Chicago Holiday Rentals

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Check prices for these dates

Tonight
10 Mar - 11 Mar
Tomorrow
11 Mar - 12 Mar
This weekend
14 Mar - 16 Mar
Next weekend
21 Mar - 23 Mar

Holiday Rentals in Chicago

Sentral Michigan Avenue
Interior

Sentral Michigan Avenue

4.0 star property
9.2 out of 10, Wonderful, (695)
"Amazing and clean experience I highly recommend "
The price is S$237
includes taxes & fees
12 Mar - 13 Mar
Sentral Michigan Avenue
Sonder South Wabash
Living area

Sonder South Wabash

3.5 star property
9.0 out of 10, Wonderful, (447)
"Amazing space - I'll be requesting the same one in the summer :) Spacious and clean! Absolutely loved the view of Willis Tower from our room. Excellent stay!"
The price is S$147
includes taxes & fees
1 Apr - 2 Apr
Sonder South Wabash
Sonder The Burnham Apartments
Marina

Sonder The Burnham Apartments

3.5 star property
8.8 out of 10, Excellent, (146)
"⭐️⭐️⭐️⭐️⭐️ Had a fantastic stay at Sonder Chicago West Loop during my business trip! The location was perfect for meetings, and I loved having the extra space. The studio felt more like an apartment—super clean, spacious, and well-appointed with stylish decor. The kitchen was fully stocked and well-maintained, making the stay even more comfortable. The reception area was great for getting work done before check-in, and the luggage room lockers were a huge plus. The app-based entry system was...
The price is S$197
includes taxes & fees
1 Apr - 2 Apr
Sonder The Burnham Apartments
Sonder Market Hall
Interior

Sonder Market Hall

3.5 star property
8.6 out of 10, Excellent, (263)
"The room was amazing. I’ll definitely stay here again!"
The price is S$167
includes taxes & fees
1 Apr - 2 Apr
Sonder Market Hall
Level Chicago – Old Town
Front of property – evening/night

Level Chicago – Old Town

4.0 star property
9.0 out of 10, Wonderful, (291)
"The Place was Great, Clean, inviting, Hip, Comfortable and relaxing. Will definitely be back and would highly recommend a stay here"
The price is S$284
includes taxes & fees
12 Mar - 13 Mar
Level Chicago – Old Town
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, (373)
"Very nice "
The price is S$268
includes taxes & fees
12 Mar - 13 Mar
Kasa Magnificent Mile Chicago
Comfort Inn Chicago Wind Creek Casino
Desk, laptop workspace, blackout curtains, free WiFi

Comfort Inn Chicago Wind Creek Casino

2.5 star property
3.8 out of 10, (6)
"False advertising, based off the pictures, the new hotel was an old run down hotel. I called the number and there was not even a greeting. The man that answered just said hello and I was thinking is this the correct number. Finally I said I’m calling a hotel number if this it, then he said oh yes this is hotel. I asked where it was and he said we’re here in the court yard and I looked and said nope, nothing like the pictures so I left and booked with IHG Matteson, IL, new and clean"
The price is S$139
includes taxes & fees
18 Mar - 19 Mar
Comfort Inn Chicago Wind Creek Casino
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, (262)
"realy great place and very close to everything"
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, (141)
"Loved it Had to leave early but loved "
The price is S$178
includes taxes & fees
8 Apr - 9 Apr
Sonder Jewelers Row
Kasa River North Chicago
Exterior

Kasa River North Chicago

4.0 star property
9.6 out of 10, Exceptional, (128)
"We had an overall wodnerful experience. We were celebrating a milestone birthday and was perfect for a group of 4! The room was beautiful and close to everything!! We will definitely come back. "
The price is S$183
includes taxes & fees
20 Mar - 21 Mar
Kasa River North Chicago
The Neighborhood Hotel-Little Italy
50-inch Smart TV with satellite channels

The Neighborhood Hotel-Little Italy

3.5 star property
9.8 out of 10, Exceptional, (136)
"This place is amazing. So relaxing and comforting. The host is so accommodating and responsive. Everything was great to the point that I did not even want to leave! I shall be back. "
The Neighborhood Hotel-Little Italy
Sonder The Plymouth
City view from property

Sonder The Plymouth

3.5 star property
8.2 out of 10, Very good, (92)
"This is the best Sonder property we've ever stayed at!! The location is perfect for Chicago. We had a few different questions during our stay and we always received immediate and thorough answers by using the chat button in the app. Would definitely stay here again!"
The price is S$153
includes taxes & fees
1 Apr - 2 Apr
Sonder The Plymouth
Sonder The Opal
Exterior

Sonder The Opal

3.5 star property
8.4 out of 10, Very good, (30)
"We loved the location in River North with shops around plenty of nice restaurants. Walkable and good buses around. Apartment was very nice, we were 5 adults. A bit noisy because of bar nearby ( it depends of your tolerance to noise. Some of us were disturbed some heard nothing). We enjoyed our stay !"
The price is S$200
includes taxes & fees
24 Mar - 25 Mar
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, (42)
"I loved how easy it was to find and the instructions to access was easy to follow"
The price is S$186
includes taxes & fees
7 Apr - 8 Apr
Sonder Greektown
Wrigleyville Suites
Living area

Wrigleyville Suites

2.0 star property
10.0 out of 10, Exceptional, (2)
The price is S$172
includes taxes & fees
12 Mar - 13 Mar
Wrigleyville Suites
Sonder Onterie
Miscellaneous

Sonder Onterie

3.5 star property
10.0 out of 10, Exceptional, (8)
"The stove, washer/drier, plates, silverwear, beds, everything was obviously cleaned throughly. Was very impressed with how spotless everything was"
The price is S$167
includes taxes & fees
8 Apr - 9 Apr
Sonder Onterie
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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Other types of properties in Chicago you may be interested in

River Hotel
View from property

River Hotel

4.0 star property
8.8 out of 10, Excellent, (3888)
"Like it"
The price is S$150
includes taxes & fees
23 Mar - 24 Mar
River Hotel
L7 Chicago by LOTTE
Exterior

L7 Chicago by LOTTE

4.5 star property
9.6 out of 10, Exceptional, (1826)
"Great position professional staff Clean and well run"
The price is S$255
includes taxes & fees
12 Mar - 13 Mar
L7 Chicago by LOTTE
Congress Plaza Hotel
Aerial view

Congress Plaza Hotel

3.5 star property
7.8 out of 10, Good, (8608)
"Awesome in overall. "
The price is S$179
includes taxes & fees
23 Mar - 24 Mar
Congress Plaza Hotel
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.

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 fascinating museums. The array of shops and acclaimed art scene are some other things you might want to check out while you're here.

How many holiday rentals are there in Chicago?

With 1298 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 Soldier Field.

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.