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The largest city in the American state of Illinois, holiday rental accommodation in Chicago is a magnet to anyone with a passion for urban culture, and being renowned for its wealth of history and architecture, acondo or apartment rental in Chicago is not something that would appeal to those seeking a situation of silence and seclusion! In truth, an atmosphere of peace can be easily enjoyed without ever having to leave your holiday accommodation in Chicago, and never being far from one of the city's numerous state parks means you'll easily be able to discover a truly quiet corner in which to relax and take a break away from the hustle and bustle of everyday life on the streets of what must be the most famous city in Illinois. Condo and apartment rentals in Chicago can also satisfy the needs of those who simply can't do without a little natural beauty to soften the hard edges of an urban environment, and being situated on the shores of Lake Michigan can even promise to add a little sun, sea and sand to your vacation experience! But that would only be likely from May to October when temperatures can rise to around 30°C otherwise you might need to pack your thermal underwear, as during the deepest part of winter it's almost guaranteed that you'll see snow settling on the window sills of your holiday accommodation in Chicago.

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Favorite
    Viewed 47 times in the last 48 hours
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    avg/night
    (2 nights minimum)
    Apartment #1148015vb
    Favorite
      Viewed 39 times in the last 48 hours
      Exceptional! 5/5
      (10 reviews)
      avg/night
      (30 nights minimum)
      Apartment #860493vb
      10
      Favorite
        Viewed 76 times in the last 48 hours
        Premier Partner
        Wonderful! 4.8/5
        (58 reviews)
        avg/night
        (2 nights minimum)
        Condo #290256vb
        58
        Favorite
          Viewed 48 times in the last 48 hours
          Premier Partner
          Wonderful! 4.8/5
          (57 reviews)
          avg/night
          (3 nights minimum)
          Condo #265424vb
          57
          Favorite
            Viewed 17 times in the last 48 hours
            Wonderful! 4.8/5
            (47 reviews)
            avg/night
            (3 nights minimum)
            Apartment #3790035
            47
            Favorite
              Viewed 72 times in the last 48 hours
              Exceptional! 5/5
              (8 reviews)
              avg/night
              (27 nights minimum)
              Condo #499693vb
              8
              Favorite
                Viewed 27 times in the last 48 hours
                avg/night
                (31 nights minimum)
                Townhome #836942vb
                2
                Favorite
                  Viewed 35 times in the last 48 hours
                  Wonderful! 4.8/5
                  (72 reviews)
                  avg/night
                  (3 nights minimum)
                  Apartment #3768288
                  72
                  Favorite
                    Viewed 24 times in the last 48 hours
                    Excellent! 4.7/5
                    (52 reviews)
                    avg/night
                    (3 nights minimum)
                    Apartment #3751630
                    52
                    Favorite
                      Viewed 35 times in the last 48 hours
                      Premier Partner
                      Excellent! 4.6/5
                      (47 reviews)
                      avg/night
                      (2 nights minimum)
                      Condo #622632vb
                      47
                      Favorite
                        Viewed 32 times in the last 48 hours
                        Wonderful! 4.8/5
                        (65 reviews)
                        avg/night
                        (3 nights minimum)
                        Condo #296798
                        65
                        Favorite
                          Viewed 50 times in the last 48 hours
                          Excellent! 4.4/5
                          (21 reviews)
                          avg/night
                          Apartment #836457vb
                          21
                          Favorite
                            Viewed 21 times in the last 48 hours
                            Premier Partner
                            Excellent! 4.5/5
                            (12 reviews)
                            svg-lightning
                            avg/night
                            (3 nights minimum)
                            Apartment #845524vb
                            12
                            Favorite
                              Viewed 31 times in the last 48 hours
                              Wonderful! 4.9/5
                              (24 reviews)
                              avg/night
                              (2 nights minimum)
                              Apartment #903748vb
                              24
                              Favorite
                                Viewed 11 times in the last 48 hours
                                Wonderful! 4.9/5
                                (62 reviews)
                                avg/night
                                (3 nights minimum)
                                Condo #939473
                                62
                                Favorite
                                  Viewed 34 times in the last 48 hours
                                  Premier Partner
                                  Exceptional! 5/5
                                  (24 reviews)
                                  avg/night
                                  (3 nights minimum)
                                  Condo #3627370
                                  24
                                  Favorite
                                    Viewed 98 times in the last 48 hours
                                    Wonderful! 4.9/5
                                    (85 reviews)
                                    svg-lightning
                                    avg/night
                                    (2 nights minimum)
                                    Condo #679790vb
                                    85
                                    Favorite
                                      Viewed 19 times in the last 48 hours
                                      Excellent! 4.7/5
                                      (52 reviews)
                                      avg/night
                                      (3 nights minimum)
                                      Apartment #3833362
                                      52
                                      Favorite
                                        Viewed 39 times in the last 48 hours
                                        Wonderful! 4.8/5
                                        (137 reviews)
                                        avg/night
                                        (2 nights minimum)
                                        Condo #147152vb
                                        137
                                        Favorite
                                          Viewed 101 times in the last 48 hours
                                          Exceptional! 5/5
                                          (15 reviews)
                                          avg/night
                                          (2 nights minimum)
                                          Apartment #1093980vb
                                          15
                                          Favorite
                                            Viewed 21 times in the last 48 hours
                                            Premier Partner
                                            Exceptional! 5/5
                                            (28 reviews)
                                            avg/night
                                            (3 nights minimum)
                                            Condo #844695vb
                                            28
                                            Favorite
                                              Viewed 31 times in the last 48 hours
                                              Exceptional! 5/5
                                              (76 reviews)
                                              avg/night
                                              (2 nights minimum)
                                              Apartment #627209vb
                                              76
                                              Favorite
                                                Viewed 14 times in the last 48 hours
                                                Good! 3.7/5
                                                (23 reviews)
                                                avg/night
                                                Apartment #852509vb
                                                23
                                                Favorite
                                                  Viewed 41 times in the last 48 hours
                                                  Exceptional! 5/5
                                                  (23 reviews)
                                                  avg/night
                                                  Condo #4131192
                                                  23
                                                  Favorite
                                                    Viewed 42 times in the last 48 hours
                                                    Excellent! 4.4/5
                                                    (17 reviews)
                                                    avg/night
                                                    Apartment #874916vb
                                                    17
                                                    Favorite
                                                      Viewed 11 times in the last 48 hours
                                                      Wonderful! 4.8/5
                                                      (21 reviews)
                                                      avg/night
                                                      (2 nights minimum)
                                                      Apartment #821841vb
                                                      21
                                                      Favorite
                                                        Wonderful! 4.8/5
                                                        (11 reviews)
                                                        avg/night
                                                        (3 nights minimum)
                                                        Apartment #875365vb
                                                        11
                                                        Favorite
                                                          Viewed 21 times in the last 48 hours
                                                          Exceptional! 5/5
                                                          (55 reviews)
                                                          svg-lightning
                                                          avg/night
                                                          (3 nights minimum)
                                                          Condo #501599vb
                                                          55
                                                          Favorite
                                                            Wonderful! 4.9/5
                                                            (79 reviews)
                                                            View details for price
                                                            (3 nights minimum)
                                                            Condo #3720918
                                                            79
                                                            Favorite
                                                              Viewed 12 times in the last 48 hours
                                                              Wonderful! 4.8/5
                                                              (13 reviews)
                                                              avg/night
                                                              (2 - 3 nights minimum)
                                                              Apartment #4424184
                                                              13
                                                              Favorite
                                                                Viewed 28 times in the last 48 hours
                                                                Wonderful! 4.8/5
                                                                (83 reviews)
                                                                avg/night
                                                                (2 nights minimum)
                                                                Apartment #301852vb
                                                                83
                                                                Favorite
                                                                  Viewed 12 times in the last 48 hours
                                                                  Very Good! 4.1/5
                                                                  (29 reviews)
                                                                  avg/night
                                                                  Apartment #870916vb
                                                                  29
                                                                  Favorite
                                                                    Viewed 22 times in the last 48 hours
                                                                    Premier Partner
                                                                    Wonderful! 4.9/5
                                                                    (51 reviews)
                                                                    avg/night
                                                                    (3 nights minimum)
                                                                    House #571144vb
                                                                    51
                                                                    Favorite
                                                                      Viewed 19 times in the last 48 hours
                                                                      Very Good! 4.1/5
                                                                      (22 reviews)
                                                                      avg/night
                                                                      Apartment #819229vb
                                                                      22
                                                                      Favorite
                                                                        Viewed 35 times in the last 48 hours
                                                                        Exceptional! 5/5
                                                                        (48 reviews)
                                                                        svg-lightning
                                                                        avg/night
                                                                        Apartment #864022vb
                                                                        48
                                                                        Favorite
                                                                          Viewed 6 times in the last 48 hours
                                                                          Wonderful! 4.9/5
                                                                          (14 reviews)
                                                                          avg/night
                                                                          (4 nights minimum)
                                                                          Condo #849791vb
                                                                          14
                                                                          Favorite
                                                                            Viewed 12 times in the last 48 hours
                                                                            Very Good! 4/5
                                                                            (18 reviews)
                                                                            avg/night
                                                                            Apartment #895525vb
                                                                            18
                                                                            Favorite
                                                                              Viewed 15 times in the last 48 hours
                                                                              Excellent! 4.4/5
                                                                              (5 reviews)
                                                                              avg/night
                                                                              (2 nights minimum)
                                                                              Studio #4304772
                                                                              5
                                                                              Favorite
                                                                                Viewed 33 times in the last 48 hours
                                                                                Excellent! 4.7/5
                                                                                (14 reviews)
                                                                                avg/night
                                                                                (2 nights minimum)
                                                                                Townhome #985945vb
                                                                                14
                                                                                Favorite
                                                                                  Viewed 39 times in the last 48 hours
                                                                                  Wonderful! 4.8/5
                                                                                  (119 reviews)
                                                                                  svg-lightning
                                                                                  avg/night
                                                                                  (2 nights minimum)
                                                                                  Apartment #578762vb
                                                                                  119
                                                                                  Favorite
                                                                                    Wonderful! 4.9/5
                                                                                    (26 reviews)
                                                                                    avg/night
                                                                                    (3 nights minimum)
                                                                                    Apartment #695418vb
                                                                                    26
                                                                                    Favorite
                                                                                      Viewed 19 times in the last 48 hours
                                                                                      Premier Partner
                                                                                      Exceptional! 5/5
                                                                                      (43 reviews)
                                                                                      avg/night
                                                                                      (2 nights minimum)
                                                                                      House #840552vb
                                                                                      43
                                                                                      Favorite
                                                                                        Viewed 14 times in the last 48 hours
                                                                                        Premier Partner
                                                                                        Excellent! 4.7/5
                                                                                        (29 reviews)
                                                                                        avg/night
                                                                                        (2 nights minimum)
                                                                                        Apartment #4146480
                                                                                        29
                                                                                        Favorite
                                                                                          Viewed 16 times in the last 48 hours
                                                                                          Excellent! 4.7/5
                                                                                          (39 reviews)
                                                                                          avg/night
                                                                                          (3 nights minimum)
                                                                                          Apartment #4016534
                                                                                          39
                                                                                          Favorite
                                                                                            Viewed 10 times in the last 48 hours
                                                                                            Excellent! 4.6/5
                                                                                            (23 reviews)
                                                                                            avg/night
                                                                                            (1 - 6 nights minimum)
                                                                                            House #4325287
                                                                                            23
                                                                                            Favorite
                                                                                              Viewed 48 times in the last 48 hours
                                                                                              Wonderful! 4.9/5
                                                                                              (93 reviews)
                                                                                              avg/night
                                                                                              (3 nights minimum)
                                                                                              Condo #411142vb
                                                                                              93
                                                                                              Favorite
                                                                                                Viewed 62 times in the last 48 hours
                                                                                                Wonderful! 4.8/5
                                                                                                (19 reviews)
                                                                                                avg/night
                                                                                                (3 nights minimum)
                                                                                                House #717983vb
                                                                                                19
                                                                                                Favorite
                                                                                                  Viewed 28 times in the last 48 hours
                                                                                                  Excellent! 4.7/5
                                                                                                  (19 reviews)
                                                                                                  avg/night
                                                                                                  (2 nights minimum)
                                                                                                  Apartment #967904vb
                                                                                                  19
                                                                                                  Favorite
                                                                                                    Viewed 39 times in the last 48 hours
                                                                                                    Wonderful! 4.9/5
                                                                                                    (49 reviews)
                                                                                                    svg-lightning
                                                                                                    avg/night
                                                                                                    Apartment #856957vb
                                                                                                    49
                                                                                                    Favorite
                                                                                                      Viewed 30 times in the last 48 hours
                                                                                                      Premier Partner
                                                                                                      Excellent! 4.6/5
                                                                                                      (21 reviews)
                                                                                                      avg/night
                                                                                                      (7 nights minimum)
                                                                                                      Apartment #724537vb
                                                                                                      21

                                                                                                      Holiday Accommodation Chicago (300+)