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 15% in commissions and service fees on Houfy.

Most viewed vacation rentals in Chicago

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2 Bedroom + Office - Honeycomb Workspace

2 Bedroom + Office - Honeycomb Workspace

Apartment • 
2 Bedrooms • 1 Bathroom
5IconIconIconIconIcon5 reviews
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Ashland 2

Ashland 2

Condo • 
3 Bedrooms • 1 Bathroom

Search vacation rentals in Chicago

Search vacation rentals, beach rentals and condos in Chicago, IL, United States

Recommended vacation rentals in Chicago

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MFL 2 West

MFL 2 West

Apartment • 
3 Bedrooms • 2 Bathrooms
4.95IconIconIconIconIcon206 reviews
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Chicago 2BR Condo- King Sleep Number

Chicago 2BR Condo- King Sleep Number

Condo • 
2 Bedrooms • 1 Bathroom
4.63IconIconIconIconIcon8 reviews
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Luxury Chicago TH 10 Mins To DWTWN RSV Now!

Luxury Chicago TH 10 Mins To DWTWN RSV Now!

Townhome • 
3 Bedrooms • 2 Bathrooms
4.79IconIconIconIconIcon29 reviews
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Chicago  2Br 90s Condo - Very Kid Friendly

Chicago 2Br 90s Condo - Very Kid Friendly

Condo • 
2 Bedrooms • 1 Bathroom
4.5IconIconIconIconIcon4 reviews
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Chicago  2Br Condo -Nature Themed Downtown Access

Chicago 2Br Condo -Nature Themed Downtown Access

Apartment • 
2 Bedrooms • 1 Bathroom
5IconIconIconIconIcon2 reviews
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Chicago  2Br Condo - Downtown Access

Chicago 2Br Condo - Downtown Access

Condo • 
2 Bedrooms • 1 Bathroom
5IconIconIconIconIcon3 reviews
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MFL 2 East

MFL 2 East

Apartment • 
4 Bedrooms • 3 Bathrooms
4.93IconIconIconIconIcon120 reviews
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MFL 3 East

MFL 3 East

Apartment • 
4 Bedrooms • 4 Bathrooms
4.99IconIconIconIconIcon93 reviews
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Hyde Park 2BR UChicago Medical Museums 20% OFF

Hyde Park 2BR UChicago Medical Museums 20% OFF

Apartment • 
2 Bedrooms • 1 Bathroom
5IconIconIconIconIcon4 reviews
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2BD/1 BA with summer patio in quiet Roscoe Village

2BD/1 BA with summer patio in quiet Roscoe Village

Vacation Home • 
2 Bedrooms • 1 Bathroom
4.97IconIconIconIconIcon98 reviews
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Luxurious Condo in Top Rated Neighborhood

Luxurious Condo in Top Rated Neighborhood

Apartment • 
1 Bedroom • 1 Bathroom
4.46IconIconIconIconIcon28 reviews
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Large Cozy 3BR near UChicago Medical Midway Museum

Large Cozy 3BR near UChicago Medical Midway Museum

Apartment • 
3 Bedrooms • 1 Bathroom
5IconIconIconIconIcon8 reviews

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