Chicago Holiday Rentals

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Holiday Rentals in Chicago

Sentral Michigan Avenue
Interior
Sentral Michigan Avenue
4.0 star property
9.2 out of 10, Wonderful, (592)
"We stayed stayed at the Sentral for a business/family trip. This hotel is beautiful and accommodating. Sandra at the front desk was the sweetest and made check in a breeze, even allowing us to check in early. The room was clean, however there was a burn mark on the kitchen floor and it appeared as it was not vacuumed. Otherwise the room was wonderful, we would definitely stay here again! "
The price is AU$238
includes taxes & fees
24 Nov - 25 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 AU$101
includes taxes & fees
22 Dec - 23 Dec
Sonder Market Hall
Sonder South Wabash
Superior Apartment, 1 Bedroom, Balcony, City View | Living area
Sonder South Wabash
3.5 star property
9.0 out of 10, Wonderful, (395)
"Nice"
The price is AU$218
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 AU$395
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 AU$208
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 AU$226
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 AU$224
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 AU$145
includes taxes & fees
8 Dec - 9 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 AU$226
includes taxes & fees
19 Dec - 20 Dec
Sonder The Plymouth
Luxury Home Away From Your Home
Fridge, microwave, oven, stovetop
Luxury Home Away From Your Home
9.0 out of 10, Wonderful, (116)
"Had a great time at Ms. Linnie’s place! She was incredibly responsive and helpful. The house was clean and comfortable, and I loved that there were 2 full bathrooms! I was a little nervous about the neighborhood as we were definitely looked at as outsiders, but no one bothered us and we walked to Maxwell Street Polish and back just fine (which is fantastic, btw). I did love the gated yard in back with two parking spots, so we had our own space. Would definitely stay again!"
Luxury Home Away From Your Home
Walking distance to restaurants, shops and Lake Michigan,
Exterior
Walking distance to restaurants, shops and Lake Michigan,
9.6 out of 10, Exceptional, (173)
"Good location clean"
Walking distance to restaurants, shops and Lake Michigan,
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 AU$243
includes taxes & fees
18 Dec - 19 Dec
Sonder The Opal
LakeHouse
Fridge, microwave, oven, stovetop
LakeHouse
10.0 out of 10, Exceptional, (13)
"Overall great experience! Great home, I love the decor of the entire home. And I will definitely recommend to others and will book again "
LakeHouse
51st Floor MagMile Penthouse - VIEWS, Fireplace, Balcony, Pool, WiFi
Outdoor pool
51st Floor MagMile Penthouse - VIEWS, Fireplace, Balcony, Pool, WiFi
10.0 out of 10, Exceptional, (212)
"A big, beautiful, immaculate, wonderfully furnished space 51 floors above the city. Everything in the owner's description is true. Watching the sun rise over the lake from that height was a treat. Also being able to walk to restaurants, Navy Pier, river tours, great blues clubs, plus hop the subway just a few doors away. The door staff was very helpful in stashing our luggage on both sides of our stay (be sure to "show them some kindness" for that service). "
51st Floor MagMile Penthouse - VIEWS, Fireplace, Balcony, Pool, WiFi
Experience Chicago living near United Center
Fridge, microwave, oven, stovetop
Experience Chicago living near United Center
9.4 out of 10, Exceptional, (12)
"Our family stayed for a corporate training and we had a great experience. The neighborhood wasn't the best but we felt very secure with having a garage to use. Very thankful for the quick communication! from the p "
Experience Chicago living near United Center
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 AU$258
includes taxes & fees
12 Dec - 13 Dec
Sonder Greektown
Wrigley/Southport Corridor Garden Oasis +parking!
Exterior
Wrigley/Southport Corridor Garden Oasis +parking!
9.8 out of 10, Exceptional, (66)
"This little apartment is close to my cousin in Wrigleyville and a perfect location to get downtown and to see a Bears game (they are terrible right now). Entry instructions were easy and apartment was very clean."
Wrigley/Southport Corridor Garden Oasis +parking!
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, (8135)
"It is an old building so We were very pleased with how clean the rooms were. Tub drained slowly but did not affect our shower schedules. Radiator was a little confusing but it didn’t bother is because the weather was beautiful. Will stay again"
The price is AU$154
includes taxes & fees
24 Nov - 25 Nov
Congress Plaza Hotel
River Hotel
View from property
River Hotel
4.0 star property
8.8 out of 10, Excellent, (3549)
"Everything was great! Staff was friendly and check in was super easy! I will stay again "
The price is AU$189
includes taxes & fees
22 Dec - 23 Dec
River Hotel
The Westin Michigan Avenue Chicago
Exterior
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 AU$297
includes taxes & fees
22 Dec - 23 Dec
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

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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.

What are some of the best holiday rentals that Chicago has to offer?

Roxan Corner: This highly rated holiday home rental in Chicago offers a patio, a garden and a BBQ to help you feel perfectly comfortable in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. Other favourite homes for rent in Chicago are Updated Forest Park 3 BR Bungalow and Beautiful 6BR mansion, 4 parking spots, sleeps 21! Walk to Wrigley & the lake!.

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.