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Chicago Vacation Rentals(234)

234 Results
3 - 5 night minimum stay
(105)
  • 2 BR,
  • 2 BA,
  • Sleeps 6
3 - 5 night minimum stay
(11)
  • 3 BR,
  • 2 BA,
  • Sleeps 8
3 night minimum stay
(60)
  • 2 BR,
  • 2 BA,
  • Sleeps 6
    Book it Now
    2 - 4 night minimum stay
    (7)
    • 2 BR,
    • 1 BA,
    • Sleeps 6
    $260 - $450
    per night
    3 - 5 night minimum stay
    (10)
    • 1 BR,
    • 1 BA,
    • Sleeps 4
    2 - 4 night minimum stay
    (23)
    • 2 BR,
    • 2 BA,
    • Sleeps 6
    2 - 4 night minimum stay
    (37)
    • 4 BR,
    • 3 BA,
    • 1 HF BA,
    • Sleeps 24
    3 night minimum stay
    (36)
    • 2 BR,
    • 2 BA,
    • Sleeps 6
      Book it Now
      3 night minimum stay
      (58)
      • 2 BR,
      • 2 BA,
      • Sleeps 6
        Book it Now
        3 night minimum stay
        (63)
        • 2 BR,
        • 2 BA,
        • Sleeps 6
          Book it Now
          3 night minimum stay
          (24)
          • 2 BR,
          • 2 BA,
          • Sleeps 6
            Book it Now
            2 night minimum stay
            (18)
            • 3 BR,
            • 2 BA,
            • 1 HF BA,
            • Sleeps 8
            3 night minimum stay
            (7)
            • 2 BR,
            • 2 BA,
            • Sleeps 6
              Book it Now
              2 - 4 night minimum stay
              (5)
              • 1 BR,
              • 1 BA,
              • Sleeps 6
              Special Offer! Huge savings of $20 off a day for Winter bookings! January 6 - March 1
              2 - 5 night minimum stay
              (12)
              • 2 BR,
              • 2 BA,
              • Sleeps 6
              3 night minimum stay
              (4)
              • 2 BR,
              • 2 BA,
              • Sleeps 6
                Book it Now
                (10)
                • 3 BR,
                • 2 BA,
                • Sleeps 10
                2 - 5 night minimum stay
                (19)
                • 2 BR,
                • 2 BA,
                • Sleeps 6
                2 night minimum stay
                (9)
                • 2 BR,
                • 2 BA,
                • Sleeps 8
                Special Offer! LOWEST PRICE FOR AMAZING GOLD COAST STAY! $199.00 a night! January 3 - March 1
                2 - 4 night minimum stay
                (4)
                • 3 BR,
                • 2 BA,
                • Sleeps 8
                2 - 3 night minimum stay
                (80)
                • 3 BR,
                • 2 BA,
                • Sleeps 6
                Special Offer! NEW YEARS SPECIAL GREYSTONE MANSION!!!! $699.00 whole house January 3 - March 1
                3 night minimum stay
                (6)
                • 1 BR,
                • 1 BA,
                • Sleeps 4
                3 night minimum stay
                2 Reviews
                • 2 BR,
                • 2 BA,
                • Sleeps 6
                  Book it Now
                  3 night minimum stay
                  2 Reviews
                  • 2 BR,
                  • 2 BA,
                  • Sleeps 6
                    Book it Now
                    Special Offer! Amazing Streeterville location in the heart of Chicago! January 20 - February 3
                    3 - 5 night minimum stay
                    (4)
                    • 2 BR,
                    • 2 BA,
                    • Sleeps 4
                    Special Offer! Winter Special $99/n + fees January 7 - March 31
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