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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. Gold Coast Lake Michigan Corner Stidio
    $1,800
    Chicago
  6. Wisconsin Dells - Glacier Canyon Nov 20-22 w/8 waterpark wristbands
    $299
    Wisconsin Dells
  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. Cabin for rent
    $200
    seveirville
  10. 4 Bdrm Private Pool/Spa Home
    $4,000
    Palm Desert
  11. New Years Eve and Independence Day week
    $800
    Wisconsin Dells, Wi.
  12. Smokey Mountain Fall vacatiion
    $850
    Gaitlinburg
  13. Modern Recent home
    $125
    Chicago
  14. Perfect for groups
    $0
    Chicago, IL
  15. Ideally located in West Lakeview withing walking distance to Wrigley Field
    $135
    Chicago, IL
  16. Perfect for groups
    $0
    Chicago, IL
  17. Visiting the Evanston area for 3 days or more? Check us out.
    $269
    Evanston IL
  18. 2 Bedroom 16x80 Manufactured Home
    $2,150
    St. Cloud, Fl.
  19. Perfect for groups
    $135
    Chicago, IL
  20. Perfect for groups
    $135
    Chicago, IL
  21. Perfect for groups
    $135
    Chicago, IL
  22. Perfect for groups
    $135
    Chicago, IL
  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 weekly $ 375
    $395
    Bartlett ILLINOIS 60103
  25. Wisconsin Dells - Glacier Canyon Oct 27-30 w/8 waterpark wristbands
    $199
    Wisconsin Dells
  26. Wisconsin Dells - Glacier Canyon Oct 21-23 w/8 waterpark wristbands
    $199
    Wisconsin Dells
  27. Scottsdale Arizona Luxury Condominium Pool Side Clubhouse view
    $5,500
    scottsdale
  28. Hotel rooms available discounted rates
    $0
    city of chicago
  29. 3br -Tropical Caribbean Vacation this Winter St John US Virgin Islands
    $5,899
    St John USVI
  30. Furnished motel style suite, No Deposit daily $ 75.00 weekly $ 350
    $395
    Bartlett ILLINOIS 60103
  31. WELL-MAINTAINED CONDO
    $1,300
    Schaumburg
  32. Perfect for groups
    $150
    Chicago, IL
  33. ~*~ Luxury FL Beach Rental 6br/5ba/over 3k sqft/sleeps 16 ~*~
    $0
    Cape San Blas, FL
  34. Condo - Bradenton Florida - Seasonal Rental
    $1,600
    Bradenton
  35. A Home Away From Home
    $150
    Chicago
  36. Perfect for groups
    $150
    Chicago, IL
  37. New construction elevator building
    $150
    Chicago, IL
  38. Amazing Southern City Views Spacious 1 Bed 1 Bath
    $1,350
    Chicago
  39. ROOM 4 RIOT FEST
    $200
    Douglass Park
  40. A Vacation Rental Home Away from Home
    $150
    Chicago, IL
  41. Just steps from vibrant downtown Naperville
    $1,300
    Naperville
  42. 3 bedroom, 2 bath residence offers private outdoor space
    $4,408
    Chicago