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  • Showing 1-50 of 300+
Additional fees apply. Taxes may be added.
    Excellent! 4.5/5
    (53 reviews)
    $67
    avg/night
    • 1 BR
    • 1 BA
    • Sleeps 4
    Apartment #690239vb
    53
    Viewed 29 times in the last 48 hours
      Excellent! 4.3/5
      (12 reviews)
      avg/night
      • 2 BR
      • 2 BA
      • Sleeps 5
      Apartment #4047746
      12
      Viewed 60 times in the last 48 hours
        Wonderful! 4.9/5
        (80 reviews)
        avg/night
        • 3 BR
        • 2 BA
        • 1 HF BA
        • Sleeps 8
        Apartment #578762vb
        80
        Viewed 95 times in the last 48 hours
          Wonderful! 4.9/5
          (12 reviews)
          avg/night
          • 2 BR
          • 1 BA
          • Sleeps 4
          Apartment #780506vb
          12
          Viewed 14 times in the last 48 hours
            Wonderful! 4.9/5
            (36 reviews)
            avg/night
            • 2 BR
            • 2 BA
            • Sleeps 6
            Apartment #408313vb
            36
            Viewed 53 times in the last 48 hours
              Wonderful! 4.8/5
              (50 reviews)
              avg/night
              • 4 BR
              • 4 BA
              • Sleeps 12
              Condo #679790vb
              50
              Viewed 70 times in the last 48 hours
                Excellent! 4.7/5
                (92 reviews)
                avg/night
                • 2 BR
                • 2 BA
                • Sleeps 4
                Condo #222038
                92
                Viewed 28 times in the last 48 hours
                  Exceptional! 5.0/5
                  (28 reviews)
                  avg/night
                  • 3 BR
                  • 2 BA
                  • Sleeps 6
                  Apartment #470476vb
                  28
                  Viewed 25 times in the last 48 hours
                    Excellent! 4.6/5
                    (83 reviews)
                    avg/night
                    • 2 BR
                    • 2 BA
                    • Sleeps 8
                    Apartment #179389vb
                    83
                    Viewed 60 times in the last 48 hours
                      Wonderful! 4.9/5
                      (35 reviews)
                      avg/night
                      • 1 BR
                      • 1 BA
                      • Sleeps 4
                      Apartment #3790035
                      35
                      Viewed 17 times in the last 48 hours
                        Wonderful! 4.8/5
                        (37 reviews)
                        avg/night
                        • 3 BR
                        • 1 BA
                        • Sleeps 5
                        Apartment #600158vb
                        37
                        Viewed 13 times in the last 48 hours
                          Wonderful! 4.8/5
                          (45 reviews)
                          avg/night
                          • 3 BR
                          • 2 BA
                          • Sleeps 8
                          Condo #290256vb
                          45
                          Viewed 30 times in the last 48 hours
                            Excellent! 4.7/5
                            (15 reviews)
                            avg/night
                            • 1 BR
                            • 1 BA
                            • Sleeps 3
                            Apartment #4146480
                            15
                            Viewed 11 times in the last 48 hours
                              Wonderful! 4.9/5
                              (53 reviews)
                              avg/night
                              • 2 BR
                              • 2 BA
                              • Sleeps 6
                              Condo #3720918
                              53
                              Viewed 29 times in the last 48 hours
                                Excellent! 4.7/5
                                (40 reviews)
                                avg/night
                                • 2 BR
                                • 1 BA
                                • 1 HF BA
                                • Sleeps 8
                                Apartment #3645846
                                40
                                Viewed 20 times in the last 48 hours
                                  • 2 BR
                                  • 1 BA
                                  • Sleeps 5
                                  Condo #3861165
                                  19
                                  Viewed 26 times in the last 48 hours
                                    Exceptional! 5.0/5
                                    (125 reviews)
                                    avg/night
                                    • 3 BR
                                    • 2 BA
                                    • Sleeps 8
                                    Apartment #422128vb
                                    125
                                    Viewed 28 times in the last 48 hours
                                      Wonderful! 4.8/5
                                      (13 reviews)
                                      avg/night
                                      • Studio
                                      • 1 BA
                                      • Sleeps 2
                                      Apartment #742485vb
                                      13
                                      Viewed 25 times in the last 48 hours
                                        Excellent! 4.7/5
                                        (21 reviews)
                                        $93
                                        avg/night
                                        • 2 BR
                                        • 1 BA
                                        • Sleeps 4
                                        Apartment #588228vb
                                        21
                                        Viewed 17 times in the last 48 hours
                                          Wonderful! 4.9/5
                                          (56 reviews)
                                          avg/night
                                          • 4 BR
                                          • 2 BA
                                          • Sleeps 10
                                          House #595328vb
                                          56
                                          Viewed 39 times in the last 48 hours
                                            Exceptional! 5.0/5
                                            (58 reviews)
                                            avg/night
                                            • 4 BR
                                            • 2 BA
                                            • Sleeps 10
                                            Apartment #627209vb
                                            58
                                            Viewed 48 times in the last 48 hours
                                              Excellent! 4.7/5
                                              (34 reviews)
                                              $86
                                              avg/night
                                              • 1 BR
                                              • 1 BA
                                              • Sleeps 4
                                              Apartment #3751630
                                              34
                                              Viewed 21 times in the last 48 hours
                                                Wonderful! 4.8/5
                                                (42 reviews)
                                                avg/night
                                                • 2 BR
                                                • 1 BA
                                                • 1 HF BA
                                                • Sleeps 6
                                                Apartment #271945
                                                42
                                                Viewed 11 times in the last 48 hours
                                                  Exceptional! 5.0/5
                                                  (13 reviews)
                                                  avg/night
                                                  • 3 BR
                                                  • 2 BA
                                                  • Sleeps 6
                                                  Apartment #723132vb
                                                  13
                                                  Viewed 35 times in the last 48 hours
                                                    Wonderful! 4.9/5
                                                    (20 reviews)
                                                    avg/night
                                                    • 2 BR
                                                    • 2 BA
                                                    • Sleeps 6
                                                    Apartment #653828vb
                                                    20
                                                    Viewed 22 times in the last 48 hours
                                                      $82
                                                      avg/night
                                                      • Studio
                                                      • 1 BA
                                                      • Sleeps 2
                                                      Apartment #471498vb
                                                      3
                                                      Viewed 9 times in the last 48 hours
                                                        Wonderful! 4.8/5
                                                        (45 reviews)
                                                        avg/night
                                                        • 6 BR
                                                        • 3 BA
                                                        • Sleeps 18
                                                        Condo #682966vb
                                                        45
                                                        Viewed 66 times in the last 48 hours
                                                          Wonderful! 4.8/5
                                                          (56 reviews)
                                                          avg/night
                                                          • 3 BR
                                                          • 2 BA
                                                          • Sleeps 12
                                                          House #376549vb
                                                          56
                                                          Viewed 17 times in the last 48 hours
                                                            Exceptional! 5.0/5
                                                            (23 reviews)
                                                            avg/night
                                                            • 3 BR
                                                            • 2 BA
                                                            • Sleeps 6
                                                            Townhome #3917584
                                                            23
                                                            Viewed 21 times in the last 48 hours
                                                              Excellent! 4.5/5
                                                              (75 reviews)
                                                              avg/night
                                                              • 2 BR
                                                              • 2 BA
                                                              • Sleeps 10
                                                              Condo #400905vb
                                                              75
                                                              Viewed 21 times in the last 48 hours
                                                                Wonderful! 4.9/5
                                                                (17 reviews)
                                                                avg/night
                                                                • 2 BR
                                                                • 1 BA
                                                                • Sleeps 7
                                                                Apartment #792973vb
                                                                17
                                                                Viewed 18 times in the last 48 hours
                                                                  Wonderful! 4.9/5
                                                                  (74 reviews)
                                                                  avg/night
                                                                  • 2 BR
                                                                  • 2 BA
                                                                  • Sleeps 6
                                                                  Apartment #358020
                                                                  74
                                                                  Viewed 30 times in the last 48 hours
                                                                    Very Good! 4.2/5
                                                                    (15 reviews)
                                                                    avg/night
                                                                    • 1 BR
                                                                    • 1 BA
                                                                    • Sleeps 3
                                                                    Apartment #836462vb
                                                                    15
                                                                    Viewed 78 times in the last 48 hours
                                                                      Wonderful! 4.9/5
                                                                      (17 reviews)
                                                                      avg/night
                                                                      • 1 BR
                                                                      • 1 BA
                                                                      • Sleeps 5
                                                                      Apartment #784869vb
                                                                      17
                                                                      Viewed 11 times in the last 48 hours
                                                                        Wonderful! 4.8/5
                                                                        (17 reviews)
                                                                        avg/night
                                                                        • 2 BR
                                                                        • 2 BA
                                                                        • Sleeps 6
                                                                        Condo #735859vb
                                                                        17
                                                                        Viewed 38 times in the last 48 hours
                                                                          Exceptional! 5.0/5
                                                                          (20 reviews)
                                                                          avg/night
                                                                          • 4 BR
                                                                          • 1 BA
                                                                          • 2 HF BA
                                                                          • Sleeps 8
                                                                          House #776608vb
                                                                          20
                                                                          Viewed 45 times in the last 48 hours
                                                                            Excellent! 4.7/5
                                                                            (42 reviews)
                                                                            avg/night
                                                                            • 2 BR
                                                                            • 1 BA
                                                                            • Sleeps 4
                                                                            Apartment #445608vb
                                                                            42
                                                                            Viewed 26 times in the last 48 hours
                                                                              Wonderful! 4.9/5
                                                                              (9 reviews)
                                                                              avg/night
                                                                              • 3 BR
                                                                              • 2 BA
                                                                              • Sleeps 6
                                                                              Apartment #653830vb
                                                                              9
                                                                              Viewed 16 times in the last 48 hours
                                                                                Excellent! 4.6/5
                                                                                (31 reviews)
                                                                                avg/night
                                                                                • 4 BR
                                                                                • 2 BA
                                                                                • Sleeps 11
                                                                                Condo #685840vb
                                                                                31
                                                                                Viewed 13 times in the last 48 hours
                                                                                  Exceptional! 5.0/5
                                                                                  (231 reviews)
                                                                                  avg/night
                                                                                  • 1 BR
                                                                                  • 1 BA
                                                                                  • Sleeps 4
                                                                                  Condo #65673vb
                                                                                  231
                                                                                  Viewed 16 times in the last 48 hours
                                                                                    Wonderful! 4.9/5
                                                                                    (29 reviews)
                                                                                    avg/night
                                                                                    • 2 BR
                                                                                    • 2 BA
                                                                                    • Sleeps 6
                                                                                    Condo #376149vb
                                                                                    29
                                                                                    Viewed 9 times in the last 48 hours
                                                                                      Wonderful! 4.9/5
                                                                                      (140 reviews)
                                                                                      avg/night
                                                                                      • 3 BR
                                                                                      • 2 BA
                                                                                      • Sleeps 8
                                                                                      Condo #7757vb
                                                                                      140
                                                                                      Viewed 32 times in the last 48 hours
                                                                                        Excellent! 4.5/5
                                                                                        (24 reviews)
                                                                                        avg/night
                                                                                        • 3 BR
                                                                                        • 2 BA
                                                                                        • Sleeps 8
                                                                                        Condo #622632vb
                                                                                        24
                                                                                        Viewed 20 times in the last 48 hours
                                                                                          Wonderful! 4.9/5
                                                                                          (11 reviews)
                                                                                          avg/night
                                                                                          • 1 BR
                                                                                          • 1 BA
                                                                                          • Sleeps 4
                                                                                          Condo #4037980
                                                                                          11
                                                                                          Viewed 86 times in the last 48 hours
                                                                                            • 1 BR
                                                                                            • 1 BA
                                                                                            • Sleeps 2
                                                                                            Apartment #4005449
                                                                                            2
                                                                                              Wonderful! 4.8/5
                                                                                              (12 reviews)
                                                                                              avg/night
                                                                                              • 1 BR
                                                                                              • 1 BA
                                                                                              • Sleeps 3
                                                                                              Apartment #4146120
                                                                                              12
                                                                                              Viewed 8 times in the last 48 hours
                                                                                                Exceptional! 5.0/5
                                                                                                (24 reviews)
                                                                                                avg/night
                                                                                                • 3 BR
                                                                                                • 2 BA
                                                                                                • Sleeps 6
                                                                                                Apartment #398923vb
                                                                                                24
                                                                                                Viewed 10 times in the last 48 hours
                                                                                                  • 3 BR
                                                                                                  • 2 BA
                                                                                                  • Sleeps 8
                                                                                                  Apartment #4055734
                                                                                                  20
                                                                                                  Viewed 7 times in the last 48 hours
                                                                                                    • Studio
                                                                                                    • 1 BA
                                                                                                    • Sleeps 2
                                                                                                    Condo #459707vb
                                                                                                    15
                                                                                                      Wonderful! 4.8/5
                                                                                                      (44 reviews)
                                                                                                      avg/night
                                                                                                      • 2 BR
                                                                                                      • 2 BA
                                                                                                      • Sleeps 6
                                                                                                      Condo #265424vb
                                                                                                      44
                                                                                                      Viewed 34 times in the last 48 hours
                                                                                                      • 1 - 50 of 300+

                                                                                                      Chicago: Vacation Rentals (1,245)

                                                                                                       

                                                                                                      Recent Chicago Reviews

                                                                                                      Great view and convenient location

                                                                                                      5 of 5
                                                                                                      We love the property and all the amenities. The instructions on where the key was were wrong but we soon figured it out. Really enjoyed the view.
                                                                                                      • Submitted: Nov 30, 2016
                                                                                                      • Stayed: Nov 2016

                                                                                                      Great place to stay in the Windy City!

                                                                                                      4 of 5
                                                                                                      Our family of 6 enjoyed this great home. We had 3 generations (grandparents, kids, grandkids) in town to celebrate a 70th birthday - and this was a perfect place to set up camp. Plenty of room for all of us and it was nice to have living space/kitchen so that we could be together. We didn't spend much time exploring the neighborhood, but it was nice and not too noisy. House is on a quiet, tree-lined street. The home is in an older building, so many of the finishes are quite dated - this didn't bother us at all. Beds were comfortable, nice big towels, hooks in all of the rooms for helping with storage (which I love!). We had everything we needed - and it was just a short uber ride into the city.
                                                                                                      • Submitted: Nov 28, 2016
                                                                                                      • Stayed: Nov 2016

                                                                                                      Great place for family get together

                                                                                                      5 of 5
                                                                                                      We had a great stay in this condo last week. It was very easy for people to get to, whether by train from O'Hare, car, or taxi. It was very clean and comfortable for everyone. Brett does a great job to make you feel welcome! I would certainly come back, if I ever need to come to Chicago again.
                                                                                                      • Submitted: Nov 27, 2016
                                                                                                      • Stayed: Nov 2016