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Chicago Vacation Rentals

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    All 18 Rentals in Chicago
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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.
    West Town
    2 Bedrooms, Sleeps 6Quick View
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    The following rentals are within 15 miles of Chicago.
    Hyde Park
    3 Bedrooms, Sleeps 6Quick View
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    Glenview
    1 Bedroom, Sleeps 2Quick View
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    Oak Park
    5 of 5 bubbles
    1 Review
    3 Bedrooms, Sleeps 6Quick View
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    • Air Conditioning
    • Private Yard
    • Grill
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    Pet friendly
    Kid friendly
    Smoking allowed
    Excellent of 5 bubbles
    Reviewed 2 weeks ago
    This was a beautiful home, very modern! The house provided all of the comforts of home! The owner was very accommodating and super nice. This was our first trip to the Chicago...
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    About this property
    Oak Park Duplex. This charming Oak Park Duplex offers a quiet relaxing environment to unwind after a busy day of site seeing in Chicago or enjoying the historic beauty of Oak Park. The home has been divided into two units. The top two floors (Duplex) are the rental space above a garden...
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    Oak Park, Illinois 60304
    Rental Home - 3 Bedrooms, 1 Bathroom, Sleeps 6
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    Wilmette
    3 Bedrooms, Sleeps 10Quick 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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    Evanston
    1 Bedroom, Sleeps 3Quick View
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    • Private Yard
    • Internet Access
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    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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    Location Information
    Evanston, Illinois 60203
    Private Room - 1 Bedroom, 2 Bathrooms, Sleeps 3
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    Evanston
    3 Bedrooms, Sleeps 6Quick View
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    • Terrace
    • Wi-Fi
    • Grill
    • Washer
    • Shared Yard
    • Air Conditioning
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Suite Home Chicago at AMLI Evanston offers fully furnished apartments. Rates include housekeeping, all taxes, high speed wireless internet, expanded cable, all utilities, linens, towels, and first class customer service. Located near the heart of Evanston and just blocks away from Lake Michigan,...
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    Location Information
    Evanston, Illinois 60202
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    River Grove
    1 Bedroom, Sleeps 2Quick View
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    • Air Conditioning
    • Satellite TV
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    Pet friendly
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    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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    Forest Park
    1 Bedroom, Sleeps 4Quick 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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    Location Information
    Forest Park, Illinois 60130
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Lincolnwood
    1 Bedroom, Sleeps 2Quick View
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    • Secure Parking
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    Pet friendly
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    Smoking allowed
    About this property
    Hi ! This is a beautifully furnished room in a beautiful area of Chicago ! It is a gorgeous condo, with a Target across the street and a doorman here aswell. The room you are renting is incredibly spacious, and you have your own bathroom too! It's a dream! 16 foot ceilings, in unit washer and...
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    Lincolnwood, Illinois 60645
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Condo
    Oak Park
    2 Bedrooms, Sleeps 4Quick View
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    • Satellite TV
    • Air Conditioning
    • Wi-Fi
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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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    Location Information
    Oak Park, Illinois 60302
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    Hyde Park
    1 Bedroom, Sleeps 6Quick View
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    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    I have a extra room in my basement that I am renting out. The renter will have full access of the basement. There is a fulll bath and a laundry room. The only restriction is that pets are not allowed and that I ask the renter to please keep their shoes off in the house. If there is any additional...
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    Location Information
    Hyde Park, Illinois 60609
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 6
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    Oak Park
    1 Bedroom, Sleeps 1Quick 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, Sleeps 1Quick 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...
    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, Sleeps 1Quick 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, Sleeps 1Quick View
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    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
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    Oak Park
    4 Bedrooms, Sleeps 1Quick 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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    Location Information
    Oak Park, Illinois 60302
    Rental Home - 4 Bedrooms, 2 Bathrooms, Sleeps 1
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    Hyde Park
    1 Bedroom, Sleeps 2Quick View
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    • Parking
    • Shared Indoor Pool
    • Air Conditioning
    • Wi-Fi
    • Private Yard
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The perfect one bedroom for two! Just a hop to Navy Pier, Lake Michigan, Magnificent Mile, tons of restaurants and bars, museums, the bean, and easy access to public transit and plenty more. In need of parking? Ask about the attached garage parking for as low as $36 per day!
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    Location Information
    Hyde Park, Illinois 60615
    Condo/Apartment - 1 Bedroom, 2 Bathrooms, Sleeps 2
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    • Peak travel: March
    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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