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2026-06-07

2026-06-08

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Chicago holiday rentals

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109 properties found

  • Envitae Hotel 4Br Luxury Modern Apartments

    853 West Blackhawk Street, Chicago, United States ( Show map )

    The 6-room Envitae Hotel 4Br Luxury Modern Apartments Chicago villa boasts a location approximately a 5-minute walk from the PRYSM Nightclub and offers…

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    From US$ 309
    price for 1 night
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  • Gorgeous 5 Bedroom Gem With Games

    7928 South Ada Street, Chicago, United States ( Show map )

    The 2-bedroom Gorgeous 5 Bedroom Gem With Games Chicago villa offers proximity to such city sites as Saint Sabina Roman Catholic Church, located only…

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    From US$ 1685
    price for 1 night
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  • Perfect Location Across From Park & Train Station

    244 North Hamlin Avenue, Chicago, United States ( Show map )

    Situated about a 20-minute walk from Gladys Park, the 4-bedroom Perfect Location Across From Park & Train Station Villa Chicago entices guests to explore…

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    From US$ 325
    price for 1 night
    Book Now From US$ 325
  • Boutique Garden House Chicago 3-Story Sleeps 12

    7131 South Michigan Avenue, Chicago, United States ( Show map )

    The 3-bedroom Boutique Garden House Chicago 3-Story Sleeps 12 Villa offers proximity to nearby tourist spots, such as First Progressive Church of Christ…

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    From US$ 539
    price for 1 night
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  • Northside Famlynest Lincoln Sq 4Br 2Ba 2P Rare Find

    2713 West Balmoral Avenue, Chicago, United States ( Show map )

    The 2-bedroom Northside Famlynest Lincoln Sq 4Br 2Ba 2P Rare Find Villa Chicago is located around a 25-minute walk from the Andersonville neighborhood…

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    From US$ 270
    price for 1 night
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  • Roscoe Village Family Hideaway

    1811 West Eddy Street, Chicago, United States ( Show map )

    Located nearly 5 minutes' walk from Loba Pastry + Coffee, the 3-bedroom Roscoe Village Family Hideaway Chicago villa offers quick access to various city attractions…

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  • Lincoln Park Living - 3 Queen Beds - Sleeps 6

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

    Situated about 25 minutes on foot from the 35 - acre Lincoln Park Zoo, the 1-bedroom Lincoln Park Living - 3 Queen Beds - Sleeps 6 Chicago…

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    From US$ 112
    price for 1 night
    Book Now From US$ 112
  • Stylish Chicago Retreat: Walk To Loyola University

    6242 N Kenmore Ave Unit D, Chicago, United States ( Show map )

    Located nearly 5 minutes' walk from Mundelein College, the 4-bedroom Stylish Chicago Retreat Walk To Loyola University villa offers quick access to various city…

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  • Beautifully Renovated House 10 Mins From Downtown

    4244 South Prairie Avenue, Chicago, United States ( Show map )

    Situated in the Bronzeville district, 6 km from the premier natural-history Field Museum, Beautifully Renovated House 10 Mins From Downtown Villa Chicago comes with…

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    From US$ 654
    price for 1 night
    Book Now From US$ 654
  • The Village Inn By Dakota Gal Digs

    2111 North Kenmore Avenue Unit 1, Chicago, United States ( Show map )

    Along with Wi-Fi and parking, The Village Inn By Dakota Gal Digs Chicago villa offers proximity to the tall skyscraper "Willis Tower", located 4.9…

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    From US$ 973
    price for 1 night
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  • 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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  • 2 Mi To South Shore Beach: Urban Retreat W/ Yard

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

    Situated 2.6 km from the Sprawling hands-on Museum of Science and Industry, 2 Mi To South Shore Beach : Urban Retreat W/ Yard Chicago villa…

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  • Lincoln Park Living - Suite 1

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

    The 2-bedroom Lincoln Park Living - Suite 1 Chicago villa offers easy access to such tourist spots as Rosa's Lounge, located just a 6-minute…

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    From US$ 227
    price for 1 night
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  • Spacious Row Home Next Transit Near Downtown W Parking

    3133 West Fulton Street, Chicago, United States ( Show map )

    The 3-bedroom Spacious Row Home Next Transit Near Downtown W Parking Chicago offers quick access to such city attractions as 345 Art Gallery, located…

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    From US$ 452
    price for 1 night
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  • Entire Building-Walk To Lincoln Park Or The Beach

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

    The 5-bedroom Entire Building-Walk To Lincoln Park Or The Beach Chicago villa is situated within easy reach of Rotofugi Gallery, featuring such comforts…

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    From US$ 1347
    price for 1 night
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  • Lincoln Park Living - Suite 2

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

    Situated a 5-minute walk from the petite South Lakeview Playground Park, Lincoln Park Living - Suite 2 Chicago villa entices guests with views of the…

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    From US$ 178
    price for 1 night
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  • Magnificent New Home W/8 Beds & Free Parking

    2019 North Bingham Street, Chicago, United States ( Show map )

    The 3-bedroom Magnificent New Home W/8 Beds & Free Parking Chicago offers quick access to such tourist spots as the live music venue "Congress…

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    From US$ 301
    price for 1 night
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  • 5Br 5Ba Architectural Estate-Theatre Gym Rooftop

    1856 North Fairfield Avenue, Chicago, United States ( Show map )

    5Br 5Ba Architectural Estate-Theatre Gym Rooftop Chicago villa offers swift access to various city sites, such as Katherine Anne Confections, situated approximately 5 minutes'…

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  • Spacious 5-Br House Near Transit W Parking

    1868 South Millard Avenue, Chicago, United States ( Show map )

    The 3-bedroom Spacious 5-Br House Near Transit W Parking Chicago villa offers easy access to such tourist spots as Blessed Sacrament Catholic Youth…

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    From US$ 677
    price for 1 night
    Book Now From US$ 677
  • 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$ 1049
    price for 1 night
    Book Now From US$ 1049