-Sleeps-Up-To-6.h91086437.Hotel-Information)

Brighton Park

8.6/10

Excellent

(21 reviews)

"Clean and nice. My son loved the arcade game. Would stay again "

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

Nichole S.

[](https://www.expedia.com/Chicago-Hotels-Sunflower-Apt-10-Min-From-Downtown-Chicago-Sleeps-Up-To-6.h91086437.Hotel-Information)

![Game room](https://images.trvl-media.com/lodging/97000000/96480000/96479300/96479287/w1350h899x0y1-b9b7a110.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/97000000/96480000/96479300/96479287/w1349h899x1y1-922f1c40.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior detail](https://images.trvl-media.com/lodging/97000000/96480000/96479300/96479287/3bda02c5.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/97000000/96480000/96479300/96479287/w1350h899x0y1-7f0cda99.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### W Pershing · Large Chicago Apt 3 Bed | 12 Min Downtown | Arcade

[](https://www.expedia.com/Chicago-Hotels-W-Pershing-Large-Chicago-Apt-3-Bed-12-Min-Downtown-Arcade.h96479287.Hotel-Information)

Brighton Park

9.4/10

Exceptional

(9 reviews)

"Great location, spacious, and family friendly. Had cousins over and they had a blast playing the video games. "

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

Jessica H.

$232 nightly

$260 total

Mar 23 - Mar 24

Total with taxes and fees

[](https://www.expedia.com/Chicago-Hotels-W-Pershing-Large-Chicago-Apt-3-Bed-12-Min-Downtown-Arcade.h96479287.Hotel-Information)

![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 | 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)

![Garden](https://images.trvl-media.com/lodging/77000000/76270000/76267500/76267438/ccaab668.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

(1,107 reviews)

"The kitchen was great and check-in was easy."

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

Marshal

$152 nightly

$178 total

Apr 1 - Apr 2

Total with taxes and fees

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

![Interior](https://images.trvl-media.com/lodging/50000000/49100000/49092500/49092456/cf096b64.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)

![Dining](https://images.trvl-media.com/lodging/50000000/49100000/49092500/49092456/64fce148.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### A quiet stay while you are away

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

Oak Park

9.8/10

Exceptional

(35 reviews)

"Everything was very comfortable and Jay did a great job of showing the house. I would definitely come back again"

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

Fred D.

$210 nightly

$241 total

Apr 13 - Apr 14

Total with taxes and fees

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

![TV](https://images.trvl-media.com/lodging/117000000/116800000/116792900/116792834/e8c7e2dc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/117000000/116800000/116792900/116792834/5e4daba6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV](https://images.trvl-media.com/lodging/117000000/116800000/116792900/116792834/bb8a78a9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/117000000/116800000/116792900/116792834/c7d9d0bd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Nice 1BR Spot, Unwind & Relax

[](https://www.expedia.com/Chicago-Hotels-Furnished-1-Bedroom-Sunlit-Space.h116792834.Hotel-Information)

Lincoln Square

9.8/10

Exceptional

(28 reviews)

"Very clean & cozy! Conveniently located by great shopping & restaurants!"

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

SHERI C.

$159 nightly

$176 total

Mar 22 - Mar 23

Total with taxes and fees

[](https://www.expedia.com/Chicago-Hotels-Furnished-1-Bedroom-Sunlit-Space.h116792834.Hotel-Information)

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

![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)

![Exterior detail](https://images.trvl-media.com/lodging/109000000/108220000/108219500/108219403/e79449bd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/109000000/108220000/108219500/108219403/dfa31946.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

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

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

Robertsdale

9.6/10

Exceptional

(22 reviews)

"I had a fun stay "

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

Jusu K.

$160 nightly

$179 total

Mar 23 - Mar 24

Total with taxes and fees

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

![Iron/ironing board, WiFi](https://images.trvl-media.com/lodging/117000000/116800000/116793100/116793093/bfe9ce5f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/117000000/116800000/116793100/116793093/017a65ce.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV](https://images.trvl-media.com/lodging/117000000/116800000/116793100/116793093/a91f2fad.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, oven, stovetop, coffee/tea maker](https://images.trvl-media.com/lodging/117000000/116800000/116793100/116793093/bd243cfa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Uptown Studio Gem Sum

[](https://www.expedia.com/Chicago-Hotels-Uptown-Studio-Gem-Sum.h116793093.Hotel-Information)

Uptown

7.4/10

Good

(6 reviews)

"The neighborhood was perfect for me. I’d like to book the same property again because of the location.The only problem was checking in. The address was wrong and if I wasn’t raised in that part of Chicago I would have been very confused.Plus I checked in late at night. It wasn’t an easy process. Next time it will be diffeeent."

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

Darryl C.

$174 nightly

$195 total

Mar 22 - Mar 23

Total with taxes and fees

[](https://www.expedia.com/Chicago-Hotels-Uptown-Studio-Gem-Sum.h116793093.Hotel-Information)

![Interior](https://images.trvl-media.com/lodging/100000000/99670000/99665400/99665339/w904h683x60y0-0a03c909.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/100000000/99670000/99665400/99665339/w908h683x58y0-c6e60f75.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/100000000/99670000/99665400/99665339/w438h683x287y0-7bc85031.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/100000000/99670000/99665400/99665339/w507h683x259y0-1739d42c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Oak Park Queen

[](https://www.expedia.com/Chicago-Hotels-Oak-Park-Queen.h99665339.Hotel-Information)

Oak Park

8.2/10

Very Good

(33 reviews)

"The property was very clean and comfortable. Good location. The owner was responsive."

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

Susan S.

$197 nightly

$226 total

Mar 22 - Mar 23

Total with taxes and fees

[](https://www.expedia.com/Chicago-Hotels-Oak-Park-Queen.h99665339.Hotel-Information)

![Property grounds](https://images.trvl-media.com/lodging/106000000/105890000/105888000/105887915/322fd87f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/106000000/105890000/105888000/105887915/8a1e71e2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/106000000/105890000/105888000/105887915/06df6711.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/106000000/105890000/105888000/105887915/87e615f7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### 2-bedroom apartment just 2 minutes drive to Wrigley Field

[](https://www.expedia.com/Chicago-Hotels-2-Bedroom-Apartment-Just-2-Minutes-Drive-To-Wrigley-Field.h105887915.Hotel-Information)

North Center

9.6/10

Exceptional

(63 reviews)

"Nice property, great location, super helpful host!"

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

Carin O.

$267 nightly

$330 total

Mar 22 - Mar 23

Total with taxes and fees

[](https://www.expedia.com/Chicago-Hotels-2-Bedroom-Apartment-Just-2-Minutes-Drive-To-Wrigley-Field.h105887915.Hotel-Information)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/46000000/45890000/45886100/45886096/074854f6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/46000000/45890000/45886100/45886096/b2e3ba0b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/46000000/45890000/45886100/45886096/d6df8cf6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![2 bedrooms, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/46000000/45890000/45886100/45886096/715ba83d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Cozy, Comfortable and Convenient apartment. Close to everything!

[](https://www.expedia.com/Chicago-Hotels-Cozy.h45886096.Hotel-Information)

Oak Park

9.8/10

Exceptional

(73 reviews)

"Apartment is as advertised. Nicely stocked, large, clean, comfortable, nice natural light, quiet, great location, full size appliances, easy access. "

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

Susan G.

$261 nightly

$299 total

Mar 25 - Mar 26

Total with taxes and fees

[](https://www.expedia.com/Chicago-Hotels-Cozy.h45886096.Hotel-Information)

![TV, offices](https://images.trvl-media.com/lodging/117000000/116800000/116793100/116793043/afe63d9a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/117000000/116800000/116793100/116793043/e3efb27d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, offices](https://images.trvl-media.com/lodging/117000000/116800000/116793100/116793043/19144195.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/117000000/116800000/116793100/116793043/8ec83200.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Modern Comfort: 1BR Unit w/ Laundry

[](https://www.expedia.com/Chicago-Hotels-Stylish-1BR-In-West-Loop.h116793043.Hotel-Information)

Downtown Chicago

9.2/10

Wonderful

(15 reviews)

"Great host comfortable bed close to restaurants and parks"

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

Alana C.

$179 nightly

$199 total

Mar 22 - Mar 23

Total with taxes and fees

[](https://www.expedia.com/Chicago-Hotels-Stylish-1BR-In-West-Loop.h116793043.Hotel-Information)

![Interior](https://images.trvl-media.com/lodging/117000000/116800000/116793000/116792993/ca2aa0d7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/117000000/116800000/116793000/116792993/9c142ace.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Shower, hair dryer](https://images.trvl-media.com/lodging/117000000/116800000/116793000/116792993/96d438b5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/117000000/116800000/116793000/116792993/e4a26e6f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Your Perfect 2BR Home

[](https://www.expedia.com/Chicago-Hotels-Your-Perfect-2BR-Home.h116792993.Hotel-Information)

Near West Side

8.4/10

Very Good

(15 reviews)

"Great location! "

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

Kourtney K.

$207 nightly

$229 total

Mar 23 - Mar 24

Total with taxes and fees

[](https://www.expedia.com/Chicago-Hotels-Your-Perfect-2BR-Home.h116792993.Hotel-Information)

![Smart TV, books](https://images.trvl-media.com/lodging/84000000/83580000/83571000/83570994/f8b770f6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, books](https://images.trvl-media.com/lodging/84000000/83580000/83571000/83570994/8b428166.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/84000000/83580000/83571000/83570994/822df8f5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/84000000/83580000/83571000/83570994/ef7d4602.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Chic Suite/Mins to L Train /Laundry/Free Parking

[](https://www.expedia.com/Chicago-Hotels-Chic-SuiteMins-To-L-Train-LaundryFree-Parking.h83570994.Hotel-Information)

Oak Park

9.6/10

Exceptional

(60 reviews)

"Comfortable bed, spacious rooms and clean."

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

Michael W.

$173 nightly

$198 total

Mar 25 - Mar 26

Total with taxes and fees

[](https://www.expedia.com/Chicago-Hotels-Chic-SuiteMins-To-L-Train-LaundryFree-Parking.h83570994.Hotel-Information)

![Interior](https://images.trvl-media.com/lodging/123000000/122120000/122119700/122119695/8e2390b0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/123000000/122120000/122119700/122119695/w4032h2772x0y0-82beddf3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/123000000/122120000/122119700/122119695/788521e9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/123000000/122120000/122119700/122119695/85daceee.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Cozy Garden Suite minutes from O'hare and Rosemont + Free Parking

[](https://www.expedia.com/Chicago-Hotels-Cozy-Garden-Suite-Minutes-From-Ohare-And-Rosemont-Free-Parking.h122119695.Hotel-Information)

Northlake

10/10

Exceptional

(7 reviews)

"Had a great experience here, and also close to the airport!"

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

Yafeat D.

$115 nightly

$123 total

Mar 22 - Mar 23

Total with taxes and fees

[](https://www.expedia.com/Chicago-Hotels-Cozy-Garden-Suite-Minutes-From-Ohare-And-Rosemont-Free-Parking.h122119695.Hotel-Information)

![TV, offices](https://images.trvl-media.com/lodging/117000000/116800000/116793000/116792936/7d7ccc69.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/117000000/116800000/116793000/116792936/93c17f93.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Shower, hair dryer](https://images.trvl-media.com/lodging/117000000/116800000/116793000/116792936/c6bb5c1b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/117000000/116800000/116793000/116792936/a5975d89.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Sun-Drenched 1BR Apartment

[](https://www.expedia.com/Chicago-Hotels-Sun-Drenched-1BR-Apartment.h116792936.Hotel-Information)

Downtown Chicago

10/10

Exceptional

(2 reviews)

"Host was very friendly and informative. Place was clean and close to lots of fun. Trains loud and busy but knew that going in. "

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

Tyler B.

$178 nightly

$198 total

Mar 25 - Mar 26

Total with taxes and fees

[](https://www.expedia.com/Chicago-Hotels-Sun-Drenched-1BR-Apartment.h116792936.Hotel-Information)

![1 bedroom, iron/ironing board, travel crib, WiFi](https://images.trvl-media.com/lodging/120000000/119140000/119131900/119131874/b10cb31b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/120000000/119140000/119131900/119131874/368bd483.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, iron/ironing board, travel crib, WiFi](https://images.trvl-media.com/lodging/120000000/119140000/119131900/119131874/b56ca762.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV](https://images.trvl-media.com/lodging/120000000/119140000/119131900/119131874/b754723c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### West Loop Living – Bright 1BR

[](https://www.expedia.com/Chicago-Hotels-West-Loop-Living-Bright-1BR.h119131874.Hotel-Information)

Downtown Chicago

10/10

Exceptional

(8 reviews)

"Great communication and hosts. Location and unit was perfect."

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

Greg C.

$179 nightly

$199 total

Mar 22 - Mar 23

Total with taxes and fees

[](https://www.expedia.com/Chicago-Hotels-West-Loop-Living-Bright-1BR.h119131874.Hotel-Information)

![TV](https://images.trvl-media.com/lodging/117000000/116800000/116792900/116792861/255dfec9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, iron/ironing board, travel crib, WiFi](https://images.trvl-media.com/lodging/117000000/116800000/116792900/116792861/7523a52a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/117000000/116800000/116792900/116792861/fce51bf6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV](https://images.trvl-media.com/lodging/117000000/116800000/116792900/116792861/bea75315.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### 1BR Apartment in Chicago

[](https://www.expedia.com/Chicago-Hotels-1BR-Apartment-In-Chicago.h116792861.Hotel-Information)

North Center

9.0/10

Wonderful

(17 reviews)

"Very clean and the host was easy to work with. "

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

Scott S.

$175 nightly

$194 total

Apr 6 - Apr 7

Total with taxes and fees

[](https://www.expedia.com/Chicago-Hotels-1BR-Apartment-In-Chicago.h116792861.Hotel-Information)

![Interior](https://images.trvl-media.com/lodging/118000000/117520000/117515200/117515137/d8e9b0e1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/118000000/117520000/117515200/117515137/a410264a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/118000000/117520000/117515200/117515137/6c271db9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/118000000/117520000/117515200/117515137/57a172f1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### River North Rooftop With In and Out Parking 3

[](https://www.expedia.com/Chicago-Hotels-River-North-Rooftop-With-In-Out-Parking-3.h117515137.Hotel-Information)

Downtown Chicago

9.6/10

Exceptional

(4 reviews)

"We had a very comfortable stay here. The hosts are exceptionally communicative and helpful. Loved having a place to park my car, and the hosts set it up so my license plate was recognized at the gate so that parking was free. The unit was very clean and spacious. Note, the kitchen does not have pots or pans to cook, so plan on eating out!"

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

Jennifer M.

$448 nightly

$506 total

Mar 22 - Mar 23

Total with taxes and fees

[](https://www.expedia.com/Chicago-Hotels-River-North-Rooftop-With-In-Out-Parking-3.h117515137.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=2026-04-02&endDate=2026-04-03&regionId=553248635976475403&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true)

## 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=2026-06-17&d1=2026-06-17&endDate=2026-06-20&d2=2026-06-20&lodging=APART_HOTEL)

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=2026-06-17&d1=2026-06-17&endDate=2026-06-20&d2=2026-06-20&lodging=APARTMENT)

Cottages

[](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=2026-06-17&d1=2026-06-17&endDate=2026-06-20&d2=2026-06-20&lodging=COTTAGE)

Condos

[](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=2026-06-17&d1=2026-06-17&endDate=2026-06-20&d2=2026-06-20&lodging=CONDO)

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## Top Southwest Side Hotel Reviews

![Hilton Chicago/Magnificent Mile Suites](https://images.trvl-media.com/lodging/1000000/20000/18600/18514/a215cd17_y.jpg)

### Hilton Chicago/Magnificent Mile Suites

10/10 Excellent

"Absolutely amazing! "

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

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

### Hilton Chicago

10/10 Excellent

"Nice and clean "

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

![The Wade](https://images.trvl-media.com/lodging/1000000/10000/1400/1346/109a2156_y.jpg)

### The Wade

10/10 Excellent

"Had a very lovely experience. The bed are very comfortable and a lovely view of the lake."

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

![Aloft Chicago Mag Mile](https://images.trvl-media.com/lodging/27000000/27000000/26998800/26998765/58ac280a_y.jpg)

### Aloft Chicago Mag Mile

6/10 Okay

"The pool table could use a maintenance on the sticks were broken also some of our towels in the second room were dirty room 2211 overall was a nice stay we enjoy it . Staff was very friendly and helpful ."

[](https://expedia.com/Chicago-Hotels-Aloft-Chicago-Mag-Mile.h26998765.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

"It was a wonderful visit with not one complaint about the amenities, cleanliness or staff!"

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

![Courtyard by Marriott Chicago Magnificent Mile](https://images.trvl-media.com/lodging/1000000/990000/982600/982517/7705f099_y.jpg)

### Courtyard by Marriott Chicago Magnificent Mile

10/10 Excellent

"The staff were very friendly and helpful."

[](https://expedia.com/Chicago-Hotels-Courtyard-By-Marriott-Chicago-Magnificent-Mile.h982517.Hotel-Information)

![Congress Plaza Hotel](https://images.trvl-media.com/lodging/1000000/10000/6500/6452/11b63ec2_y.jpg)

### Congress Plaza Hotel

10/10 Excellent

"I spent 2 nights and everything was great. I'll be back!"

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

![Embassy Suites by Hilton Chicago Downtown River North](https://images.trvl-media.com/lodging/1000000/20000/11600/11580/24d28405_y.jpg)

### Embassy Suites by Hilton Chicago Downtown River North

8/10 Good

"Good room lower floor was a little close to the street and a little loud but it’s Chicago so to be expected. Breakfast was good and the room was clean."

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

![Palmer House a Hilton Hotel](https://images.trvl-media.com/lodging/1000000/10000/8100/8079/9d783fbd_y.jpg)

### Palmer House a Hilton Hotel

10/10 Excellent

"Beautiful property, great resturant on site, an the pool and spa was amazing."

[](https://expedia.com/Chicago-Hotels-Palmer-House-A-Hilton-Hotel.h8079.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 $106 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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- [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

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- [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)
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- [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)
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- [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)
- [South Side Beach Hotels](https://expedia.com/South-Side-Hotels-Beach-Hotel.0-0-d553248635074842823-tBeachHotel.Travel-Guide-Filter-Hotels)
- [Hotels in Chicago Union Station](https://expedia.com/Chicago-Union-Station-Hotels.d6129885.Travel-Guide-Hotels)
- [North Suburbs Pet-friendly Hotels](https://expedia.com/North-Suburbs-Hotels-Pet-Friendly-Hotel.0-0-d6059336-tPetfriendlyHotel.Travel-Guide-Filter-Hotels)
- [North Suburbs Hotels with Suites](https://expedia.com/North-Suburbs-Hotels-Hotel-Suites.0-0-d6059336-tHotelSuites.Travel-Guide-Filter-Hotels)

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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