Chicago: Vacation Rental By Owner

Showing 20 Of 526 Vacation Rentals
  • Property-1 Image 1
    Apartment Select Dates for Price
    • 2 Bed
    • 1 Baths
    Chicago, IL

    Hyde Park is home to the University of Chicago, the kind of place where they discover the universe is expanding. Expand your own cultural universe when you stay... ...more

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

    When you stay at this spacious top-floor three-bedroom suite in Wicker Park, you’ll be the guest of permanent residents Bill Murray and John Oliver—or their... ...more

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

    Studio living doesn’t have to be the cramped yet sparse nightmare of your younger years: this hip, modern unit manages to pack every amenity and home comfort you... ...more

  • Property-4 Image 1
    Apartment Select Dates for Price
    • 1 Baths
    • (2) Exceptional
    Chicago, IL

    If you’re a science buff, this is the perfect spot for you—just a four-minute walk from the Museum of Science and Industry. Catch a few exhibits at the Museum,... ...more

  • Property-5 Image 1
    Apartment $79 / Nightly
    • 1 Bed
    • 1 Baths
    • (4) Very Good
    Chicago, IL

    Crisp and clean, this Ravenswood one-bedroom has a luxurious queen bed, full kitchen, tons of natural light, and a pretty serious leather chair. In fact, it’s... ...more

  • Property-6 Image 1
    Apartment Select Dates for Price
    • 1 Bed
    • 1 Baths
    • (3) Very Good
    Chicago, IL

    This simple, modern one bedroom Hyde Park suite has a lot going for it: luxurious queen bed, full kitchen, spacious living area, and even a work corner and desk.... ...more

  • Property-7 Image 1
    Apartment $166 / Nightly
    • 1 Bed
    • 1 Baths
    • (1) Exceptional
    Chicago, IL

    When it comes to simple comfort, this place has everything you need. Minimalist decor, retro kitchen, and classy furnishings keep this no-nonsense spot modern and... ...more

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

    Get cozy with a stay at this welcoming two bedroom suite in Hyde Park. Decorated in soft earth-tones and neutrals, this suite boasts hardwood flooring, updated... ...more

  • Property-9 Image 1
    Apartment Select Dates for Price
    • 1 Bed
    • 2 Baths
    • (5) Exceptional
    Chicago, IL

    A sense of glamour pervades this South Loop suite with a magnificent view of the Chicago skyline. Polished with art deco flair, this one-bedroom loft possesses... ...more

  • Property-10 Image 1
    Apartment Select Dates for Price
    • 2 Bed
    • 1 Baths
    Chicago, IL

    This is acute place to stay that appeals to anyone. Triangulate your position in one of Chicago’s hottest neighborhoods with this... ...more

  • Property-11 Image 1
    Apartment Select Dates for Price
    • 1 Bed
    • 1 Baths
    • (1) Very Good
    Chicago, IL

    This spacious one-bedroom home includes a full kitchen, one bathroom, and marble stoned bathroom. Enjoy extra lounge space in the large bedroom, luxury fixtures,... ...more

  • Property-12 Image 1
    Apartment Select Dates for Price
    • 1 Baths
    • (1) Exceptional
    Chicago, IL

    Just a long line drive and outfielder’s throw away from fabled Wrigley Field (home of the Chicago Cubs, doncha know?) this home away from home (plate) has all the... ...more

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

    Steep yourself in city luxury with this suite located in the South Loop. With high ceilings, granite countertops, a private balcony, and even a rooftop pool, this... ...more

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

    Enjoy green space galore with this apartment! Overlooking Jackson Park, a 600-acre green space that borders Lake Michigan and provides city-dwellers with a... ...more

  • Property-15 Image 1
    Apartment Select Dates for Price
    • 3 Bed
    • 1 Baths
    • (1) Exceptional
    Chicago, IL

    You’ve had some bright ideas in your time, but securing this airy, spacious three-bedroom unit in Lakeview is sure to rank as one of the more luminous bulbs ever... ...more

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

    Views galore! This cozy corner 2-bedroom apartment features a beautiful panoramic view of all Hyde Park has to offer. Take full advantage of a spacious living... ...more

  • Property-17 Image 1
    Apartment Select Dates for Price
    • 2 Bed
    • 1 Baths
    Chicago, IL

    Seeking city views from the comfort of a Chicago apartment? Look no further than this lavish corner suite. With an abundance of natural lighting, bold leather... ...more

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

    Welcome to Chicago, home of the World Series Champs, the Cubs. Our 1BR/1BA condo is a perfect place to stay on any Chicago getaway, whether business or vacation.... ...more

  • Property-19 Image 1
    Condo $450 / Nightly
    • 3 Bed
    • 2 Baths
    • (184) Wonderful
    Chicago, IL

    Beautifully furnished Three Bedroom, Two Bath. Walking distance from the lakefront, and a short bus ride to Michigan Avenue. First Floor Condominium Unit, New... ...more

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

    NEW as of 3-18-2019 - La Buena Vida was designed for you to enjoy. Located just 1/2 block from Lake Shore Drive and the best beach scene on Lake Michigan in... ...more

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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 July, where prices hit an average of $142 a night. In June, prices will hit an average low of $205 per night.