Chicago Holiday Rentals

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

This weekend
Next weekend

Holiday Rentals in Chicago

Sentral Michigan Avenue

4.0 star property
9.2 out of 10, Wonderful, (839)
"Great stay!"
The price is S$317
includes taxes & fees
18 Aug - 19 Aug
Sentral Michigan Avenue

Sonder by Marriott Bonvoy Market Hall Apartments West Loop

3.5 star property
8.4 out of 10, Very good, (326)
"Super cool spot in a great part of the city."
The price is S$217
includes taxes & fees
17 Aug - 18 Aug
Sonder by Marriott Bonvoy Market Hall Apartments West Loop

Level Chicago – Old Town

4.0 star property
9.0 out of 10, Wonderful, (329)
"Hotel was nice"
The price is S$704
includes taxes & fees
30 Jul - 31 Jul
Level Chicago – Old Town

Kasa Magnificent Mile Chicago

4.0 star property
9.4 out of 10, Exceptional, (447)
"Nice views and convenient location to transit and dining"
Kasa Magnificent Mile Chicago

Sonder by Marriott Bonvoy South Wabash Apartments South Loop

3.5 star property
8.8 out of 10, Excellent, (579)
"Great place and location. "
The price is S$275
includes taxes & fees
21 Aug - 22 Aug
Sonder by Marriott Bonvoy South Wabash Apartments South Loop

Kasa South Loop Chicago

4.0 star property
9.4 out of 10, Exceptional, (320)
"Great stay"
Kasa South Loop Chicago

Sonder by Marriott Bonvoy The Burnham Apartments Loop

3.5 star property
9.0 out of 10, Wonderful, (196)
"Fantastically located snd brilliantly appointed aparthotel. Absolutely perfect for our stay, where we were competing at the HYROX world championships. The room was super spacious and had all amenities you could wish for. "
The price is S$331
includes taxes & fees
17 Aug - 18 Aug
Sonder by Marriott Bonvoy The Burnham Apartments Loop

Sonder by Marriott Bonvoy The Plymouth Apartments Loop

3.5 star property
8.0 out of 10, Very good, (119)
"Super convenient location. Lots of parking options and able to walk to all sites in this area."
The price is S$210
includes taxes & fees
4 Aug - 5 Aug
Sonder by Marriott Bonvoy The Plymouth Apartments Loop

The Gem Museum Suites

3.5 star property
9.6 out of 10, Exceptional, (77)
"Excellent hotel. Would stay again."
The price is S$339
includes taxes & fees
5 Aug - 6 Aug
The Gem Museum Suites

The Neighborhood Hotel-Little Italy

4.0 star property
9.8 out of 10, Exceptional, (177)
"Great spot. "
The Neighborhood Hotel-Little Italy

Sonder by Marriott Bonvoy Jewelers Row Apartments Millenium Park

3.5 star property
8.2 out of 10, Very good, (169)
"Great location. Clean (very clean) and comfortable apartments with everything you need. Cons: soundproofing from the city center is weak, all sounds are heard quite well. In terms of price per room ratio - a super option. I will book next time, and I recommend it to everyone."
The price is S$242
includes taxes & fees
17 Aug - 18 Aug
Sonder by Marriott Bonvoy Jewelers Row Apartments Millenium Park

Kasa River North Chicago

4.0 star property
9.6 out of 10, Exceptional, (156)
"Great location and very clean! Will definitely be staying again. "
Kasa River North Chicago

Sonder by Marriott Bonvoy The Opal Apartments River North

3.5 star property
8.6 out of 10, Excellent, (42)
"Our stay was amazing. "
The price is S$269
includes taxes & fees
27 Jul - 28 Jul
Sonder by Marriott Bonvoy The Opal Apartments River North

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

2.5 star property
3.6 out of 10, (48)
"the property is under renovation it should not be open. There were no amenities, i.e., ice. The room was clean. "
The price is S$123
includes taxes & fees
4 Aug - 5 Aug
Comfort Inn Chicago Southland I-80 & I-294 Near Casino

Wrigleyville Suites

2.0 star property
9.4 out of 10, Exceptional, (8)
"Absolutely loved staying here! Would 10/10 recommend this place!"
The price is S$194
includes taxes & fees
23 Jul - 24 Jul
Wrigleyville Suites

Sonder by Marriott Bonvoy Greektown Apartments

3.5 star property
8.8 out of 10, Excellent, (56)
"Great location, easy stay!"
The price is S$332
includes taxes & fees
17 Aug - 18 Aug
Sonder by Marriott Bonvoy Greektown Apartments
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.
Save an average of 15% on thousands of hotels when you're signed in

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.

How many holiday rentals are there in Chicago?

With 1485 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.