Chicago Vacation Rentals

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Check prices for these dates

In two weeks
Dec 5 - Dec 7
In two months
Jan 16 - Jan 18
In three months
Feb 13 - Feb 15
In four months
Mar 13 - Mar 15

Vacation Rentals in Chicago

Indoor pool
Sentral Michigan Avenue

Aparthotel in Downtown Chicago

4.0 star property
9.2 out of 10, Wonderful, (987)
"Loved my stay! Staff was amazing and the apartment had everything to make you feel like home. "
United States
Nicole
The price is NT$3,148
NT$4,613 total
includes taxes & fees
Dec 7 - Dec 8
Sentral Michigan Avenue
Front of property - evening/night
Level Chicago – Old Town

Aparthotel in Downtown Chicago

4.0 star property
9.0 out of 10, Wonderful, (386)
"Property was clean, centrally located with wonderful staff. Will definitely stay again."
United States
Michelle
Level Chicago – Old Town
Business center
Kasa River North Chicago

Aparthotel in Downtown Chicago

4.0 star property
9.4 out of 10, Exceptional, (179)
"Awesome stay "
United States
Sally
Kasa River North Chicago
Free WiFi, bed sheets
Chicago luxury home suites

Aparthotel in Downtown Chicago

2.0 star property
10.0 out of 10, Exceptional, (1)
"This was Amazing stay I have ever had in my life. Wonderful host, super clean. Stunning views, close to everything that you would needed. "
New Zealand
Moha
The price is NT$9,373
NT$11,003 total
includes taxes & fees
Nov 24 - Nov 25
Chicago luxury home suites
Studio | Private kitchen | Fridge, oven, coffee/tea maker, toaster
River West, Third Floor Chicago by 747 Lofts

Aparthotel in West Town

2.0 star property
9.0 out of 10, Wonderful, (17)
"Overall solid property, I will return."
United States
Fletcher
The price is NT$1,978
NT$4,357 total
includes taxes & fees
Nov 30 - Dec 1
River West, Third Floor Chicago by 747 Lofts
Apartment (4 Bedrooms) | Interior
Walk to Wrigley Field! Townhouse w/ Pool Table

Apartment in Lakeview

3.0 star property
The price is NT$6,749
NT$18,748 total
includes taxes & fees
Dec 1 - Dec 2
Walk to Wrigley Field! Townhouse w/ Pool Table
Living area
Wrigleyville Suites

Aparthotel in Lakeview

2.0 star property
9.6 out of 10, Exceptional, (26)
"Excellent location and very clean! Would stay again!"
United States
Jacob
The price is NT$2,489
NT$2,921 total
includes taxes & fees
Nov 24 - Nov 25
Wrigleyville Suites
Classic Apartment | Private kitchen
Stylish Apartment near Chicago Downtown

Aparthotel in Bridgeport

2.0 star property
The price is NT$7,780
NT$12,360 total
includes taxes & fees
Dec 1 - Dec 2
Stylish Apartment near Chicago Downtown
Interior
Art Villa

Aparthotel in West Town

5.0 star property
10.0 out of 10, Exceptional, (2)
" "
United States
tomonobu
Art Villa
Studio | Exterior
Ground Floor Studios in Chicago by 747 Lofts

Aparthotel in West Town

2.0 star property
9.0 out of 10, Wonderful, (21)
"The stay lacked in shelf space as well as other amenities that could be useful. "
United States
Zugeily
Ground Floor Studios in Chicago by 747 Lofts
Studio | Exterior
Chicago Third Floor Studio by 747 Lofts

Aparthotel in West Town

2.0 star property
9.6 out of 10, Exceptional, (5)
"Cute little studio that was clean. There was a nice size kitchen and was close to our activities in the West loop of Chicago. There was also assistance with parking located in the lofts."
United States
Jennifer
The price is NT$2,768
NT$8,058 total
includes taxes & fees
Nov 29 - Nov 30
Chicago Third Floor Studio by 747 Lofts
Studio | Private kitchen | Fridge, oven, coffee/tea maker, toaster
Chicago Second Floor Studio by 747 Lofts

Aparthotel in West Town

2.0 star property
8.8 out of 10, Excellent, (13)
"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
Barbara
Chicago Second Floor Studio by 747 Lofts
House (3 Bedrooms) | Floor plan
Spacious 3BR Home Firepit & Grill

Cottage in Miller Beach

2.0 star property
The price is NT$4,843
NT$13,110 total
includes taxes & fees
Nov 30 - Dec 1
Spacious 3BR Home Firepit & Grill
House (3 Bedrooms) | Interior
Classic Forest Park Foursquare < 1 Mi to Blue Line

Cottage in Forest Park

3.0 star property
The price is NT$5,436
NT$12,034 total
includes taxes & fees
Nov 25 - Nov 26
Classic Forest Park Foursquare < 1 Mi to Blue Line
Suite, 2 Bedrooms, Kitchen (Three Beds, Washer/Dryer) | Private kitchen | Full-size fridge, microwave, stovetop, dishwasher
The Gem Museum Suites

Aparthotel in Downtown Evanston

3.5 star property
9.4 out of 10, Exceptional, (96)
"Great stay. The studio is small but has everything necessary."
United States
Julia
The price is NT$5,680
NT$6,503 total
includes taxes & fees
Nov 23 - Nov 24
The Gem Museum Suites
Comfort Double Room | Desk, laptop workspace, blackout drapes, free WiFi
Comfort Inn Chicago Southland I-80 & I-294 Near Casino

Aparthotel in Harvey

3.0 star property
3.8 out of 10, (67)
"Good "
United States
Abel
The price is NT$2,271
NT$2,565 total
includes taxes & fees
Nov 25 - Nov 26
Comfort Inn Chicago Southland I-80 & I-294 Near Casino
Front of property
Spacious 3BR House With Firepit & Grill, Near Beach

Cottage in Miller Beach

2.0 star property
5.0 out of 10, (2)
"It is a beautiful residence. This is a relatively new residence, evidenced by all the brand new with tags furniture, lamps, appliances etc. No internet or cable, which was sort of a downer. Did not get the code until 15 minutes after check in time. No coffee or silverware. We only found one spoon. "
United States
Kaitlyn
The price is NT$4,695
NT$11,417 total
includes taxes & fees
Dec 21 - Dec 22
Spacious 3BR House With Firepit & Grill, Near Beach
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

Warwick Allerton - Chicago

Warwick Allerton - Chicago

10/10 Excellent
"Great staff, rooms, and views"
Taylor 2-night trip
Posted 7 hours ago
Warwick Allerton - 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
  • Use the map to find apartments and other holiday homes in the Chicago neighbourhood you prefer
  • 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 Field Museum of Natural History, or you can choose a more secluded option if you want a relaxing stay. Tourists who visit Chicago like the notable monuments and entertainment choices. The array of shops and fascinating museums are some other things you might want to check out while you're here.

How many vacation rentals are there in Chicago?

With 1137 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 Lake Michigan 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 Wrigley Field.

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.