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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 15 Rentals in Chicago
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    The following rentals are within 10 miles of Chicago.
    Oak Park Beauty Sleeps 1 to 8 Guests1 / 14
    (1)Excellent
    Oak Park
    3 Bedrooms, 1 Bathroom, Sleeps 9 Quick View
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    Historic Chicago Style Bungalow Business Ready1 / 25
    (3)Very good
    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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    Forest Park
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Air Conditioning
    • Wi-Fi
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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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    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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    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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    Oak Park, Illinois 60302
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    Humphrey Homestay - Yellow Room, Bed 11 / 7
    (1)Excellent
    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
    Reviewed October 4, 2017
    If you are looking for an accommodation in Chicago, I recommend you the Humphrey Homestay located in the west of the city. You will settle in Oak Park, a wealthy village marking...
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    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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    Forest Park
    4 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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    • Central Heating
    • Grill
    • Terrace
    • DVD Player
    • Balcony
    • Housekeeping Included
    • Patio
    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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    Oak Park
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Parking
    • Air Conditioning
    • Wi-Fi
    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 - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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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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    Oak Park
    1 Bedroom, 2 Bathrooms, Sleeps 1 Quick 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...
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    Location Information
    Oak Park, Illinois 60302
    Rental Home - 1 Bedroom, 2 Bathrooms, Sleeps 1
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    Lincolnwood
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Central Heating
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    My place is a short walk to Kimball CTA Brown Line, which will get you downtown in about 30 minutes. My place is good for couples, solo adventurers, and business travelers. One bedroom with TV, large living room with TV and wireless Bluetooth soundbar if you want to play music, nice kitchen with...
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    Location Information
    Lincolnwood, Illinois 60625
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Oak Park
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Amenities & Details
    • Air Conditioning
    • Wi-Fi
    • Cable/satellite TV
    • Parking
    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
    4 Bedrooms, 2 Bathrooms, Sleeps 1 Quick View
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    Amenities & Details
    • Wi-Fi
    • Grill
    • Washer
    • Housekeeping Included
    • Cable/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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    Show Prices
    Payment Protection
    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
    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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