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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+
Additional service fee may apply.
    Excellent! 4.5/5
    (57 reviews)
    avg/night
    • 1 BR
    • 1 BA
    • Sleeps 4
    Apartment #690239vb
    57
    Viewed 95 times in the last 48 hours
      Excellent! 4.6/5
      (86 reviews)
      avg/night
      • 2 BR
      • 2 BA
      • Sleeps 8
      Apartment #179389vb
      86
      Viewed 83 times in the last 48 hours
        Excellent! 4.3/5
        (12 reviews)
        avg/night
        • 2 BR
        • 2 BA
        • Sleeps 5
        Apartment #4047746
        12
        Viewed 193 times in the last 48 hours
          Excellent! 4.7/5
          (15 reviews)
          avg/night
          • Studio
          • 1 BA
          • Sleeps 2
          Multiple rentals Apartment #4261388
          15
          Viewed 40 times in the last 48 hours
            Wonderful! 4.9/5
            (87 reviews)
            avg/night
            • 3 BR
            • 2 BA
            • Separate Toilet
            • Sleeps 8
            Apartment #578762vb
            87
            Viewed 173 times in the last 48 hours
              Excellent! 4.7/5
              (93 reviews)
              avg/night
              • 2 BR
              • 2 BA
              • Sleeps 4
              Condo #222038
              93
              Viewed 86 times in the last 48 hours
                Excellent! 4.7/5
                (44 reviews)
                avg/night
                • 2 BR
                • 1 BA
                • Sleeps 4
                Apartment #445608vb
                44
                Viewed 41 times in the last 48 hours
                  Wonderful! 4.8/5
                  (59 reviews)
                  avg/night
                  • 4 BR
                  • 4 BA
                  • Sleeps 12
                  Condo #679790vb
                  59
                  Viewed 197 times in the last 48 hours
                    Excellent! 4.6/5
                    (16 reviews)
                    avg/night
                    • 1 BR
                    • 1 BA
                    • Sleeps 3
                    Apartment #4146480
                    16
                    Viewed 52 times in the last 48 hours
                      Excellent! 4.7/5
                      (40 reviews)
                      avg/night
                      • 2 BR
                      • 1 BA
                      • Sleeps 5
                      Apartment #3833362
                      40
                      Viewed 93 times in the last 48 hours
                        Wonderful! 4.9/5
                        (35 reviews)
                        avg/night
                        • 1 BR
                        • 1 BA
                        • Sleeps 4
                        Apartment #3790035
                        35
                        Viewed 46 times in the last 48 hours
                          Wonderful! 4.9/5
                          (51 reviews)
                          avg/night
                          • 3 BR
                          • 2 BA
                          • Sleeps 8
                          Condo #296798
                          51
                          Viewed 49 times in the last 48 hours
                            Excellent! 4.6/5
                            (36 reviews)
                            avg/night
                            • 1 BR
                            • 1 BA
                            • Sleeps 4
                            Apartment #3751630
                            36
                            Viewed 45 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 74 times in the last 48 hours
                                Wonderful! 4.9/5
                                (53 reviews)
                                avg/night
                                • 2 BR
                                • 2 BA
                                • Sleeps 6
                                Condo #3720918
                                53
                                Viewed 62 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! 4.9/5
                                    (37 reviews)
                                    avg/night
                                    • 2 BR
                                    • 2 BA
                                    • Sleeps 6
                                    Apartment #408313vb
                                    37
                                    Viewed 56 times in the last 48 hours
                                      Wonderful! 4.9/5
                                      (39 reviews)
                                      avg/night
                                      • 3 BR
                                      • 2 BA
                                      • Sleeps 8
                                      Condo #939473
                                      39
                                      Viewed 40 times in the last 48 hours
                                        Wonderful! 4.9/5
                                        (74 reviews)
                                        avg/night
                                        • 2 BR
                                        • 2 BA
                                        • Sleeps 6
                                        Apartment #358020
                                        74
                                        Viewed 96 times in the last 48 hours
                                          Wonderful! 4.8/5
                                          (46 reviews)
                                          avg/night
                                          • 3 BR
                                          • 2 BA
                                          • Sleeps 8
                                          Condo #290256vb
                                          46
                                          Viewed 228 times in the last 48 hours
                                            Exceptional! 5.0/5
                                            (59 reviews)
                                            avg/night
                                            • 4 BR
                                            • 2 BA
                                            • Sleeps 10
                                            Apartment #627209vb
                                            59
                                            Viewed 97 times in the last 48 hours
                                              Wonderful! 4.9/5
                                              (58 reviews)
                                              avg/night
                                              • 4 BR
                                              • 2 BA
                                              • Sleeps 11
                                              House #595328vb
                                              58
                                              Viewed 174 times in the last 48 hours
                                                Wonderful! 4.9/5
                                                (14 reviews)
                                                avg/night
                                                • Studio
                                                • 1 BA
                                                • Sleeps 2
                                                Apartment #742485vb
                                                14
                                                Viewed 83 times in the last 48 hours
                                                  Exceptional! 5.0/5
                                                  (13 reviews)
                                                  avg/night
                                                  • 3 BR
                                                  • 2 BA
                                                  • Sleeps 6
                                                  Apartment #723132vb
                                                  13
                                                  Viewed 82 times in the last 48 hours
                                                    Wonderful! 4.9/5
                                                    (16 reviews)
                                                    avg/night
                                                    • 1 BR
                                                    • 2 BA
                                                    • Sleeps 2
                                                    Apartment #864022vb
                                                    16
                                                    Viewed 105 times in the last 48 hours
                                                      Wonderful! 4.8/5
                                                      (12 reviews)
                                                      avg/night
                                                      • 1 BR
                                                      • 1 BA
                                                      • Sleeps 3
                                                      Apartment #4146120
                                                      12
                                                      Viewed 44 times in the last 48 hours
                                                        Excellent! 4.7/5
                                                        (22 reviews)
                                                        avg/night
                                                        • 2 BR
                                                        • 1 BA
                                                        • Sleeps 4
                                                        Apartment #588228vb
                                                        22
                                                        Viewed 66 times in the last 48 hours
                                                          Exceptional! 5.0/5
                                                          (25 reviews)
                                                          avg/night
                                                          • 3 BR
                                                          • 2 BA
                                                          • Sleeps 6
                                                          Townhome #3917584
                                                          25
                                                          Viewed 29 times in the last 48 hours
                                                            Wonderful! 4.8/5
                                                            (23 reviews)
                                                            avg/night
                                                            • 2 BR
                                                            • 2 BA
                                                            • Sleeps 6
                                                            Apartment #3795191
                                                            23
                                                            Viewed 100 times in the last 48 hours
                                                              Wonderful! 4.8/5
                                                              (19 reviews)
                                                              avg/night
                                                              • 2 BR
                                                              • 2 BA
                                                              • Sleeps 6
                                                              Condo #735859vb
                                                              19
                                                              Viewed 107 times in the last 48 hours
                                                                Exceptional! 5.0/5
                                                                (127 reviews)
                                                                avg/night
                                                                • 3 BR
                                                                • 2 BA
                                                                • Sleeps 8
                                                                Apartment #422128vb
                                                                127
                                                                Viewed 50 times in the last 48 hours
                                                                  Wonderful! 4.9/5
                                                                  (21 reviews)
                                                                  avg/night
                                                                  • 2 BR
                                                                  • 2 BA
                                                                  • Sleeps 6
                                                                  Apartment #653828vb
                                                                  21
                                                                  Viewed 36 times in the last 48 hours
                                                                    Wonderful! 4.9/5
                                                                    (18 reviews)
                                                                    avg/night
                                                                    • 1 BR
                                                                    • 1 BA
                                                                    • Sleeps 5
                                                                    Apartment #784869vb
                                                                    18
                                                                    Viewed 37 times in the last 48 hours
                                                                      Exceptional! 5.0/5
                                                                      (22 reviews)
                                                                      avg/night
                                                                      • 5 BR
                                                                      • 1 BA
                                                                      • Separate Toilet
                                                                      • Sleeps 10
                                                                      Condo #776608vb
                                                                      22
                                                                      Viewed 179 times in the last 48 hours
                                                                        Exceptional! 5.0/5
                                                                        (29 reviews)
                                                                        avg/night
                                                                        • 3 BR
                                                                        • 2 BA
                                                                        • Sleeps 6
                                                                        Apartment #470476vb
                                                                        29
                                                                        Viewed 48 times in the last 48 hours
                                                                          Excellent! 4.5/5
                                                                          (76 reviews)
                                                                          avg/night
                                                                          • 2 BR
                                                                          • 2 BA
                                                                          • Sleeps 10
                                                                          Condo #400905vb
                                                                          76
                                                                          Viewed 62 times in the last 48 hours
                                                                            Wonderful! 4.8/5
                                                                            (43 reviews)
                                                                            avg/night
                                                                            • 2 BR
                                                                            • 1 BA
                                                                            • Separate Toilet
                                                                            • Sleeps 6
                                                                            Apartment #271945
                                                                            43
                                                                            Viewed 39 times in the last 48 hours
                                                                              Wonderful! 4.8/5
                                                                              (49 reviews)
                                                                              avg/night
                                                                              • 6 BR
                                                                              • 3 BA
                                                                              • Sleeps 18
                                                                              Condo #682966vb
                                                                              49
                                                                              Viewed 72 times in the last 48 hours
                                                                                Excellent! 4.7/5
                                                                                (66 reviews)
                                                                                avg/night
                                                                                • 1 BR
                                                                                • 1 BA
                                                                                • Sleeps 4
                                                                                Condo #177026vb
                                                                                66
                                                                                Viewed 49 times in the last 48 hours
                                                                                  Wonderful! 4.8/5
                                                                                  (59 reviews)
                                                                                  avg/night
                                                                                  • 3 BR
                                                                                  • 2 BA
                                                                                  • Sleeps 12
                                                                                  House #376549vb
                                                                                  59
                                                                                  Viewed 75 times in the last 48 hours
                                                                                    Wonderful! 4.9/5
                                                                                    (12 reviews)
                                                                                    avg/night
                                                                                    • 3 BR
                                                                                    • 2 BA
                                                                                    • Sleeps 6
                                                                                    Apartment #653830vb
                                                                                    12
                                                                                    Viewed 21 times in the last 48 hours
                                                                                      Excellent! 4.3/5
                                                                                      (14 reviews)
                                                                                      avg/night
                                                                                      • 2 BR
                                                                                      • 2 BA
                                                                                      • Sleeps 6
                                                                                      Apartment #593610vb
                                                                                      14
                                                                                      Viewed 54 times in the last 48 hours
                                                                                        Wonderful! 4.9/5
                                                                                        (13 reviews)
                                                                                        avg/night
                                                                                        • 1 BR
                                                                                        • 1 BA
                                                                                        • Sleeps 4
                                                                                        Condo #4037980
                                                                                        13
                                                                                        Viewed 201 times in the last 48 hours
                                                                                          Excellent! 4.7/5
                                                                                          (38 reviews)
                                                                                          avg/night
                                                                                          • 3 BR
                                                                                          • 1 BA
                                                                                          • Sleeps 5
                                                                                          Apartment #600158vb
                                                                                          38
                                                                                          Viewed 31 times in the last 48 hours
                                                                                            Wonderful! 4.8/5
                                                                                            (42 reviews)
                                                                                            avg/night
                                                                                            • 4 BR
                                                                                            • 2 BA
                                                                                            • Sleeps 10
                                                                                            Apartment #3768288
                                                                                            42
                                                                                            Viewed 65 times in the last 48 hours
                                                                                              Wonderful! 4.8/5
                                                                                              (62 reviews)
                                                                                              avg/night
                                                                                              • 2 BR
                                                                                              • 1 BA
                                                                                              • Sleeps 6
                                                                                              Apartment #301852vb
                                                                                              62
                                                                                              Viewed 30 times in the last 48 hours
                                                                                                Wonderful! 4.9/5
                                                                                                (19 reviews)
                                                                                                avg/night
                                                                                                • 2 BR
                                                                                                • 1 BA
                                                                                                • Sleeps 7
                                                                                                Apartment #792973vb
                                                                                                19
                                                                                                Viewed 79 times in the last 48 hours
                                                                                                  Excellent! 4.7/5
                                                                                                  (23 reviews)
                                                                                                  avg/night
                                                                                                  • 3 BR
                                                                                                  • 1 BA
                                                                                                  • Sleeps 8
                                                                                                  Apartment #4016534
                                                                                                  23
                                                                                                  Viewed 54 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 44 times in the last 48 hours
                                                                                                      Exceptional! 5.0/5
                                                                                                      (6 reviews)
                                                                                                      avg/night
                                                                                                      • 2 BR
                                                                                                      • 2 BA
                                                                                                      • Sleeps 6
                                                                                                      Apartment #4172462
                                                                                                      6
                                                                                                      Viewed 43 times in the last 48 hours
                                                                                                      • 1 - 50 of 300+

                                                                                                      Chicago Holiday Apartments & Rentals (300+)