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craigslist

Vacation Rentals in Chicago

  1. see also
  2. Wyndham Glacier Canyon at The Wilderness Waterpark 1/2-4 in 3 bdrm
    $699
    north chicagoland
  3. Hotel rooms available discounted rates
    $0
    Chicago
  4. Condo for rent
    $1,300
    Chicago
  5. Condo for rent
    $1,300
    Chicago
  6. Waterfront Cottages with boats
    $135
    Barryton
  7. Furnished Vacation Rental in Scottsdale, Arizona
    $7,000
    Scottsdale
  8. Marriott's Aruba Ocean Club (July 20, 2026 to July 27, 2026)
    $2,700
    Palm Beach Aruba
  9. FURNISHED LAKEVIEW 2 BEDROOM UNIT AVAILABLE 12/12-1/3 OR LONGER!
    $750
    LAKEVIEW / ROSCOE VILLAGE
  10. Spacious one bedroom in the heart of Downtown Evanston.
    $1,600
    Evanston
  11. LAST MINUTE DEAL 2BR Glacier Canyon! (Thursday-Sunday 12/11-12/14)
    $0
    Only $190/ night TOTAL
  12. Old Naples Florida resort rental. Near Beach. Jan 10th thru Jan 17th
    $1,500
    Naples
  13. Modern Recent home
    $125
    Chicago
  14. Cabin for rent
    $200
    smoky mountains
  15. Cabin for rent
    $200
    smoky mountains
  16. Cabin for rent
    $200
    smoky mountains
  17. Cabin for rent smoky mtns
    $125
    New Lenox
  18. Old Naples Florida Resort rental. 3 weeks starting March 2026.
    $2,700
    Naples
  19. 2 Bedroom 16x80 Manufactured Home
    $2,150
    St. Cloud, Fl.
  20. 3BED/4Bath Unique Home Available Dec 15-Dec 28, Jan 10 - Feb 20 June 14-26
    $1,050
    Chicago
  21. Hotel rooms available discounted rates
    $0
    city of chicago
  22. Furnished motel style suite, No Deposit daily $ 75.00 weekly $395
    $395
    Bartlett ILLINOIS 60103
  23. Furnished motel style suite, No Deposit daily $ 75.00 weekly $395
    $395
    Bartlett ILLINOIS 60103
  24. Furnished motel style suite, No Deposit daily $ 75.00 week;y 395.00
    $395
    Bartlett ILLINOIS 60103
  25. Furnished motel style suite, No Deposit daily $ 75.00 weekly $350
    $395
    Bartlett ILLINOIS 60103
  26. Furnished motel style suite, No Deposit daily $ 75.00 weekly $350
    $395
    Bartlett ILLINOIS 60103
  27. Furnished motel style suite, No Deposit daily $ 75.00 weekly $350
    $395
    Bartlett ILLINOIS 60103
  28. Furnished motel style suite, No Deposit daily $ 75.00 weekly $350
    $395
    Bartlett ILLINOIS 60103
  29. Furnished motel style suite, No Deposit daily $ 75.00 weekly $350
    $395
    Bartlett ILLINOIS 60103
  30. Furnished motel style suite, No Deposit daily $ 75.00 weekly $395
    $395
    Bartlett ILLINOIS 60103
  31. Furnished motel style suite, No Deposit $ 70 daily $ 395 weekly
    $395
    Bartlett ILLINOIS 60103
  32. Furnished motel style suite, No Deposit daily $ 75.00 weekly $ 390
    $390
    Bartlett ILLINOIS 60103
  33. Furnished motel style suite, No Deposit daily $ 75.00 weekly $395
    $395
    Bartlett ILLINOIS 60103
  34. SKI WEEKEND IN MICHIGAN / MOUNTAIN RUN AT BOYNE
    $0
    BOYNE FALLS, MICHIGAN
  35. JANUARY GETAWAY TO MEXICO
    $0
    Puerto Vallarta
  36. Wisconsin Dells - Glacier Canyon Jan 22-24 w/8 waterpark wristbands
    $299
    Wisconsin Dells
  37. Wisconsin Dells - Glacier Canyon Jan 25-28 w/10 waterpark wtbnds
    $299
    Wisconsin Dells
  38. Wisconsin Dells - Glacier Canyon Jan 9-11 w/8 waterpark wristbands
    $299
    Wisconsin Dells
  39. Twin Bay Resort Cabin Rentals
    $0
    Tomahawk/ Lake Nokomis
  40. Wisconsin Dells - Glacier Canyon Jan 4-7, 2026 w/10 waterpark wtbnds
    $299
    Wisconsin Dells
  41. 118 Douglas Ave
    $1,000
    Naperville
  42. Art Deco 1BR Co-op with Lake Views, Designer Interior & Balcony - Prime Gold C
    $1,700
    Chicago
  43. 2 Bedroom Aframe
    $0
    city of chicago
  44. Orr Mn winter Log cabin rental snowmobile fishing
    $250
    Orr
  45. SUNDARA SPA - 2BR Condo in WISCONSIN DELLS
    $190
    Baraboo
  46. 3br 2bath beach condo
    $0
    Panama City beach florida
  47. Visiting the Evanston area for 3 days or more? Check us out.
    $269
    Evanston IL
  48. 6mo sublet - gorgeous 1bd 1ba top floor
    $2,250
    849 North Franklin St, # 1205, Chicago, IL
  49. SPECTACULAR CONDO WITH INCREDIBLE DOWNTOWN VIEWS!
    $1,780
    city of chicago
  50. Graciously scaled one bedroom condo!!
    $1,870
    city of chicago
  51. The heart of the Gold Coast.
    $1,920
    city of chicago
  52. WOW! RIVER NORTH'S FINEST!
    $1,790
    city of chicago
  53. Its worth it!!
    $1,915
    city of chicago
  54. THIS IS THE ONE!!
    $1,960
    city of chicago
  55. Right in the heart of River North.
    $1,830
    city of chicago
  56. This unit can be your best pick.
    $1,725
    city of chicago
  57. All new and Exquisite.
    $1,825
    city of chicago
  58. Rare updated custom condo!!
    $1,900
    city of chicago
  59. One of a kind!
    $1,895
    city of chicago
  60. Holiday Vacay
    $1
    Wis Dells
  61. Manasota Key Condo
    $0
    Englewood
  62. New Years Eve and Independence Day week
    $800
    Wisconsin Dells, Wi.
  63. Escape the cold this winter - Enjoy January to March in Sonoma Ca.
    $6,500
    Sonoma
  64. 11-22 Arrival- Christmas Mountain Resort -Wis Dells
    $649
    Wisconsin Dells
  65. Your Perfect Arizona Vacation Home Awaits!
    $0
    Fantastic Vacation Properties in Phoenix, Scottsdale and Gle
  66. PUEBLO BONITO ROSE RESORT
    $4,000
    Chicago
  67. LQQK Thanksgiving 2 bedroom wisconsin dells
    $649
    Wisconsin Dells
  68. ~*~ Luxury FL Beach Rental 6br/5ba/over 3k sqft/sleeps 16 ~*~
    $0
    Cape San Blas, FL
  69. LQQK Thanksgiving 2 bedroom- Wisconsin Dells
    $649
    Wisconsin Dells