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Chicago Vacation Rentals

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29 rentals in Chicago.
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Nice apartment two bedrooms

Theater District, Downtown / The Loop, Central
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Möblierte 1-Zimmer-Apartment in N State St & W Illinois St Chicago

Near North Side, Central
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Furnished 1-Bedroom Apartment at N State St & W Illinois St Chicago

Near North Side, Central
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Eingerichtete Studio-Apartment in W Grand Ave & N State St Chicago

Near North Side, Central
0 bedrooms
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Möblierte 1-Zimmer-Apartment in N State St & W Illinois St Chicago

Near North Side, Central
0 bedrooms
0 bathrooms
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Möblierte 1-Zimmer-Apartment in N State St & W Illinois St Chicago

Near North Side, Central
0 bedrooms
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Eingerichtete Studio-Apartment in W Grand Ave & N State St Chicago

Near North Side, Central
0 bedrooms
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Fornito Monolocale a W Grand Ave & N State St Chicago

Near North Side, Central
0 bedrooms
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Möblierte 1-Zimmer-Apartment in N State St & W Illinois St Chicago

Near North Side, Central
0 bedrooms
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Eingerichtete Studio-Apartment in W Grand Ave & N State St Chicago

Near North Side, Central
0 bedrooms
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Möblierte 3-Zimmer Stadthaus in N Wells St & W Scott St Chicago

Near North Side, Old Town, Central
0 bedrooms
0 bathrooms
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Επιπλωμένο Διαμέρισμα με 1 υπνοδωμάτιο στο Ν State St & W Illinois St Σικάγο

Near North Side, Central
0 bedrooms
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Eingerichtete Studio-Apartment in W Grand Ave & N State St Chicago

Near North Side, Central
0 bedrooms
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Furnished 1-Bedroom Apartment at N State St & W Illinois St Chicago

Near North Side, Central
0 bedrooms
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Möblierte 2-Zimmer-Apartment in W Grand Ave & N State St Chicago

Near North Side, Central
0 bedrooms
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Möblierte 1-Zimmer-Apartment in N State St & W Illinois St Chicago

Near North Side, Central
0 bedrooms
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Furnished Studio Apartment at W Grand Ave & N State St Chicago

Near North Side, Central
0 bedrooms
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Luxuriöse Downtown Riverwalk Condo (3 Betten)

Downtown / The Loop, Central
0 bedrooms
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Ferienwohnung Chicago

Downtown / The Loop, Central
0 bedrooms
0 bathrooms
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Penthouse mit Blick auf den See

Edgewater Beach, Edgewater, Far North Side
0 bedrooms
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sweet home chicago

Chatham, Far Southeast Side
0 bedrooms
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Wyndham Grand Chicago Riverfront 1 Bedroom

Theater District, Downtown / The Loop, Central
0 bedrooms
0 bathrooms
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Beautiful two bedroom. Apt in Hyde park

Kenwood, South Side
0 bedrooms
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Luxury Apartment Downton Chicago

South Loop, Prairie Avenue Historic District (Prairie District), Near South Side, Central
0 bedrooms
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Near Downtown and McCormick Place

Chinatown, South Side, Armour Square
0 bedrooms
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1BR Condo near Lake, Aragon

Uptown, Far North Side
0 bedrooms
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West Loop 2 bed 2 Bath Blackhawks Bulls!

West Side, Near West Side, West Loop
0 bedrooms
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Luxury Penthouse South Loop

South Loop, Near South Side, Central
0 bedrooms
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cozy one bedroom apt / mccormick place/bronzevill

Chinatown, South Side, Armour Square
0 bedrooms
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Frequently Asked Questions about Chicago





Chicago Vacation Rentals
Planning a visit to Chicago? A Chicago vacation rental is a great hotel alternative. From modern apartments on the Magnificent Mile to cozy coach houses in Lincoln Park and everything in between, we’ve got a wide variety of Chicago vacation rentals so there’s sure to be one that’s just right for you. Whatever your budget, we’ll help you find a great deal. Plus, you can book with confidence - we have plenty of unbiased user reviews of Chicago vacation rentals!
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Chicago Vacation Rentals
Planning a visit to Chicago? A Chicago vacation rental is a great hotel alternative. From modern apartments on the Magnificent Mile to cozy coach houses in Lincoln Park and everything in between, we’ve got a wide variety of Chicago vacation rentals so there’s sure to be one that’s just right for you. Whatever your budget, we’ll help you find a great deal. Plus, you can book with confidence - we have plenty of unbiased user reviews of Chicago vacation rentals!
Chicago family vacations
Chicago is a great city for families and a vacation home rental makes it easy to explore all that the second city has to offer. If it’s baseball season, catch a Chicago Cubs game at historic Wrigley Field, one of the oldest ball parks in the country. Or take the kids out to Navy Pier, which features amusement rides, shops and restaurants right on Lake Michigan. If you’re kids are animal lovers, visit the Great Ape House at the Lincoln Park Zoo, where admission is still free. Or see dinosaurs at The Field Museum of Natural History.
Chicago attractions
There's plenty to do in Chicago and a vacation rental in the city will put you within walking distance of most of the city's many attractions. Art lovers will enjoy the Art Institute of Chicago where they can browse the large collection of impressionist and post-impressionist paintings before heading to the newer Modern Wing. After, you’ll want to head over to nearby Millennium Park, which features public art and cultural events year-round. During the warmer months, find a spot on the sand at Oak Street Beach, a great place to people watch with views of downtown skyscrapers and Lake Michigan.
Chicago day trips
For those who want to explore Chicago beyond the city center, there are plenty of short getaways worth exploring, all within an hour or two of your vacation rental. Nearby Oak Park is home to the Frank Lloyd Wright Home and Studio. It’s also the birthplace of Ernest Hemingway. For those looking for outdoor adventure, head south to Starved Rock State Park where you can hike miles of trails through rolling hills or go fishing, boating or horseback riding. Other popular getaways include Lake Geneva in southern Wisconsin or the shores along Lake Michigan outside the city.
Saving money on Chicago vacation rentals
Whether you want to stay in a chic downtown apartment rental in Chicago or a spacious house in the suburbs, we can help you find a deal that fits your budget. There are discounts on every type of property to help you get the most bang for your buck.