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Holiday 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.
    All 22 Rentals in Chicago
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    The following rentals are within 30 kilometers of Chicago.
    Historic Chicago Style Bungalow Business Ready1 / 25
    (2)Excellent
    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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    Evanston
    1 Bedroom, 2 Bathrooms, Sleeps 3 Quick View
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    Glencoe
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Washer
    • Patio
    • Grill
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    Pet friendly
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    Smoking allowed
    About this property
    Large and sun-filled family home on Chicago's beautiful north shore with easy access to Lake Michigan beaches, Chicago Botanic Garden and downtown Chicago. Our home offers many inviting spaces, whether you would like to relax in the spacious backyard and patio, enjoy the living room with...
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    Glencoe, Illinois 60022
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    Just north of Chicago1 / 8
    (18)Excellent
    Winnetka
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • DVD Player
    • Air Conditioning
    • Parking
    • Internet Access
    • Patio
    • Washer
    • Satellite TV
    • Shared Garden
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 18 May 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 23 November 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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    Winnetka, Illinois 60093
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Wilmette
    3 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    • 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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    Lombard
    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • Grill
    • DVD Player
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Eclectic furniture, comfortable beds, large yard, 25 minutes to down town Chicago, walking distance to shopping, restaurants and grocery. Large all weather room seats 18. There is only one other house on the block and it is a dead end street so very quiet, adorned by large trees, there is also...
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    Lombard, DuPage County 60148
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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    Burr Ridge
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Washer
    • Air Conditioning
    • Grill
    • DVD Player
    • Internet Access
    • Satellite TV
    • Hot Tub
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    If you’re seeking the perfect spot for your business retreat or family gathering, look no further than this 3-bedroom, 2-bathroom vacation rental house in Burr Ridge! With accommodations for 6 throughout 4,000 square feet of beautifully-appointed living space and a large yard on 5 well-groomed...
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    Burr Ridge, DuPage County 60517
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Downers Grove
    6 Bedrooms, 5 Bathrooms, Sleeps 15 Quick View
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    • Air Conditioning
    • Wi-Fi
    • DVD Player
    • Washer
    • Patio
    • Parking
    • Satellite TV
    • Grill
    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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    Downers Grove, DuPage County 60516
    Holiday Rental House - 6 Bedrooms, 5 Bathrooms, Sleeps 15
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    Oak Park
    3 Bedrooms, 1 Bathroom, Sleeps 9 Quick View
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    • Wi-Fi
    • Parking
    • Housekeeping Included
    • Grill
    • Patio
    • Washer
    • Satellite TV
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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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    Location Information
    Oak Park, Illinois 60302
    Condo/Apartment - 3 Bedrooms, 1 Bathroom, Sleeps 9
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    River Grove
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Air Conditioning
    • Satellite TV
    • Parking
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    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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    River Grove, Illinois 60171
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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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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    Condo
    Oak Park
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • 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
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    Des Plaines
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Central Heating
    • Balcony
    • Housekeeping Included
    • DVD Player
    • Terrace
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Very Clean and Large 2 bed, 1 bath apartment 20 minutes north of downtown Chicago. and 10 minutes from O'Hare Airport. 1st floor, one king bed, two twin beds. Large fully equipped kitchen and Free parking, WiFi, Roku TV, DVD, Wii and Laundry on site (fee). Always fresh towels and linens for...
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    Des Plaines, Illinois 60016
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Calumet Park
    Studio, 2 Bathrooms, Sleeps 8 Quick View
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    • Grill
    • Satellite TV
    • Internet Access
    • Parking
    • Washer
    • DVD Player
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This 3 bedroom, 2 bath townhouse is located in the quiet South end of Stone Harbor. Close to Clarks Market, local eateries and the Bird Sanctuary. Located within an easy walk to one of the most popular beaches on the island. Two bedrooms, a hall bath, laundry area and den are all located on the...
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    Calumet Park, Illinois 08247
    Condo/Apartment - 2 Bathrooms, Sleeps 8
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    Oak Park
    1 Bedroom, 2 Bathrooms, Sleeps 1 Quick View
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    • 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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    Oak Park, Illinois 60302
    Holiday Rental House - 1 Bedroom, 2 Bathrooms, Sleeps 1
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    Riverdale
    Studio, 2 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Grill
    • Satellite TV
    • Air Conditioning
    • Internet Access
    • Washer
    • Parking
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This 3 bedroom, 2 bath upside down style townhouse is located in the South end of Stone Harbor. Close to Clarks Market, local eateries and the Bird Sanctuary. Located within a quick walk to one of the island's most popular beaches.Two bedrooms, a hall bath, laundry area and den are all located on...
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    Location Information
    Riverdale, Illinois 08247
    Condo/Apartment - 2 Bathrooms, Sleeps 8
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    Lombard
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Washer
    • DVD Player
    • Grill
    • Central Heating
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    My place is 30 minutes from downtown Chicago. Located 8 minutes from Oakbrook Center Mall and 15 min from Wheaton College. Plenty of restaurants and dining and family-friendly activities nearby. Large backyard and deck that's great for pets and entertaining! This cozy house gets tons of sunlight...
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    Location Information
    Lombard, DuPage County 60148
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, 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 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...
    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, 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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    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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    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...
    View all property information
    Location Information
    Oak Park, Illinois 60302
    Holiday Rental House - 1 Bedroom, 2 Bathrooms, Sleeps 1
    Make Enquiry
    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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