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craigslist

Vacation Rentals in Chicago

  1. see also
  2. Waterfront Cottages with boats
    $135
    Barryton
  3. 4BR/2BA Vacation Pool Rental Home near Walt Disney World
    $0
    6 miles to Disneyworld
  4. New Years Eve and Independence Day week
    $800
    Wisconsin Dells, Wi.
  5. Wyndham Glacier Canyon at The Wilderness 9/19-21 in 2 bdrm deluxe
    $575
    north chicagoland
  6. ~*~ Luxury FL Beach Rental 6br/5ba/over 3k sqft/sleeps 16 ~*~
    $0
    Cape San Blas, FL
  7. Wisconsin Dells Labor Day week weekend Christmas Mountain resort
    $749
    Wisconsin Dells
  8. Marriott's Aruba Ocean Club (July 20, 2026 to July 27, 2026)
    $2,700
    Palm Beach Aruba
  9. Charming 1 bedroom condo plus parking spot!!
    $1,299
    Evanston
  10. Stunning 1BR condo in SoNo West!
    $1,800
    Chicago
  11. LUXURY FAMILY HOME W/THREE OUTDOOR DECKS AND HOT TUB
    $250
    Chicago
  12. MAGNIFICENT CUSTOM-BUILT HOME IN PERFECT SPOT
    $1
    2155 W Huron St, Chicago
  13. Great 1br/1ba in downtown evanston
    $1,350
    Evanston
  14. Wisconsin Dells Vacay Condos booking now. Choose 1 or 2 BR. Lakefront
    $0
    Wisconsin Dells
  15. 3 bedroom, 2 bath residence offers private outdoor space
    $4,408
    Chicago
  16. 3 bedroom, 2 bath residence offers private outdoor space
    $4,408
    Chicago
  17. *Private Wrigleyville Coach House - Perfect for Groups!*
    $150
    Chicago, IL
  18. Perfect for groups
    $135
    Chicago, IL
  19. *Private Wrigleyville Coach House - Perfect for Groups!*
    $150
    Chicago, IL
  20. Perfect for groups
    $135
    Chicago, IL
  21. 4 Bdrm Private Pool/Spa Home
    $4,000
    Palm Desert
  22. Hotel rooms available discounted rates
    $0
    city of chicago
  23. Highly updated 1bed/1bath condo
    $1,200
    Chicago
  24. Heritage Harbor vacation rental - Ottawa vacation rental
    $189
    Ottawa, IL
  25. Southwest Florida Waterfront Paradise
    $5,500
    Punta Gorda
  26. 2 Bedroom 16x80 Manufactured Home
    $2,150
    St. Cloud, Fl.
  27. 3 bedroom, 2 bath residence offers private outdoor space
    $4,408
    Chicago
  28. Visiting the Evanston area for 3 days or more? Check us out.
    $269
    Evanston IL