Chicago Holiday Rentals

    Plan, book, stay with confidence
    bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    Sign in
    today icon
    Change your mind
    Book hotels with free cancellation

Holiday Rentals in Chicago

Sentral Michigan Avenue
Interior
Sentral Michigan Avenue
4.0 star property
9.2 out of 10, Wonderful, (592)
"Great stay. Will stay again!"
The price is S$208
includes taxes & fees
25 Nov - 26 Nov
Sentral Michigan Avenue
Sonder Market Hall
Interior
Sonder Market Hall
3.5 star property
8.6 out of 10, Excellent, (208)
"Easiest check in and check out process "
The price is S$88
includes taxes & fees
22 Dec - 23 Dec
Sonder Market Hall
Sonder South Wabash
Living area
Sonder South Wabash
3.5 star property
9.0 out of 10, Wonderful, (395)
"Nice"
The price is S$191
includes taxes & fees
19 Dec - 20 Dec
Sonder South Wabash
Kasa Magnificent Mile Chicago
49-inch Smart TV with digital channels, TV, streaming services
Kasa Magnificent Mile Chicago
4.0 star property
9.2 out of 10, Wonderful, (332)
"Fantastic location with great proximity to shopping, restaurants, and sights. Well equipped, clean, spacious rooms, "
Kasa Magnificent Mile Chicago
The Neighborhood Hotel-Little Italy
50-inch Smart TV with satellite channels
The Neighborhood Hotel-Little Italy
3.5 star property
9.6 out of 10, Exceptional, (101)
"Excellent place to stay! "
The Neighborhood Hotel-Little Italy
Level Chicago – Old Town
Front of property – evening/night
Level Chicago – Old Town
4.0 star property
9.0 out of 10, Wonderful, (269)
"Beautiful place with amazing amenities. Perfect stay for adults or families alike! Highly recommend!"
The price is S$345
includes taxes & fees
24 Nov - 25 Nov
Level Chicago – Old Town
Found Chicago powered by Sonder
Exterior
Found Chicago powered by Sonder
3.5 star property
7.6 out of 10, Good, (176)
"Excellent location, amazing price. No nonsense stay, you only get the basics here but very clean and simple. Pros: no carpet in rooms, no extra frilly pillows or curtains, all surfaces look like they can be easily wiped down and disinfected. You can actually open the windows. Self serve toiletry station. Coded locks instead of keys. Great location close to restaurants and bus stops. THE PRICE!!! Cons: non responsive staff in person and online, sometimes no staff at all. No view, stuffy room...
The price is S$183
includes taxes & fees
17 Dec - 18 Dec
Found Chicago powered by Sonder
Sonder The Burnham Apartments
Marina
Sonder The Burnham Apartments
3.5 star property
8.8 out of 10, Excellent, (114)
"Very convenient location, the apartment was impeccable "
The price is S$198
includes taxes & fees
16 Dec - 17 Dec
Sonder The Burnham Apartments
Kasa South Loop Chicago
42-inch Smart TV with digital channels, TV, streaming services
Kasa South Loop Chicago
4.0 star property
9.4 out of 10, Exceptional, (233)
"Amazing stay!"
Kasa South Loop Chicago
Sonder Jewelers Row
Free toiletries, hair dryer, towels, soap
Sonder Jewelers Row
3.5 star property
8.2 out of 10, Very good, (132)
"I so enjoyed staying on jewelers row at the Sonder property In Chicago. It was very close to the places I was visiting so I could walk everywhere. It was noisy because of the L train, yes, but when you’re inside, you Barely hear the train. I felt very safe getting into the building and getting up to my room. It was so well appointed. You thought of everything! I just wish I had longer than three days in Chicago and I hope to come back. I would rent the same apartment again without a doubt!"
The price is S$217
includes taxes & fees
11 Dec - 12 Dec
Sonder Jewelers Row
Kasa River North Chicago
Exterior
Kasa River North Chicago
4.0 star property
9.6 out of 10, Exceptional, (100)
"First pick for my first trip to Chicago. I felt safe and I was able to walk to the diner, mall and restaurants. Highly recommend this place!"
The price is S$137
includes taxes & fees
10 Dec - 11 Dec
Kasa River North Chicago
Sonder The Plymouth
City view from property
Sonder The Plymouth
3.5 star property
8.2 out of 10, Very good, (83)
"Our stay was pleasant and the 3 rooms and 3 bathrooms were perfect for five people."
The price is S$198
includes taxes & fees
19 Dec - 20 Dec
Sonder The Plymouth
Sonder The Opal
Exterior
Sonder The Opal
3.5 star property
8.4 out of 10, Very good, (25)
"Stayed here twice - great place to stay when visiting. Easily walkable to shops, attractions and dining! "
The price is S$214
includes taxes & fees
18 Dec - 19 Dec
Sonder The Opal
Sonder Greektown
40-inch flat-screen TV with digital channels, TV
Sonder Greektown
3.5 star property
9.0 out of 10, Wonderful, (33)
"Everything was Excellent! The property was beautiful and most of all very CLEAN!!! The way everything was set up on site , to check-in and check-out was a very seamless process. The property was also very spacious, the beds were very big in size, super comfy, and having the three bathrooms in each bedroom was a such a plus. Greek neighborhood was a wonderful and smart location, everything is walking distance: for any coffee connoisseurs: Ground up Coffee is superb, Target is only a couple blocks...
The price is S$225
includes taxes & fees
12 Dec - 13 Dec
Sonder Greektown
Ground Floor Studios in Chicago by 747 Lofts
Exterior
Ground Floor Studios in Chicago by 747 Lofts
2.0 star property
9.8 out of 10, Exceptional, (11)
"Its was in a good location for anyone who has family close by. Bed was wonderful. "
Ground Floor Studios in 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.
Don't see what you're looking for?
See all available properties in Chicago
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Other types of properties in Chicago you may be interested in

Congress Plaza Hotel
Lobby
Congress Plaza Hotel
3.5 star property
7.8 out of 10, Good, (8135)
"Great staff made the stay worth it. Will go back when I return to Chicago."
The price is S$134
includes taxes & fees
25 Nov - 26 Nov
Congress Plaza Hotel
River Hotel
View from property
River Hotel
4.0 star property
8.8 out of 10, Excellent, (3549)
"Highly recommend ."
The price is S$165
includes taxes & fees
22 Dec - 23 Dec
River Hotel
The Westin Michigan Avenue Chicago
View from room
The Westin Michigan Avenue Chicago
4.5 star property
8.6 out of 10, Excellent, (1005)
"The staff was very welcoming. The rooms were clean. Great location and view! Good cocktails!"
The price is S$259
includes taxes & fees
25 Nov - 26 Nov
The Westin Michigan Avenue Chicago
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.
Beautiful view of the beach with palm trees

Black Friday: Members save 30%+

Members save 30%+ on selected hotels until 4 Dec (property time) with our Black Friday deals. Stay by 15 Dec 2025.
Unlock Black Friday deals

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 1217 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.