A river with a yellow boat, surrounded by tall buildings and a bridge.

Chicago country houses

We found 1,398 country houses — enter your dates for availability

Explore Chicago mansion rentals

Image of Spacious Budget-friendly Room w/ Kitchenette Ideal for Extended or Short Stays

Premier Host

Spacious Budget-friendly Room w/ Kitchenette Ideal for Extended or Short Stays

Sleeps 2 · 1 bedroom · 1 bathroom

Image of LakeHouse with rooftop and views of lake.

Premier Host

LakeHouse with rooftop and views of lake.

Sleeps 12 · 3 bedrooms · 3 bathrooms

Image of 4BR Modern Urban Escape, Walk to Zoo, Lakefront & Red Line

Premier Host

4BR Modern Urban Escape, Walk to Zoo, Lakefront & Red Line

Sleeps 10 · 4 bedrooms · 3 bathrooms

Image of Your Home Away From Home! Outdoor Pool, Pets Allowed, Near Lindholm Park!

Premier Host

Your Home Away From Home! Outdoor Pool, Pets Allowed, Near Lindholm Park!

Sleeps 3 · 1 bedroom · 1 bathroom

Image of ENVITAE Hotel, 4BR Luxury Modern Apartments

Premier Host

ENVITAE Hotel, 4BR Luxury Modern Apartments

Sleeps 10 · 4 bedrooms · 3 bathrooms

Image of Pleasant 3-bedroom house with occupied basement separate entrance.

Pleasant 3-bedroom house with occupied basement separate entrance.

Sleeps 6 · 3 bedrooms · 1 bathroom

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