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2026-02-27

2026-02-28

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Chicago holiday rentals

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95 properties found

  • 5 Bedroom Huge House In Best Location Parking Fireplace Back Yard

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

    Located nearly a 20-minute walk from Lake Michigan, the 4-bedroom 5 Bedroom Huge House In Best Location Parking Fireplace Back Yard Chicago villa…

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    From US$ 1924
    price for 1 night
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  • Romantic 3 Bed Home In The Heart Of The Park

    5923 South Indiana Avenue, Chicago, United States ( Show map )

    2-bedroom Romantic 3 Bed Home In The Heart Of The Park offers proximity to such city sites as Greater Metropolitan MB Church, located just…

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    From US$ 393
    price for 1 night
    Book Now From US$ 393
  • River North Hideaway With Amazing Views And Parking

    1 E Huron St, Chicago, United States ( Show map )

    Positioned about 600 metres from bustling shopping destinations such as the fancy high-rise Shops at Northbridge Mall, River North Hideaway With Amazing Views And…

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    From US$ 264
    price for 1 night
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  • Logan Square Oasis

    2508 N Spaulding Ave, Chicago, United States ( Show map )

    Nestled 4.9 km from the 184 - acre Garfield Park Conservatory, Logan Square Oasis With Parking! The 2-bedroom villa is located a short distance from…

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    From US$ 142
    price for 1 night
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  • Charming Home In Portage Park

    4109 North Narragansett Avenue, Chicago, United States ( Show map )

    The 2-bedroom Charming Home In Portage Park Chicago offers easy access to such tourist spots as Chicago Latvian Zion Lutheran Church, located only a…

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    From US$ 107
    price for 1 night
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  • Chicago Treasure 4 Bed Getaway

    712 North Willard Court, Chicago, United States ( Show map )

    Offering a location 2.2 km from deep-dish pizza restaurants in Chicago|Chicago-style Pizza|a Chicago-style pizza, Chicago Treasure 4 Bed Getaway Villa…

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    From US$ 231
    price for 1 night
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  • Chicago New 2Br Home W 3 Beds And Highspeed Internet

    West Potomac Avenue 1731, Chicago, United States ( Show map )

    Chicago New 2Br Home W 3 Beds And Highspeed Internet offers quick access to such city attractions as Foxtrot Market, located merely 6 minutes' walk…

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    From US$ 139
    price for 1 night
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  • Windy City Getaway - 3Br 2Ba Chicago Townhouse Home

    3721 North Milwaukee Avenue, Chicago, United States ( Show map )

    Positioned within a 6-km distance of bustling shopping destinations such as Architectural Artifacts, the 3-bedroom Windy City Getaway - 3BR 2BA Chicago Townhouse home…

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    From US$ 304
    price for 1 night
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  • Woodlawn Oasis

    6433 South Minerva Avenue, Chicago, United States ( Show map )

    The 3-bedroom Woodlawn Oasis Chicago villa offers quick access to such city attractions as Woodlawn Baptist Church, located a mere 400 metres away. The…

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    From US$ 364
    price for 1 night
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  • Modern 3Br Near Mccormick & South Loop

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

    Situated 3.2 km from the Skydeck Chicago, Modern 3Br Near Mccormick & South Loop Villa Chicago features a patio with views of the city. This Chicago…

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  • Newly Updated Vintage 6 Bedroom Single Family Home Home

    825 S Claremont, Chicago, United States ( Show map )

    Situated 3.8 km from Skydeck Chicago, the 2-bedroom Newly Updated Vintage 6 Bedroom Single Family Home Home Chicago entices guests to explore various tourist…

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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 villa offers quick access to such tourist spots as Saint Sabina Roman Catholic Church, situated just…

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    From US$ 370
    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 merely a 6-minute walk from Midwest Athletic Club, the 4-bedroom Perfect Location Across From Park & Train Station Villa Chicago entices guests with…

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    From US$ 358
    price for 1 night
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  • Designer Themed 4 Bedroom In Best Location With Patio And Fireplace

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

    Located about 5 minutes' walk from The Noble Horse Theatre, the 3-bedroom Designer Themed 4 Bedroom In Best Location With Patio And Fireplace Chicago…

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    From US$ 479
    price for 1 night
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  • Roscoe Village Family Hideaway

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

    The 3-bedroom Roscoe Village Family Hideaway offers easy access to such tourist spots as Cuyler Covenant Church, located a mere 5 minutes' stroll away.

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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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  • Stylish Chicago Retreat Walk To Loyola University

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

    Located 19 minutes' stroll from the energetic urban Kathy Osterman Beach, the 4-bedroom Stylish Chicago Retreat, Walk To Loyola University provides access to various…

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  • The Avondale Guesthouse

    2973 North Elston Avenue, Chicago, United States ( Show map )

    Positioned 10 minutes by car from bustling shopping destinations such as Architectural Artifacts, 1-bedroom The Avondale Guesthouse offers guests to use parking. This Chicago…

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    From US$ 165
    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 )

    Boasting a location merely 1.5 km from Eckhart Park, the 3-bedroom Art Downtown Fulton Market Entire 3 Bedroom Home Sleep10 Private Garage Roof Ev…

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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 )

    Located 7 km from Wright Plus Housewalk, the 2-bedroom New Modern 3Br, Gym, Workspace, Quiet Location entices guests to relax in a Jacuzzi. The…

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    From US$ 147
    price for 1 night
    Book Now From US$ 147