Chicagoland, IL Pet-Friendly Vacation Rentals, Apartments, & More - 558 Rentals Available

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1 / 37

Chicago Apartment
4 BR / 2 BA / Sleeps 8 4 8 3 night min stay
Apartment / 4 Bedrooms / Sleeps 8
4 bedrooms 2 bathrooms Sleeps 8
High Speed Internet • Dishwasher • Microwave
"Great place to stay. Close to the train, lots of great restaurants, all within close walking distance. It also had available street parking for our car. The owner meet us when we arrived and answered all of our questions. He also gave us ..."
- Randy Waskowiak, Nebraska
(1) Excellent (1 review)
1 / 25

Chicago Home
7 BR / 2.5 BA / Sleeps 20 7 20 Min stay varies
Home / 7 Bedrooms / Sleeps 20
7 bedrooms 2.5 bathrooms Sleeps 20
High Speed Internet • Dishwasher • Microwave
"I cannot say enough about this experience. We had rented another property for a party for my daughter's 18th birthday which turned out to be a scam. I had been in contact with Anna about this property, but the other was cheaper and met our needs. When..."
- Kathryn Murray Kzeski, Chicago, IL USA
(4) Excellent (4 reviews)
1 / 30

Chicago Condo
6 BR / 2 BA / Sleeps 16 6 16 3 night min stay
Condo / 6 Bedrooms / Sleeps 16
6 bedrooms 2 bathrooms Sleeps 16
High Speed Internet • Dishwasher • Microwave
"Great place, exactly as pictured. Our stay was enjoyable and hassle free. Owner was easily reached via email/text if needed."
- Courtney Armstrong, Milwaukee, WI
(4) Excellent (4 reviews)
1 / 14

Palatine Home
6 BR / 5 BA / Sleeps 13 6 13 90 night min stay
Home / 6 Bedrooms / Sleeps 13
6 bedrooms 5 bathrooms Sleeps 13
High Speed Internet • Dishwasher • Microwave
"A group of 12 brothers, sons, cousins and friends have gotten together every fall for a guys' getaway for the last 27 years. We stayed at your home this year and everything was perfect. Plenty of sleeping arrangements for the group. We enjoyed the..."
- Donna Tews, Illinois
(1) Excellent (1 review)
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