Chicago Holiday Rentals

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Holiday Rentals in Chicago

Interior
Sentral Michigan Avenue
4.0 star property
9.2 out of 10, Wonderful, (404)
"Super nice and well kept. Right in the heart of downtown Chicago. Highly recommended!"
The price is S$237
per night
28 May - 29 May
Sentral Michigan Avenue
Interior
Sonder Market Hall
3.5 star property
8.2 out of 10, Very good, (79)
"It was an excellent stay. I didn’t understand the Sonder model—no front desk and electronic check in. However once I got beyond that shock I didn’t mind it. I know some folks would find the setup disconcerting. I would stay in a Sonder hotel again."
The price is S$215
per night
28 May - 29 May
Sonder Market Hall
49-inch Smart TV with digital channels, TV, streaming services
Kasa Magnificent Mile Chicago
4.0 star property
9.2 out of 10, Wonderful, (223)
"Everything was great. From easy check in to easy check out. The room was very nice and cozy. Very clean. Amazing view of downtown from the bedroom and balcony. I will be staying here again! "
Kasa Magnificent Mile Chicago
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City view from property
Sonder South Wabash
3.5 star property
8.8 out of 10, Excellent, (295)
"Overall the stay was amazing. We will definitely be booking here again."
The price is S$307
per night
28 May - 29 May
Sonder South Wabash
Exterior
Sonder The Burnham
3.5 star property
8.8 out of 10, Excellent, (55)
"Convenient and easy to access"
The price is S$307
per night
28 May - 29 May
Sonder The Burnham
Interior
Found Chicago powered by Sonder
3.5 star property
7.6 out of 10, Good, (127)
"I enjoyed the fact that everything was close. The hotel was cleaned but I never saw a personal member. The code to enter didn't work and people inside had to help fellow clients to enter."
The price is S$350
per night
12 Jun - 13 Jun
Found Chicago powered by Sonder
Front of property – evening/night
Level Chicago – Old Town
4.0 star property
8.8 out of 10, Excellent, (207)
"Nice"
The price is S$344
per night
27 May - 28 May
Level Chicago – Old Town
50-inch Smart TV with satellite channels
The Neighborhood Hotel-Little Italy
2.0 star property
9.8 out of 10, Exceptional, (30)
"Beautiful, spacious, clean rooms. Cozy safe neighborhood. Prompt and responsive communication. Would absolutely stay here again!!"
The Neighborhood Hotel-Little Italy
1 bedroom, premium bedding, pillow-top beds, desk
WoodSpring Suites Chicago Addison
2.5 star property
6.0 out of 10, (184)
"Very nice property "
The price is S$103
per night
23 May - 24 May
WoodSpring Suites Chicago Addison
Exterior
Sonder Jewelers Row
3.5 star property
8.2 out of 10, Very good, (101)
"The entire experience was fantastic. Clear instructions in how to get into the building and the apartment, fully stocked kitchen and extremely comfortable bed"
The price is S$310
per night
28 May - 29 May
Sonder Jewelers Row
Exterior
Kasa River North Chicago
4.0 star property
9.6 out of 10, Exceptional, (65)
"Very clean and comfortable. Great location very close to an L stop. Walkable to shopping and the lake front and river walk"
Kasa River North Chicago
Living area
Kasa South Loop Chicago
4.0 star property
9.4 out of 10, Exceptional, (161)
"Highly recommend! Amazing view of the city and the lake, clean and quiet yet close to everything. Thoughtfully furnished with nice surprises like power strips, white noise machine in bedroom, electric kettle etc. It was ideal and we’d stay there again. "
Kasa South Loop Chicago
City view from property
Sonder The Plymouth
3.5 star property
8.4 out of 10, Very good, (66)
"Great place to stay and visit Chicago on foot. The property was exactly what we hoped for. "
The price is S$416
per night
13 Jun - 14 Jun
Sonder The Plymouth
Full-sized fridge, oven, stovetop, dishwasher
Sonder The Opal
3.5 star property
8.0 out of 10, Very good, (12)
"Overall: A nice stay in a great part of town. Pros: Walking distance to almost everything downtown Chicago. Check-in is easy, but not the most intuitive instructions for the building codes. Spacious and clean room. Cons: The view. DO NOT let the pictures of the property deceive you… Unless you are on the top floor, the view is not very good. Also, says there’s rooftop access but no way to get to the roof (door locked). The walls are thin inside the apartment. Layout was a bit bizarre. Advert...
The price is S$367
per night
29 May - 30 May
Sonder The Opal
40-inch flat-screen TV with digital channels, TV
Sonder Greektown
3.5 star property
8.8 out of 10, Excellent, (29)
"LOCATION was terrific - central and close to all our 'outings'. Downside was NOT being able to control the thermostat. And NO response to any of our efforts to contact the property manger(s)."
The price is S$453
per night
28 May - 29 May
Sonder Greektown
Exterior
Ground Floor Studios in Chicago by 747 Lofts
2.0 star property
10.0 out of 10, Exceptional, (7)
"Easy to check in, good information for parking in the area. The place was clean and nice."
The price is S$165
per night
22 May - 23 May
Ground Floor Studios in Chicago by 747 Lofts
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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.

Other types of properties in Chicago you may be interested in

Lobby
Congress Plaza Hotel
3.5 star property
7.6 out of 10, Good, (6748)
"Close to everything. Great historic hotel is absolutely beautiful. Great location "
The price is S$235
per night
27 May - 28 May
Congress Plaza Hotel
Front of property
Warwick Allerton - Chicago
4.0 star property
7.8 out of 10, Good, (2587)
"I really enjoyed my stay, I felt safe and comfortable "
The price is S$194
per night
27 May - 28 May
Warwick Allerton - Chicago
Exterior
The Westin Michigan Avenue Chicago
4.5 star property
8.6 out of 10, Excellent, (1003)
"We had a wonderful time in Chicago! This property was located in such a great area and easy walking to all the things we wanted to do...and eat. :)"
The price is S$353
per night
23 May - 24 May
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.

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 1366 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 Art Institute of Chicago and CIBC Theatre, whereas Grant Park and Millennium Park are a couple of picturesque spots to enjoy the outdoors. You can also visit some other popular places in town, such as Navy Pier and Wrigley 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.

Recent reviews of Chicago properties
Expedia verified reviews

Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

5/5 Excellent
"The property is lovely and beautifully maintained. Our room was very comfortable and nicely furnished. We would definitely stay there again. Price was reasonable and while a bit removed from the busier areas, the quiet was wonderful"
A verified traveller stayed at Hotel Felix River North/Magnificent Mile
Posted 12 hours ago
Hotel Felix River North/Magnificent Mile