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2026-02-26

2026-02-27

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Chicago holiday rentals

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80 properties found

  • 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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  • 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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  • 3-Story Townhome Free Parking Private Patio Washer-Dryer

    344 West Dickens Avenue, Chicago, United States ( Show map )

    Situated just a 6-minute walk from Siblings, the 2-bedroom 3-Story Townhome Free Parking Private Patio Washer-Dryer Chicago villa entices guests with…

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    From US$ 237
    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 )

    Situated nearly 5 minutes' walk from Mariano Plaza, the 5-bedroom Spectacular Gilded Age 6 Bedroom Gold Coast Mansion With Deck Chicago villa offers easy…

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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 )

    Situated 2.6 km from Chicago Riverwalk, Large Condo With Outdoor Deck In Historic Chicago District Home entices guests to explore various tourist attractions in the…

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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, 2Br Travelers Favorite Modern Villa Chicago offers opportunities for windsurfing, hiking, and cycling in the area. Austin…

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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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  • Wicker Park 4Bd 3Ba, Steps From Cta, Parking Incl Home

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

    Wicker Park 4Bd 3Ba, Steps From Cta, Parking Incl Home Chicago provides easy access to various city attractions, such as Foxtrot Market, situated 5 minutes'…

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  • Cute And Cozy Chicago Modern Condo

    1625 W Superior St 3F, Chicago, Il 60622, Usa, Chicago, United States ( Show map )

    Situated 16 minutes on foot from United Center, the 1-bedroom Cute And Cozy Chicago Modern Condo villa provides access to numerous tourist attractions in…

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    From US$ 526
    price for 1 night
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  • Quiet Chicago Townhome Walk To Subway Stations

    220 N Laporte Ave 1, Chicago, United States ( Show map )

    Positioned at a distance of 4.9 km from bustling shopping destinations such as Komoda Gift Shop, Quiet Chicago Townhome - 7 Mi To Downtown! The 1…

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  • 2 Mi To Red Line Chicago Home Near Sherman Park

    5205 S May St, Chicago, United States ( Show map )

    2 Mi To Red Line Chicago Home Near Sherman Park offers quick access to such tourist spots as Pillar Of Truth Evanglistic Church Of God…

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  • 3Br Gym Workspace Chicago Condo

    3656 North Osage Avenue Unit 2, Chicago, United States ( Show map )

    Situated within a 15-minute drive of Frank Lloyd Wright Home and Studio, 3Br Gym Workspace Chicago Condo entices guests to explore various tourist attractions…

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    From US$ 440
    price for 1 night
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  • Lincoln Park Living - 3 Queen Beds - Sleeps 6

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

    Located right by Rotofugi Gallery, the 1-bedroom Lincoln Park Living - 3 Queen Beds - Sleeps 6 gives easy access to various tourist attractions in the…

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    From US$ 139
    price for 1 night
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  • Bronzeville 42 Art & Hospitality

    615 East 42Nd Street, Chicago, United States ( Show map )

    Situated 2.5 km from Kimbark Plaza Shopping Center, Bronzeville 42 Art & Hospitality Chicago villa provides access to numerous tourist attractions in the area. Located in…

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  • Top 1 Rated 4Br Lincoln Park House - King Bed

    210 W St Paul Ave, Chicago, Il 60614, Usa, Chicago, United States ( Show map )

    Along with proximity to Chicago History Museum, located only a 6-minute walk away, the 2-bedroom Top 1 Rated 4Br Lincoln Park House - King…

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  • Zen Escape-Chicago'S Urban Oasis

    841 North Mozart Street, Chicago, United States ( Show map )

    Along with Wi-Fi and parking, Zen Escape-Chicago'S Urban Oasis Villa offers proximity to Willis Tower, located nearly 15 minutes away by car. Situated…

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    From US$ 79
    price for 1 night
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  • Charming & Bright Multilevel Townhome With Parking

    Chicago, United States ( Show map )

    Charming & Bright Multilevel Townhome With Parking Chicago villa offers quick access to such tourist spots as Eva's Cafe, situated just 5 minutes' walk away. Millennium…

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  • 3 Bedroom Spacious Home In Ideal Location W Free Parking Back Yard Pets Welcome

    1426 North North Park Avenue, Chicago, United States ( Show map )

    Situated approximately 5 minutes on foot from Old Town Ale House, the 3-bedroom 3 Bedroom Spacious Home In Ideal Location W Free Parking Back…

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    From US$ 949
    price for 1 night
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  • Wrigley 4Br Home, Sleeps 10

    3623 N Ashland Ave, Chicago, United States ( Show map )

    Positioned a 16-minute stroll from bustling shopping destinations such as Gallagher Way, Wrigley 4Br Home, Sleeps 10 offers guests to use a car park.

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    From US$ 398
    price for 1 night
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