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, (624)
"I have stayed at this property 3 times now and every time has been amazing. They have become the only place I will stay at in the city. The location is great with a parking garage around the corner at is very cheap. You get so many more amenities than a hotel and is an overall great experience. I highly recommend."
The price is AU$253
includes taxes & fees
23 Dec - 24 Dec
Sentral Michigan Avenue
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, (342)
"The property location was great. The room was very spacious. The only knock was there was not a tv in the bedroom."
Kasa Magnificent Mile Chicago
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, (407)
"The stay was great."
The price is AU$233
includes taxes & fees
12 Jan - 13 Jan 2025
Sonder South Wabash
Sonder Market Hall
Interior

Sonder Market Hall

3.5 star property
8.6 out of 10, Excellent, (228)
"Very nice place for the cost. Could hear outside and inside noises but noise doesn’t bother me. Would stay here again."
The price is AU$106
includes taxes & fees
21 Jan - 22 Jan 2025
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, (277)
"I loved the amenities available to us - garage parking, washer/dryer in unit, full kitchen and fully furnished. Staff were polite and helpful. Great location"
The price is AU$364
includes taxes & fees
3 Jan - 4 Jan 2025
Level Chicago – Old Town
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, (246)
"Nice and clean. Great stay with Target and other shops in walking distance. "
Kasa South Loop Chicago
Kasa River North Chicago
Exterior

Kasa River North Chicago

4.0 star property
9.6 out of 10, Exceptional, (109)
"Great stay overall"
The price is AU$240
includes taxes & fees
2 Jan - 3 Jan 2025
Kasa River North Chicago
Sonder The Burnham Apartments
Marina

Sonder The Burnham Apartments

3.5 star property
9.0 out of 10, Wonderful, (122)
"Wonderful place with some personality "
The price is AU$236
includes taxes & fees
19 Jan - 20 Jan 2025
Sonder The Burnham Apartments
Found Chicago powered by Sonder
Exterior

Found Chicago powered by Sonder

3.5 star property
7.6 out of 10, Good, (179)
"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$227
includes taxes & fees
13 Jan - 14 Jan 2025
Found Chicago powered by Sonder
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, (110)
"Absolutely loved loved loved my stay here!! It feels more like a personal home rather than a hotel. It’s very private, has tons of space, and felt very safe. "
The Neighborhood Hotel-Little Italy
Sonder Jewelers Row
Free toiletries, hair dryer, towels, soap

Sonder Jewelers Row

3.5 star property
8.2 out of 10, Very good, (136)
"Sonder check in experience as a first timer was super easy! Great instructions and no issues entering or exiting the property. Property was in great condition with all the amenities you could need. Only downside was the cigar bar downstairs... you could at certain times of day smell the cigar scent in our room upstairs. Not a huge issue, but if you were sensitive to the smell it would not be ideal."
The price is AU$193
includes taxes & fees
13 Jan - 14 Jan 2025
Sonder Jewelers Row
Sonder The Plymouth
City view from property

Sonder The Plymouth

3.5 star property
8.4 out of 10, Very good, (87)
"Loved the location. "
The price is AU$194
includes taxes & fees
16 Jan - 17 Jan 2025
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, (174)
"We were very pleased with the property. Stayed there over the Thanksgiving holiday & weekend while visiting my older daughter. Nice neighborhood & easy location to get to other parts of the city. Everything was as depicted in the description and communication with management was excellent. Would stay here again."
Walking distance to restaurants, shops and Lake Michigan,
Sonder The Opal
Exterior

Sonder The Opal

3.5 star property
8.6 out of 10, Excellent, (27)
"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 AU$194
includes taxes & fees
12 Jan - 13 Jan 2025
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, (36)
"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$237
includes taxes & fees
13 Jan - 14 Jan 2025
Sonder Greektown
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
Wrigley/Southport Corridor Garden Oasis +parking!
Exterior

Wrigley/Southport Corridor Garden Oasis +parking!

9.8 out of 10, Exceptional, (67)
"Very clean and comfortable place!"
Wrigley/Southport Corridor Garden Oasis +parking!
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, (213)
"Excited about our trip to Chicago and was not disappointed. Communication was very good from the homeowner location is perfect we had a fantastic time would recommend this for anyone wanting to enjoy downtown Chicago"
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
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
2 bars/lounges, sports bar, sports bar

Congress Plaza Hotel

3.5 star property
7.8 out of 10, Good, (8289)
"Wallpaper in lobby is old. No working ice machines to be found."
The price is AU$196
includes taxes & fees
23 Dec - 24 Dec
Congress Plaza Hotel
River Hotel
View from property

River Hotel

4.0 star property
8.8 out of 10, Excellent, (3631)
"This hotel is great! The staff helped us check in early and provided us with a river view room. My friend and I were both very happy^^ Although it’s close to the busy road, the room is not noisy. The location of the hotel is also very good, making our travel convenient."
The price is AU$175
includes taxes & fees
21 Jan - 22 Jan 2025
River Hotel
Hyatt Regency Chicago
2 bars/lounges

Hyatt Regency Chicago

4.0 star property
9.2 out of 10, Wonderful, (3125)
"I loved my stay. One of the best hotels in the city. "
The price is AU$324
includes taxes & fees
5 Jan - 6 Jan 2025
Hyatt Regency 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 Field Museum of Natural History, 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 entertainment choices. 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?

Luxury Home Away From Your Home: This highly rated holiday home rental in Chicago is equipped with a BBQ, air conditioning and cable TV to help you feel comfortable during your stay. It has 3 bedrooms, as well as a kitchen with a fridge, a stovetop and a microwave, so that you can cook with friends or family. Other favourite homes for rent in Chicago are LakeHouse and Stunning / Spacious 6BD Home + garage - Bucktown!.

How many holiday rentals are there in Chicago?

With 1280 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 Maggie Daley 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 Naval Base Great Lakes.

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.