Chicago Holiday Rentals

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Check prices for these dates

In two weeks
5 Jun - 7 Jun
In two months
17 Jul - 19 Jul
In three months
14 Aug - 16 Aug
In four months
11 Sept - 13 Sept

Our top choices for Chicago holiday rentals

Dining room

Kasa Magnificent Mile Chicago

Kasa Magnificent Mile Chicago
4.0 star property
Downtown Chicago
9.4 out of 10, Exceptional, (760 reviews)
"Great place to stay."
United States
Benedictine
The price is HK$1,227
HK$1,900 total
includes taxes & fees
24 May - 25 May
Kasa Magnificent Mile Chicago
Indoor pool

Sentral Michigan Avenue

Sentral Michigan Avenue
4.0 star property
Downtown Chicago
9.2 out of 10, Wonderful, (1,165 reviews)
"Spacious apartment with stunning view. A great stay!!"
United States
Tina
The price is HK$1,192
HK$1,629 total
includes taxes & fees
25 May - 26 May
Sentral Michigan Avenue
Full-sized fridge, microwave, oven, stovetop

Level Chicago – Old Town

Level Chicago – Old Town
4.0 star property
Downtown Chicago
9.0 out of 10, Wonderful, (478 reviews)
"Beautiful clean place. Great safe location within proximity to restaurants and transportation around the city with fantastic views. Would recommend and stay here again. "
Canada
Lissa
The price is HK$1,371
HK$1,802 total
includes taxes & fees
26 May - 27 May
Level Chicago – Old Town
Living area

Wrigleyville Suites

Wrigleyville Suites
2.0 star property
Lakeview
9.2 out of 10, Wonderful, (37 reviews)
"We had a great stay! Perfect location for cubs games and hanging out in wrigleyville."
United States
Kate
The price is HK$1,621
HK$1,903 total
includes taxes & fees
21 May - 22 May
Wrigleyville Suites
Interior

Cabin 105 by 747 Lofts

Cabin 105 by 747 Lofts
2.0 star property
West Town
10.0 out of 10, Exceptional, (1 review)
The price is HK$985
HK$1,676 total
includes taxes & fees
10 Jun - 11 Jun
Cabin 105 by 747 Lofts
Private kitchen

River West, Third Floor Chicago by 747 Lofts

River West, Third Floor Chicago by 747 Lofts
2.0 star property
West Town
9.0 out of 10, Wonderful, (18 reviews)
"Cvs. Dunkin Donuts. Pizza pie all 1-2 blocks walking distance "
United States
Paul
The price is HK$961
HK$2,404 total
includes taxes & fees
21 May - 22 May
River West, Third Floor Chicago by 747 Lofts
Living area

Ground Floor Studios in Chicago by 747 Lofts

Ground Floor Studios in Chicago by 747 Lofts
2.0 star property
West Town
9.0 out of 10, Wonderful, (22 reviews)
"Its was in a good location for anyone who has family close by. Bed was wonderful. "
United States
Susan
Ground Floor Studios in Chicago by 747 Lofts
Private kitchen

Chicago Third Floor Studio by 747 Lofts

Chicago Third Floor Studio by 747 Lofts
2.0 star property
West Town
9.8 out of 10, Exceptional, (7 reviews)
"Clean, easy to check in, all the household items you’d expect"
United States
Jason
The price is HK$961
HK$2,404 total
includes taxes & fees
21 May - 22 May
Chicago Third Floor Studio by 747 Lofts
Exterior

River West, Second Floor Chicago by 747 Lofts

River West, Second Floor Chicago by 747 Lofts
2.0 star property
West Town
9.6 out of 10, Exceptional, (4 reviews)
"I need to somewhere to stay for a night in Chicago and found this place. It had a varying level of reviews but found the property more the suitable for what I paid. Easy to follow instructions to get in, clean, and convienent. They even provide ear plugs to drown out the sounds of the city."
United States
Anonymous traveller
The price is HK$961
HK$2,404 total
includes taxes & fees
21 May - 22 May
River West, Second Floor Chicago by 747 Lofts
Breakfast, lunch, dinner served; Greek cuisine

The Gem Museum Suites

The Gem Museum Suites
3.5 star property
Downtown Evanston
9.4 out of 10, Exceptional, (119 reviews)
"Perfect place to stay!"
United States
Anton
The price is HK$1,184
HK$1,356 total
includes taxes & fees
26 May - 27 May
The Gem Museum Suites
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

The Chicago Hotel Collection - Magnificent Mile

The Chicago Hotel Collection - Magnificent Mile

10/10 Excellent
"love the location of this property everything is so easy access the staff are soo nice. We love the Rooftop bar so much in there.Love the view and the rooms are so clean and big. The "
Justin Lance 2-night trip
Posted 2 hours ago
The Chicago Hotel Collection - Magnificent Mile

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 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 entertainment choices. 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?

ENVITAE Hotel, 4BR Luxury Modern Apartments: This highly rated holiday home rental in Chicago is located in the city centre, and offers a BBQ, air conditioning and laundry facilities to help you feel perfectly comfortable 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 Charming 2-bedroom house in Maywood with WiFi, AC full basement with sofa bed and Warm & Spacious 4BR Home Long Stays Welcome.

How many holiday rentals are there in Chicago?

With 939 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 Grant Park 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 Navy Pier.

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.