Holiday Homes in Chicago

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Featured Holiday Homes in Chicago

Our top choices for Chicago holiday homes

Amazing 3-bedroom house with WiFi and AC in awesome Chicago

Amazing 3-bedroom house with WiFi and AC in awesome Chicago

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

7.4 out of 10, Good, (8)
"The house was immaculate and very spacious. Beautifully decorated. The neighborhood was easy to get in and out of and close enough to downtown. Would highly recommend."
The price is AU$374
includes taxes & fees
8 Sept - 9 Sept
Charming 2-bedroom house in Maywood with WiFi, AC full basement with sofa bed

Sleeps 18+, 8BR Kids Room, Game Room, Gym & Theater

6.0 out of 10, (2)
"Great space for large groups. Park across the street is a great "feature"."
The price is AU$1,382
includes taxes & fees
30 Sept - 1 Oct
Sleeps 18+, 8BR Kids Room, Game Room, Gym & Theater

Rumble In the Jungle Charming 3-bedroom house in nice Addison with AC, WiFi

8.0 out of 10, Very good, (3)
"Only complaint was the fact that the yard was not cut and the grass needed to maintained"
The price is AU$707
includes taxes & fees
23 Sept - 24 Sept
Rumble In the Jungle Charming 3-bedroom house in nice Addison with AC, WiFi

North Chi Retreat-Near Navel base-Sauna,Pool, Airhokey, grill,King bed,Tikki Bar

9.6 out of 10, Exceptional, (4)
"Home was cute and as advertised, outdoor area great for families to relax. Only recommendation to have some information at the home for guests in the event the alarm system is activated so it can be acknowledged quickly. "
North Chi Retreat-Near Navel base-Sauna,Pool, Airhokey, grill,King bed,Tikki Bar

4BR Retreat w/ Theater, Game Room & Backyard

7.4 out of 10, Good, (9)
The price is AU$768
includes taxes & fees
23 Sept - 24 Sept
4BR Retreat w/ Theater, Game Room & Backyard

Riverfront Libertyville Retreat w/ Outdoor Kitchen

8.6 out of 10, Excellent, (30)
"Thank you very much"
Riverfront Libertyville Retreat w/ Outdoor Kitchen

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

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

Great 3 bedroom rental unit near Logan Square

9.6 out of 10, Exceptional, (53)
"Cozy place to stay with a VERY QUICK response from host. Great location in quiet neighborhood. I would stay here again in a heartbeat. "
Great 3 bedroom rental unit near Logan Square

Chic and Spacious Bi-level 3BD in Bucktown!

2.0 star property
9.8 out of 10, Exceptional, (8)
"Property was comfortable, clean, and in a great location."
Chic and Spacious Bi-level 3BD in Bucktown!

Breathtaking home close to Schaumburg, Chicago

9.8 out of 10, Exceptional, (66)
"Fit our whole family nicely."
Breathtaking home close to Schaumburg, Chicago

Des Plaines Vacation Rental w/ Spacious Backyard!

9.0 out of 10, Wonderful, (16)
"Easy access good parking clean well stocked but very small three bedroom house with nice outdoor sitting and eating area near Rosemont"
Des Plaines Vacation Rental w/ Spacious Backyard!

Belmont House, Classy & Chic/walk to Wrigley Field

9.4 out of 10, Exceptional, (50)
"Great bang for your buck. Great area and great communication "
Belmont House, Classy & Chic/walk to Wrigley Field

New home w/view & party deck - 2nd Floor

3.0 star property
10.0 out of 10, Exceptional, (25)
"Great location. Host was accessible and prompt to respond. "
New home w/view & party deck - 2nd Floor

A Home Away From Home!

9.6 out of 10, Exceptional, (7)
"Great place to stay. Host responded quickly to questions. Location was good and neighbor was quite. "
A Home Away From Home!

Entire 3 Bedroom Cozy Unit

9.6 out of 10, Exceptional, (21)
"This property was comfortable and convenient for our attendance at the Navy boot camp graduation. "
Entire 3 Bedroom Cozy Unit

Master qtr close to nature & easy urban facilities

9.8 out of 10, Exceptional, (61)
"Great spot."
The price is AU$314
includes taxes & fees
3 Sept - 4 Sept
Master qtr close to nature & easy urban facilities

Clarendon Hills Top Floor

6.8 out of 10, (10)
"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

✽ Charming Cottage ✽ close to College/Town/Station

10.0 out of 10, Exceptional, (47)
"We loved how cute this house was! It was very convenient for visiting our daughter and nice to have plenty of space and amenities. Our host was very prompt communication. Would definitely stay here again!"
The price is AU$484
includes taxes & fees
4 Sept - 5 Sept
✽ Charming Cottage ✽ close to College/Town/Station

Family frndly TwnHm by navy base

2.0 star property
9.6 out of 10, Exceptional, (21)
"Great little place to stay near the base. "
Family frndly TwnHm by navy 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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Top Chicago Hotel Reviews

Find out more about Chicago

Find out more about Chicago

Chicago Holiday Homes information

Number of reviews
Accommodation
988 Holiday Homes
Lowest Price
AU$314
Highest Price
AU$1,382

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