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Chicago Holiday Rentals

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Our top choices for Chicago holiday rentals

Sentral Michigan Avenue

Sentral Michigan Avenue
4.0 star property
Downtown Chicago
9.2 out of 10, Wonderful, (1,198 reviews)
"Great location"
United States
JAVIER
The price is HK$1,299
HK$1,755 total
includes taxes & fees
1 Jul - 2 Jul
Sentral Michigan Avenue

Level Chicago – Old Town

Level Chicago – Old Town
4.0 star property
Downtown Chicago
9.0 out of 10, Wonderful, (496 reviews)
"Very clean and loved the location and amenities with the store on the first floor was fantastic"
United States
Kimberly
The price is HK$1,889
HK$2,411 total
includes taxes & fees
30 Jun - 1 Jul
Level Chicago – Old Town

Wrigleyville Suites

Wrigleyville Suites
2.0 star property
Lakeview
9.0 out of 10, Wonderful, (38 reviews)
"We had a great stay! Perfect location for cubs games and hanging out in wrigleyville."
United States
Kate
The price is HK$1,834
HK$2,154 total
includes taxes & fees
29 Jun - 30 Jun
Wrigleyville Suites

Ground Floor Studios in Chicago by 747 Lofts

Ground Floor Studios in Chicago by 747 Lofts
2.0 star property
West Town
8.6 out of 10, Excellent, (23 reviews)
"Great area and surprisingly nice room!"
United States
Michael
The price is HK$921
HK$1,598 total
includes taxes & fees
8 Jul - 9 Jul
Ground Floor Studios in Chicago by 747 Lofts

The Gem Museum Suites

The Gem Museum Suites
3.5 star property
Downtown Evanston
9.4 out of 10, Exceptional, (147 reviews)
"Perfect place to stay!"
United States
Anton
The price is HK$1,757
HK$2,011 total
includes taxes & fees
12 Jul - 13 Jul
The Gem Museum Suites

The Oak Park Loft

The Oak Park Loft
2.0 star property
Oak Park
10.0 out of 10, Exceptional, (6 reviews)
"Good location, nice neighborhood, restaurants close"
United States
Linda
The price is HK$1,392
HK$2,465 total
includes taxes & fees
30 Jun - 1 Jul
The Oak Park Loft

Historic Oak Park Home

Historic Oak Park Home
2.0 star property
Oak Park
10.0 out of 10, Exceptional, (5 reviews)
"The owner was awesome. Convenient parking and beautiful area! Will definitely make a reservation again."
United States
Janette
The price is HK$1,686
HK$2,801 total
includes taxes & fees
30 Jun - 1 Jul
Historic Oak Park Home

Historic Oak Park Residence

Historic Oak Park Residence
2.0 star property
Oak Park
9.6 out of 10, Exceptional, (12 reviews)
"The house is in an amazing neighborhood, easy access to subway, extremely clean and great follow-up and follow through communication with owner!"
United States
Ann-Marie
The price is HK$2,005
HK$3,166 total
includes taxes & fees
28 Jun - 29 Jun
Historic Oak Park Residence

At Home in Oak Park

At Home in Oak Park
3.5 star property
Oak Park
9.4 out of 10, Exceptional, (10 reviews)
"Great place, clean, and very accommodating! "
United States
Theresa
The price is HK$1,700
HK$2,816 total
includes taxes & fees
22 Jul - 23 Jul
At Home in Oak Park
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

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!

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Frequently asked questions

Can I find holiday rentals in Chicago?

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

What are some of the best holiday rentals that Chicago has to offer?

4BR Modern Urban Escape, Walk to Zoo, Lakefront & Red Line: This highly rated holiday home rental in Chicago is located in the city centre, and has a balcony, a BBQ and air conditioning to put you at ease in your new surroundings. It has 4 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. Other favourite homes for rent in Chicago are ENVITAE Hotel, 4BR Luxury Modern Apartments and King Comfort apartment, Quiet, Clean, AC & WiFi.

How many holiday rentals are there in Chicago?

With 889 Expedia holiday rentals, you're guaranteed 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 Wrigley Field and Michigan Avenue.

What are holiday rentals like in Chicago?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Chicago. Holiday rentals offer extras like WiFi and washers and dryers so you'll have everything you want. If you're concerned about a sanitised environment, holiday rentals can offer a sense of safety away from public hotel lifts and lobbies bustling with people while still allowing you a great travel experience. You'll also get more space in a holiday rental than in a hotel, which is another reason why a holiday rental is a popular option for a small group gathering.