Holiday Homes in Northwest Side

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 Northwest Side

"The place was perfect for our stay in Chicago!"

"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 place"

includes taxes & fees

5 Aug - 6 Aug

"Loved the place and host was super helpful when needed! "

"Clean and in a nice neighborhood "

"Easy to get to and very clean. Also check in and out was easy as well. "

"Lots of good food and close to transit! Amazing little spot."

"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. "

"Great spot."

includes taxes & fees

28 July - 29 July

"Great location in a beautiful part of town. Walk to Wrigley. Place was great for 2 families to hang out. "

"We enjoyed this old house! It was clean & furnished well. Owner very accessible & easy to work with. Would definitely stay here again!"

"The large number of bedrooms provides privacy for a lot of people."

"Three weeks later tries to say we didn't pay when we have emails/proof saying otherwise. We checked in at the time, and some guy just comes in the backdoor with towels. Upon checkout, says we didn't leave the key & they had to get a locksmith - we literally saw someone come in with a key (man with towels at check in). Scary neighborhood, misleading advertising, terrible communication. "

"It’s a beautiful home, it had everything we needed. It was nice and comfortable!!! Me and my family enjoyed our stay!!!"

"Very comfortable home. Location was great. Owners were very responsive and helpful. A storm on our last day unfortunately left us without power, owner was great at keeping us informed of status. Already went to book for our next trip but someone beat us to it. "

"The house was in a nice neighborhood and was very roomy and comfortable. Will be back."

"The space - number of rooms and bathrooms - was great for a big group. We were able to sleep multiple families comfortably with no issues getting ready with the number of bathrooms. There was plenty of free street parking close, so we also didn't have any problems finding parking for all our cars. Some more specific instructions on how to use the key pad (to enter and lock) would be helpful, but otherwise no complaints! I would recommend this Vrbo! "