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

Chicago guest houses

We found 5 guest houses — enter your dates for availability

Explore Chicago guest house rentals

Image of Sentral Michigan Avenue

Sentral Michigan Avenue

Image of Kasa Lake Shore Chicago

Kasa Lake Shore Chicago

Sleeps 2 · 1 bedroom · 1 bathroom

Image of Kasa Magnificent Mile Chicago

Kasa Magnificent Mile Chicago

Sleeps 2 · 1 bedroom · 1 bathroom

Image of The Gem Museum Suites

The Gem Museum Suites

Sleeps 6 · 1 bedroom

Image of Level Chicago – Old Town

Level Chicago – Old Town

Sleeps 4 · 1 bedroom · 1 bathroom

Image of The Neighborhood Hotel-Little Italy

The Neighborhood Hotel-Little Italy

Sleeps 3 · 1 bedroom

Find spaces that suit your style

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Condo/Apartment

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Chalet

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All the privacy of home
Enjoy full kitchens, laundry, pools, gardens and more
More for less
More space, more privacy, more amenities — more value