Chicago which includes a high-rise building and a city as well as a family

Holiday Homes in Chicago

Change your mind

Book hotels with free cancellation

Treat yourself

Be picky

Search almost a million properties worldwide

Check prices for these dates

Next weekend

In two weeks

In one month

In two months

Featured Holiday Homes in Chicago

"Very nice place "

includes taxes & fees

26 Aug - 27 Aug

"Very nice and newly remodeled property. Would definitely recommend. Property owner was pleasant and attended to maintenance issues promptly. Pool table and air hockey tables were fun to play on. There is even a sauna on the property but we did not use it. Great location for being near the Naval base."

Desk, iron/ironing board, free WiFi, bed sheets

"We had a fantastic stay! The property was perfect for kids — safe, clean, and had plenty of space to play. The outdoor space is perfect for morning coffee, lounging, afternoon cocktails, and dinner under the stars. This location was unbeatable, close to everything we wanted to do. Couldn’t have asked for a better spot for a family getaway in the city. Highly recommend!"

"Very communicative and good host for sure!"

includes taxes & fees

19 Aug - 20 Aug

"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. "

"Only complaint was the fact that the yard was not cut and the grass needed to maintained"

includes taxes & fees

9 Sept - 10 Sept

"Nice location outside of Chicago, cozy and clean, good communication, would definitely recommend! "

"Great house,great location,close to a lot of attractions and bars. Owners was egged to help and responded quickly to all our questions "

includes taxes & fees

20 Aug - 21 Aug

8 bedrooms, desk, iron/ironing board, travel cot

"When I booked this property it was the intention to have a joyful time with my family for an extended family event. We were unable to access the property the day of causing me to spend an extra 600 for us to stay at another hotel after spending 2 hours on the phone with customer service. To top it off we were harassed by the next door neighbor who attempted to take pictures of our vehicle and report to us that this property was considered an illegal listing. Once we gained entry the property was...

includes taxes & fees

19 Aug - 20 Aug

4 bedrooms, iron/ironing board, free WiFi, bed sheets

"Excellent location, right by the zoo, the place is well stocked and clean, in a nice neighborhood. Close to attractions and easy to go to other western suburbs of Chicago. Has everything we needed :). The host was great with communicating and was able to allow us to borrow a pack n play as well. Would stay again! "

includes taxes & fees

26 Aug - 27 Aug

"Everything was as it was described. Very nice "

"Host was perfect an house was perfect!!! It's my second time renting an I will be back again!!"

"Comfortable beds and room for everyone. Nice quiet neighborhood and a great home away from home. Would stay there again. Host was very easy to work with and responded quickly to questions. "

Smart TV, music library, video library, stereo

"Had fun"

"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. "