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craigslist

Holiday Rentals in Chicago

  1. see also
  2. Wyndham Glacier Canyon at The Wilderness 9/19-21 in 2 bdrm deluxe
    $575
    north chicagoland
  3. ~*~ Luxury FL Beach Rental 6br/5ba/over 3k sqft/sleeps 16 ~*~
    $0
    Cape San Blas, FL
  4. Wisconsin Dells Labor Day week weekend Christmas Mountain resort
    $749
    Wisconsin Dells
  5. Marriott's Aruba Ocean Club (July 20, 2026 to July 27, 2026)
    $2,700
    Palm Beach Aruba
  6. Charming 1 bedroom condo plus parking spot!!
    $1,299
    Evanston
  7. Stunning 1BR condo in SoNo West!
    $1,800
    Chicago
  8. LUXURY FAMILY HOME W/THREE OUTDOOR DECKS AND HOT TUB
    $250
    Chicago
  9. MAGNIFICENT CUSTOM-BUILT HOME IN PERFECT SPOT
    $1
    2155 W Huron St, Chicago
  10. Great 1br/1ba in downtown evanston
    $1,350
    Evanston
  11. Wisconsin Dells-Glacier Canyon Sept 1-4 3 bdrm Pres w/8 wristbands
    $399
    Wisconsin Dells
  12. Wisconsin Dells Vacay Condos booking now. Choose 1 or 2 BR. Lakefront
    $0
    Wisconsin Dells
  13. 2 Bedroom Aframe
    $0
    city of chicago
  14. $$$ HUNTING LAND FOR RENT $$$
    $1,475
    Kankakee
  15. 3 bedroom, 2 bath residence offers private outdoor space
    $4,408
    Chicago
  16. Deer Hunting Land For Rent
    $750
    Homer Glen
  17. Waterfront Cottages with boats
    $135
    Barryton
  18. Wisconsin Dells - Glacier Canyon September 1-4 w/10 waterpark wrstbds
    $299
    Wisconsin Dells
  19. Wisconsin Dells - Glacier Canyon Sept 8-11 w/10 waterpark wtbnds
    $299
    Wisconsin Dells
  20. Wisconsin Dells - Glacier Canyon Sept 19-21 w/10 waterpark wristbands
    $349
    Wisconsin Dells
  21. 3 bedroom, 2 bath residence offers private outdoor space
    $4,408
    Chicago
  22. 3/ 2br - Fisherman's dream for rent
    $1,350
    northwest suburbs
  23. Fisherman's Dream for rent
    $1,350
    northwest suburbs
  24. *Private Wrigleyville Coach House - Perfect for Groups!*
    $150
    Chicago, IL
  25. Perfect for groups
    $135
    Chicago, IL
  26. *Private Wrigleyville Coach House - Perfect for Groups!*
    $150
    Chicago, IL
  27. Perfect for groups
    $135
    Chicago, IL
  28. 4 Bdrm Private Pool/Spa Home
    $4,000
    Palm Desert
  29. Hotel rooms available discounted rates
    $0
    city of chicago
  30. Highly updated 1bed/1bath condo
    $1,200
    Chicago
  31. Welcome to our Magical Woods
    $50
    west chicagoland
  32. Beautiful Garden Unit near Wrigleyville
    $3,350
    North Center
  33. Heritage Harbor vacation rental - Ottawa vacation rental
    $189
    Ottawa, IL
  34. Marriott Aruba Ocean Club &Divi in Aruba for rent Christmas/New Years
    $0
    city of chicago
  35. 2br - 1446ft2 - Hawaii Big Island Vacation Rental (Senior Discount fo
    $0
    Waikoloa
  36. Southwest Florida Waterfront Paradise
    $5,500
    Punta Gorda
  37. 2 Bedroom 16x80 Manufactured Home
    $2,150
    St. Cloud, Fl.
  38. 3 bedroom, 2 bath residence offers private outdoor space
    $4,408
    Chicago
  39. Visiting the Evanston area for 3 days or more? Check us out.
    $269
    Evanston IL
  40. Wisconsin Dells - Glacier Canyon Sept 26-28 w/ 4 waterpark wristbands
    $299
    Wisconsin Dells
  41. Wisconsin Dells - Glacier Canyon Sept 12-14 w/8 waterpark wtbnds
    $299
    Wisconsin Dells
  42. JANUARY GETAWAY TO MEXICO
    $0
    Puerto Vallarta
  43. Wisconsin Dells - Glacier Canyon Sept 15-18 w/10 waterpark wristbands
    $249
    Wisconsin Dells
  44. 4BR/2BA Vacation Pool Rental Home near Walt Disney World
    $0
    6 miles to Disneyworld
  45. Vacational East River Rd Unit
    $135
    Norridge