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Chicago Vacation Rentals

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    All 18 Rentals in Chicago
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    The following rentals are within 20 miles of Chicago.
    Beautifully Remodeled 3 BR Townhouse near Chicago1 / 30
    (2)Excellent
    Wilmette
    3 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    Oak Park Bungalow1 / 20
    (3)Very good
    Oak Park
    3 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    Oak Park Beauty Sleeps 1 to 8 Guests1 / 14
    (1)Excellent
    Oak Park
    3 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    Forest Park
    4 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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    Amenities & Details
    • Wi-Fi
    • Housekeeping Included
    • Parking
    • DVD Player
    • Grill
    • Balcony
    • Patio
    • Central Heating
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Charming private apartment in the heart of Forest Park! Perfect mix of cozy, chic, & antique! Long term or a quick weekend away! Ideal for couples, solo adventurers, business travelers, families, big groups, even pets! Four bedrooms, spacious living area, beautiful backyard garden with seating for...
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    Forest Park, Illinois 60130
    Condo/Apartment - 4 Bedrooms, 1 Bathroom, Sleeps 5
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    Just north of Chicago1 / 8
    (18)Excellent
    Winnetka
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Washer
    • Wi-Fi
    • Private Yard
    • Air Conditioning
    • Secure Parking
    • Patio
    • DVD Player
    • 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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    Lincolnwood
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Cable/satellite TV
    • Washer
    • Air Conditioning
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    At this Sonder, you'll love the stunning architectural details, luxurious hardwood floors, and a spacious balcony. Located in Lakeview, known for its amazing eateries and relaxed cafes. House Rules 1. All bookings require a security deposit of $300 or more. You will not be charged for this in...
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    Location Information
    Lincolnwood, Illinois 60613
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Downers Grove
    6 Bedrooms, 5 Bathrooms, Sleeps 15 Quick View
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    • Air Conditioning
    • Wi-Fi
    • Private Outdoor Pool (Heated)
    • DVD Player
    • Washer
    • Grill
    • Cable/satellite TV
    • Patio
    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
    • Cable/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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    Condo
    Oak Park
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Cable/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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    Lincolnwood
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Waterfront
    • Wi-Fi
    • Balcony
    • Patio
    • Terrace
    • Cable/satellite TV
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Adeline's Sea Moose hosts over night stays for yacht enthusiasts! This 68 ft luxury charter yacht is one of the few sizable multi-level private Charter yachts in Chicago, and that was built and has maintained a true private yacht. Great care has been taken to uphold the integrity of her styling....
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    Location Information
    Lincolnwood, Illinois 60712
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    Oak Park
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    Amenities & Details
    • 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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    Romantic Burr Ridge Home on 5 Manicured Acres!1 / 24
    (1)Very good
    Burr Ridge
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • DVD Player
    • Washer
    • Cable/satellite TV
    • Wi-Fi
    • Air Conditioning
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    ** Please note that there are exterior cameras surveying the perimeter of this property ** If you’re seeking the perfect spot for a business retreat or family gathering, look no further than this 3-bed, 2-bath Burr Ridge vacation rental! With sleeping for 6 throughout 4,000 square feet of...
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    Location Information
    Burr Ridge, Illinois 60517
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Oak Park
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Amenities & Details
    • Cable/satellite TV
    • Wi-Fi
    • Parking
    • Air Conditioning
    • Private Yard
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    - Safe and quiet residential area by the Oak Park Arts District - Many art shops, two cafes, Italian restaurant and family-friendly activities all within walking distance. - Space is master bedroom on the 2nd floor - Free parking on premise - 15-20 mins Chicago Loop/Downtown by car - 2 mins walk to...
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    Location Information
    Oak Park, Illinois 60304
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Oak Park
    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    • Parking
    • Air Conditioning
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Beautiful Oak Park, IL home of Earnest Hemingway and Frank Lloyd Wright. We boast beautiful homes, superb restaurants, shops and we are next door to Chicago a world class city!! Welcome to my home where you will find comfortable beds, refreshments, conversation and a warm feeling of being...
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    Location Information
    Oak Park, Illinois 60302
    Private Room - 1 Bedroom, 1 Bathroom, Sleeps 3
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    Lombard
    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Washer
    • Central Heating
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Completely renovated, beautiful 4 Bedroom 2 Bath home. Located close to all amenities, grocery store, restaurants Giordano’s famous deep dish pizzeria, Mike Ditka’s steakhouse, Yorktown mall & luxurious Oakbrook shopping mall. Total 5 beds: 2 Queens, 1 twin, 2 queen airbeds (available by request)....
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    Location Information
    Lombard, DuPage County 60148
    Rental Home - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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    Evanston
    1 Bedroom, 2 Bathrooms, Sleeps 3 Quick View
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    Amenities & Details
    • 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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    Location Information
    Evanston, Illinois 60203
    Private Room - 1 Bedroom, 2 Bathrooms, Sleeps 3
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    Lincolnwood
    2 Bedrooms, 3 Bathrooms, Sleeps 4 Quick View
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    Amenities & Details
    • DVD Player
    • Balcony
    • Terrace
    • Air Conditioning
    • Cable/satellite TV
    • Wi-Fi
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Excitement bustles around Chicago as you approach this 2-bedroom, 2.5-bathroom vacation rental townhome! With room to host 4 on beds and other sleeping arrangements, this 3-story home offers 2 living areas, a gourmet kitchen, 2-car garage, and sophisticated decor, creating a luxury accommodation in...
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    Location Information
    Lincolnwood, Illinois 60660
    Rental Home - 2 Bedrooms, 3 Bathrooms, Sleeps 4
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    Summit
    3 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • DVD Player
    • Air Conditioning
    • Cable/satellite TV
    • Grill
    • Washer
    • Hot Tub
    • Patio
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The Map in the ad is wrong and Trip Advisor can't fix it. We are located in the Bridgeport neighborhood just south of downtown Chicago and just West of Guaranteed Rate Field, home of the Chicago White Sox. We are located 5 miles due south from our city center, and 3 miles from our convention...
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    Location Information
    Summit, Illinois 60501
    Condo/Apartment - 3 Bedrooms, 1 Bathroom, Sleeps 6
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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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