Title: West Side Vacation Rentals from $643: Search Short-Term Rentals | Expedia.com

[West Side Travel Guide](https://expedia.com/West-Side.dx553248635976475400)[Hotels in West Side](https://expedia.com/West-Side-Hotels.d553248635976475400.Travel-Guide-Hotels)[Flights to West Side](https://expedia.com/Cheap-Flights-To-West-Side.d553248635976475400.Travel-Guide-Flights)[Things to do in West Side](https://expedia.com/Things-To-Do-In-West-Side.d553248635976475400.Travel-Guide-Activities)[Car Rentals in West Side](https://expedia.com/Car-Rentals-In-West-Side.d553248635976475400.Car-Rental-Guide)[West Side Vacation Packages](https://expedia.com/West-Side.d553248635976475400.Destination-Travel-Guides)

![](https://images.trvl-media.com/place/6182807/509620c2-aaab-4d64-9d41-76a439dcdfa9.jpg?impolicy=fcrop&w=1200&h=500&q=medium)

![](https://images.trvl-media.com/place/6182807/509620c2-aaab-4d64-9d41-76a439dcdfa9.jpg?impolicy=fcrop&w=1200&h=500&q=medium)

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## Check prices for these dates

In two weeks

[Apr 24 - Apr 26](https://www.expedia.com/Hotel-Search?regionId=553248635976475400&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 two months

[Jun 5 - Jun 7](https://www.expedia.com/Hotel-Search?regionId=553248635976475400&startDate=2026-06-05&endDate=2026-06-07&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In three months

[Jul 3 - Jul 5](https://www.expedia.com/Hotel-Search?regionId=553248635976475400&startDate=2026-07-03&endDate=2026-07-05&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In four months

[Jul 31 - Aug 2](https://www.expedia.com/Hotel-Search?regionId=553248635976475400&startDate=2026-07-31&endDate=2026-08-02&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

## Our top choices for West Side vacation rentals

![Studio | Living area](https://images.trvl-media.com/lodging/89000000/88880000/88878700/88878619/811b307f.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/89000000/88880000/88878700/88878619/d56c0426.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Studio | Exterior](https://images.trvl-media.com/lodging/89000000/88880000/88878700/88878619/2f31fc87.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, oven, coffee/tea maker, toaster](https://images.trvl-media.com/lodging/89000000/88880000/88878700/88878619/3f16049a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Chicago Second Floor Studio by 747 Lofts

[](https://www.expedia.com/Chicago-Hotels-Full-Kitchen.h88878619.Hotel-Information)

West Town

8.8/10

Excellent

(13 reviews)

"Great location, convenient to downtown and blue line to airport. Everything necessary in unit, comfortable temperature and full kitchen with unique grocery store nearby."

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

Barbara

$198 nightly

$233 total

Apr 9 - Apr 10

Total with taxes and fees

[](https://www.expedia.com/Chicago-Hotels-Full-Kitchen.h88878619.Hotel-Information)

![Studio | Exterior](https://images.trvl-media.com/lodging/89000000/88870000/88870000/88869909/dcb2ce26.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/89000000/88870000/88870000/88869909/1d5178cf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Studio | Iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/89000000/88870000/88870000/88869909/63b4bd8e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Studio | Living area](https://images.trvl-media.com/lodging/89000000/88870000/88870000/88869909/ffc89aa4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Ground Floor Studios in Chicago by 747 Lofts

[](https://www.expedia.com/Chicago-Hotels-Stylish-Studio-Offers-The-Perfect-Location-For-Your-Windy-City-Wanderings-747-Lofts-Cabin-101-Hotel-Room.h88869909.Hotel-Information)

West Town

9.0/10

Wonderful

(21 reviews)

"Its was in a good location for anyone who has family close by. Bed was wonderful. "

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

Susan

$188 nightly

$221 total

Apr 9 - Apr 10

Total with taxes and fees

[](https://www.expedia.com/Chicago-Hotels-Stylish-Studio-Offers-The-Perfect-Location-For-Your-Windy-City-Wanderings-747-Lofts-Cabin-101-Hotel-Room.h88869909.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, 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, 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)

### Sentral Michigan Avenue

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

Downtown Chicago

9.2/10

Wonderful

(1,126 reviews)

"Clean spacious my go to vacation spot all year around "

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

xavier

$160 nightly

$188 total

Apr 12 - Apr 13

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)

![Front of property - evening/night](https://images.trvl-media.com/lodging/40000000/39810000/39805900/39805843/8a983359.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)

![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)

### Level Chicago – Old Town

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

Downtown Chicago

9.0/10

Wonderful

(456 reviews)

"Would definitely stay again. Everything was great!"

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

Michelle

$248 nightly

$291 total

Apr 12 - Apr 13

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)

![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)

![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)

![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

9.6/10

Exceptional

(187 reviews)

"Nice area if you are renting a car, be aware that you would have to pay for street parking or go over a few blocks and park in a parking lot."

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

Daysha

$197 nightly

$231 total

Apr 13 - Apr 14

Total with taxes and fees

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

(110 reviews)

"This is a fantastic hotel with super friendly staff"

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

German

$202 nightly

$232 total

Apr 8 - Apr 9

Total with taxes and fees

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

![Private kitchen](https://images.trvl-media.com/lodging/105000000/104320000/104315700/104315648/6dcfa9e1.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)

### Wrigleyville Suites

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

Lakeview

9.4/10

Exceptional

(31 reviews)

"Great location and space ! Will use again "

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

Vanessa

$95 nightly

$112 total

Apr 8 - Apr 9

Total with taxes and fees

[](https://www.expedia.com/Chicago-Hotels-Wrigleyville-Suites.h104315648.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) | Lounge](https://images.trvl-media.com/lodging/95000000/94680000/94670100/94670079/13874d20.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)

![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)

### 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

$391 nightly

$448 total

Apr 17 - Apr 18

Total with taxes and fees

[](https://www.expedia.com/Chicago-Hotels-Historic-Oak-Park-Residence.h94670079.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=2026-04-21&endDate=2026-04-22&regionId=553248635976475400&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true)

## Find vacation rentals that suit your style

Villas

[](https://www.expedia.com/Hotel-Search?destination=West+Side%2C+Illinois%2C+United+States+of+America&regionId=553248635976475400&latLong=41.876968%2C-87.708186&adults=2&startDate=2026-07-06&d1=2026-07-06&endDate=2026-07-09&d2=2026-07-09&lodging=VILLA)

Private vacation homes

[](https://www.expedia.com/Hotel-Search?destination=West+Side%2C+Illinois%2C+United+States+of+America&regionId=553248635976475400&latLong=41.876968%2C-87.708186&adults=2&startDate=2026-07-06&d1=2026-07-06&endDate=2026-07-09&d2=2026-07-09&lodging=VACATION_HOME)

Condos

[](https://www.expedia.com/Hotel-Search?destination=West+Side%2C+Illinois%2C+United+States+of+America&regionId=553248635976475400&latLong=41.876968%2C-87.708186&adults=2&startDate=2026-07-06&d1=2026-07-06&endDate=2026-07-09&d2=2026-07-09&lodging=CONDO)

Aparthotels

[](https://www.expedia.com/Hotel-Search?destination=West+Side%2C+Illinois%2C+United+States+of+America&regionId=553248635976475400&latLong=41.876968%2C-87.708186&adults=2&startDate=2026-07-06&d1=2026-07-06&endDate=2026-07-09&d2=2026-07-09&lodging=APART_HOTEL)

Cottages

[](https://www.expedia.com/Hotel-Search?destination=West+Side%2C+Illinois%2C+United+States+of+America&regionId=553248635976475400&latLong=41.876968%2C-87.708186&adults=2&startDate=2026-07-06&d1=2026-07-06&endDate=2026-07-09&d2=2026-07-09&lodging=COTTAGE)

Apartments

[](https://www.expedia.com/Hotel-Search?destination=West+Side%2C+Illinois%2C+United+States+of+America&regionId=553248635976475400&latLong=41.876968%2C-87.708186&adults=2&startDate=2026-07-06&d1=2026-07-06&endDate=2026-07-09&d2=2026-07-09&lodging=APARTMENT)

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## Top West Side Hotel Reviews

![Crowne Plaza Chicago West Loop by IHG](https://images.trvl-media.com/lodging/2000000/1300000/1293300/1293276/871940a9_y.jpg)

### Crowne Plaza Chicago West Loop by IHG

4/10 Poor

"Disappointed by the brand , room delivered with the toilet dirty not even flushed out . TV remote control was sticky . Room indicated to have a sofa bed but was in reality only a small sofa not convertible. Breakfast provided and was a good quality . Asked for extra towels never arrived to room. Overall not a good experience "

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

![Hyatt Place Chicago Medical/University District](https://images.trvl-media.com/lodging/54000000/53170000/53166000/53165905/3edad5a6_y.jpg)

### Hyatt Place Chicago Medical/University District

10/10 Excellent

"Very nice hotel in a historic Cook County Hospital building."

[](https://expedia.com/Chicago-Hotels-Hyatt-Place-Chicago-MedicalUniversity-District.h53165905.Hotel-Information)

![Homewood Suites by Hilton Chicago West Loop Fulton Mkt Area](https://images.trvl-media.com/lodging/16000000/15820000/15816100/15816026/0f7d6f35_y.jpg)

### Homewood Suites by Hilton Chicago West Loop Fulton Mkt Area

10/10 Excellent

"Very nice place, clean and great staff."

[](https://expedia.com/Chicago-Hotels-Homewood-Suites-By-Hilton-Chicago-Downtown-West-Loop.h15816026.Hotel-Information)

![Hyatt House Chicago West Loop](https://images.trvl-media.com/lodging/36000000/35840000/35834300/35834237/d1cc0289_y.jpg)

### Hyatt House Chicago West Loop

10/10 Excellent

"Everything was great… "

[](https://expedia.com/Chicago-Hotels-Hyatt-House-Chicago-West-Loop.h35834237.Hotel-Information)

![The Neighborhood Hotel-Little Italy](https://images.trvl-media.com/lodging/97000000/96300000/96299500/96299486/042dd182_y.jpg)

### The Neighborhood Hotel-Little Italy

6/10 Okay

"clean "

[](https://expedia.com/Chicago-Hotels-The-Neighborhood-Hotel-Little-Italy.h96299486.Hotel-Information)

![Hampton Inn & Suites Chicago Medical District UIC](https://images.trvl-media.com/lodging/103000000/102240000/102236700/102236658/4f2b2c13_y.jpg)

### Hampton Inn & Suites Chicago Medical District UIC

10/10 Excellent

"Perfect location and hotel "

[](https://expedia.com/Chicago-Hotels-Hampton-Inn-Suites-Chicago-Medical-District-Uic.h102236658.Hotel-Information)

![The Robey, Chicago, a Member of Design Hotels](https://images.trvl-media.com/lodging/16000000/15760000/15758200/15758132/b85ded61_y.jpg)

### The Robey, Chicago, a Member of Design Hotels

4/10 Poor

"We stayed in the room in the apex of the triangle. The square footage is reduced by poles supporting the overhead loft bed and a tv that juts out from the wall. It’s like the place is booby trapped. The only storage is under the loft bed so plan on smacking your head at least once until you learn to keep squatting and ducking. The water from the shower trickles into the floor. It gets slippery. All the employees I encountered were very friendly and easy going. The room was expensive…fees and taxes were added on to the Expedia cost at the end of the stay. "

[](https://expedia.com/Chicago-Hotels-The-Robey.h15758132.Hotel-Information)

![Hampton Inn Chicago West Loop Fulton Market Area](https://images.trvl-media.com/lodging/16000000/15850000/15849800/15849775/3ff1c0b3_y.jpg)

### Hampton Inn Chicago West Loop Fulton Market Area

10/10 Excellent

"Upon arriving we were greeted with gratitude from the kind staff along with a perfectly stocked bar and clean room. Highly recommend. :)"

[](https://expedia.com/Chicago-Hotels-Hampton-Inn-Chicago-Downtown-West-Loop.h15849775.Hotel-Information)

![LIVN - West Loop Chicago](https://images.trvl-media.com/lodging/126000000/125890000/125889300/125889222/c4f97193_y.jpg)

### LIVN - West Loop Chicago

10/10 Excellent

"Clean room"

[](https://expedia.com/Chicago-Hotels-LIVN-West-Loop-Chicago.h125889222.Hotel-Information)

## Find out more about West Side

**Everything you need to know about West 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 West 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 West Side vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

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

Whenever you want to travel, a warm welcome awaits you in West 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 West 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 $643 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 West Side rentals**

At Expedia, we put the best West 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 West 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 West 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 West 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.

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- [Apartments in West Side ](https://expedia.com/West-Side-Apartments.d553248635976475400-aaApartments.Travel-Guide-Accommodation)
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- [Hostels in West Side ](https://expedia.com/West-Side-Hostels.d553248635976475400-aaHostels.Travel-Guide-Accommodation)
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### Expedia's Latest Trends

Hotels

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Cars

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Packages

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

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