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Vacation Rentals in Chicago

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    All 18 Rentals in Chicago
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    The following rentals are within 15 kilometres of Chicago.
    Oak Park Bungalow1 / 20
    (6)Very good
    Oak Park
    3 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    Charming apartment, fantastic location! Spacious 4 bedroom, a rare find!1 / 13
    (2)Very good
    Forest Park
    4 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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    Sleep Aboard Adeline’s Sea Moose: 68 ft Private Yacht Rentals Chicago Downtown1 / 15
    (1)Excellent
    Lincolnwood
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Lincolnwood
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Washer
    • Wi-Fi
    • Air Conditioning
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Contemporary living in Uptown Chicago. Panoramic views of Lake Michigan and downtown Chicago. Enjoy your time in the Bryn Mawr historic district of Uptown surrounded by local shops, cafes and a 3 minute walk to the beach. There are also restaurants and bars just about 10 min walk. Here you’ll find...
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    Lincolnwood, Illinois 60660
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    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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    • Wi-Fi
    • Parking
    • Housekeeping Included
    • Grill
    • Patio
    • Washer
    • Cable/satellite TV
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 30 October 2017
    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 6
    Forest Park
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Air Conditioning
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    Pet friendly
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    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
    Hyde Park
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Parking
    • Cable/satellite TV
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    • DVD Player
    • Private Garden
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    • Washer
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    If you like a unique vibe, good energy, cool experience, eat or learn how to make Sushi or European food, wine, smoothies, fun activities, and tours or just relax in the front of the tv our home is for you! This listing is perfect option for small groups, families, students, organize events and...
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    Hyde Park, Illinois 60637
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    Forest Park
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Central Heating
    • Grill
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    Pet friendly
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    About this property
    ******************************************* Summary ******************************************* 1300 SF renovated APT is 2-3 min away from 290 highway, which takes you downtown in minutes! This property has 3 bedrooms, & 2 bathrooms. Master suite has a king, and the other 2 bedrooms have a Queen....
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    Location Information
    Forest Park, Illinois 60130
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
    Condo
    Oak Park
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Cable/satellite TV
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    Pet friendly
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    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
    Cicero
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    About this property
    Hello our home located 15 minutes drive to downtown Chicago , the place is brand new with all new beds sheets towels the room you will be renting out is have key that you can use to lock your stuff in the room , kitchen living room and bathroom shared with other guest if there is any during your...
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    Cicero, Illinois 60623
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Cicero
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Air Conditioning
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Hello our home located 15 minutes drive to downtown Chicago , the place is brand new with all new beds sheets towels the room you will be renting out is have key that you can use to lock your stuff in the room , kitchen living room and bathroom shared with other guest if there is any during your...
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    Location Information
    Cicero, Illinois 60623
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 2
    Lincolnwood
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    About this property
    Perfect location in Chicago's famous Wrigleyville! Beautiful 3 bedroom, 3 bath on the 1st floor (duplex down) of a Chicago walk-up with high end amenities located in the heart of Wrigleyville. Perfect location for a weekend getaway, business trip, Chicago Cubs game. Fast Wi-Fi included. 1,100+ sq....
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    Lincolnwood, Illinois 60613
    Condo/Apartment - 3 Bedrooms, 3 Bathrooms, Sleeps 8
    Berwyn
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Pet friendly
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    Smoking allowed
    About this property
    Searching for a friendly neighborhood steps away from tons of public amenities and 20 min drive to DT Chicago? Find this at our lively renovated safe and comfortable three bedroom apartment. Plenty of space for stretching and recharge, you will feel right at home with total access to a freshly...
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    Berwyn, Illinois 60402
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
    Lincolnwood
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Cable/satellite TV
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Elegant, spacious and fully furnished 1st floor apartment features 2 bed/1bath. Located on quiet residential street in West Rogers Park, on far North Side of Chicago. Guests will have entire apartment at their disposal during their stay. Tons of natural light. Gourmet kitchen with high end...
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    Lincolnwood, Illinois 60645
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
    Lincolnwood
    2 Bedrooms, 3 Bathrooms, Sleeps 4 Quick View
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    • 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
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 4
    Oak Park
    2 Bedrooms, 1 Bathroom, Sleeps 7 Quick View
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    • Washer
    • Balcony
    • Terrace
    • Air Conditioning
    • Wi-Fi
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Perfect location in one of Chicago's trendiest neighborhoods, Logan Square! Beautiful 2 bedroom, 1 bathroom unit on the 1st floor of a Chicago walk-up with high end amenities located in the Logan Square. Perfect location for a weekend getaway, business trip (12 minute to Logan Square CTA Blue Line...
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    Oak Park, Illinois 60647
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 7
    Oak Park
    3 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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    • Air Conditioning
    • Cable/satellite TV
    • Secure Parking
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    • Private Garden
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This beautifully decorated three bedroom apartment comes with private entry, secured free parking, cable, internet, security & stainless steel appliances. Located on a quiet tree-lined street, with well manicured landscaping we are 5 minutes from the I290 Expressway, 15 minutes from downtown...
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    Oak Park, Illinois 60644
    Condo/Apartment - 3 Bedrooms, 1 Bathroom, Sleeps 5
    Oak Park
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Private Garden
    • Secure Parking
    • Air Conditioning
    • Cable/satellite TV
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This property is unique in alot of ways its in Chicago and walking distance to oak park a suburb of Chicago close to public TRANSPORTATION that will .you to go downtown Chicago and Chicagoland suburbs like oak park river forest etc.with a romantic jetted bathtub.if you like nightlife...
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    Location Information
    Oak Park, Illinois 60644
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
    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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