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Chicago Vacation Rentals

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    All 24 Rentals in Chicago
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    The following rentals are within 15 miles of Chicago.
    Beautifully Remodeled 3 BR Townhouse near Chicago1 / 60
    (1)Excellent
    Wilmette
    3 Bedrooms, 2 Bathrooms, Sleeps 10 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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    Oak Park
    3 Bedrooms, 1 Bathroom, Sleeps 9 Quick View
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    Oak Park
    5 Bedrooms, 3 Bathrooms, Sleeps 11 Quick View
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    • Private Yard
    • Secure Parking
    • Wi-Fi
    • Air Conditioning
    • 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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    Oak Park, Illinois 60302
    Rental Home - 5 Bedrooms, 3 Bathrooms, Sleeps 11
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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
    • Wi-Fi
    • Satellite TV
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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
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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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    Oak Park, Illinois 60302
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    River Grove
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Air Conditioning
    • Satellite TV
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    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
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Evanston
    Studio, 1 Bathroom, Sleeps 4 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Great area Nice room can sleep 2 couples or two people, nice remodeled bathroom and Kitchen , walking distance from train 5 minutes walk License or registration number City registration pending
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    Location Information
    Evanston, Illinois 60626
    Condo/Apartment - 1 Bathroom, Sleeps 4
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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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    Evanston
    Studio, 1 Bathroom, Sleeps 2 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This is a sweet and sensation room with a very comfortable new full size bed and a desk so you can work in your computer, Nice kitchen and any dishes and pots you need for cooking. This place is very private and the entire apartment is rented Airbnb. Good for business trip, students or simply to...
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    Location Information
    Evanston, Illinois 60626
    Condo/Apartment - 1 Bathroom, Sleeps 2
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    Evanston
    Studio, 1 Bathroom, Sleeps 2 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Renovated room with new bed and mattress, nice laptop desk, ceiling fan, nice size closet, lock on the door for privacy, very nice and remodeled kitchen and bathroom. 2 short blocks away to Morse red line, about 25 minutes to downtown Chicago, buses that run 24 hours, close to the lakefront,...
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    Location Information
    Evanston, Illinois 60626
    Condo/Apartment - 1 Bathroom, Sleeps 2
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    Evanston
    Studio, 1 Bathroom, Sleeps 1 Quick View
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    • Wi-Fi
    • Air Conditioning
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Comfortable and completed remodeled Studio apartment, it has a nice queen side bed, a full side sofa bed, a computer desk, a high chair and table. remodeled private bathroom, spacious closet, fresh linen, shampoo, soap. This studio is 5 minutes walking distance to train, 4 blocks from beach,...
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    Location Information
    Evanston, Illinois 60626
    Condo/Apartment - 1 Bathroom, Sleeps 1
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    Oak Park
    4 Bedrooms, 2 Bathrooms, Sleeps 1 Quick View
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    • Wi-Fi
    • Grill
    • Washer
    • Housekeeping Included
    • Satellite TV
    • Private Yard
    • 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...
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    Location Information
    Oak Park, Illinois 60302
    Rental Home - 4 Bedrooms, 2 Bathrooms, Sleeps 1
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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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    • Balcony
    • Wi-Fi
    • Terrace
    • Patio
    • Grill
    • Private Yard
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 2 weeks ago
    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
    Rental Home - 1 Bedroom, 2 Bathrooms, Sleeps 1
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    Evanston
    Studio, 1 Bathroom, Sleeps 2 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This is a very nice room it has private entrance brand new furniture, close to everything you need, shopping, restaurants, bars, museums, Beach, transportation. This apartment is share with other airbnb guests. Very private not a place if you want to socialize with the host or hang out. This a very...
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    Location Information
    Evanston, Illinois 60626
    Condo/Apartment - 1 Bathroom, Sleeps 2
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    Evanston
    Studio, 1 Bathroom, Sleeps 2 Quick View
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This is a nice room with new furniture, private bedroom. Private room has full sized bed, If you are looking to hang out with the host or looking to feel like a family home. this is not the place for you. This place is very private and the other tenants in the apartment are also airbnb guest, This...
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    Location Information
    Evanston, Illinois 60626
    Condo/Apartment - 1 Bathroom, Sleeps 2
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    Evanston
    Studio, 1 Bathroom, Sleeps 2 Quick View
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Nice and cozy private bedroom. Private room has full sized bed with nice space Nice kitchen and any dishes and pots you need for cooking. This place is very private and the entire apartment is rented Airbnb. Good for business trip, students or simply to spent some time in Chicago. It is located on...
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    Location Information
    Evanston, Illinois 60626
    Condo/Apartment - 1 Bathroom, Sleeps 2
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    Evanston
    Studio, 1 Bathroom, Sleeps 2 Quick View
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Renovated room with new bed and mattress, nice laptop desk, ceiling fan, nice size closet, lock on the door for privacy, very nice and remodeled kitchen and bathroom. 2 short blocks away to Morse red line, about 25 minutes to downtown Chicago, buses that run 24 hours, close to the lakefront,...
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    Location Information
    Evanston, Illinois 60626
    Condo/Apartment - 1 Bathroom, Sleeps 2
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    Evanston
    Studio, 1 Bathroom, Sleeps 2 Quick View
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Nice Private room with closet space a very nice Kitchen, comfortable and roomy. Hotel style room. No smoking Not suitable for pets No parties or events Not safe or suitable for children (0-12 years) Check in is anytime after 3PM
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    Location Information
    Evanston, Illinois 60626
    Condo/Apartment - 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 Yard
    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
    Rental Home - 1 Bedroom, 2 Bathrooms, Sleeps 1
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    Oak Park
    1 Bedroom, 2 Bathrooms, Sleeps 1 Quick View
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    Payment Protection
    Amenities & Details
    • Balcony
    • Patio
    • Air Conditioning
    • Wi-Fi
    • Private Yard
    • 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
    Rental Home - 1 Bedroom, 2 Bathrooms, Sleeps 1
    Make Inquiry
    Oak Park
    1 Bedroom, 2 Bathrooms, Sleeps 1 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Grill
    • Terrace
    • Balcony
    • Private Yard
    • 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
    Rental Home - 1 Bedroom, 2 Bathrooms, Sleeps 1
    Make Inquiry
    Evanston
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Amenities & Details
    • Private Yard
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Warm and welcoming family building. It is a 2 apartment building, 2 bedroom, one bath on each floor. located 1 block north of Howard St. With easy access to St. Francis Hospital. L train station is approx 3 blocks away. CTA buses a block away. Eclectic and great restaurants around the block on...
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    Location Information
    Evanston, Illinois 60202
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Chicago Flight and Weather Info
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    Additional Chicago Info

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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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