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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 15 miles of Chicago.
    Beautifully Remodeled 3 BR Townhouse near Chicago1 / 30
    (2)Excellent
    Wilmette
    3 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    Oak Park Bungalow1 / 20
    (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 6 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 October 30, 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
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    Stay and play like a local1 / 24
    (1)Excellent
    Lincolnwood
    5 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • Parking
    • Wi-Fi
    • Washer
    • Air Conditioning
    • Private Yard
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed January 21, 2018
    My family and I stayed at the property twice from Christmas Eve until January 7th, as my son was going through basic training at the Navy Recruit Training Center at Great Lakes...
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    About this property
    Stay and play like a Chicago local in our Northside home. With easy access to Ravenswood, Lincoln Square, Andersonville and Wrigleyville neighborhoods, your options are unlimited! Walk to Gompers Park play tennis or swim. get groceries at nearby Jewel, dine at authentic Mexican restaurants....
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    Lincolnwood, Illinois 60630
    Rental Home - 5 Bedrooms, 3 Bathrooms, Sleeps 10
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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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    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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    Location Information
    Forest Park, Illinois 60130
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Evanston
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Air Conditioning
    • Cable/satellite TV
    • Wi-Fi
    • Parking
    • Private Yard
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Location, Location ,Location. Walk to many restaurants and stores. Take the Clark bus to Cubs Park. One mile to Foster Beach. Bikes for rent nearby. Great apartment to relax and sleep. This is a second floor walk up apartment. We are close to Lake Shore Drive. The CTA Red line, Berwyn stop is...
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    Location Information
    Evanston, Illinois 60640
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Lincolnwood
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Waterfront
    • Wi-Fi
    • Balcony
    • Patio
    • Terrace
    • Cable/satellite TV
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Adeline's Sea Moose hosts over night stays for yacht enthusiasts! This 68 ft luxury charter yacht is one of the few sizable multi-level private Charter yachts in Chicago, and that was built and has maintained a true private yacht. Great care has been taken to uphold the integrity of her styling....
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    Location Information
    Lincolnwood, Illinois 60712
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    Oak Park
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Air Conditioning
    • Wi-Fi
    • Cable/satellite TV
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    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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    Condo
    Oak Park
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Cable/satellite TV
    • Air Conditioning
    • Wi-Fi
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    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
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    Lincolnwood
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Cable/satellite TV
    • Washer
    • Air Conditioning
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    At this Sonder, you'll love the stunning architectural details, luxurious hardwood floors, and a spacious balcony. Located in Lakeview, known for its amazing eateries and relaxed cafes. Lakeview has plenty to offer within walking distance. Try out Toons Bar & Grill or Tango Sur for some of...
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    Location Information
    Lincolnwood, Illinois 60613
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Evanston
    1 Bedroom, 2 Bathrooms, Sleeps 3 Quick View
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    • Private Yard
    • Internet Access
    • Air Conditioning
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The Pinewoods Retreat is home to a small artist community including musicians, painters and acrobats. Here you will find an eclectic yet quiet escape from the fast paced city. We take great pride in the peaceful environment that we have created here and welcome you to share in our retreat. Please...
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    Location Information
    Evanston, Illinois 60203
    Private Room - 1 Bedroom, 2 Bathrooms, Sleeps 3
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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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    Lincolnwood
    2 Bedrooms, 3 Bathrooms, Sleeps 4 Quick View
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    Amenities & Details
    • 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
    Rental Home - 2 Bedrooms, 3 Bathrooms, Sleeps 4
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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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