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Chicago Vacation Rentals

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    Don't let other travelers get your favorite Chicago area vacation rental. You're so close to securing your perfect getaway. Book today.
    All 16 Rentals in Chicago
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    The following rentals are within 15 miles of Chicago.
    Historic Chicago Style Bungalow Business Ready1 / 25
    (2)Excellent
    Popular84 views in the past week
    Oak Park
    3 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    Oak Park
    1 Bedroom, 2 Bathrooms, Sleeps 1 Quick View
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    Oak Park
    1 Bedroom, 2 Bathrooms, Sleeps 1 Quick View
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    Oak Park
    1 Bedroom, 2 Bathrooms, Sleeps 1 Quick View
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    • Balcony
    • Wi-Fi
    • Terrace
    • Patio
    • Grill
    • Private Yard
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Located just west of Chicago - Oak Park is a historic neighborhood 30 minutes from downtown. Humphrey Homestay provides a residence for international students or medical students completing rotations in the Chicagoland area. We provide home cooked meals, all utilities including high speed wifi, in...
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    Oak Park, Illinois 60302
    Rental Home - 1 Bedroom, 2 Bathrooms, Sleeps 1
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    Forest Park
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Air Conditioning
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Spacious 1 bedroom suite with a big screen TV, a super comfy bed & the convenience of cooking your own meals (oven, frig & microwave in your kitchen). Located on a wonderfully quiet residential block, very close to public trans and expressway. Downtown Chicago & O'Hare airport are one train ride...
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    Forest Park, Illinois 60130
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Beautifully Remodeled 3 BR Townhouse near Chicago1 / 60
    (1)Excellent
    Wilmette
    3 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    • Patio
    • Grill
    • Parking
    • Wi-Fi
    • Air Conditioning
    • Private Yard
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 4 weeks ago
    Very great home! Relaxing, extremely clean & so much space! Overall made my stay back home a delightful experiance!
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    About this property
    Contemporary 3 BR Townhouse with granite-countertop kitchen and a peaceful, private backyard in the safe and beautiful Wilmette neighborhood. Walk to Walgreens, Fresh Mart, and many shops & restaurants. Just 1 min. to 94 Highway Lake Ave. Exit, 10 min. to Lake Michigan & Botanic Garden, and 20 min....
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    Wilmette, Illinois 60091
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 10
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    Condo
    Oak Park
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Satellite TV
    • Air Conditioning
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    When traveling and looking for an upscale location. Oak Park offer a great traveler great food, entertainment, relaxing environment. Safe and a wide array of guided tours, Frank Lloyd Widget homes is just the start. My condo has two room with king bed half bath master bedroom, 2 bedroom has queen...
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    Oak Park, Illinois 60302
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    Oak Park
    4 Bedrooms, 2 Bathrooms, Sleeps 1 Quick View
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    • Wi-Fi
    • Grill
    • Washer
    • Housekeeping Included
    • Satellite TV
    • Private Yard
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Located just west of Chicago - Oak Park is a historic neighborhood 30 minutes from downtown. Humphrey Homestay provides a residence for international students or medical students completing rotations in the Chicagoland area. We provide home cooked meals, all utilities including high speed wifi, in...
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    Oak Park, Illinois 60302
    Rental Home - 4 Bedrooms, 2 Bathrooms, Sleeps 1
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    River Grove
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Air Conditioning
    • Satellite TV
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The house is partially SHARED and a few blocks from the Metra Station as well as buses. You’ll love this place because of the location, the ambiance, and the outdoors space. It is good for couples, solo adventurers, and business travelers. River Grove community is nice and quiet, just that perfect...
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    River Grove, Illinois 60171
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Oak Park
    5 Bedrooms, 3 Bathrooms, Sleeps 11 Quick View
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    • Private Yard
    • Secure Parking
    • Wi-Fi
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    • Satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This house is simply beautiful on a tree lined street located in the Historic District of Oak Park. This home is spacious, comfortable, with nice art pieces, bright and clean. Central air conditioning. Huge privacy fenced yard with a trampoline and grill, patio. 10 minutes from downtown Chicago,...
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    Location Information
    Oak Park, Illinois 60302
    Rental Home - 5 Bedrooms, 3 Bathrooms, Sleeps 11
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    Oak Park
    1 Bedroom, 2 Bathrooms, Sleeps 1 Quick View
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    Amenities & Details
    • Grill
    • Wi-Fi
    • Balcony
    • Terrace
    • Patio
    • Private Yard
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Located just west of Chicago - Oak Park is a historic neighborhood 30 minutes from downtown. Humphrey Homestay provides a residence for international students or medical students completing rotations in the Chicagoland area. We provide home cooked meals, all utilities including high speed wifi, in...
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    Location Information
    Oak Park, Illinois 60302
    Rental Home - 1 Bedroom, 2 Bathrooms, Sleeps 1
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    Evanston
    1 Bedroom, 2 Bathrooms, Sleeps 3 Quick View
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    • Private Yard
    • Internet Access
    • Air Conditioning
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The Pinewoods Retreat is home to a small artist community including musicians, painters and acrobats. Here you will find an eclectic yet quiet escape from the fast paced city. We take great pride in the peaceful environment that we have created here and welcome you to share in our retreat. Please...
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    Evanston, Illinois 60203
    Private Room - 1 Bedroom, 2 Bathrooms, Sleeps 3
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    Hyde Park
    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    • Private Yard
    • Secure Parking
    • Air Conditioning
    • Internet Access
    • Washer
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    One bedroom garden condo located in the North Kenwood/Oakland community in Chicago. Direct views of Lake Michigan and one block away from Lake Shore Drive. Easy access to beach and lakefront bike and running paths. Centered within a 5-7 minute radius to downtown, Museum Campus, McCormick Place...
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    Location Information
    Hyde Park, Illinois 60653
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 3
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    Oak Park
    3 Bedrooms, 1 Bathroom, Sleeps 9 Quick View
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    Amenities & Details
    • Wi-Fi
    • Parking
    • Housekeeping Included
    • Grill
    • Patio
    • Washer
    • Satellite TV
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Come relax in OAK PARK (OP) after a long day of shopping on Michigan Avenue, sightseeing in Chicago, or family gatherings. Just 10 minutes from downtown Chicago, Oak Park, and our flat offers the best of both worlds at a price you can afford. Just blocks from 2 train lines to Chicago. Pristine,...
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    Location Information
    Oak Park, Illinois 60302
    Condo/Apartment - 3 Bedrooms, 1 Bathroom, Sleeps 9
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    Oak Park
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Patio
    • Grill
    • Central Heating
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Eclectic Artists Flat Close2Chicago & Fitzgerald's Live Music Club Located near the Oak Park Arts District, this living space is located on the second floor of a brick home. The flat is colorful and filled with art with an eclectic ambiance. Very large rooms and spacious bathroom. 1.5 Baths. A...
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    Location Information
    Oak Park, Illinois 60304
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Calumet Park
    Studio, 2 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Grill
    • Satellite TV
    • Internet Access
    • Parking
    • Washer
    • DVD Player
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This 3 bedroom, 2 bath townhouse is located in the quiet South end of Stone Harbor. Close to Clarks Market, local eateries and the Bird Sanctuary. Located within an easy walk to one of the most popular beaches on the island. Two bedrooms, a hall bath, laundry area and den are all located on the...
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    Location Information
    Calumet Park, Illinois 08247
    Condo/Apartment - 2 Bathrooms, Sleeps 8
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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.

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