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Chicago Holiday Rentals

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    Don't let other travellers get your favourite Chicago area holiday 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 15 kilometres of Chicago.
    Forest Park
    1 Bedroom, 1 Bathroom, Sleeps 4 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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    Forest Park
    4 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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    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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    Amenities & Details
    • Wi-Fi
    • Parking
    • Housekeeping Included
    • Grill
    • Patio
    • Washer
    • Cable/satellite TV
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 3 weeks ago
    We enjoyed our one-night stay at the house. The hosts were wonderful, the house was immaculately clean, everything was provided for. Plenty of linens and blankets, the kitchen...
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    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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    Oak Park, Illinois 60302
    Condo/Apartment - 3 Bedrooms, 1 Bathroom, Sleeps 9
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    Oak Park
    5 Bedrooms, 3 Bathrooms, Sleeps 11 Quick View
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    Amenities & Details
    • Private Garden
    • Secure Parking
    • Wi-Fi
    • Air Conditioning
    • Cable/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
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 11
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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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    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
    Holiday Rental House - 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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    Amenities & Details
    • Balcony
    • Wi-Fi
    • Terrace
    • Patio
    • Grill
    • Private Garden
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 4 October 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
    Holiday Rental House - 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 Garden
    • 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
    Holiday Rental House - 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 Garden
    • 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
    Holiday Rental House - 1 Bedroom, 2 Bathrooms, Sleeps 1
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    Oak Park
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Amenities & Details
    • 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, 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
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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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 Garden
    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
    Holiday Rental House - 1 Bedroom, 2 Bathrooms, Sleeps 1
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    Oak Park
    4 Bedrooms, 2 Bathrooms, Sleeps 1 Quick View
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    Payment Protection
    Amenities & Details
    • Wi-Fi
    • Grill
    • Washer
    • Housekeeping Included
    • Cable/satellite TV
    • Private Garden
    • 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
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 1
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    Lincolnwood
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Amenities & Details
    • 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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    Chicago Holiday Rentals

    Located on the shores of Lake Michigan, Chicago is a stunning city bursting with attractions. Accommodation can be pricey, but choosing a rental property rather than a hotel is the ideal way to save money. Whether you prefer a spacious apartment in the city centre or a family house in a quieter area, you will feel relaxed and be able to organise your schedule as it suits you. You will of course find a host of restaurants catering to all tastes, but when you are tired of eating out, you can prepare your own food in a fully equipped kitchen.

    Chicago attractions

    You might not know where to begin seeing the sights of Chicago, so take a trolley tour to give you and your family an overview. A Wellenda Boat tour along the Chicago River and Lake Michigan is another wonderful way to see the city's architecture. Don't miss the Magnificent Mile, where the John Hancock Observatory offers spectacular views of the skyscrapers and Lake Michigan beyond. Art lovers should make a beeline for the Art Institute of Chicago, with its world-class collections of French and American Impressionists and Dutch Masters. The whole family will enjoy a visit to Millennium Park, where the star attractions are the Crown Fountain and the Chicago Bean, an enormous silver sculpture. You can try out the restaurant there, and you might be lucky enough to catch a music festival as well.

    Chicago holiday rentals for families

    Animal lovers must find time to visit Lincoln Park Zoo, where the Regenstein African Ape Centre, the Kovler Lion House and the Primate House will impress. The youngest members of the family will find the sea lions and penguins especially entertaining to watch. Before you leave Lincoln Park, children will love a visit to Adams Playground. If the weather calls for an indoor activity, head for Chicago Children's Museum at Navy Pier with its interactive exhibits. When you feel like a break from the city, spend some time on one of Lake Michigan's beaches, where you can swim, sunbathe, or go kayaking or canoeing.

    Budget holiday rentals in Chicago

    For a holiday in a vibrant city, Chicago is hard to beat. Hotels can be expensive, but renting your accommodation is the ideal low-cost alternative. Decide whether you would rather be in the city centre within walking distance of the attractions or in the quieter suburbs. Then have a look at our range of apartments and houses and choose the one that suits you best. It's worth reading through our unbiased customer reviews to help you. After that, you can look forward to what promises to be a holiday to remember in Chicago.

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