Chicago Vacation Rentals

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Check prices for these dates

In two weeks
Mar 6 - Mar 8
In two months
Apr 17 - Apr 19
In three months
May 15 - May 17
In four months
Jun 12 - Jun 14

Our top choices for Chicago vacation rentals

Indoor pool

Sentral Michigan Avenue

Sentral Michigan Avenue
4.0 star property
Downtown Chicago
9.2 out of 10, Wonderful, (1,084 reviews)
"Best full kitchen multi-room family lodging"
United States
Lee
The price is ￥16,788
￥24,201 total
includes taxes & fees
Feb 23 - Feb 24
Sentral Michigan Avenue
Full-size fridge, microwave, oven, stovetop

Level Chicago – Old Town

Level Chicago – Old Town
4.0 star property
Downtown Chicago
9.0 out of 10, Wonderful, (429 reviews)
"Clean, nice amenities and great staff."
United States
Sydnee
Level Chicago – Old Town
TV, offices

Complete 1BR Fully Furnished Home

Complete 1BR Fully Furnished Home
Downtown Chicago
The price is ￥13,473
￥30,277 total
includes taxes & fees
Mar 2 - Mar 3
Complete 1BR Fully Furnished Home
Interior

River North Rooftop With In and Out Parking 3

River North Rooftop With In and Out Parking 3
Downtown Chicago
9.6 out of 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
Jennifer M.
The price is ￥16,125
￥49,190 total
includes taxes & fees
Feb 19 - Feb 20
River North Rooftop With In and Out Parking 3
Lounge

Kasa River North Chicago

Kasa River North Chicago
4.0 star property
Downtown Chicago
9.6 out of 10, Exceptional, (183 reviews)
"Awesome stay "
United States
Sally
Kasa River North Chicago
Desk, iron/ironing board, travel crib, WiFi

Chic Studio in the Heart of the Gold Coast

Chic Studio in the Heart of the Gold Coast
Downtown Chicago
10.0 out of 10, Exceptional, (5 reviews)
"The communication was really effective and made for a smooth check in and check out process. Host was friendly and made great recommendations, 10/10 would stay again!"
United States
Seynabou
The price is ￥10,258
￥24,980 total
includes taxes & fees
Feb 23 - Feb 24
Chic Studio in the Heart of the Gold Coast
1 bedroom, iron/ironing board, travel crib, WiFi

West Loop Living – Bright 1BR

West Loop Living – Bright 1BR
Downtown Chicago
10.0 out of 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
Jeffrey
The price is ￥10,564
￥26,871 total
includes taxes & fees
Feb 23 - Feb 24
West Loop Living – Bright 1BR
TV, offices

Sun-Drenched 1BR Apartment

Sun-Drenched 1BR Apartment
Downtown Chicago
10.0 out of 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
Tyler B.
The price is ￥10,564
￥26,871 total
includes taxes & fees
Feb 23 - Feb 24
Sun-Drenched 1BR Apartment
TV, offices

Modern Comfort: 1BR Unit w/ Laundry

Modern Comfort: 1BR Unit w/ Laundry
Downtown Chicago
9.2 out of 10, Wonderful, (15 reviews)
"Great host comfortable bed close to restaurants and parks"
United States
Alana C.
The price is ￥10,564
￥26,871 total
includes taxes & fees
Feb 23 - Feb 24
Modern Comfort: 1BR Unit w/ Laundry
1 bedroom, WiFi, bed sheets

1BR Modern Luxe Apt with In-Unit Laundry

1BR Modern Luxe Apt with In-Unit Laundry
Downtown Chicago
10.0 out of 10, Exceptional, (1 review)
"Great experience for me and my wife I would definitely come back "
United States
ShowtimeFam1
The price is ￥13,626
￥30,456 total
includes taxes & fees
Mar 2 - Mar 3
1BR Modern Luxe Apt with In-Unit Laundry
Fridge, microwave, oven, stovetop

Sleek 1BR Apartment w/ In-unit Laundry

Sleek 1BR Apartment w/ In-unit Laundry
Downtown Chicago
10.0 out of 10, Exceptional, (1 review)
"I was a little hesitant since I didn’t see any reviews, and was bit nervous. However, all that was put to rest when we arrived. Everything was as described and the photos were accurate. It was clean and minimalistic. Nice space for two for a week. Having the full kitchen was great. About 15 min walk to the brown line and 25 to the blue Line and not a lot of restaurants close by is about the only complaint. Bed could have been more comfortable too."
United States
Anonymous traveler
The price is ￥11,942
￥28,676 total
includes taxes & fees
Feb 25 - Feb 26
Sleek 1BR Apartment w/ In-unit Laundry
Exterior

Spacious 4BR Central Apartment w/ Skyline Views

Spacious 4BR Central Apartment w/ Skyline Views
Near North Side
10.0 out of 10, Exceptional, (9 reviews)
"Great location, comfortable room, welcoming host."
United States
Treseanne A.
The price is ￥107,017
￥185,337 total
includes taxes & fees
Mar 2 - Mar 3
Spacious 4BR Central Apartment w/ Skyline Views
TV, offices

Stylish Gold Coast 1BR with Vintage Flair

Stylish Gold Coast 1BR with Vintage Flair
Downtown Chicago
The price is ￥10,564
￥26,871 total
includes taxes & fees
Feb 24 - Feb 25
Stylish Gold Coast 1BR with Vintage Flair
Interior

Your Perfect 2BR Home

Your Perfect 2BR Home
Near West Side
8.2 out of 10, Very Good, (14 reviews)
"Great location! "
United States
Kourtney K.
The price is ￥13,320
￥33,160 total
includes taxes & fees
Feb 23 - Feb 24
Your Perfect 2BR Home
TV, offices

Smart & Stylish 2-Bedroom Unit

Smart & Stylish 2-Bedroom Unit
Lakeview
9.4 out of 10, Exceptional, (3 reviews)
"Good, walkable neighborhood. Nice room. "
United States
Dawn N.
The price is ￥17,300
￥37,058 total
includes taxes & fees
Mar 10 - Mar 11
Smart & Stylish 2-Bedroom Unit
1 bedroom, iron/ironing board, free WiFi, bed sheets

Cozy studio in Andersonville Chicago

Cozy studio in Andersonville Chicago
Edgewater
9.6 out of 10, Exceptional, (62 reviews)
"Great room and host"
United States
Kathy T.
The price is ￥9,952
￥21,727 total
includes taxes & fees
Feb 24 - Feb 25
Cozy studio in Andersonville Chicago
TV, offices

Stylish and Roomy 2BR in Chicago

Stylish and Roomy 2BR in Chicago
Edgewater
9.0 out of 10, Wonderful, (14 reviews)
"Location was perfect for the weekend festivities. The unit was clean and well appointed. Communication with the host was easy and timely. "
United States
Maribeth
The price is ￥11,176
￥29,883 total
includes taxes & fees
Feb 23 - Feb 24
Stylish and Roomy 2BR in Chicago
Property grounds

2-bedroom apartment just 2 minutes drive to Wrigley Field

2-bedroom apartment just 2 minutes drive to Wrigley Field
North Center
9.6 out of 10, Exceptional, (58 reviews)
"Nice property, great location, super helpful host!"
United States
Carin O.
The price is ￥13,641
￥39,694 total
includes taxes & fees
Feb 23 - Feb 24
2-bedroom apartment just 2 minutes drive to Wrigley Field
2 bedrooms, iron/ironing board, travel crib, WiFi

Prime Location! 2BR Near Wrigley

Prime Location! 2BR Near Wrigley
Lakeview
9.6 out of 10, Exceptional, (8 reviews)
"Everything was clean, really walkable area also"
United States
Anthony E.
The price is ￥10,717
￥29,346 total
includes taxes & fees
Feb 23 - Feb 24
Prime Location! 2BR Near Wrigley
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.
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Top Chicago Hotel Reviews

Hyatt Regency Chicago

Hyatt Regency Chicago

10/10 Excellent
"Yes but hot"
Melissa 3-night trip
Posted 7 hours ago
Hyatt Regency Chicago

Find out more about Chicago

Search for holiday rentals in Chicago on Expedia! You can easily find your home rentals, villas, holiday apartments in Chicago using one of the methods below:

  • View our selection of featured holiday rentals in Chicago
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  • Enter your travel dates to view the best deals on holiday rentals in Chicago while they last

Look no further and take a look at our great range of rental properties in Chicago!

Frequently asked questions

Can I find vacation rentals in Chicago?

Yes, we give you a choice of vacation rentals in Chicago near Six Flags Great America, or you can choose a more secluded option if you want a relaxing stay. Tourists who visit Chicago like the notable monuments and fascinating museums. The array of shops and acclaimed art scene are some other things you might want to check out while you're here.

What are some of the best vacation rentals in Chicago?

A Home Away From Home!: This highly rated vacation home rental in Chicago offers a fireplace, a garden, and air-conditioning to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a dishwasher, a stovetop, and a microwave. Other favorite homes for rent in Chicago are Belmont House, Classy & Chic/walk to Wrigley Field and Comfy 4 bedroom Apartment in the center of CHICAGO! 15 mins from Downtown!.

How many vacation rentals are there in Chicago?

With 955 Expedia vacation rentals, you're sure to find just the right place for your Chicago stay.

What can I see and do in Chicago?

Cultural attractions include CIBC Theatre and Symphony Center, whereas Millennium Park and Grant Park are a couple of picturesque spots to enjoy the outdoors. You can also visit some other popular places in town, such as Michigan Avenue and United Center.

What are vacation rentals like in Chicago?

Vacation rentals are private properties you can stay in for a short or long stay in Chicago. Vacation rentals provide amenities like WiFi and washers and dryers so you'll feel just like you're staying in your own home. If you're concerned about cleanliness, vacation rentals can provide a sense of security away from public hotel elevators and busy front desks while still allowing you the enjoyment of travel. You'll also get more space in a vacation rental than in a traditional hotel, which is another reason why a vacation rental is a great option for a family trip or a small group gathering.