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craigslist

Vacation Rentals in Chicago

  1. see also
  2. Condo - Bradenton Florida - Seasonal Rental
    $1,500
    Bradenton
  3. Escape Winter in Oceanfront Penthouse
    $3,995
    North Myrtle Beach
  4. 3 bedroom, 2 bath residence offers private outdoor space
    $150
    Chicago
  5. Located in one of the most desired neighborhoods in Chicago
    $3,000
    Chicago
  6. Christie Lodge Timeshare Week for Sale (Avon near Vail) - $750
    $0
    Avon, CO.
  7. Fall Colors Waterfront Cottages
    $135
    Barryton
  8. Wyndham Glacier Canyon at The Wilderness Waterpar11/7-9 in 2 bdrm
    $595
    north chicagoland
  9. Furnished motel style suite, No Deposit daily $ 75.00 weekly $ 390
    $390
    Bartlett ILLINOIS 60103
  10. Furnished motel style suite, No Deposit daily $ 75.00 weekly $395
    $395
    Bartlett ILLINOIS 60103
  11. Furnished motel style suite, No Deposit daily $ 75.00 week;y 395.00
    $395
    Bartlett ILLINOIS 60103
  12. Furnished motel style suite, No Deposit daily $ 75.00 weekly $ 390
    $390
    Bartlett ILLINOIS 60103
  13. Furnished motel style suite, No Deposit daily $ 75.00 weekly $ 375
    $375
    Bartlett ILLINOIS 60103
  14. Furnished motel style suite, No Deposit daily $ 75.00 weekly $395
    $395
    Bartlett ILLINOIS 60103
  15. Furnished motel style suite, No Deposit $ 70 daily $ 395 weekly
    $395
    Bartlett ILLINOIS 60103
  16. Furnished motel style suite, No Deposit daily $ 75.00 weekly $ 350
    $395
    Bartlett ILLINOIS 60103
  17. Furnished motel style suite, No Deposit daily $ 75.00 weekly $ 375
    $395
    Bartlett ILLINOIS 60103
  18. Cabin for rent
    $200
    seveirville
  19. Marriott's Aruba Ocean Club (July 20, 2026 to July 27, 2026)
    $2,700
    Palm Beach Aruba
  20. Wisconsin Dells - Glacier Canyon Nov 9-11 w/8 waterpark wristbands
    $249
    Wisconsin Dells
  21. Wisconsin Dells - Glacier Canyon Nov 4-7 w/10 waterpark wtbnds
    $249
    Wisconsin Dells
  22. Wisconsin Dells - Glacier Canyon Nov 2-7 w/10 waterpark wtbnds
    $249
    Wisconsin Dells
  23. Wisconsin Dells - Glacier Canyon Dec 8-12 w/10 waterpark wtbnds
    $249
    Wisconsin Dells
  24. Wisconsin Dells - Glacier Canyon Dec 15-18 w/10 waterpark wtbnds
    $249
    Wisconsin Dells
  25. Wisconsin Dells - Glacier Canyon Dec 15-20 w/10 waterpark wtbnds
    $249
    Wisconsin Dells
  26. Modern Recent home
    $125
    Chicago
  27. Hotel rooms available discounted rates
    $0
    city of chicago
  28. 2 Bedroom Aframe
    $0
    city of chicago
  29. Wisconsin Dells - Glacier Canyon Oct 30- Nov 1 w/10 waterpark wtbnds
    $299
    Wisconsin Dells
  30. New Years Eve and Independence Day week
    $800
    Wisconsin Dells, Wi.
  31. WELL-MAINTAINED CONDO
    $1,300
    Schaumburg
  32. TOWNHOME FOR THANKSGIVING FAMILY GATHERING
    $0
    CHRISTMAS MOUNTAIN / WISCONSIN DELLS
  33. JANUARY GETAWAY TO MEXICO
    $0
    Puerto Vallarta
  34. Old Naples Florida resort rental. Near Beach. Jan 10th thru Jan 17th
    $1,800
    Naples
  35. Perfect for large group
    $150
    Chicago
  36. PUEBLO BONITO ROSE RESORT
    $4,000
    Chicago
  37. Perfect for groups
    $135
    Chicago, IL
  38. Perfect for groups
    $135
    Chicago, IL
  39. Gold Coast Lake Michigan Corner Stidio
    $1,800
    Chicago
  40. Wisconsin Dells - Glacier Canyon Nov 20-22 w/8 waterpark wristbands
    $299
    Wisconsin Dells
  41. Modern and Well-Equipped Cabin in Minocqua, WI.
    $0
    Gurnee
  42. 5 STAR RESORT - GREAT Amenities + Full Kitchen
    $900
    WORLDWIDE
  43. Wisconsin Dells-Glacier Canyon Nov 6-8 2 bdrm Pres w/ 6 wristbands
    $299
    Wisconsin Dells
  44. 4 Bdrm Private Pool/Spa Home
    $4,000
    Palm Desert
  45. Wisconsin dells Glacier canyon
    $0
    Fredonia
  46. Wisconsin Dells - Glacier Canyon Oct 31-Nov 2 w/ 4 wrtpk wristbands
    $249
    Wisconsin Dells
  47. Smokey Mountain Fall vacatiion
    $850
    Gaitlinburg
  48. Attention snowmobilers
    $3,500
    Presque Isle
  49. rci points for sale
    $200
    fredonia
  50. Vacation home available for rent
    $3,195
    Chicago
  51. Assistance for right girl or couple
    $0
    city of chicago
  52. Perfect for groups
    $0
    Chicago, IL
  53. Ideally located in West Lakeview withing walking distance to Wrigley Field
    $135
    Chicago, IL
  54. Perfect for groups
    $0
    Chicago, IL
  55. Visiting the Evanston area for 3 days or more? Check us out.
    $269
    Evanston IL
  56. $$$ Part time work to cover Rent for Ladies18-35 Apply now $$$$$
    $0
    city of chicago
  57. 2 Bedroom 16x80 Manufactured Home
    $2,150
    St. Cloud, Fl.
  58. Perfect for groups
    $135
    Chicago, IL
  59. Perfect for groups
    $135
    Chicago, IL
  60. Perfect for groups
    $135
    Chicago, IL
  61. Perfect for groups
    $135
    Chicago, IL
  62. Wisconsin Dells - Glacier Canyon Oct 27-30 w/8 waterpark wristbands
    $199
    Wisconsin Dells
  63. Wisconsin Dells - Glacier Canyon Oct 21-23 w/8 waterpark wristbands
    $199
    Wisconsin Dells
  64. Scottsdale Arizona Luxury Condominium Pool Side Clubhouse view
    $5,500
    scottsdale
  65. 3br -Tropical Caribbean Vacation this Winter St John US Virgin Islands
    $5,899
    St John USVI
  66. $1,800 / 1br - New Years Ski Adventure (12/26/25-1/2/26)
    $1,800
    Vail, CO
  67. Lovely unit
    $1,600
    Chicago
  68. WINTER VACATION HOME
    $3,000
    Minocqua
  69. Perfect for groups
    $150
    Chicago, IL
  70. ~*~ Luxury FL Beach Rental 6br/5ba/over 3k sqft/sleeps 16 ~*~
    $0
    Cape San Blas, FL