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craigslist

Vacation Rentals in Chicago

  1. see also
  2. Wyndham Glacier Canyon The Wilderness Waterpark in 2 bdrm 10/23-25
    $599
    north chicagoland
  3. 1-bedroom apartment in the South Loop -
    $1,890
    1408 S Wabash Ave, Chicago, IL
  4. EXTENDED WEEKEND SPECIAL 8/20-2/24; WHEELCHAIR ACCESSIBLE; SAVE $400
    $375
    WOODLAND PARK, BITELY, MI
  5. B
    $210
    New Lenox
  6. Wis Dells Glacier Canyon Fri 8/28 to Mon8/31/26 3Br/2Ba Deluxe
    $0
    west chicagoland
  7. Twin Bay Resort Cabin Rentals
    $0
    Tomahawk/ Lake Nokomis
  8. Florida Beach Front Condo: Winter stays!
    $1,438
    Indian Rocks Beach
  9. $$$ HUNTING LAND FOR RENT $$$
    $1,175
    Pontiac
  10. Sheraton Vistana Resort
    $1,695
    Orlando
  11. MINOCQUA WINTER VACATION HOME-RENT
    $3,000
    Squirrel Lake
  12. Wisconsin Dells - Glacier Canyon Sept 1-4 w/10 waterpark wristbands
    $299
    Wisconsin Dells
  13. Move-in ready
    $1,300
    Naperville
  14. Sherman Plaza
    $1,280
    Evanston
  15. Park views
    $1,330
    Chicago
  16. Spectacular Views! On the Beach!!!
    $1,438
    Indian Rocks Beach
  17. Delray Beach Florida-Lakes of Delray 2027 Winter Rental
    $4,500
    Delray Beach
  18. Wisconsin Dells-Glacier Canyon Sept 10-12 2 bdrm Pres w/ 6 wrstbnd
    $329
    Wisconsin Dells
  19. Vacation
    $1,380
    Evanston
  20. Dont miss
    $1,350
    Evanston
  21. Vacation
    $1,300
    Naperville
  22. Visiting the Evanston area for 3 days or more? Check us out.
    $269
    Evanston IL
  23. Heritage Harbor vacation rental - Ottawa vacation rental
    $189
    Ottawa, IL
  24. New Years at Vail skiing week & also Valentine week
    $750
    Vail or Wisconsin Dells, Wi.
  25. RETREAT, RELAX & REJUVENATE on Lake . . . 2 hours from Chicago
    $175
    Edgerton, WI
  26. Lollapalooza weekend airbnb
    $2,700
    Chicago
  27. 1-bedroom apartment in the River North
    $2,000
    58 W Superior Str, Unit 11, Chicago, IL
  28. 2 Bedroom 16x80 Manufactured Home
    $2,150
    St. Cloud, Fl.
  29. Wisconsin Dells Vacay Condos. Choose 1 or 2 BR. Lake/beachfront/pools
    $0
    Wisconsin Dells
  30. Wisconsin Dells - Glacier Canyon Nov 22-5 w/10 waterpark wtbnds
    $299
    Wisconsin Dells
  31. Wisconsin Dells - Glacier Canyon Sept 2-4 w/10 waterpark wtbnds
    $350
    Wisconsin Dells
  32. Schaumburg Executive Rental Suite Fully Furnished with Kitchen
    $0
    Schaumburg