Chicago Holiday Rentals

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Holiday Rentals in Chicago

Sentral Michigan Avenue

4.0 star property
9.2 out of 10, Wonderful, (882)
"Great stay!"
The price is AU$304
includes taxes & fees
3 Sept - 4 Sept
Sentral Michigan Avenue

Sonder by Marriott Bonvoy Market Hall Apartments West Loop

3.5 star property
8.2 out of 10, Very good, (344)
"Great stay!"
The price is AU$229
includes taxes & fees
3 Sept - 4 Sept
Sonder by Marriott Bonvoy Market Hall Apartments West Loop

Level Chicago – Old Town

4.0 star property
9.0 out of 10, Wonderful, (339)
"A lot of good food options walkable distance. "
Level Chicago – Old Town

Kasa Magnificent Mile Chicago

4.0 star property
9.4 out of 10, Exceptional, (472)
"Great location and great property will stay again "
Kasa Magnificent Mile Chicago

The Neighborhood Hotel-Little Italy

4.0 star property
9.6 out of 10, Exceptional, (190)
"Property was extremely comfortable in a great area."
The Neighborhood Hotel-Little Italy

Sonder by Marriott Bonvoy South Wabash Apartments South Loop

3.5 star property
8.8 out of 10, Excellent, (618)
"I would stay again. "
The price is AU$198
includes taxes & fees
3 Sept - 4 Sept
Sonder by Marriott Bonvoy South Wabash Apartments South Loop

Sonder by Marriott Bonvoy The Burnham Apartments Loop

3.5 star property
9.0 out of 10, Wonderful, (207)
"Great location, room was very nice. Vent in the bathroom wasn’t working and the walls are paper thin so you can hear other people talking loud. Otherwise a great stay! "
The price is AU$275
includes taxes & fees
3 Sept - 4 Sept
Sonder by Marriott Bonvoy The Burnham Apartments Loop

Kasa South Loop Chicago

4.0 star property
9.4 out of 10, Exceptional, (330)
"Great stay"
Kasa South Loop Chicago

The Gem Museum Suites

3.5 star property
9.4 out of 10, Exceptional, (83)
"Super nice hotel and staff "
The price is AU$359
includes taxes & fees
2 Sept - 3 Sept
The Gem Museum Suites

Sonder by Marriott Bonvoy The Plymouth Apartments Loop

3.5 star property
7.8 out of 10, Good, (131)
"Super convenient location. Lots of parking options and able to walk to all sites in this area."
The price is AU$304
includes taxes & fees
2 Sept - 3 Sept
Sonder by Marriott Bonvoy The Plymouth Apartments Loop

Sonder by Marriott Bonvoy Jewelers Row Apartments Millenium Park

3.5 star property
8.2 out of 10, Very good, (173)
"Great location!!!"
The price is AU$244
includes taxes & fees
3 Sept - 4 Sept
Sonder by Marriott Bonvoy Jewelers Row Apartments Millenium Park

Wrigleyville Suites

2.0 star property
9.6 out of 10, Exceptional, (14)
"Excellent location and very clean! Would stay again!"
The price is AU$219
includes taxes & fees
20 Aug - 21 Aug
Wrigleyville Suites

Comfort Inn Chicago Southland I-80 & I-294 Near Casino

2.5 star property
3.6 out of 10, (51)
"Property is advertised as a Comfort Inn, but is actually undergoing the transformation of becoming a Comfort Inn. It is still very much so operating as a motel on the south side of Chicago. Be safe. "
The price is AU$147
includes taxes & fees
3 Sept - 4 Sept
Comfort Inn Chicago Southland I-80 & I-294 Near Casino

Sonder by Marriott Bonvoy The Opal Apartments River North

3.5 star property
8.4 out of 10, Very good, (47)
"Great location. Apartment had all the amenities needed. Felt safe. Only not so good part was that being in downtown, it wasn't super quiet at times. Would stay here again without a doubt."
The price is AU$229
includes taxes & fees
1 Sept - 2 Sept
Sonder by Marriott Bonvoy The Opal Apartments River North

Kasa River North Chicago

4.0 star property
9.6 out of 10, Exceptional, (163)
"Great location and very clean! Will definitely be staying again. "
Kasa River North Chicago

Clean & Equipped 1BR Apt

8.2 out of 10, Very good, (13)
"Good experience. Would stay there again "
The price is AU$314
includes taxes & fees
9 Sept - 10 Sept
Clean & Equipped 1BR Apt

Charming 2BR in Vibrant Lakeview

8.8 out of 10, Excellent, (9)
The price is AU$358
includes taxes & fees
25 Aug - 26 Aug
Charming 2BR in Vibrant Lakeview

Sleeps 18+, 8BR Kids Room, Game Room, Gym & Theater

6.0 out of 10, (2)
"Great space for large groups. Park across the street is a great "feature"."
The price is AU$1,371
includes taxes & fees
25 Aug - 26 Aug
Sleeps 18+, 8BR Kids Room, Game Room, Gym & Theater

Cozy, Fully Set-Up 1BR Space

8.8 out of 10, Excellent, (15)
"Great place! 15 min walk to Wrigley "
The price is AU$320
includes taxes & fees
20 Aug - 21 Aug
Cozy, Fully Set-Up 1BR Space

Huge Projector and Designated Workspace - Near Wrigley!

The price is AU$438
includes taxes & fees
25 Aug - 26 Aug
Huge Projector and Designated Workspace - 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

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?

Charming 2-bedroom house in Maywood with WiFi, AC full basement with sofa bed: This highly rated holiday home rental in Chicago offers a patio, a BBQ and air conditioning to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a dishwasher, a stovetop and a microwave. Other favourite homes for rent in Chicago are North Chi Retreat-Near Navel base-Sauna,Pool, Airhokey, grill,King bed,Tikki Bar and Sleeps 18+, 8BR Kids Room, Game Room, Gym & Theater.

How many holiday rentals are there in Chicago?

With 1514 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 Michigan Avenue 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.