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Chicago: Vacation Rental By Owner

Search result 1 to 20 Of 548
  • Property-1 Image 1
    Studio Select Dates for Price
    • 1Baths
    Chicago, IL

    Same day reservations accepted! Just send an inquiry and I'll make it happen. This is an amazing studio in the gold coast near everything! This is 2 blocks away... ...more

  • Property-2 Image 1
    Studio Select Dates for Price
    • 1Baths
    Chicago, IL

    Sun-filled third floor studio on a quiet and safe culdesac, tucked around the corner from the best of Hyde Park. 7 min walk to the Metra, 20 mins to downtown by... ...more

  • Property-3 Image 1
    Apartment Select Dates for Price
    • 3Bed
    • 2Baths
    • (1) Exceptional
    Chicago, IL

    • Luxury apartment located In Irving Park • 12 minutes to Aragon Ballroom • 12 minutes to Wrigley Field • 18 minutes to Chicago Downtown • Complimentary quality... ...more

  • Property-4 Image 1
    Apartment Select Dates for Price
    • 3Bed
    • 1Baths
    Chicago, IL

    Come and enjoy Chicago. Stay in your own apartment set up for you and your small group to lounge and get a comfortable nights rest every night. Whether you’re... ...more

  • Property-5 Image 1
    Apartment Select Dates for Price
    • 3Bed
    • 1Baths
    Chicago, IL

    Our family-friendly apartment will welcome you with all the amenities you will need for your Chicago visit. Located in the heart of Little Italy, easily a 5... ...more

  • Property-6 Image 1
    Condo Select Dates for Price
    • 3Bed
    • 1Baths
    • (1) Exceptional
    Chicago, IL

    We have 3 night min. Please don't ask or try for 1 or 2 night booking we will not accept and decline your request. Thank you. Located in Chicago’s Andersonville... ...more

  • Property-7 Image 1
    Apartment Select Dates for Price
    • 3Bed
    • 1Baths
    Chicago, IL

    Spacious stay in the Bridgeport Neighborhood. Short drive to The McCormick Place & Chinatown. Short drive to Downtown, Millenium Park, United Center and walking... ...more

  • Property-8 Image 1
    Apartment Select Dates for Price
    • 3Bed
    • 2Baths
    • (1) Exceptional
    Chicago, IL

    Stunning 2,500 square foot brick-and-timber luxury loft with 15 foot ceilings located in the heart of the vibrant West Loop neighborhood. This designer 3 bedroom... ...more

  • Property-9 Image 1
    Apartment Select Dates for Price
    • 3Bed
    • 1Baths
    Chicago, IL

    Gracefully furnished and conveniently located vintage Chicago! Enjoy a neighborhood feel with easy access to O'Hare, downtown, and everything in between. Walk to... ...more

  • Property-10 Image 1
    Apartment Select Dates for Price
    • 3Bed
    • 3Baths
    • (3) Very Good
    Chicago, IL

    This newly renovated, luxurious three bedroom loft is located in the heart of Downtown in a safe neighborhood with a lot of restaurants, cafes, and nightlife. It... ...more

  • Property-11 Image 1
    House Select Dates for Price
    • 3Bed
    • 1Baths
    Chicago, IL

    Entire spacious second floor apartment on a quiet street - 3 minutes from expressway, 6 minutes from Chinatown, 10 minutes from downtown. CTA bus runs one block... ...more

  • Property-12 Image 1
    Condo Select Dates for Price
    • 1Bed
    • 1Baths
    Chicago, IL

    Trendy midcentury space in hip Logan Square. Just steps away from the hottest neighborhood in Chicago. Hot restaurants, shops and bars just a block away. Guests... ...more

  • Property-13 Image 1
    Apartment Select Dates for Price
    • 6Bed
    • 7Baths
    Chicago, IL

    Connected by a hallway, these two, separate luxurious 3 BDR lofts combine to make a massive 5,000 sq. ft. 6 BDR mega-home perfect for bigger groups looking for a... ...more

  • Property-14 Image 1
    Apartment Select Dates for Price
    • 2Bed
    • 1Baths
    Chicago, IL

    This large sunny unit is nestled in the heart of the up-and-coming Woodlawn area. Steps away from the University of Chicago School & Hospitals, Washington Park,... ...more

  • Property-15 Image 1
    Apartment Select Dates for Price
    • 2Bed
    • 2Baths
    Chicago, IL

    • 75 Transit Score (Transit is convenient for most trips.) • 74 Bike Score (Very Bikeable ) • Super Fast Business wi-fi • Fully equipped kitchen • Extremely safe... ...more

  • Property-16 Image 1
    Apartment Select Dates for Price
    • 3Bed
    • 1Baths
    Chicago, IL

    • Private room in a freshly remodeled Luxury 3BR apartment located In Irving Park • 12 minutes to Aragon Ballroom • 10 minutes to Logan Square • 18 minutes to... ...more

  • Property-17 Image 1
    House Select Dates for Price
    • 5Bed
    • 2Baths
    • (3) Exceptional
    Chicago, IL

    This 5BR Chicago Brewing District haven is perfect for your next Chicago adventure. Newly renovated and walking distance from some of the best breweries in... ...more

  • Property-18 Image 1
    Condo Select Dates for Price
    • 1Bed
    • 1Baths
    Chicago, IL

    Property Location With a stay at this condo in Chicago (Logan Square), you'll be within a 15-minute drive of DePaul University-Lincoln Park and Humboldt Park.... ...more

  • Property-19 Image 1
    House Select Dates for Price
    • 4Bed
    • 2Baths
    Chicago, IL

    This beautiful two-story unit is tucked away on a quiet tree lined city block! Ukrainian Village is one of the hottest neighborhoods in Chicago and the United... ...more

  • Property-20 Image 1
    Apartment Select Dates for Price
    • 3Bed
    • 1Baths
    • (1)
    Chicago, IL

    Located on the 2nd floor, this unique spacious apartment in Chicago has accommodations with free WiFi, 5 miles from Wrigley Field, 7 miles from Lincoln Park Zoo... ...more

Vacation Rental Filters are an easy way to help you personalize your search to find the ideal rental in Chicago. Many accommodations in Chicago provide "Non Smoking Only", there are 705, or there are 608 of Vacation Rentals in Chicago with a "Pets Not Allowed", there are also 557 with "Children Welcome", which is another great reason to visit Chicago.

We analyzed price data and rendered them in this graph, which shows vacation rental prices for the next twelve months in Chicago. The most expensive month of the next 12 months is in January, where prices hit an average of $275 a night. In December, prices will hit an average low of $150 per night.