Title: West Side Vacation Rentals from $292: 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)

![Discover the lush greenery and tranquil environment at Garfield Park Conservatory in Chicago, Illinois, showcasing diverse plant life](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

[Mar 20 - Mar 22](https://www.expedia.com/Hotel-Search?regionId=553248635976475400&startDate=2026-03-20&endDate=2026-03-22&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In two months

[May 1 - May 3](https://www.expedia.com/Hotel-Search?regionId=553248635976475400&startDate=2026-05-01&endDate=2026-05-03&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In three months

[May 29 - May 31](https://www.expedia.com/Hotel-Search?regionId=553248635976475400&startDate=2026-05-29&endDate=2026-05-31&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In four months

[Jun 26 - Jun 28](https://www.expedia.com/Hotel-Search?regionId=553248635976475400&startDate=2026-06-26&endDate=2026-06-28&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

![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.

$206 nightly

$231 total

Mar 9 - Mar 10

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)

![Shower, hair dryer](https://images.trvl-media.com/lodging/120000000/119140000/119131900/119131874/4fcb7f04.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)

### West Loop Living – Bright 1BR

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

Downtown Chicago

10/10

Exceptional

(7 reviews)

"Well-outfitted, nice apartment. Nearby (walkable) Jewel-Osco grocery, restaurants, and pay-parking. Moderate noise from nearby Chicago "L" Green Line."

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

Jeffrey

$206 nightly

$231 total

Mar 4 - Mar 5

Total with taxes and fees

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

![](https://images.trvl-media.com/lodging/127000000/126870000/126868500/126868475/7317fe0e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![](https://images.trvl-media.com/lodging/127000000/126870000/126868500/126868475/9c319c8d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![](https://images.trvl-media.com/lodging/127000000/126870000/126868500/126868475/ced2d469.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![](https://images.trvl-media.com/lodging/127000000/126870000/126868500/126868475/d5ece405.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### LIVN West Loop Chicago

[](https://www.expedia.com/Chicago-Hotels-LIVN-West-Loop-Chicago.h126868475.Hotel-Information)

Downtown Chicago

$246 nightly

$291 total

Apr 1 - Apr 2

Total with taxes and fees

[](https://www.expedia.com/Chicago-Hotels-LIVN-West-Loop-Chicago.h126868475.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/117000000/116800000/116793100/116793043/8ec83200.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/117000000/116800000/116793100/116793043/143f3ef1.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)

### 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.

$206 nightly

$231 total

Mar 4 - Mar 5

Total with taxes and fees

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

![1 bedroom, WiFi, bed sheets](https://images.trvl-media.com/lodging/120000000/119140000/119131900/119131871/e255803d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/120000000/119140000/119131900/119131871/2e28ea21.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/120000000/119140000/119131900/119131871/4b4ff505.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Shower, hair dryer, towels](https://images.trvl-media.com/lodging/120000000/119140000/119131900/119131871/fe11ac9c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### 1BR Modern Luxe Apt with In-Unit Laundry

[](https://www.expedia.com/Chicago-Hotels-1BR-Modern-Luxe-Apt-With-In-Unit-Laundry.h119131871.Hotel-Information)

Downtown Chicago

10/10

Exceptional

(1 review)

"Great experience for me and my wife I would definitely come back "

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

ShowtimeFam1

$206 nightly

$231 total

Mar 4 - Mar 5

Total with taxes and fees

[](https://www.expedia.com/Chicago-Hotels-1BR-Modern-Luxe-Apt-With-In-Unit-Laundry.h119131871.Hotel-Information)

![](https://images.trvl-media.com/lodging/127000000/126870000/126868500/126868474/62ffbce8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![](https://images.trvl-media.com/lodging/127000000/126870000/126868500/126868474/d2e56ab7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![](https://images.trvl-media.com/lodging/127000000/126870000/126868500/126868474/36bcad50.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![](https://images.trvl-media.com/lodging/127000000/126870000/126868500/126868474/b85e3bee.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### LIVN West Loop Chicago

[](https://www.expedia.com/Chicago-Hotels-LIVN-West-Loop-Chicago.h126868474.Hotel-Information)

Downtown Chicago

$171 nightly

$202 total

Apr 1 - Apr 2

Total with taxes and fees

[](https://www.expedia.com/Chicago-Hotels-LIVN-West-Loop-Chicago.h126868474.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)

![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/117000000/116800000/116793000/116792993/9c142ace.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/117000000/116800000/116793000/116792993/8da5334e.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

8.2/10

Very Good

(14 reviews)

"Great location! "

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

Kourtney K.

$223 nightly

$247 total

Mar 4 - Mar 5

Total with taxes and fees

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

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/106000000/105560000/105552500/105552490/w1350h899x0y1-0e2db60e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/106000000/105560000/105552500/105552490/w1349h899x1y1-7309c990.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/106000000/105560000/105552500/105552490/edfa1c05.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, desk, iron/ironing board, travel crib](https://images.trvl-media.com/lodging/106000000/105560000/105552500/105552490/0395dfa5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Cozy Boho Chicago - 10 Minutes to Downtown Chicago

[](https://www.expedia.com/Chicago-Hotels-Cozy-Boho-Chicago-10-Minutes-To-Downtown-Chicago.h105552490.Hotel-Information)

Lawndale

10/10

Exceptional

(8 reviews)

"Wonderful space and convenient location. Really responsive host and super quiet neighborhood! "

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

Jess S.

$183 nightly

$205 total

Mar 9 - Mar 10

Total with taxes and fees

[](https://www.expedia.com/Chicago-Hotels-Cozy-Boho-Chicago-10-Minutes-To-Downtown-Chicago.h105552490.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)

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

![Studio | Iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/89000000/88910000/88902500/88902456/380b6682.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

$203 nightly

$238 total

Mar 6 - Mar 7

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)

![Smart TV](https://images.trvl-media.com/lodging/116000000/115430000/115420400/115420356/b4ab2028.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/116000000/115430000/115420400/115420356/46461bf5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/116000000/115430000/115420400/115420356/cf70ee87.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/116000000/115430000/115420400/115420356/1246de2d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### NEW Private West Loop 1br with Backyard near Green Line and CTA

[](https://www.expedia.com/Chicago-Hotels-NEW-Private-West-Loop-1br-With-Backyard-Near-Green-Line-And-CTA.h115420356.Hotel-Information)

East Garfield Park

9.6/10

Exceptional

(4 reviews)

"Very cozy stay. Host was great with communication and the place has everything needed. Would definitely book here again!"

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

Eric H.

$168 nightly

$207 total

Mar 4 - Mar 5

Total with taxes and fees

[](https://www.expedia.com/Chicago-Hotels-NEW-Private-West-Loop-1br-With-Backyard-Near-Green-Line-And-CTA.h115420356.Hotel-Information)

![Interior](https://images.trvl-media.com/lodging/109000000/108480000/108474000/108473931/w1349h899x1y1-02d8b93f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/109000000/108480000/108474000/108473931/w1350h899x0y1-546ed985.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/109000000/108480000/108474000/108473931/w1350h899x0y1-d9f91130.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/109000000/108480000/108474000/108473931/w1350h899x0y1-cd80dee1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### 10 Minutes to Downtown Chicago - Sleeps 12 - King Beds - Games and Arcades

[](https://www.expedia.com/Chicago-Hotels-10-Minutes-To-Downtown-Chicago-Sleeps-12-King-Beds-Games-And-Arcades.h108473931.Hotel-Information)

Lawndale

8.8/10

Excellent

(3 reviews)

"While it was a great price, you get what you pay for. "

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

Deya R.

$290 nightly

$325 total

Apr 1 - Apr 2

Total with taxes and fees

[](https://www.expedia.com/Chicago-Hotels-10-Minutes-To-Downtown-Chicago-Sleeps-12-King-Beds-Games-And-Arcades.h108473931.Hotel-Information)

![Interior](https://images.trvl-media.com/lodging/119000000/118310000/118306200/118306109/a943eff7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/119000000/118310000/118306200/118306109/907c775c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, books, offices](https://images.trvl-media.com/lodging/119000000/118310000/118306200/118306109/fc588142.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/119000000/118310000/118306200/118306109/51989ea6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Flexhome West Town • Urban 2BR · Easy Parking

[](https://www.expedia.com/Chicago-Hotels-Flexhome-West-Town-2BR-Apt-T1.h118306109.Hotel-Information)

West Town

9.6/10

Exceptional

(5 reviews)

"Awesome location, great views and comfortable."

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

Steve L.

$220 nightly

$255 total

Mar 29 - Mar 30

Total with taxes and fees

[](https://www.expedia.com/Chicago-Hotels-Flexhome-West-Town-2BR-Apt-T1.h118306109.Hotel-Information)

![TV](https://images.trvl-media.com/lodging/126000000/125080000/125073100/125073089/7ac3b0ec.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/126000000/125080000/125073100/125073089/04b81adb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![2 bedrooms, desk, WiFi](https://images.trvl-media.com/lodging/126000000/125080000/125073100/125073089/d0ac6aae.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/126000000/125080000/125073100/125073089/48ee2988.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### 15 mins DT| HumboldtPark Gem | Sleeps 8 | FreePark

[](https://www.expedia.com/Chicago-Hotels-15-Mins-DT-HumboldtPark-Gem-Sleeps-8-FreePark.h125073089.Hotel-Information)

West Town

10/10

Exceptional

(1 review)

$104 nightly

$109 total

Mar 4 - Mar 5

Total with taxes and fees

[](https://www.expedia.com/Chicago-Hotels-15-Mins-DT-HumboldtPark-Gem-Sleeps-8-FreePark.h125073089.Hotel-Information)

![Interior](https://images.trvl-media.com/lodging/117000000/116800000/116793000/116792914/672545d9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV](https://images.trvl-media.com/lodging/117000000/116800000/116793000/116792914/05d0e593.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/117000000/116800000/116793000/116792914/904b24c8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![3 bedrooms, iron/ironing board, travel crib, WiFi](https://images.trvl-media.com/lodging/117000000/116800000/116793000/116792914/3944b711.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### 3BR Complete and Spacious Apt

[](https://www.expedia.com/Chicago-Hotels-3BR-Complete-And-Spacious-Apt.h116792914.Hotel-Information)

West Town

8.8/10

Excellent

(13 reviews)

"This is such a steal of a price for this beautiful place! We had a great stay. Amazing location, plenty of square footage, and the hosts are incredibly helpful. You really don’t have to do much to check out like some VRBOs either! Would definitely stay again. "

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

Alec

$262 nightly

$292 total

Mar 4 - Mar 5

Total with taxes and fees

[](https://www.expedia.com/Chicago-Hotels-3BR-Complete-And-Spacious-Apt.h116792914.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/89000000/88910000/88902300/88902260/48649b7d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/89000000/88910000/88902300/88902260/33934a73_edited_05cd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/89000000/88910000/88902300/88902260/9e56bc31_edited_8e5b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/89000000/88910000/88902300/88902260/15c79dc3_edited_9263.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Cabin 308 by 747 Lofts

[](https://www.expedia.com/Chicago-Hotels-Cabin-308-By-747-Lofts.h88902260.Hotel-Information)

West Town

9.4/10

Exceptional

(17 reviews)

"Stayed here to go to a concert, location is extremely convenient. Bed was comfortable and place was exactly what we needed! Definitely booking again"

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

Rachelle A.

$192 nightly

$227 total

Mar 6 - Mar 7

Total with taxes and fees

[](https://www.expedia.com/Chicago-Hotels-Cabin-308-By-747-Lofts.h88902260.Hotel-Information)

![Dining](https://images.trvl-media.com/lodging/111000000/110690000/110681900/110681813/d1e56d63.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/111000000/110690000/110681900/110681813/164cb885.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![](https://images.trvl-media.com/lodging/111000000/110690000/110681900/110681813/ad3911c2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Hair dryer, towels](https://images.trvl-media.com/lodging/111000000/110690000/110681900/110681813/f955619a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Flexhome Wicker Park • Stylish 2BR • Prime Spot

[](https://www.expedia.com/Chicago-Hotels-Flexhome-Wicker-Park-2BR-DV4.h110681813.Hotel-Information)

West Town

9.6/10

Exceptional

(4 reviews)

"Great location. The apartment has everything you will need. Had a great time . Thanks"

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

Wayne M.

$140 nightly

$172 total

Mar 5 - Mar 6

Total with taxes and fees

[](https://www.expedia.com/Chicago-Hotels-Flexhome-Wicker-Park-2BR-DV4.h110681813.Hotel-Information)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/103000000/102350000/102347800/102347797/be907ced.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/103000000/102350000/102347800/102347797/w1277h853x0y0-b16d8c38.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, books](https://images.trvl-media.com/lodging/103000000/102350000/102347800/102347797/4d07b912.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior detail](https://images.trvl-media.com/lodging/103000000/102350000/102347800/102347797/d8a5de19.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Flexhome East Village • Modern 2BR • Quiet Street

[](https://www.expedia.com/Chicago-Hotels-Flexhome-East-Village-2BR-H1.h102347797.Hotel-Information)

West Town

9.6/10

Exceptional

(8 reviews)

"Location was great for everything we were doing in Chicago. "

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

Tom W.

$135 nightly

$167 total

Mar 5 - Mar 6

Total with taxes and fees

[](https://www.expedia.com/Chicago-Hotels-Flexhome-East-Village-2BR-H1.h102347797.Hotel-Information)

![Dining](https://images.trvl-media.com/lodging/119000000/118120000/118113500/118113406/w1350h899x0y1-e4f4e07a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, video games](https://images.trvl-media.com/lodging/119000000/118120000/118113500/118113406/w1350h899x0y1-a954e392.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/119000000/118120000/118113500/118113406/819688a1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Microwave, oven, stovetop, dishwasher](https://images.trvl-media.com/lodging/119000000/118120000/118113500/118113406/w1350h899x0y1-6b0d266e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### 5 Mins to Downtown CHI Sleeps 10 - Parking + Games

[](https://www.expedia.com/Chicago-Hotels-5-Mins-To-Downtown-CHI-Sleeps-10-Parking-Games.h118113406.Hotel-Information)

Lower West Side

10/10

Exceptional

(3 reviews)

"We loved the location, the area is awesome! Great stay, highly recommend. "

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

Db D.

$307 nightly

$345 total

Mar 18 - Mar 19

Total with taxes and fees

[](https://www.expedia.com/Chicago-Hotels-5-Mins-To-Downtown-CHI-Sleeps-10-Parking-Games.h118113406.Hotel-Information)

![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)

![Studio | Exterior](https://images.trvl-media.com/lodging/89000000/88910000/88902400/88902334/4016d076.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/89000000/88910000/88902400/88902334/52817ea9.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

$293 nightly

$344 total

Mar 16 - Mar 17

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)

![Exterior](https://images.trvl-media.com/lodging/103000000/102340000/102331000/102330932/7ab6d91a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/103000000/102340000/102331000/102330932/a2f95807.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/103000000/102340000/102331000/102330932/cdbd7000.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/103000000/102340000/102331000/102330932/46cf36e4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The Banksy-Greystone Rooftop Firepit United Center

[](https://www.expedia.com/Chicago-Hotels-The-Banksy-Greystone-Rooftop-Firepit-United-Center.h102330932.Hotel-Information)

Near West Side

$235 nightly

$281 total

Mar 8 - Mar 9

Total with taxes and fees

[](https://www.expedia.com/Chicago-Hotels-The-Banksy-Greystone-Rooftop-Firepit-United-Center.h102330932.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=2026-03-17&endDate=2026-03-18&regionId=553248635976475400&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true)

![](https://forever.travel-assets.com/flex/flexmanager/images/2026/02/06/expedia-sale-2026-desktop-us-ca.jpg?impolicy=fcrop&w=1400&h=600&q=mediumHigh)

## 

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## 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=2026-06-01&d1=2026-06-01&endDate=2026-06-04&d2=2026-06-04&lodging=VILLA)

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=2026-06-01&d1=2026-06-01&endDate=2026-06-04&d2=2026-06-04&lodging=APART_HOTEL)

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=2026-06-01&d1=2026-06-01&endDate=2026-06-04&d2=2026-06-04&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=2026-06-01&d1=2026-06-01&endDate=2026-06-04&d2=2026-06-04&lodging=CONDO)

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=2026-06-01&d1=2026-06-01&endDate=2026-06-04&d2=2026-06-04&lodging=APARTMENT)

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=2026-06-01&d1=2026-06-01&endDate=2026-06-04&d2=2026-06-04&lodging=COTTAGE)

Residences

[](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=2026-06-01&d1=2026-06-01&endDate=2026-06-04&d2=2026-06-04&lodging=RESIDENCE)

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## Top West Side Hotel Reviews

![Hampton Inn & Suites Chicago Medical District UIC](https://images.trvl-media.com/lodging/103000000/102240000/102236700/102236658/03795c9c_y.jpg)

### Hampton Inn & Suites Chicago Medical District UIC

10/10 Excellent

"Room was spotless. Very friendly front desk and cannot express how convenient and safe for a female traveling alone. "

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

![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

10/10 Excellent

"Perfect "

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

![Nobu Hotel Chicago](https://images.trvl-media.com/lodging/37000000/36480000/36475600/36475533/486e1134_y.jpg)

### Nobu Hotel Chicago

10/10 Excellent

"Has everything and more "

[](https://expedia.com/Chicago-Hotels-Nobu-Hotel-Chicago.h36475533.Hotel-Information)

![The Emily Hotel](https://images.trvl-media.com/lodging/20000000/19390000/19381200/19381112/d235a6b6_y.jpg)

### The Emily Hotel

10/10 Excellent

"Room was great. Staff were nice. Good coffee shop"

[](https://expedia.com/Chicago-Hotels-Ace-Hotel-Chicago.h19381112.Hotel-Information)

![Holiday Inn & Suites Chicago - Downtown by IHG](https://images.trvl-media.com/lodging/1000000/210000/201300/201274/9b3b5e62_y.jpg)

### Holiday Inn & Suites Chicago - Downtown by IHG

10/10 Excellent

"Pretty good"

[](https://expedia.com/Chicago-Hotels-Holiday-Inn-Suites-Chicago-Downtown.h201274.Hotel-Information)

![Hyatt House Chicago Medical/University District](https://images.trvl-media.com/lodging/50000000/49320000/49315100/49315022/689da744_y.jpg)

### Hyatt House Chicago Medical/University District

10/10 Excellent

"Clean hotel, good breakfast, close to United Center, helpful staff. Easy parking. Safe and great value for price."

[](https://expedia.com/Chicago-Hotels-Hyatt-House-Chicago-MedicalUniversity-District.h49315022.Hotel-Information)

![Hyatt Place Chicago/Wicker Park](https://images.trvl-media.com/lodging/43000000/42200000/42197500/42197417/34425b75_y.jpg)

### Hyatt Place Chicago/Wicker Park

10/10 Excellent

"Very pleased. Incredible staff. Excellent beds/linens. Very clean. Lots of choices for complimentary breakast buffet with views of the city on the 7th floor "

[](https://expedia.com/Chicago-Hotels-Hyatt-Place-ChicagoWicker-Park.h42197417.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

"Everything was great. "

[](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

"Yes"

[](https://expedia.com/Chicago-Hotels-Hyatt-House-Chicago-West-Loop.h35834237.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 $292 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.

## Explore a world of travel with Expedia

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

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- [Michigan Vacation Rentals ](https://www.expedia.com/Destinations-In-Michigan.d224.Vacation-Rental-Destinations)

- [Apartments in West Side ](https://expedia.com/West-Side-Apartments.d553248635976475400-aaApartments.Travel-Guide-Accommodation)
- [Vacation Homes in West Side ](https://expedia.com/West-Side-Private-Vacation-Homes.d553248635976475400-aaPrivateVacationHomes.Travel-Guide-Accommodation)
- [Aparthotels in West Side ](https://expedia.com/West-Side-Apart-Hotels.d553248635976475400-aaApartHotels.Travel-Guide-Accommodation)
- [Condo Rentals in West Side ](https://expedia.com/West-Side-Condos.d553248635976475400-aaCondos.Travel-Guide-Accommodation)
- [Villas in West Side ](https://expedia.com/West-Side-Villas.d553248635976475400-aaVillas.Travel-Guide-Accommodation)
- [B&B in West Side ](https://expedia.com/West-Side-Bed-And-Breakfast.d553248635976475400-aaBedAndBreakfast.Travel-Guide-Accommodation)
- [Hostels in West Side ](https://expedia.com/West-Side-Hostels.d553248635976475400-aaHostels.Travel-Guide-Accommodation)
- [Houseboats in West Side ](https://expedia.com/West-Side-Houseboats.d553248635976475400-aaHouseboats.Travel-Guide-Accommodation)

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- [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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- [Cheap Hotels in South Side](https://expedia.com/South-Side-Hotels-Cheap-Hotels.0-0-d553248635074842823-tCheapHotels.Travel-Guide-Filter-Hotels)
- [Beach Hotels in North Suburbs](https://expedia.com/North-Suburbs-Hotels-Beach-Hotel.0-0-d6059336-tBeachHotel.Travel-Guide-Filter-Hotels)
- [Hotels with an Outdoor Pool in North Suburbs](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)
- [Hotels near Grant Park](https://expedia.com/Grant-Park-Hotels.0-l507389-0.Travel-Guide-Filter-Hotels)
- [Hotels near Michigan Avenue](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)
- [Hotels near Navy Pier](https://expedia.com/Navy-Pier-Hotels.0-l6069215-0.Travel-Guide-Filter-Hotels)
- [Beach Hotels in South Side](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)
- [Pet-friendly Hotels in North Suburbs](https://expedia.com/North-Suburbs-Hotels-Pet-Friendly-Hotel.0-0-d6059336-tPetfriendlyHotel.Travel-Guide-Filter-Hotels)
- [Hotels with Suites in North Suburbs](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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