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

Holiday Homes in Chicago

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Featured Holiday Homes in Chicago and around

Our top choices for Chicago holiday homes

"The apartment looked exactly like the pictures and was very well kept. Everything was clean and functional and we didn’t have any issues. The neighborhood is very quiet and safe and also has a target nearby for quick grocery trips. Connectivity wise, there’s a busy stop within walking distance but no train stations.The host was also very responsive and helpful. We didn’t have any trouble checking in or checking out.Overall a great experience and comfortable stay."

includes taxes & fees

2 Sept - 3 Sept

"The hotel was very nice and the location was excellent. Was able to walk to many locations. Noise wasn't bad for a city experience. Hotel restaurant was very good."

includes taxes & fees

1 Sept - 2 Sept

includes taxes & fees

2 Sept - 3 Sept

includes taxes & fees

2 Sept - 3 Sept

includes taxes & fees

10 Sept - 11 Sept

includes taxes & fees

2 Sept - 3 Sept

includes taxes & fees

10 Sept - 11 Sept

"Lovely little cottage in great location with excellent restaurants close by. Had everything we needed for our stay. Kitchen was perfectly equipped and having the washer dryer was such a bonus. The communication with the landlord was very good. Would absolutely stay here again. "

includes taxes & fees

1 Sept - 2 Sept

includes taxes & fees

1 Sept - 2 Sept

includes taxes & fees

1 Sept - 2 Sept

"it was nice"

"Very nice and clean place to stay at. Great communication from property manager. I would absolutely stay here again!"

includes taxes & fees

1 Sept - 2 Sept

"Great spot."

includes taxes & fees

2 Sept - 3 Sept

1 bedroom, iron/ironing board, WiFi, bed sheets

"This was a wonderful base for the days I spent exploring Chicago. The apartment is clean and comfy and it is located right on the 'L' Brown line in a charming and vibrant neighborhood. I could zip to anywhere in the city I wanted on the L and felt very relaxed coming "home" each night."

includes taxes & fees

9 Sept - 10 Sept