Chicago vacation rentals
Vacation rentals in Chicago — enter your dates to book direct
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Book direct on Houfy and find a vacation rental that matches your expectations among all these great properties in Chicago. Each of the accommodations are being offered directly by owners and managers. Book direct and save up to 25% in commissions and service fees on Houfy.
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Most viewed vacation rentals in Chicago
Our guests viewed these book direct rentals the most.
Hyde Park 2BR UChicago Medical Museums 20% OFF
2 Bedrooms • 1 Bathroom
Chicago 2BR Condo- King Sleep Number
2 Bedrooms • 1 Bathroom
4.63
8 reviews
8 reviews
Large Cozy 3BR near UChicago Medical Midway Museum
3 Bedrooms • 1 Bathroom
Luxury Chicago TH 10 Mins To DWTWN RSV Now!
3 Bedrooms • 2 Bathrooms
4.7929 reviews
29 reviewsSearch vacation rentals in Chicago
Pet friendly vacation rentals in Chicago
Chicago 2Br Condo - Downtown Access
2 Bedrooms • 1 Bathroom
53 reviews
3 reviews
Luxurious Condo in Top Rated Neighborhood
1 Bedroom • 1 Bathroom
4.46
28 reviews
28 reviews
Chicago 2Br Condo -Nature Themed Downtown Access
2 Bedrooms • 1 Bathroom
52 reviews
2 reviews
Chicago 2Br 90s Condo - Very Kid Friendly
2 Bedrooms • 1 Bathroom
4.54 reviews
4 reviewsExplore destinations around Chicago
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