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2026-06-29

2026-06-30
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Chicago holiday rentals

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240 results

  • Roscoe Village Family Hideaway

    1811 West Eddy Street, Chicago, United States (To the map)

    To the hotel

    Book Now
  • Brownstone In Gold Coast - Downtown

    57 East Cedar Street, Chicago, United States (To the map)

    To the hotel

    Book Now
  • Goose Island Central Downtown Prime Location With Access To Patio Chi - 1

    From US$ 179

    West Augusta Boulevard 1220, Chicago, United States (To the map)

    To the hotel

    price for 1 night
    Book Now From US$ 179
  • 2 Bedroom With Soaking Tub And Onsite Parking

    841 North Mozart Street, Chicago, United States (To the map)

    To the hotel

    Book Now
  • Central Downtown Location-Modern 2Br Condo

    210 North Wells Street Unit 1401, Chicago, United States (To the map)

    To the hotel

    Book Now
  • Spacious 4-Bedroom Home With Stunning Backyard Deck In Chicago

    1850 N Neva Ave, Chicago, United States (To the map)

    To the hotel

    Book Now
  • 420 Friendly 12 Pm Check Out 1 Bedroom Basement

    From US$ 131

    8132 South Harvard Avenue, Chicago, United States (To the map)

    To the hotel

    price for 1 night
    Book Now From US$ 131
  • Townhouse In Rogers Park

    From US$ 198

    2337 W Chase Ave, Chicago, United States (To the map)

    To the hotel

    price for 1 night
    Book Now From US$ 198
  • Spacious West Town Oasis With Parking!

    1656 West Erie Street, Chicago, United States (To the map)

    To the hotel

    Book Now
  • Tuscan Charm In Chicago'S Heart

    From US$ 293

    3412 North Greenview Avenue, Chicago, United States (To the map)

    To the hotel

    price for 1 night
    Book Now From US$ 293
  • Modern Lincoln Park Hideaway 1 Bd And 1Bath

    From US$ 311

    1410 W Diversey Pkwy, Chicago, United States (To the map)

    To the hotel

    price for 1 night
    Book Now From US$ 311
  • Beautifully Remodeled Flat Downtown #3N

    From US$ 239

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

    To the hotel

    price for 1 night
    Book Now From US$ 239
  • Spectacular Gilded Age 6 Bedroom Gold Coast Mansion With Deck

    From US$ 999

    67 East Cedar Street, Chicago, United States (To the map)

    To the hotel

    price for 1 night
    Book Now From US$ 999
  • Cozy Bungalow Home In Chicago

    6200 South Campbell Avenue, Chicago, United States (To the map)

    To the hotel

    Book Now
  • Large Condo With Outdoor Deck In Historic Chicago District Home

    1729 N St Michaels, Chicago, United States (To the map)

    To the hotel

    Book Now
  • Amazing Wicker Park Penthouse With Skyline Views

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

    To the hotel

    Book Now
  • Sleeps 18 7Br Gym Game Room Theater

    From US$ 4680

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

    To the hotel

    price for 1 night
    Book Now From US$ 4680
  • 2 Mi To Red Line: Chicago Home Near Sherman Park

    5205 S May St, Chicago, United States (To the map)

    To the hotel

    Book Now
  • Nice Family Home

    4027 West 25Th Street, Chicago, United States (To the map)

    To the hotel

    Book Now
  • Designer Smart Home

    From US$ 1682

    59 West Schiller Street, Chicago, United States (To the map)

    To the hotel

    price for 1 night
    Book Now From US$ 1682