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craigslist

Vacation Rentals in Chicago

  1. see also
  2. Fall Colors Waterfront Cottages
    $135
    Barryton
  3. Stunning 1BR condo in SoNo West!
    $1,800
    Chicago
  4. Penn State Football Package
    $999
    Evanston
  5. Wisconsin Dells - Glacier Canyon Nov 20-22 w/8 waterpark wristbands
    $299
    Wisconsin Dells
  6. Modern and Well-Equipped Cabin in Minocqua, WI.
    $0
    Gurnee
  7. Wyndham Glacier Canyon at The Wilderness 10/24-26
    $695
    north chicagoland
  8. Marriott's Aruba Ocean Club (July 20, 2026 to July 27, 2026)
    $2,700
    Palm Beach Aruba
  9. 5 STAR RESORT - GREAT Amenities + Full Kitchen
    $900
    WORLDWIDE
  10. Wisconsin Dells-Glacier Canyon Nov 6-8 2 bdrm Pres w/ 6 wristbands
    $299
    Wisconsin Dells
  11. Cabin for rent
    $200
    seveirville
  12. 4 Bdrm Private Pool/Spa Home
    $4,000
    Palm Desert
  13. New Years Eve and Independence Day week
    $800
    Wisconsin Dells, Wi.
  14. Wisconsin Dells - Glacier Canyon Oct 31-Nov 2 w/ 4 wrtpk wristbands
    $249
    Wisconsin Dells
  15. Wisconsin Dells-Glacier Canyon Oct 29-Nov 1 2 Pres w/ 6 wrstbnds
    $199
    Wisconsin Dells
  16. Wisconsin Dells-Glacier Canyon Oct 27-30 3 bdrm Pres w/8 wristbands
    $249
    Wisconsin Dells
  17. Smokey Mountain Fall vacatiion
    $850
    Gaitlinburg
  18. Attention snowmobilers
    $3,500
    Presque Isle
  19. Modern Recent home
    $125
    Chicago
  20. Perfect for groups
    $0
    Chicago, IL
  21. Ideally located in West Lakeview withing walking distance to Wrigley Field
    $135
    Chicago, IL
  22. Perfect for groups
    $0
    Chicago, IL
  23. Visiting the Evanston area for 3 days or more? Check us out.
    $269
    Evanston IL
  24. Old Naples Florida resort rental. Near Beach. Jan 10th thru Jan 17th
    $1,800
    Naples
  25. 2 Bedroom 16x80 Manufactured Home
    $2,150
    St. Cloud, Fl.
  26. Perfect for groups
    $135
    Chicago, IL
  27. Perfect for groups
    $135
    Chicago, IL
  28. Perfect for groups
    $135
    Chicago, IL
  29. Perfect for groups
    $135
    Chicago, IL
  30. Furnished motel style suite, No Deposit daily $ 75.00 weekly $395
    $395
    Bartlett ILLINOIS 60103
  31. Furnished motel style suite, No Deposit daily $ 75.00 weekly $ 375
    $395
    Bartlett ILLINOIS 60103
  32. Wisconsin Dells - Glacier Canyon Oct 27-30 w/8 waterpark wristbands
    $199
    Wisconsin Dells
  33. Wisconsin Dells - Glacier Canyon Oct 21-23 w/8 waterpark wristbands
    $199
    Wisconsin Dells
  34. Scottsdale Arizona Luxury Condominium Pool Side Clubhouse view
    $5,500
    scottsdale
  35. Hotel rooms available discounted rates
    $0
    city of chicago
  36. Lovely unit
    $1,600
    Chicago
  37. Furnished motel style suite, No Deposit daily $ 75.00 weekly $ 350
    $395
    Bartlett ILLINOIS 60103
  38. Furnished motel style suite, No Deposit $ 70 daily $ 395 weekly
    $395
    Bartlett ILLINOIS 60103
  39. WINTER VACATION HOME
    $3,000
    Minocqua
  40. WELL-MAINTAINED CONDO
    $1,300
    Schaumburg
  41. Perfect for groups
    $150
    Chicago, IL
  42. ~*~ Luxury FL Beach Rental 6br/5ba/over 3k sqft/sleeps 16 ~*~
    $0
    Cape San Blas, FL
  43. Condo - Bradenton Florida - Seasonal Rental
    $1,600
    Bradenton
  44. A Home Away From Home
    $150
    Chicago
  45. Perfect for groups
    $150
    Chicago, IL
  46. New construction elevator building
    $150
    Chicago, IL
  47. Amazing Southern City Views Spacious 1 Bed 1 Bath
    $1,350
    Chicago
  48. ROOM 4 RIOT FEST
    $200
    Douglass Park
  49. A Vacation Rental Home Away from Home
    $150
    Chicago, IL
  50. Just steps from vibrant downtown Naperville
    $1,300
    Naperville
  51. 3 bedroom, 2 bath residence offers private outdoor space
    $4,408
    Chicago