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craigslist

Vacation Rentals in Chicago - City Of Chicago

  1. see also
  2. Marriott's Aruba Ocean Club (July 20, 2026 to July 27, 2026)
    $2,700
    Palm Beach Aruba
  3. Perfect for groups
    $135
    Chicago, IL
  4. Ideally located in West Lakeview withing walking distance to Wrigley Field
    $150
    Chicago, IL
  5. Perfect for groups
    $150
    Chicago, IL
  6. Ideally located in West Lakeview withing walking distance to Wrigley Field
    $150
    Chicago, IL
  7. Perfect for groups
    $150
    Chicago, IL
  8. Modern Recent home
    $125
    Chicago
  9. Hotel rooms available discounted rates
    $0
    city of chicago
  10. Superbowl Party and Final Four Accommodations
    $1,990
    10 minutes from Grand Rapids Airport
  11. PUEBLO BONITO ROSE RESORT
    $4,000
    Chicago
  12. Gorgeous Top-floor 1 bed/1 bath
    $1,300
    Chicago
  13. Perfect for groups
    $150
    Chicago, IL
  14. Condo on the beach
    $0
    7 Mile Beach
  15. New construction elevator building
    $150
    Chicago, IL
  16. Perfect for groups
    $150
    Chicago, IL
  17. Escape Winter in Oceanfront Penthouse
    $3,995
    North Myrtle Beach
  18. Located in one of the most desired neighborhoods in Chicago
    $3,000
    Chicago
  19. Perfect for large group
    $150
    Chicago
  20. Perfect for groups
    $135
    Chicago, IL
  21. Gold Coast Lake Michigan Corner Stidio
    $1,800
    Chicago
  22. 4 Bdrm Private Pool/Spa Home
    $4,000
    Palm Desert
  23. Wisconsin dells Glacier canyon
    $0
    Fredonia
  24. Smokey Mountain Fall vacatiion
    $850
    Gaitlinburg
  25. Vacation home available for rent
    $3,195
    Chicago
  26. Assistance for right girl or couple
    $0
    city of chicago
  27. Perfect for groups
    $0
    Chicago, IL
  28. Perfect for groups
    $0
    Chicago, IL