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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 22 Rentals in Chicago
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    The following rentals are within 20 miles of Chicago.
    Historic Chicago Style Bungalow Business Ready1 / 25
    (2)Excellent
    Oak Park
    3 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    Oak Park
    5 Bedrooms, 3 Bathrooms, Sleeps 11 Quick View
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    Evanston
    1 Bedroom, 2 Bathrooms, Sleeps 3 Quick View
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    Glencoe
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Washer
    • Patio
    • Grill
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Large and sun-filled family home on Chicago's beautiful north shore with easy access to Lake Michigan beaches, Chicago Botanic Garden and downtown Chicago. Our home offers many inviting spaces, whether you would like to relax in the spacious backyard and patio, enjoy the living room with...
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    Glencoe, Illinois 60022
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    Just north of Chicago1 / 8
    (18)Excellent
    Winnetka
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • DVD Player
    • Air Conditioning
    • Parking
    • Internet Access
    • Patio
    • Washer
    • Satellite TV
    • Shared Yard
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed May 17, 2017
    Loved this place. It was perfect for a family vacation for my husband, myself and our two early 20 year old sons. Cottage was very well equipped, convenient to the Metra to...
    Reviewed November 23, 2016
    Cottage is cozy, convenient to trains, and in a charming residential neighborhood. Wonderful owners too.
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    About this property
    Our 2 Bedroom Cottage has a private brick patio, full kitchen, full bath, window Ac and wifi. We are walking distance to train, buses, village of Winnetka, beaches and parks. This is a lovely, quiet, tree lined suburb 19 miles (31km) north of downtown Chicago. Trains/buses make access to Chicago...
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    Location Information
    Winnetka, Illinois 60093
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    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
    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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    Lombard
    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • Grill
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Eclectic furniture, comfortable beds, large yard, 25 minutes to down town Chicago, walking distance to shopping, restaurants and grocery. Large all weather room seats 18. There is only one other house on the block and it is a dead end street so very quiet, adorned by large trees, there is also...
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    Lombard, DuPage County 60148
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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    Burr Ridge
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Washer
    • Air Conditioning
    • Grill
    • DVD Player
    • Internet Access
    • Satellite TV
    • Hot Tub
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    If you’re seeking the perfect spot for your business retreat or family gathering, look no further than this 3-bedroom, 2-bathroom vacation rental house in Burr Ridge! With accommodations for 6 throughout 4,000 square feet of beautifully-appointed living space and a large yard on 5 well-groomed...
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    Location Information
    Burr Ridge, DuPage County 60517
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Des Plaines
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Central Heating
    • Balcony
    • Housekeeping Included
    • DVD Player
    • Terrace
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Very Clean and Large 2 bed, 1 bath apartment 20 minutes north of downtown Chicago. and 10 minutes from O'Hare Airport. 1st floor, one king bed, two twin beds. Large fully equipped kitchen and Free parking, WiFi, Roku TV, DVD, Wii and Laundry on site (fee). Always fresh towels and linens for...
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    Location Information
    Des Plaines, Illinois 60016
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Condo
    Oak Park
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Satellite TV
    • Air Conditioning
    • Wi-Fi
    Suitability
    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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    Location Information
    Oak Park, Illinois 60302
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    Downers Grove
    6 Bedrooms, 5 Bathrooms, Sleeps 15 Quick View
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    • Air Conditioning
    • Wi-Fi
    • DVD Player
    • Washer
    • Patio
    • Parking
    • Satellite TV
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This 5000 square foot classic Colonial home is located in a private cul-de-sac on an acre of picturesque greens, trees, perennial garden and in ground pool. Its western suburban Chicago location is minutes from major expressways and Metra making quick and easy access to all Chicagoland has to...
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    Location Information
    Downers Grove, DuPage County 60516
    Rental Home - 6 Bedrooms, 5 Bathrooms, Sleeps 15
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    Forest Park
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Air Conditioning
    • Wi-Fi
    • Satellite TV
    Suitability
    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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    Location Information
    Forest Park, Illinois 60130
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    River Grove
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Air Conditioning
    • Satellite TV
    • Parking
    • Wi-Fi
    Suitability
    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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    Location Information
    River Grove, Illinois 60171
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 2
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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, 2 Bathrooms, Sleeps 1 Quick View
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    Amenities & Details
    • 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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    Location Information
    Oak Park, Illinois 60302
    Rental Home - 1 Bedroom, 2 Bathrooms, Sleeps 1
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    Oak Park
    1 Bedroom, 2 Bathrooms, Sleeps 1 Quick View
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    Amenities & Details
    • Grill
    • Terrace
    • Balcony
    • Private Yard
    • Wi-Fi
    • Patio
    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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    Riverdale
    Studio, 2 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Grill
    • Satellite TV
    • Air Conditioning
    • Internet Access
    • Washer
    • Parking
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This 3 bedroom, 2 bath upside down style townhouse is located in the South end of Stone Harbor. Close to Clarks Market, local eateries and the Bird Sanctuary. Located within a quick walk to one of the island's most popular beaches.Two bedrooms, a hall bath, laundry area and den are all located on...
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    Location Information
    Riverdale, Illinois 08247
    Condo/Apartment - 2 Bathrooms, Sleeps 8
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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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    Lombard
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Washer
    • DVD Player
    • Grill
    • Central Heating
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    My place is 30 minutes from downtown Chicago. Located 8 minutes from Oakbrook Center Mall and 15 min from Wheaton College. Plenty of restaurants and dining and family-friendly activities nearby. Large backyard and deck that's great for pets and entertaining! This cozy house gets tons of sunlight...
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    Location Information
    Lombard, DuPage County 60148
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Oak Park
    4 Bedrooms, 2 Bathrooms, Sleeps 1 Quick View
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    Amenities & Details
    • 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...
    View all property information
    Location Information
    Oak Park, Illinois 60302
    Rental Home - 4 Bedrooms, 2 Bathrooms, Sleeps 1
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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...
    View all property information
    Location Information
    Oak Park, Illinois 60302
    Rental Home - 1 Bedroom, 2 Bathrooms, Sleeps 1
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    Oak Park
    1 Bedroom, 2 Bathrooms, Sleeps 1 Quick View
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    Payment Protection
    Amenities & Details
    • Balcony
    • Patio
    • Air Conditioning
    • Wi-Fi
    • Private Yard
    • Terrace
    • Grill
    • Washer
    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...
    View all property information
    Location Information
    Oak Park, Illinois 60302
    Rental Home - 1 Bedroom, 2 Bathrooms, Sleeps 1
    Make Inquiry
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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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