Chicago Vacation Rentals

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Check prices for these dates

In two weeks
31 Oct - 2 Nov
In two months
12 Dec - 14 Dec
In three months
9 Jan - 11 Jan
In four months
6 Feb - 8 Feb

Vacation Rentals in Chicago

Indoor pool
Sentral Michigan Avenue
Sentral Michigan Avenue
4.0 star property
9.2 out of 10, Wonderful, (958)
"Great location and cleanliness of rooms. Staff was extremely helpful "
The price is RM572
RM796 total
includes taxes & fees
10 Nov - 11 Nov
Sentral Michigan Avenue
Front of property – evening/night
Level Chicago – Old Town
Level Chicago – Old Town
4.0 star property
9.0 out of 10, Wonderful, (367)
"Friendly staff and great amenities "
Level Chicago – Old Town
Lobby
Sonder by Marriott Bonvoy The Burnham Apartments Loop
Sonder by Marriott Bonvoy The Burnham Apartments Loop
3.5 star property
8.8 out of 10, Excellent, (239)
"Great stay. "
The price is RM572
RM672 total
includes taxes & fees
2 Nov - 3 Nov
Sonder by Marriott Bonvoy The Burnham Apartments Loop
Business centre
Kasa River North Chicago
Kasa River North Chicago
4.0 star property
9.6 out of 10, Exceptional, (171)
"This place has everything for a multi-night stay."
Kasa River North Chicago
1 bedroom, individually decorated, individually furnished, desk
Sonder by Marriott Bonvoy Market Hall Apartments West Loop
Sonder by Marriott Bonvoy Market Hall Apartments West Loop
3.5 star property
8.0 out of 10, Very good, (384)
"Great stay!"
The price is RM464
RM545 total
includes taxes & fees
2 Nov - 3 Nov
Sonder by Marriott Bonvoy Market Hall Apartments West Loop
1 bedroom, individually furnished, desk, iron/ironing board
Sonder by Marriott Bonvoy The Opal Apartments River North
Sonder by Marriott Bonvoy The Opal Apartments River North
3.5 star property
8.4 out of 10, Very good, (53)
"Place was in a great location close to good restaurants "
The price is RM536
RM629 total
includes taxes & fees
16 Nov - 17 Nov
Sonder by Marriott Bonvoy The Opal Apartments River North
Living room
Sonder by Marriott Bonvoy Greektown Apartments
Sonder by Marriott Bonvoy Greektown Apartments
3.5 star property
8.6 out of 10, Excellent, (65)
"The kitchen had everything we needed, great space overall, safe location, clean, near everything we needed, access to bus and rail very close, we really enjoyed our stay. "
The price is RM572
RM672 total
includes taxes & fees
2 Nov - 3 Nov
Sonder by Marriott Bonvoy Greektown Apartments
50-inch flat-screen TV with digital channels, TV
Sonder by Marriott Bonvoy Jewelers Row Apartments Millenium Park
Sonder by Marriott Bonvoy Jewelers Row Apartments Millenium Park
3.5 star property
8.2 out of 10, Very good, (184)
"Place was amazing! Very centralized, all sorts of restaurants nearby, and right next to the CTA Trains which is AWESOME!"
The price is RM500
RM587 total
includes taxes & fees
9 Nov - 10 Nov
Sonder by Marriott Bonvoy Jewelers Row Apartments Millenium Park
Living area
Wrigleyville Suites
Wrigleyville Suites
2.0 star property
9.8 out of 10, Exceptional, (21)
"Excellent location and very clean! Would stay again!"
The price is RM651
RM976 total
includes taxes & fees
18 Oct - 19 Oct
Wrigleyville Suites
Private kitchen
River West, Third Floor Chicago by 747 Lofts
River West, Third Floor Chicago by 747 Lofts
2.0 star property
9.0 out of 10, Wonderful, (17)
"Overall solid property, I will return."
The price is RM473
RM865 total
includes taxes & fees
23 Oct - 24 Oct
River West, Third Floor Chicago by 747 Lofts
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

Holiday Inn Chicago Dwtn - The Mart by IHG

Holiday Inn Chicago Dwtn - The Mart by IHG

10/10 Excellent
"Erika at the front fest was amazing. So was Kevin! I will be back!"
Carrie 2-night trip
Posted 3 days ago
Holiday Inn Chicago Dwtn - The Mart by IHG

Find out more about Chicago

Search for holiday rentals in Chicago on Expedia.co.uk! 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 acclaimed theatre scene. The array of shops and fascinating museums are some other things you might want to check out while you're here.

How many holiday rentals are there in Chicago?

With 1125 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.