Holiday Homes in Chicago

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Featured Holiday Homes in Chicago

Clarendon Hills Top Floor

7.2 out of 10, Good, (7)
"The house was nice, in a quiet area. The bedrooms were great. It was a little nerve wracking when the lower unit was rented, as we didn't want to disturb them. "
Clarendon Hills Top Floor

Lincoln Park Living - Suite 2!

9.4 out of 10, Exceptional, (39)
"Great Place. Super area!"
Lincoln Park Living - Suite 2!

Charming 2-bedroom house in Maywood with WiFi, AC full basement with sofa bed

8.0 out of 10, Very good, (2)
"Very nice place "
The price is AU$381
includes taxes & fees
11 Aug - 12 Aug
Charming 2-bedroom house in Maywood with WiFi, AC full basement with sofa bed

Great 3 bedroom rental unit near Logan Square

9.6 out of 10, Exceptional, (49)
"This is a really cute property close to a lot of neighborhood restaurants and bars. The host is really nice and even moved his car for us so we could have his spot when we arrived. We would definitely stay here again. "
Great 3 bedroom rental unit near Logan Square

4BR Retreat w/ Theater, Game Room & Backyard

10.0 out of 10, Exceptional, (4)
"Great place"
The price is AU$1,005
includes taxes & fees
20 Aug - 21 Aug
4BR Retreat w/ Theater, Game Room & Backyard

Charming 2-bedroom house with WiFi in peaceful Hazel Crest

7.0 out of 10, Good, (7)
The price is AU$561
includes taxes & fees
4 Aug - 5 Aug
Charming 2-bedroom house with WiFi in peaceful Hazel Crest

Cozy 3-bedroom house in family-oriented Melrose Park.

10.0 out of 10, Exceptional, (19)
"The home was clean and Maggie was very responsive in our chat when I needed something. Very lovely. "
Cozy 3-bedroom house in family-oriented Melrose Park.

Riverfront Libertyville Retreat w/ Outdoor Kitchen

8.6 out of 10, Excellent, (30)
"Amazing property!! Great location communication with owners throughout our stay. This made our stay with our sailor perfect."
Riverfront Libertyville Retreat w/ Outdoor Kitchen

Cheerful 4 bedroom smart home w/ indoor fireplace

8.0 out of 10, Very good, (14)
"Loved the place and host was super helpful when needed! "
Cheerful 4 bedroom smart home w/ indoor fireplace

Vintage Urban Retreat

10.0 out of 10, Exceptional, (8)
"Great house,great location,close to a lot of attractions and bars. Owners was egged to help and responded quickly to all our questions "
The price is AU$907
includes taxes & fees
4 Aug - 5 Aug
Vintage Urban Retreat

Hermosa House ECO-HOME - Quiet, Peaceful 3BR + Free Parking by Logan Square

10.0 out of 10, Exceptional, (13)
"Lots of good food and close to transit! Amazing little spot."
Hermosa House ECO-HOME - Quiet, Peaceful 3BR + Free Parking by Logan Square

Stylish 5BR/3BA - 2 Units - 2 Kitchens + Parking!

Stylish 5BR/3BA - 2 Units - 2 Kitchens + Parking!

Luxury Home Away From Your Home

9.0 out of 10, Wonderful, (124)
"Property manager was very responsive and the communication was clear and helpful. The house was very clean. Although the neighborhood was very concerning, dirty with a lot of people standing on the block, no one was threatening and nothing happened during our stay. Parking on street was safe. "
Luxury Home Away From Your Home

Comfortable 2 bedroom house near Great Lakes Navy Base ideal for families

9.0 out of 10, Wonderful, (31)
"Had fun"
Comfortable 2 bedroom house near Great Lakes Navy Base ideal for families

Master qtr close to nature & easy urban facilities

9.8 out of 10, Exceptional, (58)
"Great spot."
The price is AU$335
includes taxes & fees
7 Aug - 8 Aug
Master qtr close to nature & easy urban facilities

Lincoln Park Living - Suite 1

9.6 out of 10, Exceptional, (29)
"Ideal location and plenty of beds. Communication was easy. My friends and I kept saying how lucky we were to find this place. Highly recommend! "
Lincoln Park Living - Suite 1

Urban Farmhouse near O’Hare Airport

9.4 out of 10, Exceptional, (44)
"We enjoyed this old house! It was clean & furnished well. Owner very accessible & easy to work with. Would definitely stay here again!"
Urban Farmhouse near O’Hare Airport

LakeHouse

9.2 out of 10, Wonderful, (20)
"Host was perfect an house was perfect!!! It's my second time renting an I will be back again!!"
LakeHouse

Huge Wrigleyville Beauty -10 beds and 5 baths in the heart of it all!!

4.0 star property
9.4 out of 10, Exceptional, (40)
"The large number of bedrooms provides privacy for a lot of people."
Huge Wrigleyville Beauty -10 beds and 5 baths in the heart of it all!!

Quaint Bungalow, near Great Lakes Naval Base

10.0 out of 10, Exceptional, (61)
"Great experience, lots of cooking materials "
The price is AU$517
includes taxes & fees
10 Aug - 11 Aug
Quaint Bungalow, near Great Lakes Naval Base
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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