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2026-02-28

2026-03-01

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Vacation Rentals in Chicago

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716 properties found

  • Chic & Fully Furnished 2Br Apartment - Roscoe 1

    3906 West Roscoe Street, Chicago, United States ( Show map )

    Situated merely a 6-minute stroll from Night Club, Chic & Fully Furnished 2Br Apartment - Roscoe 1 Chicago offers proximity to various nearby tourist attractions. Tony's…

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    From US$ 68
    price for 1 night
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  • Fully Furnished Extended Stay Work Or Insurance In Chicago

    5539 West Adams Street Garden, Chicago, United States ( Show map )

    The 1-room Fully Furnished Extended Stay Work Or Insurance In Chicago apartment lies just 1.3 km from the Chase Tower and within 10 minutes'…

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    From US$ 133
    price for 1 night
    Book Now From US$ 133
  • 1Br Fully Equipped & Central - Belmont Rep

    1627 West Belmont Avenue, Chicago, United States ( Show map )

    To enjoy your vacation in Chicago, stay at the 1-room 1Br Fully Equipped & Central - Belmont Rep Chicago apartment, which is about a 10-minute…

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    From US$ 156
    price for 1 night
    Book Now From US$ 156
  • Freshly Minted 2Br - Elegance & Comfort In Central Chicago

    North Elizabeth Street, Chicago, United States ( Show map )

    Situated about 10 minutes' walk from Racine underground station, the spacious 2-bedroom Freshly Minted 2BR - Elegance & Comfort in Central Chicago Apartment offers Wi-Fi…

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    From US$ 708
    price for 1 night
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  • Chateau De Woodlawn - Peaceful 3 Bedroom Apartment.

    6554 South Rhodes Avenue, Chicago, United States ( Show map )

    The 108 m^2 Chateau De Woodlawn - Peaceful 3 Bedroom Apartment. This 1-bedroom property is at a distance of 2.8 km from Smart Museum…

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    From US$ 265
    price for 1 night
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  • Beautifully Remodeled Third Floor Flat In River North - 3N

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

    Situated a mere 500 metres from St. While staying at the Chicago villa, you'll be about a 5-minute walk from Saint Luke Church of…

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    From US$ 585
    price for 1 night
    Book Now From US$ 585
  • City Charm Studio Apt In Chicago - Kenwood 205

    5532 South Kenwood Avenue, Chicago, United States ( Show map )

    City Charm Studio Apt In Chicago - Kenwood 205 is located nearly 15 minutes on foot from Museum of Science and Industry and within 800 metres…

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    From US$ 170
    price for 1 night
    Book Now From US$ 170
  • Iklektik House // Bluejay

    2334 West Erie Street 1F, Chicago, United States ( Show map )

    Situated 2.8 km from City Winery, the spacious 1-bedroom Iklektik House // Bluejay Apartment Chicago provides convenient access to numerous nearby attractions. A 10-minute…

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    From US$ 207
    price for 1 night
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  • Chic South Loop 2Br Apartment With Gym And Optional Parking Near Grant Park, Mccormick Place, Museum Campus & Downtown

    61 East 21St Street Unit 617, Chicago, United States ( Show map )

    Situated nearly a 25-minute stroll from the Illinois Institute of Technology, the spacious 84 m² Chic South Loop 2Br Apartment With Gym And Optional…

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    From US$ 324
    price for 1 night
    Book Now From US$ 324
  • Vibrant 1Br Apartment In Roscoe Village - Marshfield N3

    3429 North Marshfield Avenue, Chicago, United States ( Show map )

    Vibrant 1Br Apartment In Roscoe Village - Marshfield N3 Chicago is situated 5 minutes' walk from Loba Pastry + Coffee and 25 km from Midway International airport.

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    From US$ 266
    price for 1 night
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  • Modern And Minimalist Studio Apartment - Bstone 105 And 108 Rep

    5514 South Blackstone Avenue, Chicago, United States ( Show map )

    Modern And Minimalist Studio Apartment - Bstone 105 And 108 Rep Chicago is also located just a 9-minute walk from Rockefeller Memorial Chapel. Frank Lloyd…

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    From US$ 178
    price for 1 night
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  • Chicago Studio Unit Cozy & Convenient - Bstone 226 Rep

    5514 South Blackstone Avenue, Chicago, United States ( Show map )

    To enjoy your vacation in Chicago, stay at the 1-room Chicago Studio Unit Cozy & Convenient - Bstone 226 Rep, which is just 1.1 km from…

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    From US$ 78
    price for 1 night
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  • A Home Away From Home!

    8858 South Constance Avenue, Chicago, United States ( Show map )

    Staying at the 3-bedroom A Home Away From Home! This accommodation is within 20 km of Chicago Midway International airport and around a 15…

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  • Well-Appointed Cozy Portage Park Apt, Dogs, Kids, Free Parking, 420 Compliant

    4134 North Mason Avenue Floor 2, Chicago, United States ( Show map )

    Staying at the 93 m^2 Well-Appointed Cozy Portage Park Apt, Dogs, Kids, Free Parking, 420 Compliant Apartment Chicago, guests can relax on a…

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    From US$ 101
    price for 1 night
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  • Mccormick Place 420-Friendly 3Br-2Ba With Optional Parking - Sleeps 8

    2001 South State Street, Chicago, United States ( Show map )

    To enjoy your vacation in Chicago, stay at Mccormick Place 420-Friendly 3Br-2Ba With Optional Parking - Sleeps 8 Chicago apartment, which is 2.4 km…

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    From US$ 585
    price for 1 night
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  • Flexhome Avondale 3Br Duplex Apt W2

    2947 N Wisner Ave, Chicago, Il 60618, Usa, Chicago, United States ( Show map )

    The 2-room Flexhome Avondale 3Br Duplex Apt W2 - Read Info Chicago offers easy entry to such city sights as Half Italian, situated 450 metres…

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    From US$ 143
    price for 1 night
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  • Comfy Retreat In Rogers Park, Prime Location!

    6443 N Hamilton Ave Unit 1G, Chicago, United States ( Show map )

    To enjoy your vacation in Chicago, stay at the spacious 70 m^2 Comfy Retreat In Rogers Park, Prime Location! The 1-bedroom apartment is…

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    From US$ 283
    price for 1 night
    Book Now From US$ 283
  • Townhome

    5434 North Kenmore Avenue, Chicago, United States ( Show map )

    Andersonville is just 1.2 km from the 3-room Townhome Chicago, while Edge Theater is situated nearby. Nearly 5 minutes' walk from Berwyn tube station…

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    From US$ 81
    price for 1 night
    Book Now From US$ 81
  • The Logandale: Huge Mid-Century Home, Sleeps 15

    2920 North Gresham Avenue, Chicago, United States ( Show map )

    3-bedroom The Logandale: Huge Mid-Century Home, Sleeps 15 offers easy access to such tourist spots as Saint Wenceslaus Roman Catholic Church, located only…

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    From US$ 698
    price for 1 night
    Book Now From US$ 698
  • Stunning 5Br Home In Heart Of Chicago With 2 Rooftops

    1307 North Bell Avenue, Chicago, United States ( Show map )

    Stunning 5Br Home In Heart Of Chicago With 2 Rooftops provides easy access to various city attractions, such as Buzz Killer Espresso, situated 6 minutes'…

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    From US$ 1501
    price for 1 night
    Book Now From US$ 1501