Search Holiday Rentals in Chicago

Top Holiday Rentals in Chicago

Sentral Michigan Avenue
Interior
Sentral Michigan Avenue
4.0 star property
9.2 out of 10, Wonderful, (570)
"Great neiborhood "
The price is ₹11,275
₹15,703 total
includes taxes & fees
27 Oct - 28 Oct
Sentral Michigan Avenue
Sonder Market Hall
Interior
Sonder Market Hall
3.5 star property
8.6 out of 10, Excellent, (187)
"Perfect for staying close to the United Center!"
The price is ₹7,052
₹8,278 total
includes taxes & fees
21 Nov - 22 Nov
Sonder Market Hall
Sonder South Wabash
36-inch flat-screen TV with digital channels, TV
Sonder South Wabash
3.5 star property
9.0 out of 10, Wonderful, (383)
"Clean and well located. We had access to the green and red line trains a few stops away from the loop. Entering the building was easy and convenient. Apartment was clean and spacious!! "
The price is ₹13,138
₹15,422 total
includes taxes & fees
14 Nov - 15 Nov
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, (322)
"Great location. Well equipped and well maintained. Worked really well, especially for the weekend of the marathon."
Kasa Magnificent Mile Chicago
Level Chicago – Old Town
Front of property – evening/night
Level Chicago – Old Town
4.0 star property
9.0 out of 10, Wonderful, (265)
"We had a lovely stay! Amenities were next level! Lots in area to access as well! Perfect in every regard!"
The price is ₹19,069
₹23,815 total
includes taxes & fees
10 Nov - 11 Nov
Level Chicago – Old Town
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, (86)
"We liked every bit of our stay at The Neighborhood Hotel in Little Italy. would stay again if the opportunity came our way. We've stayed in more than 25 home rentals and our time in your hotel would rank tied for #1. If I had a complaint, I would add that the key pads used for entry were very hard to see at night!, sometimes requiring three or more failed attempts."
The Neighborhood Hotel-Little Italy
Found Chicago powered by Sonder
Exterior
Found Chicago powered by Sonder
3.5 star property
7.6 out of 10, Good, (169)
"The location is great, the hotel is clean and nice. I liked everything👍👍👍"
The price is ₹10,460
₹12,279 total
includes taxes & fees
20 Nov - 21 Nov
Found Chicago powered by Sonder
Sonder The Burnham
Marina
Sonder The Burnham
3.5 star property
8.8 out of 10, Excellent, (108)
"I stayed in the Burnham and it was amazing! Aesthetically gorgeous, clean, stocked with necessary amenities. Even the bed linen was high quality! This will be my place of choice whenever I’m in the area!!"
The price is ₹12,057
₹14,154 total
includes taxes & fees
27 Oct - 28 Oct
Sonder The Burnham
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, (218)
"Great property. Good size condo. Dining all around to go to. Target right around the corner. Not many places to "shop", but a short ride. Only issue I had was my condo had a strange smell. They told me they would be addressing it though."
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, (130)
"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 ₹12,250
₹14,380 total
includes taxes & fees
11 Nov - 12 Nov
Sonder Jewelers Row
Kasa River North Chicago
Exterior
Kasa River North Chicago
4.0 star property
9.6 out of 10, Exceptional, (97)
"great layout and views w private balcony highly recommended!"
The price is ₹10,745
₹12,614 total
includes taxes & fees
31 Oct - 1 Nov
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, (81)
"It was myself and 3,other ladies that flew into Chicago for the AKIRA fashion show! The venue was only a 10 min walk from Sonder. We all had worked all day and took the last flight out. When we arrived we were ready to eat and crash! We loved the self check-in option. They sent ez to follow instructions, Everything was keyless which provided quick ins and outs and you don’t have to think about keeping up with keys or cards every time you walk out the door. Upon entry you are greeted with the...
The price is ₹12,767
₹14,987 total
includes taxes & fees
12 Nov - 13 Nov
Sonder The Plymouth
Sonder The Opal
Exterior
Sonder The Opal
3.5 star property
8.2 out of 10, Very good, (22)
"Great location. Good amenities with full kitchen and laundry facilities. "
The price is ₹12,761
₹14,980 total
includes taxes & fees
27 Oct - 28 Oct
Sonder The Opal
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)
"Easy to check in, good information for parking in the area. The place was clean and nice."
Ground Floor Studios in Chicago by 747 Lofts
Sonder Greektown
40-inch flat-screen TV with digital channels, TV
Sonder Greektown
3.5 star property
9.0 out of 10, Wonderful, (33)
"The place was awesome, they had to kick out the people before me, so getting my room was a little bit late "
Sonder Greektown
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

Congress Plaza Hotel
Lobby
Congress Plaza Hotel
3.5 star property
7.8 out of 10, Good, (7964)
"We loved our stay at the Congress!! Me. Steve out front was ana amazing help with our bags, the other gentleman who were apart of the concierge service were great as well. Mr. Bill in the bar was always great. The stay was all around amazing for us. We were two female travelers and felt safe the entire time and were close to so much. "
The price is ₹12,040
₹14,133 total
includes taxes & fees
31 Oct - 1 Nov
Congress Plaza Hotel
River Hotel
View from property
River Hotel
4.0 star property
8.8 out of 10, Excellent, (3491)
"Great and right downtown. Lobby is shared with the hotel next to it, they are merged older buildings. They’ve done a great job with them being older hotels."
The price is ₹11,342
₹13,314 total
includes taxes & fees
29 Oct - 30 Oct
River Hotel
Club Quarters Hotel, Central Loop, Chicago
Superior Room, 1 Queen Bed, Kitchenette | Premium bedding, in-room safe, desk, laptop workspace
Club Quarters Hotel, Central Loop, Chicago
4.0 star property
8.6 out of 10, Excellent, (3216)
"Very close to many attractions. "
The price is ₹11,307
₹13,273 total
includes taxes & fees
29 Oct - 30 Oct
Club Quarters Hotel, Central Loop, 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.

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 1215 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.