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craigslist

Vacation Rentals in Chicago

  1. see also
  2. Stunning 1BR condo in SoNo West!
    $1,800
    Chicago
  3. Wyndham Glacier Canyon at The Wilderness 10/24-26
    $695
    north chicagoland
  4. Marriott's Aruba Ocean Club (July 20, 2026 to July 27, 2026)
    $2,700
    Palm Beach Aruba
  5. 5 STAR RESORT - GREAT Amenities + Full Kitchen
    $900
    WORLDWIDE
  6. New Years Eve and Independence Day week
    $800
    Wisconsin Dells, Wi.
  7. Modern Recent home
    $125
    Chicago
  8. Old Naples Florida resort rental. Near Beach. Jan 10th thru Jan 17th
    $1,800
    Naples
  9. Scottsdale Arizona Luxury Condominium Pool Side Clubhouse view
    $5,500
    scottsdale
  10. $1,800 / 1br - New Years Ski Adventure (12/26/25-1/2/26)
    $1,800
    Vail, CO
  11. WELL-MAINTAINED CONDO
    $1,300
    Schaumburg
  12. 3br 2bath beach condo
    $0
    Panama City beach florida
  13. Condo - Bradenton Florida - Seasonal Rental
    $1,600
    Bradenton
  14. Amazing Southern City Views Spacious 1 Bed 1 Bath
    $1,350
    Chicago
  15. Just steps from vibrant downtown Naperville
    $1,300
    Naperville