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2026-04-21

2026-04-22

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Chicago holiday rentals

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104 properties found

  • Art Downtown Fulton Market Entire 3 Bedroom Home Sleep10 Private Garage Roof Ev Tesla

    467 North Armour Street, Chicago, United States ( Show map )

    Located just 7 minutes' walk from Santa Maria Addolorata Parish, the 3-bedroom Art Downtown Fulton Market Entire 3 Bedroom Home Sleep10 Private Garage Roof…

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  • New Modern 3Br, Gym, Workspace, Quiet Location

    3656 N Osage Ave Unit 3, Chicago, Il 60634, Usa, Chicago, United States ( Show map )

    During the stay at the 2-bedroom New Modern 3Br, Gym, Workspace, Quiet Location Chicago villa, guests can indulge in a Jacuzzi or visit the…

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    From US$ 147
    price for 1 night
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  • 2 Mi To South Shore Beach Urban Retreat With Yard

    1653 E 70Th St, Chicago, United States ( Show map )

    2 Mi To South Shore Beach Urban Retreat With Yard Chicago villa offers proximity to nearby tourist spots, such as the Sprawling hands-on Museum…

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  • Entire Building-Walk To Lincoln Park Or The Beach

    1147 West Diversey Parkway, Chicago, United States ( Show map )

    Situated a stone's throw from Rotofugi Gallery, the 5-bedroom Entire Building-Walk To Lincoln Park Or The Beach Chicago villa offers easy access to…

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    From US$ 1713
    price for 1 night
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  • 4 Bedroom Home In Best Location Parking Fireplace Back Yard Pets Welcome

    329 West Schiller Street, Chicago, United States ( Show map )

    Situated within 5 minutes' walk of Eva's Cafe, the 4-bedroom 4 Bedroom Home In Best Location Parking Fireplace Back Yard Pets Welcome Chicago offers…

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    From US$ 502
    price for 1 night
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  • Personal Gym Luxury Balcony Condo

    5105 N East River Rd Unit 3F, Chicago, Il 60656, Usa, Chicago, United States ( Show map )

    The 1-bedroom Personal Gym Luxury Balcony Condo Chicago villa is located around 10 minutes by car from Rosemont Theatre, giving access to various tourist…

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    From US$ 233
    price for 1 night
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  • Near Lake & Museum • Modern • Game Area

    2714 E 76Th Pl, Chicago, Il 60649, Usa, Chicago, United States ( Show map )

    Located 3.3 km from the Jackson Bark Park, Near Lake & Museum • Modern • Game Area Chicago villa provides access to various tourist attractions in the vicinity.

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    From US$ 277
    price for 1 night
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  • Stylish 3Br Gem In Prime Location

    2550 South Wabash Avenue, Chicago, United States ( Show map )

    Staying at Stylish 3Br Gem In Prime Location Villa Chicago, guests can easily reach the Buckingham Fountain, located approximately 3 km away. The Chicago villa…

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  • 2 Newly Built Luxury Condos With Private Roofdeck

    811 N Sedgwick St, Chicago, United States ( Show map )

    Located within a 500-metre distance of the Carl Hammer Gallery, 2 Newly Built Luxury Condos With Private Roofdeck Chicago villa offers a patio with…

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    From US$ 607
    price for 1 night
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  • Victorian Mansion In Garfield Park

    3461 W Adams St, Chicago, United States ( Show map )

    Situated approximately 7 km from the tall skyscraper "Willis Tower", the 1-bedroom Victorian Mansion In Garfield Park Villa Chicago provides access to numerous tourist…

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    From US$ 162
    price for 1 night
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  • Spectacular Gilded Age 6 Bedroom Gold Coast Mansion With Deck

    67 East Cedar Street, Chicago, United States ( Show map )

    Staying at the 5-bedroom Spectacular Gilded Age 6 Bedroom Gold Coast Mansion With Deck Chicago villa, guests can visit deep-dish pizza restaurants in…

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    From US$ 999
    price for 1 night
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  • 420 Friendly 12 Pm Check Out 1 Bedroom Basement

    8132 South Harvard Avenue, Chicago, United States ( Show map )

    Offering a hot tub for a relaxing experience, 420 Friendly 12 Pm Check Out 1 Bedroom Basement Chicago villa is located 6 km from the…

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    From US$ 131
    price for 1 night
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  • Large Condo With Outdoor Deck In Historic Chicago District Home

    1729 N St Michaels, Chicago, United States ( Show map )

    Offering a location just 1.7 km from the 35-acre beautifully landscaped Lincoln Park Zoo, Large Condo With Outdoor Deck In Historic Chicago District Home…

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  • 2Br Travelers Favorite Modern

    5425 W Drummond Pl, Chicago, Il 60639, Usa, Chicago, United States ( Show map )

    Situated around a 5-minute stroll from Grace, the 1-bedroom 2Br Travelers Favorite Modern Villa Chicago offers quick access to numerous city landmarks nearby.

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    From US$ 261
    price for 1 night
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  • Sleeps 18 6Br Gym, Game Room And Theater

    33 S Waller Ave, Chicago, Il 60644, Usa, Chicago, United States ( Show map )

    Along with proximity to the Columbus Park Refectory, located only 7 minutes' walk away, the 3-bedroom Sleeps 18 6Br Gym, Game Room And Theater…

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    From US$ 1261
    price for 1 night
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  • Amazing Wicker Park Penthouse With Skyline Views

    1549 North Milwaukee Avenue #4, Chicago, United States ( Show map )

    Amazing Wicker Park Penthouse With Skyline Views Villa Chicago is located 6 km from the huge outdoor Cloud Gate Sculpture and provides cycling for active…

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  • Downtown Mich Ave - 6 Penthouses, Sleep 25

    820 South Michigan Avenue 1207, Chicago, United States ( Show map )

    Located right around the corner from the General John Logan Memorial, Downtown Mich Ave - 6 Penthouses, Sleep 25 Chicago villa offers a patio with a…

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  • King Bed L Cta L United Center L Near Kasama L Patio

    924 North Wolcott Avenue G, Chicago, United States ( Show map )

    Staying at King Bed L Cta L United Center L Near Kasama L Patio Villa Chicago, guests can easily reach the indoor public Shedd Aquarium…

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  • Beautifully Remodeled Flat Downtown #3N

    858 North Orleans Street #3N, Chicago, United States ( Show map )

    Situated nearly 5 minutes' walk from Durse Park, Beautifully Remodeled Flat Downtown #3N Villa Chicago offers easy access to numerous tourist spots in the area.

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    From US$ 239
    price for 1 night
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  • Wicker Park 4Bd 3Ba, Steps From Cta, Parking Incl Home

    1220 N Paulina, Chicago, United States ( Show map )

    Situated 6 km from the Wrigley Field, Wicker Park 4Bd 3Ba, Steps From Cta, Parking Incl Home Chicago provides access to numerous tourist attractions in…

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