Illinois Holiday Rentals

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Top Cities in Illinois

Top Holiday Rentals Destinations in Illinois

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

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

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

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

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

4.0 star property
9.4 out of 10, Exceptional, (246)
"Everything was great from the beginning. From the instructions on where to park and enter to how to exit. "
Kasa South Loop Chicago

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

3.5 star property
9.0 out of 10, Wonderful, (122)
"Wonderful place with some personality "
The price is AU$236
includes taxes & fees
16 Jan - 17 Jan 2025
Sonder The Burnham Apartments

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

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

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

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

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,

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

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

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!

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

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

BIG 5BR/5.5BA all ensuite baths, Hot Tub, Screen Porch.

9.6 out of 10, Exceptional, (141)
"A great place to spend the holiday with our kids, grandkids and their dogs. Rooms were comfortable. Hot tub was great. A special touch was wood was provided for the fireplace on this ultra cold holiday weekend."
BIG 5BR/5.5BA all ensuite baths, Hot Tub, Screen Porch.

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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