Title: Chicago Vacation Rentals from $106: Search Short-Term Rentals | Expedia.com

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![City of Chicago. Image of Chicago downtown and Chicago River with bridges at sunny summer day](https://images.trvl-media.com/place/178248/e6aa83ce-7ad8-43a5-9d1d-b055eefa7e78.jpg?impolicy=fcrop&w=1200&h=500&q=medium)

![](https://images.trvl-media.com/place/178248/e6aa83ce-7ad8-43a5-9d1d-b055eefa7e78.jpg?impolicy=fcrop&w=1200&h=500&q=medium)

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## Check prices for these dates

In two weeks

[Mar 27 - Mar 29](https://www.expedia.com/Hotel-Search?regionId=178248&startDate=2026-03-27&endDate=2026-03-29&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In two months

[May 8 - May 10](https://www.expedia.com/Hotel-Search?regionId=178248&startDate=2026-05-08&endDate=2026-05-10&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In three months

[Jun 5 - Jun 7](https://www.expedia.com/Hotel-Search?regionId=178248&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 four months

[Jul 3 - Jul 5](https://www.expedia.com/Hotel-Search?regionId=178248&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)

## Our top choices for Chicago vacation rentals

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

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

### Sentral Michigan Avenue

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

Downtown Chicago

9.2/10

Wonderful

(1,102 reviews)

"Best full kitchen multi-room family lodging"

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

Lee

$152 nightly

$178 total

Apr 5 - Apr 6

Total with taxes and fees

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

![Dining room](https://images.trvl-media.com/lodging/47000000/46240000/46231100/46231022/264e98f1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/47000000/46240000/46231100/46231022/b5ecc9d9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![49-inch Smart TV with digital channels, TV, streaming services](https://images.trvl-media.com/lodging/47000000/46240000/46231100/46231022/5915e3d1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Front of property](https://images.trvl-media.com/lodging/47000000/46240000/46231100/46231022/a150e313.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Kasa Magnificent Mile Chicago

[](https://www.expedia.com/Chicago-Hotels-Kasa-Chicago-River-North-Apartments.h46231022.Hotel-Information)

Downtown Chicago

9.4/10

Exceptional

(708 reviews)

"Perfect location and very clean! "

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

Latoya

$218 nightly

$256 total

Mar 10 - Mar 11

Total with taxes and fees

[](https://www.expedia.com/Chicago-Hotels-Kasa-Chicago-River-North-Apartments.h46231022.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.

$394 nightly

$451 total

Mar 18 - Mar 19

Total with taxes and fees

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

![Desk, iron/ironing board, travel crib, WiFi](https://images.trvl-media.com/lodging/121000000/120510000/120508900/120508888/7a65e5d0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/121000000/120510000/120508900/120508888/df8744f2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, offices](https://images.trvl-media.com/lodging/121000000/120510000/120508900/120508888/f0a938f2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Microwave, oven, stovetop, coffee/tea maker](https://images.trvl-media.com/lodging/121000000/120510000/120508900/120508888/1c0ee66d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Chic Studio in the Heart of the Gold Coast

[](https://www.expedia.com/Chicago-Hotels-Cozy-Gold-Coast-Studio-Stay.h120508888.Hotel-Information)

Downtown Chicago

10/10

Exceptional

(5 reviews)

"We had a wonderful stay at this Vrbo! The home was spotless, cozy, and exactly as described. The host was friendly, responsive, and made everything easy from check-in to check-out. We would absolutely stay here again. Highly recommend!"

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

Brianna K.

$195 nightly

$220 total

Mar 10 - Mar 11

Total with taxes and fees

[](https://www.expedia.com/Chicago-Hotels-Cozy-Gold-Coast-Studio-Stay.h120508888.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)

![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)

![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

(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 10 - Mar 11

Total with taxes and fees

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

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/117000000/116800000/116793000/116792936/a49da56a.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)

### 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 10 - Mar 11

Total with taxes and fees

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

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

### Level Chicago – Old Town

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

Downtown Chicago

9.0/10

Wonderful

(441 reviews)

"Clean, nice amenities and great staff."

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

Sydnee

$176 nightly

$207 total

Apr 5 - Apr 6

Total with taxes and fees

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

![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)

![Interior](https://images.trvl-media.com/lodging/117000000/116800000/116793100/116793043/e3efb27d.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 10 - Mar 11

Total with taxes and fees

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

![Exterior](https://images.trvl-media.com/lodging/118000000/117790000/117782400/117782327/ce588c2e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/118000000/117790000/117782400/117782327/13dc1926.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/118000000/117790000/117782400/117782327/9f7e92a2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, offices](https://images.trvl-media.com/lodging/118000000/117790000/117782400/117782327/92c646c0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Spacious 4BR Central Apartment w/ Skyline Views

[](https://www.expedia.com/Chicago-Hotels-4BR-Modern-Gem-Sleek.h117782327.Hotel-Information)

Near North Side

10/10

Exceptional

(9 reviews)

"Great location, comfortable room, welcoming host."

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

Treseanne A.

$911 nightly

$1,124 total

Mar 11 - Mar 12

Total with taxes and fees

[](https://www.expedia.com/Chicago-Hotels-4BR-Modern-Gem-Sleek.h117782327.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 10 - Mar 11

Total with taxes and fees

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

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

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

![Business center](https://images.trvl-media.com/lodging/67000000/66430000/66425400/66425311/825d44e9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

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

### Kasa River North Chicago

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

Downtown Chicago

9.4/10

Exceptional

(185 reviews)

"Awesome stay "

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

Sally

$243 nightly

$285 total

Apr 6 - Apr 7

Total with taxes and fees

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

![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)

![Exterior](https://images.trvl-media.com/lodging/106000000/105890000/105888000/105887915/06df6711.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

(60 reviews)

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

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

Carin O.

$247 nightly

$305 total

Mar 10 - Mar 11

Total with taxes and fees

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

![TV, video games](https://images.trvl-media.com/lodging/114000000/113520000/113517100/113517065/148e02c2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/114000000/113520000/113517100/113517065/d474c757.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, video games](https://images.trvl-media.com/lodging/114000000/113520000/113517100/113517065/649a9f12.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/114000000/113520000/113517100/113517065/d8c5cb46.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### 5 Minutes to Wrigley and Beach - Games and Arcades - Garage - Sleeps 10

[](https://www.expedia.com/Chicago-Hotels-5-Minutes-To-Wrigley-And-Beach-Games-And-Arcades-Garage-Sleeps-10.h113517065.Hotel-Information)

Lakeview

9.2/10

Wonderful

(5 reviews)

"This was a wonderful stay! The apartment was clean, well furnished, and the communication with the manager was wonderful. My son and I really enjoyed the video games, especially golden tee. The location is fantastic, giving us access to most everything in the Lincoln Park area, as well as Wrigley Field. I can’t recommend this enough. We had a wonderful time!"

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

Matthew B.

$282 nightly

$316 total

Mar 23 - Mar 24

Total with taxes and fees

[](https://www.expedia.com/Chicago-Hotels-5-Minutes-To-Wrigley-And-Beach-Games-And-Arcades-Garage-Sleeps-10.h113517065.Hotel-Information)

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

![Living area](https://images.trvl-media.com/lodging/105000000/104320000/104315700/104315648/3935f43c.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)

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

### Wrigleyville Suites

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

Lakeview

9.2/10

Wonderful

(29 reviews)

"Nice place "

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

Barry

$109 nightly

$129 total

Mar 10 - Mar 11

Total with taxes and fees

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

![TV, offices](https://images.trvl-media.com/lodging/121000000/120510000/120509000/120508914/8d052ee4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/121000000/120510000/120509000/120508914/33798ba9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, offices](https://images.trvl-media.com/lodging/121000000/120510000/120509000/120508914/fac022de.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/121000000/120510000/120509000/120508914/08b4a74d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Stylish Gold Coast 1BR with Vintage Flair

[](https://www.expedia.com/Chicago-Hotels-1BR-Gold-Coast-Vintage-Gem.h120508914.Hotel-Information)

Downtown Chicago

$206 nightly

$231 total

Mar 10 - Mar 11

Total with taxes and fees

[](https://www.expedia.com/Chicago-Hotels-1BR-Gold-Coast-Vintage-Gem.h120508914.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/w1017h1536x0y0-87b71443.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.

$176 nightly

$197 total

Mar 10 - Mar 11

Total with taxes and fees

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

![2 bedrooms, iron/ironing board, travel crib, WiFi](https://images.trvl-media.com/lodging/117000000/116800000/116792900/116792848/93b6d18a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/117000000/116800000/116792900/116792848/w1007h1024x0y0-beaf9548.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Shower](https://images.trvl-media.com/lodging/117000000/116800000/116792900/116792848/fb6a6e02.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV](https://images.trvl-media.com/lodging/117000000/116800000/116792900/116792848/2740956d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Prime Location! 2BR Near Wrigley

[](https://www.expedia.com/Chicago-Hotels-Prime-Location-2BR-Near-Wrigley.h116792848.Hotel-Information)

Lakeview

9.6/10

Exceptional

(8 reviews)

"Everything was clean, really walkable area also"

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

Anthony E.

$219 nightly

$244 total

Mar 12 - Mar 13

Total with taxes and fees

[](https://www.expedia.com/Chicago-Hotels-Prime-Location-2BR-Near-Wrigley.h116792848.Hotel-Information)

![2 bedrooms, iron/ironing board, travel crib, WiFi](https://images.trvl-media.com/lodging/117000000/116800000/116793000/116792920/ff0ac870.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/117000000/116800000/116793000/116792920/692acf21.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/117000000/116800000/116793000/116792920/93d50c3c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, offices](https://images.trvl-media.com/lodging/117000000/116800000/116793000/116792920/196f7de3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Modern 2BR with Reliable Wi-Fi

[](https://www.expedia.com/Chicago-Hotels-Modern-2BR-With-Reliable-Wi-Fi.h116792920.Hotel-Information)

Lakeview

9.0/10

Wonderful

(6 reviews)

"Great location for seeing a Cubs game. Easy to follow "

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

David A.

$219 nightly

$244 total

Mar 10 - Mar 11

Total with taxes and fees

[](https://www.expedia.com/Chicago-Hotels-Modern-2BR-With-Reliable-Wi-Fi.h116792920.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=2026-03-23&endDate=2026-03-24&regionId=829&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)

## 

The Annual Vacation Sale

Members save up to 40% on hotels and homes. Plan this year’s big trip and save.

[Book now](https://expedia.com/deals?rfrr=VR_SPRING_PROMO_178248)

## Find vacation rentals that suit your style

Aparthotels

[](https://www.expedia.com/Hotel-Search?destination=Chicago+%28and+vicinity%29%2C+Illinois%2C+United+States+of+America&regionId=178248&latLong=41.88078%2C-87.62813&adults=2&startDate=2026-06-07&d1=2026-06-07&endDate=2026-06-10&d2=2026-06-10&lodging=APART_HOTEL)

Apartments

[](https://www.expedia.com/Hotel-Search?destination=Chicago+%28and+vicinity%29%2C+Illinois%2C+United+States+of+America&regionId=178248&latLong=41.88078%2C-87.62813&adults=2&startDate=2026-06-07&d1=2026-06-07&endDate=2026-06-10&d2=2026-06-10&lodging=APARTMENT)

Cabins

[](https://www.expedia.com/Hotel-Search?destination=Chicago+%28and+vicinity%29%2C+Illinois%2C+United+States+of+America&regionId=178248&latLong=41.88078%2C-87.62813&adults=2&startDate=2026-06-07&d1=2026-06-07&endDate=2026-06-10&d2=2026-06-10&lodging=CABIN)

Private vacation homes

[](https://www.expedia.com/Hotel-Search?destination=Chicago+%28and+vicinity%29%2C+Illinois%2C+United+States+of+America&regionId=178248&latLong=41.88078%2C-87.62813&adults=2&startDate=2026-06-07&d1=2026-06-07&endDate=2026-06-10&d2=2026-06-10&lodging=VACATION_HOME)

Condos

[](https://www.expedia.com/Hotel-Search?destination=Chicago+%28and+vicinity%29%2C+Illinois%2C+United+States+of+America&regionId=178248&latLong=41.88078%2C-87.62813&adults=2&startDate=2026-06-07&d1=2026-06-07&endDate=2026-06-10&d2=2026-06-10&lodging=CONDO)

Villas

[](https://www.expedia.com/Hotel-Search?destination=Chicago+%28and+vicinity%29%2C+Illinois%2C+United+States+of+America&regionId=178248&latLong=41.88078%2C-87.62813&adults=2&startDate=2026-06-07&d1=2026-06-07&endDate=2026-06-10&d2=2026-06-10&lodging=VILLA)

Cottages

[](https://www.expedia.com/Hotel-Search?destination=Chicago+%28and+vicinity%29%2C+Illinois%2C+United+States+of+America&regionId=178248&latLong=41.88078%2C-87.62813&adults=2&startDate=2026-06-07&d1=2026-06-07&endDate=2026-06-10&d2=2026-06-10&lodging=COTTAGE)

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## Top Chicago Hotel Reviews

![Hotel Riu Plaza Chicago](https://images.trvl-media.com/lodging/103000000/102630000/102622800/102622712/3e21593f_y.jpg)

### Hotel Riu Plaza Chicago

10/10 Excellent

"Great location ans staff was amazing!!"

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

![Eurostars Magnificent Mile](https://images.trvl-media.com/lodging/2000000/1890000/1880400/1880320/8076f539_y.jpg)

### Eurostars Magnificent Mile

8/10 Good

"Great stay. Staff was slightly inattentive at times with requests for things to room."

[](https://expedia.com/Chicago-Hotels-Eurostars-Magnificent-Mile.h1880320.Hotel-Information)

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

### Congress Plaza Hotel

10/10 Excellent

"Great historic vibe, but feels old."

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

![Hyatt Centric The Loop Chicago](https://images.trvl-media.com/lodging/10000000/9070000/9069700/9069667/0ec157ec_y.jpg)

### Hyatt Centric The Loop Chicago

10/10 Excellent

"Everything was perfect. The room was cleaned dhe the staff was kind.It has a lot of stores near by the hotel."

[](https://expedia.com/Chicago-Hotels-Hyatt-Centric-The-Loop-Chicago.h9069667.Hotel-Information)

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

### Hilton Chicago

8/10 Good

"Staff was prejudice to black kids in pool area! "

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

![LondonHouse Chicago, Curio Collection by Hilton](https://images.trvl-media.com/lodging/13000000/12790000/12786700/12786616/7aab5ae1_y.jpg)

### LondonHouse Chicago, Curio Collection by Hilton

10/10 Excellent

"Didn't get to make it to spa"

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

10/10 Excellent

"Good hotel, good area ! "

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

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

### Hilton Chicago/Magnificent Mile Suites

4/10 Poor

"Room was clean, but the room was also very hot. Microwave did not work at first. They sent somebody up to fix it, but I still had to sleep in a hot room because the air was not working. I went down to ask the lady at the front desk for a microwave because my work was not working and she rushed me away assuring me that someone was coming up to fix all these issues I was having only for him to get up there take a board off the countertop to plug up the microwave and tell me to just turn the air off and turn it back on again and it should work overall it was a nice hotel very clean"

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

8/10 Good

"Clean room nice staff hotel needed some work. Pool was freezing, our door broke and kept locking us out. "

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

## Price trends for vacation rentals in Chicago

| Less expensive | More expensive | This month | Next month |
| -------------- | -------------- | ---------- | ---------- |
| January        | July           | $276       | $311       |

| Month     | Price |
| --------- | ----- |
| January   | $259  |
| February  | $270  |
| March     | $276  |
| April     | $311  |
| May       | $376  |
| June      | $372  |
| July      | $449  |
| August    | $373  |
| September | $322  |
| October   | $379  |
| November  | $288  |
| December  | $282  |

Price trend information excludes taxes and fees and is based on base rates for a nightly stay for 2 adults found in the last 7 days on our site and averaged for commonly viewed vacation rentals in Chicago. Select dates and complete search for nightly totals inclusive of taxes and fees.

## Find out more about Chicago

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

**Chicago vacation rentals: An excellent choice for every season**

Whenever you want to travel, a warm welcome awaits you in Chicago. 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 Chicago 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 Chicago rentals**

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

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- [Apartments in Chicago ](https://expedia.com/Chicago-Apartments.d178248-aaApartments.Travel-Guide-Accommodation)
- [Vacation Homes in Chicago ](https://expedia.com/Chicago-Private-Vacation-Homes.d178248-aaPrivateVacationHomes.Travel-Guide-Accommodation)
- [Condo Rentals in Chicago ](https://expedia.com/Chicago-Condos.d178248-aaCondos.Travel-Guide-Accommodation)
- [Aparthotels in Chicago ](https://expedia.com/Chicago-Apart-Hotels.d178248-aaApartHotels.Travel-Guide-Accommodation)
- [Motels in Chicago ](https://expedia.com/Chicago-Motels.d178248-aaMotels.Travel-Guide-Accommodation)
- [Cottages in Chicago ](https://expedia.com/Chicago-Cottages.d178248-aaCottages.Travel-Guide-Accommodation)
- [B&B in Chicago ](https://expedia.com/Chicago-Bed-And-Breakfast.d178248-aaBedAndBreakfast.Travel-Guide-Accommodation)
- [Guest Houses in Chicago ](https://expedia.com/Chicago-Guest-Houses.d178248-aaGuestHouses.Travel-Guide-Accommodation)
- [Villas in Chicago ](https://expedia.com/Chicago-Villas.d178248-aaVillas.Travel-Guide-Accommodation)
- [Resorts in Chicago ](https://expedia.com/Chicago-Resorts.d178248-aaResorts.Travel-Guide-Accommodation)
- [Hostels in Chicago ](https://expedia.com/Chicago-Hostels.d178248-aaHostels.Travel-Guide-Accommodation)
- [Farmstay in Chicago ](https://expedia.com/Chicago-Agritourism.d178248-aaAgritourism.Travel-Guide-Accommodation)
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- [Residences in Chicago ](https://expedia.com/Chicago-Residences.d178248-aaResidences.Travel-Guide-Accommodation)
- [Inns in Chicago ](https://expedia.com/Chicago-Inns.d178248-aaInns.Travel-Guide-Accommodation)
- [Cabin Rentals in Chicago ](https://expedia.com/Chicago-Cabins.d178248-aaCabins.Travel-Guide-Accommodation)

## Frequently asked questions

### Can I find vacation rentals in Chicago?

### What are some of the best vacation rentals in Chicago?

### How many vacation rentals are there in Chicago?

### What can I see and do in Chicago?

### What are vacation rentals like in Chicago?

### Expedia's Latest Trends

Hotels

- [Hotels near Millennium Park](https://expedia.com/Millennium-Park-Hotels.0-l6069201-0.Travel-Guide-Filter-Hotels)
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- [Hotels near United Center](https://expedia.com/United-Center-Hotels.0-l6064077-0.Travel-Guide-Filter-Hotels)
- [River North Hotels](https://expedia.com/River-North-Chicago-Hotels.0-n6350695-0.Travel-Guide-Filter-Hotels)
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- [Luxury Hotels in Downtown Chicago](https://expedia.com/Downtown-Chicago-Chicago-Hotels-Luxury-Hotel.0-n6350699-0-tLuxuryHotel.Travel-Guide-Filter-Hotels)
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- [Hotels near Soldier Field](https://expedia.com/Soldier-Field-Hotels.0-l6058043-0.Travel-Guide-Filter-Hotels)
- [The Loop Hotels](https://expedia.com/The-Loop-Chicago-Hotels.0-n800024-0.Travel-Guide-Filter-Hotels)
- [Hotels in Schaumburg](https://expedia.com/Schaumburg-Hotels.d8107.Travel-Guide-Hotels)
- [Magnificent Mile Hotels](https://expedia.com/Magnificent-Mile-Chicago-Hotels.0-n800025-0.Travel-Guide-Filter-Hotels)
- [Hotels in Rosemont](https://expedia.com/Rosemont-Hotels.d7581.Travel-Guide-Hotels)
- [Hotels in Oak Brook](https://expedia.com/Oak-Brook-Hotels.d9218.Travel-Guide-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)
- [Cheap Hotels in Downtown Chicago](https://expedia.com/Downtown-Chicago-Chicago-Hotels-Cheap-Hotels.0-n6350699-0-tCheapHotels.Travel-Guide-Filter-Hotels)
- [Hotels in Evanston](https://expedia.com/Evanston-Hotels.d8049.Travel-Guide-Hotels)
- [Hotels in Naperville](https://expedia.com/Naperville-Hotels.d9009.Travel-Guide-Hotels)
- [Hotels near Navy Pier](https://expedia.com/Navy-Pier-Hotels.0-l6069215-0.Travel-Guide-Filter-Hotels)
- [Hotels with a View in Downtown Chicago](https://expedia.com/Downtown-Chicago-Chicago-Hotels-Hotels-With-View.0-n6350699-0-tHotelswithView.Travel-Guide-Filter-Hotels)
- [Hotels in Chicago Union Station](https://expedia.com/Chicago-Union-Station-Hotels.d6129885.Travel-Guide-Hotels)
- [West Loop Hotels](https://expedia.com/West-Loop-Chicago-Hotels.0-n553248634029130868-0.Travel-Guide-Filter-Hotels)

Flights

- [Cheap Flights to Chicago](https://expedia.com/Cheap-Flights-To-OHare-Intl.d4477519.Travel-Guide-Flights)

Cars

- [Car rental Chicago Airport (MDW)](https://expedia.com/Car-Rentals-In-Midway-Intl.d5719117.Car-Rental-Guide)
- [Car rental Chicago Airport (ORD)](https://expedia.com/Car-Rentals-In-OHare-Intl.d4477519.Car-Rental-Guide)

Activities

- [Things to do in Schaumburg](https://expedia.com/Things-To-Do-In-Schaumburg.d8107.Travel-Guide-Activities)

General

- [Visit The Loop](https://expedia.com/Chicago-The-Loop.dx800024)
- [Visit Downtown Chicago](https://expedia.com/Chicago-Downtown-Chicago.dx6350699)

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