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Holidaymakers searching for holiday rentals in Chicago also enquired about apartments in Midtown Manhattan, apartments in Upper East Side and apartments in Central Park North

Make a holiday rental, home, or cottage in Chicago, USA your home away from home

Holidaymakers looking for a fantastic city break might like to try Chicago in the mid-west of the United States. Located in the state of Illinois this amazing city offers many exciting things for visitors to see and do. Here visitors will find numerous different places to stay including self catering accommodation, apartments and condos.

Things to do on holiday to Chicago, USA

This is a cycling friendly city with over 100 miles of bike lanes and 50 miles of bike paths. There are many scenic areas for visitors to explore either on two wheels or by foot and there are also horse riding opportunities available here. There are beaches located along Lake Michigan for holidaymakers to relax on in the sunshine. Swimming, canoeing and kayaking can also be enjoyed on the lake. The city offers many other sporting activities including tennis and softball and there are many golf courses located in and around the city. Chicago has numerous restaurants, bars and cafes offering an excellent selection of cuisine from around the world. Self catering holidaymakers will be able to buy food and drink from stores and markets as well as gifts and souvenirs. Chicago has some upscale shopping areas such as the Magnificent Mile and State Street.

Places to visit on holiday to Chicago, USA

Chicago has many wonderful places for holidaymakers to visit including historic buildings and attractions. Tourists can visit various museums and galleries in the city such as the Adler Planetarium and Astronomy Museum, the Field Museum of Natural History and the Shedd Aquarium. As well as the museums visitors can go to the Chicago Cultural Center, which houses the city’s visitor information center, galleries and exhibit halls. Some fantastic sculptures are well worth visiting including the Glass Fountain and the Cloud Gate. Chicago has lots of parks and gardens too with Lincoln Park the second most visited city park in the U.S. Other popular attractions here include Chicago Botanic Garden and Brookfield Zoo. Holidaymakers with a head for heights can get a great view of the city from Skydeck Chicago’s The Ledge, which is 1,350 feet from the ground.

Weather in Chicago, USA

The warmest time of the year in Chicago is July with average high temperatures of almost 29 degrees centigrade. The coldest month is January when average highs are -1 degrees centigrade and average lows are almost -11 degrees. January also see the highest amount of snowfall with an average of 10.7 inches, while august is the wettest month with an average of 4.2 inches of rainfall.

Travel to Chicago, USA

Chicago O’Hare International Airport has flights from many international airports including Amsterdam (AMS), Beijing-Capital (PEK), Brussels (BRU), Dublin (DUB), Frankfurt (FRA), London-Heathrow (LHW), Madrid (MAD), Manchester (MAN), Paris-Charles de Gaulle (CDG), Rome-Fiumicino (FCO), Tokyo-Narita (NRT), Toronto-Pearson (YYZ) and Zurich (ZRH) amongst others. There are taxi and limousine services available at the airport as well as several car rental firms.

  • Showing 1-50 of 300+
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    Excellent! 4.6/5
    (86 reviews)
    avg/night
    • 2 BR
    • 2 BA
    • Sleeps 8
    Apartment #179389vb
    86
    Viewed 71 times in the last 48 hours
      Excellent! 4.5/5
      (57 reviews)
      avg/night
      • 1 BR
      • 1 BA
      • Sleeps 4
      Apartment #690239vb
      57
      Viewed 72 times in the last 48 hours
        Wonderful! 4.9/5
        (35 reviews)
        avg/night
        • 1 BR
        • 1 BA
        • Sleeps 4
        Apartment #3790035
        35
        Viewed 74 times in the last 48 hours
          Excellent! 4.7/5
          (44 reviews)
          avg/night
          • 2 BR
          • 1 BA
          • Sleeps 4
          Apartment #445608vb
          44
          Viewed 71 times in the last 48 hours
            Excellent! 4.7/5
            (93 reviews)
            avg/night
            • 2 BR
            • 2 BA
            • Sleeps 4
            Condo #222038
            93
            Viewed 78 times in the last 48 hours
              Wonderful! 4.9/5
              (89 reviews)
              avg/night
              • 3 BR
              • 2 BA
              • Separate Toilet
              • Sleeps 8
              Apartment #578762vb
              89
              Viewed 101 times in the last 48 hours
                Wonderful! 4.8/5
                (46 reviews)
                avg/night
                • 3 BR
                • 2 BA
                • Sleeps 8
                Condo #290256vb
                46
                Viewed 139 times in the last 48 hours
                  Excellent! 4.6/5
                  (17 reviews)
                  avg/night
                  • 1 BR
                  • 1 BA
                  • Sleeps 3
                  Apartment #4146480
                  17
                  Viewed 51 times in the last 48 hours
                    Wonderful! 4.8/5
                    (60 reviews)
                    avg/night
                    • 4 BR
                    • 4 BA
                    • Sleeps 12
                    Condo #679790vb
                    60
                    Viewed 93 times in the last 48 hours
                      Wonderful! 4.9/5
                      (51 reviews)
                      avg/night
                      • 3 BR
                      • 2 BA
                      • Sleeps 8
                      Condo #296798
                      51
                      Viewed 17 times in the last 48 hours
                        Wonderful! 4.9/5
                        (19 reviews)
                        avg/night
                        • 1 BR
                        • 2 BA
                        • Sleeps 2
                        Apartment #864022vb
                        19
                        Viewed 89 times in the last 48 hours
                          Wonderful! 4.9/5
                          (14 reviews)
                          avg/night
                          • Studio
                          • 1 BA
                          • Sleeps 2
                          Apartment #742485vb
                          14
                          Viewed 73 times in the last 48 hours
                            Wonderful! 4.8/5
                            (42 reviews)
                            avg/night
                            • 4 BR
                            • 2 BA
                            • Sleeps 10
                            Apartment #3768288
                            42
                            Viewed 60 times in the last 48 hours
                              Very Good! 4.2/5
                              (17 reviews)
                              avg/night
                              • 1 BR
                              • 1 BA
                              • Sleeps 3
                              Apartment #836462vb
                              17
                              Viewed 65 times in the last 48 hours
                                Excellent! 4.7/5
                                (16 reviews)
                                avg/night
                                • Studio
                                • 1 BA
                                • Sleeps 2
                                Multiple rentals Apartment #4261388
                                16
                                Viewed 206 times in the last 48 hours
                                  Wonderful! 4.9/5
                                  (40 reviews)
                                  avg/night
                                  • 3 BR
                                  • 2 BA
                                  • Sleeps 8
                                  Condo #939473
                                  40
                                  Viewed 21 times in the last 48 hours
                                    Wonderful! 4.8/5
                                    (23 reviews)
                                    avg/night
                                    • 2 BR
                                    • 2 BA
                                    • Sleeps 6
                                    Apartment #3795191
                                    23
                                    Viewed 86 times in the last 48 hours
                                      Wonderful! 4.9/5
                                      (21 reviews)
                                      avg/night
                                      • 2 BR
                                      • 2 BA
                                      • Sleeps 6
                                      Condo #735859vb
                                      21
                                      Viewed 58 times in the last 48 hours
                                        Excellent! 4.6/5
                                        (41 reviews)
                                        avg/night
                                        • 2 BR
                                        • 1 BA
                                        • Sleeps 5
                                        Apartment #3833362
                                        41
                                        Viewed 74 times in the last 48 hours
                                          Exceptional! 5/5
                                          (59 reviews)
                                          avg/night
                                          • 4 BR
                                          • 2 BA
                                          • Sleeps 10
                                          Apartment #627209vb
                                          59
                                          Viewed 45 times in the last 48 hours
                                            Excellent! 4.7/5
                                            (67 reviews)
                                            avg/night
                                            • 1 BR
                                            • 1 BA
                                            • Sleeps 4
                                            Condo #177026vb
                                            67
                                            Viewed 27 times in the last 48 hours
                                              Wonderful! 4.9/5
                                              (54 reviews)
                                              avg/night
                                              • 2 BR
                                              • 2 BA
                                              • Sleeps 6
                                              Condo #3720918
                                              54
                                              Viewed 51 times in the last 48 hours
                                                Wonderful! 4.9/5
                                                (75 reviews)
                                                avg/night
                                                • 2 BR
                                                • 2 BA
                                                • Sleeps 6
                                                Apartment #358020
                                                75
                                                Viewed 56 times in the last 48 hours
                                                  Excellent! 4.7/5
                                                  (51 reviews)
                                                  avg/night
                                                  • 1 BR
                                                  • 1 BA
                                                  • Sleeps 4
                                                  Apartment #415005vb
                                                  51
                                                  Viewed 22 times in the last 48 hours
                                                    Wonderful! 4.8/5
                                                    (44 reviews)
                                                    avg/night
                                                    • 2 BR
                                                    • 2 BA
                                                    • Sleeps 6
                                                    Condo #265424vb
                                                    44
                                                    Viewed 73 times in the last 48 hours
                                                      Wonderful! 4.9/5
                                                      (18 reviews)
                                                      avg/night
                                                      • 1 BR
                                                      • 1 BA
                                                      • Sleeps 5
                                                      Apartment #784869vb
                                                      18
                                                      Viewed 56 times in the last 48 hours
                                                        Excellent! 4.7/5
                                                        (39 reviews)
                                                        avg/night
                                                        • 3 BR
                                                        • 1 BA
                                                        • Sleeps 5
                                                        Apartment #600158vb
                                                        39
                                                        Viewed 39 times in the last 48 hours
                                                          Exceptional! 5/5
                                                          (22 reviews)
                                                          avg/night
                                                          • 5 BR
                                                          • 1 BA
                                                          • Separate Toilet
                                                          • Sleeps 10
                                                          Condo #776608vb
                                                          22
                                                          Viewed 115 times in the last 48 hours
                                                            Excellent! 4.5/5
                                                            (8 reviews)
                                                            avg/night
                                                            • 1 BR
                                                            • 1 BA
                                                            • Sleeps 3
                                                            Apartment #836457vb
                                                            8
                                                            Viewed 51 times in the last 48 hours
                                                              Exceptional! 5/5
                                                              (6 reviews)
                                                              avg/night
                                                              • 2 BR
                                                              • 2 BA
                                                              • Sleeps 6
                                                              Apartment #4172462
                                                              6
                                                              Viewed 75 times in the last 48 hours
                                                                Excellent! 4.5/5
                                                                (76 reviews)
                                                                avg/night
                                                                • 2 BR
                                                                • 2 BA
                                                                • Sleeps 10
                                                                Condo #400905vb
                                                                76
                                                                Viewed 54 times in the last 48 hours
                                                                  Wonderful! 4.9/5
                                                                  (37 reviews)
                                                                  avg/night
                                                                  • 2 BR
                                                                  • 2 BA
                                                                  • Sleeps 6
                                                                  Apartment #408313vb
                                                                  37
                                                                  Viewed 52 times in the last 48 hours
                                                                    Excellent! 4.5/5
                                                                    (24 reviews)
                                                                    avg/night
                                                                    • 3 BR
                                                                    • 2 BA
                                                                    • Sleeps 8
                                                                    Condo #622632vb
                                                                    24
                                                                    Viewed 80 times in the last 48 hours
                                                                      Exceptional! 5/5
                                                                      (14 reviews)
                                                                      avg/night
                                                                      • 3 BR
                                                                      • 2 BA
                                                                      • Sleeps 6
                                                                      Apartment #723132vb
                                                                      14
                                                                      Viewed 55 times in the last 48 hours
                                                                        Wonderful! 4.9/5
                                                                        (13 reviews)
                                                                        avg/night
                                                                        • 2 BR
                                                                        • 1 BA
                                                                        • Sleeps 4
                                                                        Apartment #780506vb
                                                                        13
                                                                        Viewed 35 times in the last 48 hours
                                                                          Excellent! 4.6/5
                                                                          (36 reviews)
                                                                          avg/night
                                                                          • 1 BR
                                                                          • 1 BA
                                                                          • Sleeps 4
                                                                          Apartment #3751630
                                                                          36
                                                                          Viewed 54 times in the last 48 hours
                                                                            Exceptional! 5/5
                                                                            (60 reviews)
                                                                            avg/night
                                                                            • 4 BR
                                                                            • 2 BA
                                                                            • Sleeps 11
                                                                            House #595328vb
                                                                            60
                                                                            Viewed 111 times in the last 48 hours
                                                                              Exceptional! 5/5
                                                                              (6 reviews)
                                                                              avg/night
                                                                              • 1 BR
                                                                              • 1 BA
                                                                              • Sleeps 2
                                                                              Apartment #871091vb
                                                                              6
                                                                              Viewed 57 times in the last 48 hours
                                                                                Exceptional! 5/5
                                                                                (26 reviews)
                                                                                avg/night
                                                                                • 3 BR
                                                                                • 2 BA
                                                                                • Sleeps 6
                                                                                Townhome #3917584
                                                                                26
                                                                                Viewed 28 times in the last 48 hours
                                                                                  Wonderful! 4.9/5
                                                                                  (16 reviews)
                                                                                  avg/night
                                                                                  • 1 BR
                                                                                  • 1 BA
                                                                                  • Sleeps 4
                                                                                  Apartment #870614vb
                                                                                  16
                                                                                  Viewed 117 times in the last 48 hours
                                                                                    Wonderful! 4.9/5
                                                                                    (14 reviews)
                                                                                    avg/night
                                                                                    • 1 BR
                                                                                    • 1 BA
                                                                                    • Sleeps 4
                                                                                    Condo #4037980
                                                                                    14
                                                                                    Viewed 334 times in the last 48 hours
                                                                                      Excellent! 4.7/5
                                                                                      (22 reviews)
                                                                                      avg/night
                                                                                      • 2 BR
                                                                                      • 1 BA
                                                                                      • Sleeps 4
                                                                                      Apartment #588228vb
                                                                                      22
                                                                                      Viewed 44 times in the last 48 hours
                                                                                        Excellent! 4.6/5
                                                                                        (8 reviews)
                                                                                        avg/night
                                                                                        • 2 BR
                                                                                        • 2 BA
                                                                                        • Sleeps 6
                                                                                        Apartment #4172463
                                                                                        8
                                                                                        Viewed 61 times in the last 48 hours
                                                                                          Wonderful! 4.8/5
                                                                                          (62 reviews)
                                                                                          avg/night
                                                                                          • 2 BR
                                                                                          • 1 BA
                                                                                          • Sleeps 6
                                                                                          Apartment #301852vb
                                                                                          62
                                                                                          Viewed 53 times in the last 48 hours
                                                                                            Wonderful! 4.9/5
                                                                                            (21 reviews)
                                                                                            avg/night
                                                                                            • 2 BR
                                                                                            • 2 BA
                                                                                            • Sleeps 6
                                                                                            Apartment #653828vb
                                                                                            21
                                                                                            Viewed 18 times in the last 48 hours
                                                                                              Excellent! 4.7/5
                                                                                              (42 reviews)
                                                                                              avg/night
                                                                                              • 2 BR
                                                                                              • 1 BA
                                                                                              • Separate Toilet
                                                                                              • Sleeps 8
                                                                                              Apartment #3645846
                                                                                              42
                                                                                              Viewed 52 times in the last 48 hours
                                                                                                Wonderful! 4.9/5
                                                                                                (20 reviews)
                                                                                                avg/night
                                                                                                • 4 BR
                                                                                                • 2 BA
                                                                                                • Separate Toilet
                                                                                                • Sleeps 10
                                                                                                House #840552vb
                                                                                                20
                                                                                                Viewed 66 times in the last 48 hours
                                                                                                  Exceptional! 5/5
                                                                                                  (29 reviews)
                                                                                                  avg/night
                                                                                                  • 3 BR
                                                                                                  • 2 BA
                                                                                                  • Sleeps 6
                                                                                                  Apartment #470476vb
                                                                                                  29
                                                                                                  Viewed 33 times in the last 48 hours
                                                                                                    Exceptional! 5/5
                                                                                                    (127 reviews)
                                                                                                    avg/night
                                                                                                    • 3 BR
                                                                                                    • 2 BA
                                                                                                    • Sleeps 8
                                                                                                    Apartment #422128vb
                                                                                                    127
                                                                                                    Viewed 29 times in the last 48 hours
                                                                                                      Excellent! 4.6/5
                                                                                                      (71 reviews)
                                                                                                      avg/night
                                                                                                      • 1 BR
                                                                                                      • 1 BA
                                                                                                      • Sleeps 4
                                                                                                      Apartment #179390vb
                                                                                                      71
                                                                                                      Viewed 31 times in the last 48 hours
                                                                                                      • 1 - 50 of 300+

                                                                                                      Chicago Holiday Apartments & Rentals (300+)