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Chicago Holiday Rentals

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    All 15 Rentals in Chicago
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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.
    West Town
    2 Bedrooms, Sleeps 6Quick View
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    The following rentals are within 25 kilometres of Chicago.
    Oak Park
    1 Review
    3 Bedrooms, Sleeps 6Quick View
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    Evanston
    1 Bedroom, Sleeps 3Quick View
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    Hyde Park
    3 Bedrooms, Sleeps 6Quick View
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    Amenities & Details
    • Satellite TV
    • Secure Parking
    • Air Conditioning
    • Wi-Fi
    • Washer
    • Grill
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Great Townhouse at the University of Chicago Sunny, bright 3 bedroom townhouse, located across the street from University of Chicago Campus. The home has a large open concept main floor with kitchen, dinning and living room. Kitchen has a breakfast peninsula. It has two bedrooms with ample closet...
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    Location Information
    Hyde Park, Illinois 60637
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Glenview
    1 Bedroom, Sleeps 2Quick View
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    • Terrace
    • Satellite TV
    • Patio
    • Washer
    • Wi-Fi
    • Balcony
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Suite Home Chicago at ALOFT offers fully furnished apartments. Rates include housekeeping, all taxes, high speed wireless internet, expanded cable, all utilities, linens, towels, and first class customer service. - 24-hour fitness center with Precor equipment, cardio/strength machines, free...
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    Glenview, Illinois 60026
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Evanston
    3 Bedrooms, Sleeps 6Quick View
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    Amenities & Details
    • Terrace
    • Wi-Fi
    • Grill
    • Washer
    • Shared Garden
    • 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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    Evanston, Illinois 60202
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Forest Park
    1 Bedroom, Sleeps 4Quick 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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    Wilmette
    3 Bedrooms, Sleeps 10Quick View
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    Amenities & Details
    • Patio
    • Grill
    • Parking
    • Wi-Fi
    • Air Conditioning
    • Private Garden
    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
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 10
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    Oak Park
    1 Bedroom, Sleeps 1Quick 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, Sleeps 1Quick View
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    Amenities & Details
    • Balcony
    • Wi-Fi
    • Terrace
    • Patio
    • Grill
    • 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...
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    Location Information
    Oak Park, Illinois 60302
    Holiday Rental House - 1 Bedroom, 2 Bathrooms, Sleeps 1
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    River Grove
    1 Bedroom, Sleeps 2Quick View
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    Amenities & Details
    • 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
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Oak Park
    1 Bedroom, Sleeps 1Quick 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
    1 Bedroom, Sleeps 1Quick 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...
    View all property information
    Location Information
    Oak Park, Illinois 60302
    Holiday Rental House - 1 Bedroom, 2 Bathrooms, Sleeps 1
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    Condo
    Oak Park
    2 Bedrooms, Sleeps 4Quick View
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    Amenities & Details
    • 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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    Oak Park
    4 Bedrooms, Sleeps 1Quick View
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    Amenities & Details
    • Wi-Fi
    • Grill
    • Washer
    • Housekeeping Included
    • 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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    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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