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

Chicago houses

We found 1,420 houses — enter your dates for availability

Explore Chicago house rentals

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 Sleeps 18 • 8BR • Game Room • Gym • Theater

Premier Host

Sleeps 18 • 8BR • Game Room • Gym • Theater

Sleeps 18 · 8 bedrooms · 3 bathrooms

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

Image of Near Lake and Museum • Modern • Game Area

Near Lake and Museum • Modern • Game Area

Sleeps 12 · 5 bedrooms · 2+ bathrooms

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