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Vacation Rentals in Chicago

  1. see also
  2. Wis Dells Glacier Canyon Fri 8/28 to Mon8/31/26 3Br/2Ba Deluxe
    $0
    west chicagoland
  3. Twin Bay Resort Cabin Rentals
    $0
    Tomahawk/ Lake Nokomis
  4. Florida Beach Front Condo: Winter stays!
    $1,438
    Indian Rocks Beach
  5. $$$ HUNTING LAND FOR RENT $$$
    $1,175
    Pontiac
  6. EXTENDED WEEKEND SPECIAL 8/20-2/24; WHEELCHAIR ACCESSIBLE; SAVE $400
    $375
    WOODLAND PARK, BITELY, MI
  7. Sheraton Vistana Resort
    $1,695
    Orlando
  8. Come Camping!
    $50
    city of chicago
  9. MINOCQUA WINTER VACATION HOME-RENT
    $3,000
    Squirrel Lake
  10. Wyndham Glacier Canyon The Wilderness Waterpark in 2 bdrm 10/23-25
    $599
    north chicagoland
  11. Wisconsin Dells - Glacier Canyon Sept 1-4 w/10 waterpark wristbands
    $299
    Wisconsin Dells
  12. Move-in ready
    $1,300
    Naperville
  13. Sherman Plaza
    $1,280
    Evanston
  14. Park views
    $1,330
    Chicago
  15. Spectacular Views! On the Beach!!!
    $1,438
    Indian Rocks Beach
  16. Delray Beach Florida-Lakes of Delray 2027 Winter Rental
    $4,500
    Delray Beach
  17. Wisconsin Dells-Glacier Canyon Sept 10-12 2 bdrm Pres w/ 6 wrstbnd
    $329
    Wisconsin Dells
  18. Vacation
    $1,380
    Evanston
  19. Dont miss
    $1,350
    Evanston
  20. Vacation
    $1,300
    Naperville
  21. Visiting the Evanston area for 3 days or more? Check us out.
    $269
    Evanston IL
  22. B
    $210
    New Lenox
  23. cabin rental in tennessee
    $170
    pigeon forge smoky mt
  24. cabin rental in tennessee
    $170
    pigeon forge smoky mt
  25. cabin rental in tennessee
    $170
    pigeon forge smoky mt
  26. Heritage Harbor vacation rental - Ottawa vacation rental
    $189
    Ottawa, IL
  27. New Years at Vail skiing week & also Valentine week
    $750
    Vail or Wisconsin Dells, Wi.
  28. RETREAT, RELAX & REJUVENATE on Lake . . . 2 hours from Chicago
    $175
    Edgerton, WI
  29. Lollapalooza weekend airbnb
    $2,700
    Chicago
  30. 1-bedroom apartment in the River North
    $2,000
    58 W Superior Str, Unit 11, Chicago, IL
  31. 2 Bedroom 16x80 Manufactured Home
    $2,150
    St. Cloud, Fl.
  32. amazing views 1 bed, 1bath stunning and spacious
    $1,650
    1255 South State St, Unit 1305, Chicago, IL
  33. amazing views 1 bed, 1bath stunning and spacious
    $1,650
    51 E 14th St, Unit 2-502, Chicago, IL
  34. Wisconsin Dells Vacay Condos. Choose 1 or 2 BR. Lake/beachfront/pools
    $0
    Wisconsin Dells
  35. Wisconsin Dells - Glacier Canyon Nov 22-5 w/10 waterpark wtbnds
    $299
    Wisconsin Dells
  36. Wisconsin Dells - Glacier Canyon Sept 2-4 w/10 waterpark wtbnds
    $350
    Wisconsin Dells
  37. Schaumburg Executive Rental Suite Fully Furnished with Kitchen
    $0
    Schaumburg
  38. Glacier Canyon Wisconsin Dells
    $0
    Chicago
  39. 1-bedroom apartment in the South Loop -
    $2,335
    1408 S Wabash Ave, Chicago, IL