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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.

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Chicago Holiday Apartments & Rentals (300+)

  • 1 - 50 of 300+
Additional service fee may apply.
    Wonderful! 4.9/5
    (14 reviews)
    avg/night
    • 2 BR
    • 1 BA
    • Sleeps 4
    Apartment #856957vb
    14
    Viewed 50 times in the last 48 hours
      Wonderful! 4.9/5
      (11 reviews)
      avg/night
      • 1 BR
      • 1 BA
      • Sleeps 4
      Condo #4037980
      11
      Viewed 78 times in the last 48 hours
        Very Good! 4.2/5
        (15 reviews)
        avg/night
        • 1 BR
        • 1 BA
        • Sleeps 3
        Apartment #836462vb
        15
        Viewed 81 times in the last 48 hours
          Wonderful! 4.9/5
          (39 reviews)
          avg/night
          • 3 BR
          • 2 BA
          • Sleeps 8
          Condo #939473
          39
          Viewed 10 times in the last 48 hours
            avg/night
            • 1 BR
            • 1 BA
            • Sleeps 3
            Apartment #819932vb
            3
            Viewed 31 times in the last 48 hours
              avg/night
              • 3 BR
              • 2 BA
              • Separate Toilet
              • Sleeps 6
              Condo #4276593
              1
              Viewed 37 times in the last 48 hours
                Wonderful! 4.9/5
                (11 reviews)
                avg/night
                • 1 BR
                • 2 BA
                • Sleeps 2
                Apartment #864022vb
                11
                Viewed 89 times in the last 48 hours
                  Wonderful! 4.8/5
                  (11 reviews)
                  avg/night
                  • 1 BR
                  • 1 BA
                  • Sleeps 2
                  Condo #767984vb
                  11
                  Viewed 74 times in the last 48 hours
                    Excellent! 4.5/5
                    (6 reviews)
                    avg/night
                    • 1 BR
                    • 1 BA
                    • Sleeps 3
                    Apartment #836457vb
                    6
                    Viewed 28 times in the last 48 hours
                      Excellent! 4.3/5
                      (6 reviews)
                      avg/night
                      • 1 BR
                      • 1 BA
                      • Sleeps 2
                      Apartment #871119vb
                      6
                      Viewed 57 times in the last 48 hours
                        Excellent! 4.5/5
                        (53 reviews)
                        avg/night
                        • 1 BR
                        • 1 BA
                        • Sleeps 4
                        Apartment #690239vb
                        53
                        Viewed 21 times in the last 48 hours
                          Excellent! 4.4/5
                          (10 reviews)
                          avg/night
                          • 1 BR
                          • 1 BA
                          • Sleeps 5
                          Apartment #870916vb
                          10
                          Viewed 34 times in the last 48 hours
                            • 1 BR
                            • 1 BA
                            • Sleeps 3
                            Apartment #895525vb
                            6
                            Viewed 41 times in the last 48 hours
                              Exceptional! 5.0/5
                              (58 reviews)
                              avg/night
                              • 4 BR
                              • 2 BA
                              • Sleeps 10
                              Apartment #627209vb
                              58
                              Viewed 47 times in the last 48 hours
                                avg/night
                                • 4 BR
                                • 3 BA
                                • Sleeps 10
                                Barn #916963vb
                                1
                                Viewed 22 times in the last 48 hours
                                  Wonderful! 4.9/5
                                  (11 reviews)
                                  avg/night
                                  • 3 BR
                                  • 2 BA
                                  • Sleeps 6
                                  Condo #376151vb
                                  11
                                  Viewed 17 times in the last 48 hours
                                    Exceptional! 5.0/5
                                    (23 reviews)
                                    avg/night
                                    • 3 BR
                                    • 2 BA
                                    • Sleeps 6
                                    Townhome #3917584
                                    23
                                    Viewed 22 times in the last 48 hours
                                      Excellent! 4.7/5
                                      (15 reviews)
                                      avg/night
                                      • 1 BR
                                      • 1 BA
                                      • Sleeps 3
                                      Apartment #4146480
                                      15
                                      Viewed 58 times in the last 48 hours
                                        • 4 BR
                                        • 3 BA
                                        • Sleeps 11
                                        Apartment #889984vb
                                        4
                                        Viewed 9 times in the last 48 hours
                                          Very Good! 4.1/5
                                          (10 reviews)
                                          avg/night
                                          • 3 BR
                                          • 1 BA
                                          • Sleeps 6
                                          Apartment #852515vb
                                          10
                                          Viewed 30 times in the last 48 hours
                                            Excellent! 4.7/5
                                            (38 reviews)
                                            avg/night
                                            • 3 BR
                                            • 1 BA
                                            • Sleeps 5
                                            Apartment #600158vb
                                            38
                                            Viewed 16 times in the last 48 hours
                                              Excellent! 4.4/5
                                              (18 reviews)
                                              avg/night
                                              • 3 BR
                                              • 1 BA
                                              • Sleeps 7
                                              Apartment #819226vb
                                              18
                                              Viewed 35 times in the last 48 hours
                                                Excellent! 4.7/5
                                                (34 reviews)
                                                avg/night
                                                • 1 BR
                                                • 1 BA
                                                • Sleeps 4
                                                Apartment #3751630
                                                34
                                                Viewed 19 times in the last 48 hours
                                                  Good! 3.9/5
                                                  (9 reviews)
                                                  avg/night
                                                  • 2 BR
                                                  • 2 BA
                                                  • Sleeps 6
                                                  Apartment #852513vb
                                                  9
                                                  Viewed 33 times in the last 48 hours
                                                    Excellent! 4.6/5
                                                    (37 reviews)
                                                    avg/night
                                                    • 2 BR
                                                    • 1 BA
                                                    • Sleeps 5
                                                    Apartment #3833362
                                                    37
                                                    Viewed 29 times in the last 48 hours
                                                      • 3 BR
                                                      • 1 BA
                                                      • Sleeps 8
                                                      Apartment #4016534
                                                      22
                                                        Excellent! 4.6/5
                                                        (83 reviews)
                                                        avg/night
                                                        • 2 BR
                                                        • 2 BA
                                                        • Sleeps 8
                                                        Apartment #179389vb
                                                        83
                                                        Viewed 56 times in the last 48 hours
                                                          Wonderful! 4.8/5
                                                          (45 reviews)
                                                          avg/night
                                                          • 6 BR
                                                          • 3 BA
                                                          • Sleeps 18
                                                          Condo #682966vb
                                                          45
                                                          Viewed 51 times in the last 48 hours
                                                            Excellent! 4.3/5
                                                            (13 reviews)
                                                            avg/night
                                                            • 1 BR
                                                            • 1 BA
                                                            • Sleeps 3
                                                            Apartment #819227vb
                                                            13
                                                            Viewed 32 times in the last 48 hours
                                                              Excellent! 4.7/5
                                                              (13 reviews)
                                                              avg/night
                                                              • 1 BR
                                                              • 1 BA
                                                              • Sleeps 2
                                                              Apartment #870495vb
                                                              13
                                                              Viewed 32 times in the last 48 hours
                                                                avg/night
                                                                • 1 BR
                                                                • 1 BA
                                                                • Sleeps 2
                                                                House #4280611
                                                                4
                                                                Viewed 67 times in the last 48 hours
                                                                  • 1 BR
                                                                  • 1 BA
                                                                  • Sleeps 2
                                                                  Apartment #871091vb
                                                                  4
                                                                  Viewed 64 times in the last 48 hours
                                                                    avg/night
                                                                    • 1 BR
                                                                    • 1 BA
                                                                    • Sleeps 5
                                                                    Apartment #855043vb
                                                                    14
                                                                    Viewed 31 times in the last 48 hours
                                                                      • 4 BR
                                                                      • 2 BA
                                                                      • Sleeps 10
                                                                      Apartment #3768288
                                                                      41
                                                                        Wonderful! 4.8/5
                                                                        (12 reviews)
                                                                        avg/night
                                                                        • 1 BR
                                                                        • 1 BA
                                                                        • Sleeps 3
                                                                        Apartment #4146120
                                                                        12
                                                                        Viewed 7 times in the last 48 hours
                                                                          Very Good! 4.2/5
                                                                          (5 reviews)
                                                                          avg/night
                                                                          • 1 BR
                                                                          • 1 BA
                                                                          • Sleeps 2
                                                                          Studio #916837vb
                                                                          5
                                                                          Viewed 26 times in the last 48 hours
                                                                            Wonderful! 4.9/5
                                                                            (17 reviews)
                                                                            avg/night
                                                                            • 1 BR
                                                                            • 1 BA
                                                                            • Sleeps 5
                                                                            Apartment #784869vb
                                                                            17
                                                                            Viewed 5 times in the last 48 hours
                                                                              Exceptional! 5.0/5
                                                                              (125 reviews)
                                                                              avg/night
                                                                              • 3 BR
                                                                              • 2 BA
                                                                              • Sleeps 8
                                                                              Apartment #422128vb
                                                                              125
                                                                              Viewed 13 times in the last 48 hours
                                                                                Wonderful! 4.9/5
                                                                                (49 reviews)
                                                                                avg/night
                                                                                • 3 BR
                                                                                • 2 BA
                                                                                • Sleeps 8
                                                                                Condo #296798
                                                                                49
                                                                                Viewed 19 times in the last 48 hours
                                                                                  • 1 BR
                                                                                  • 1 BA
                                                                                  • Sleeps 4
                                                                                  Apartment #836456vb
                                                                                  2
                                                                                  Viewed 16 times in the last 48 hours
                                                                                    Wonderful! 4.8/5
                                                                                    (6 reviews)
                                                                                    avg/night
                                                                                    • 3 BR
                                                                                    • 2 BA
                                                                                    • Sleeps 6
                                                                                    Apartment #865945vb
                                                                                    6
                                                                                    Viewed 16 times in the last 48 hours
                                                                                      Wonderful! 4.8/5
                                                                                      (13 reviews)
                                                                                      avg/night
                                                                                      • 1 BR
                                                                                      • 1 BA
                                                                                      • Sleeps 4
                                                                                      Apartment #4101747
                                                                                      13
                                                                                      Viewed 18 times in the last 48 hours
                                                                                        Exceptional! 5.0/5
                                                                                        (28 reviews)
                                                                                        avg/night
                                                                                        • 3 BR
                                                                                        • 2 BA
                                                                                        • Sleeps 6
                                                                                        Apartment #470476vb
                                                                                        28
                                                                                        Viewed 24 times in the last 48 hours
                                                                                          Excellent! 4.5/5
                                                                                          (75 reviews)
                                                                                          avg/night
                                                                                          • 2 BR
                                                                                          • 2 BA
                                                                                          • Sleeps 10
                                                                                          Condo #400905vb
                                                                                          75
                                                                                          Viewed 22 times in the last 48 hours
                                                                                            Excellent! 4.7/5
                                                                                            (21 reviews)
                                                                                            avg/night
                                                                                            • 2 BR
                                                                                            • 1 BA
                                                                                            • Sleeps 4
                                                                                            Apartment #588228vb
                                                                                            21
                                                                                            Viewed 21 times in the last 48 hours
                                                                                              Wonderful! 4.9/5
                                                                                              (37 reviews)
                                                                                              avg/night
                                                                                              • 1 BR
                                                                                              • 1 BA
                                                                                              • Sleeps 3
                                                                                              Apartment #3863638
                                                                                              37
                                                                                              Viewed 16 times in the last 48 hours
                                                                                                Wonderful! 4.9/5
                                                                                                (36 reviews)
                                                                                                avg/night
                                                                                                • 2 BR
                                                                                                • 2 BA
                                                                                                • Sleeps 6
                                                                                                Apartment #408313vb
                                                                                                36
                                                                                                Viewed 31 times in the last 48 hours
                                                                                                  Wonderful! 4.8/5
                                                                                                  (13 reviews)
                                                                                                  avg/night
                                                                                                  • Studio
                                                                                                  • 1 BA
                                                                                                  • Sleeps 2
                                                                                                  Apartment #742485vb
                                                                                                  13
                                                                                                  Viewed 31 times in the last 48 hours
                                                                                                    • 2 BR
                                                                                                    • 2 BA
                                                                                                    • Sleeps 7
                                                                                                    Apartment #931991vb
                                                                                                    2
                                                                                                    Viewed 31 times in the last 48 hours
                                                                                                      • 3 BR
                                                                                                      • 2 BA
                                                                                                      • Sleeps 6
                                                                                                      Apartment #4252673
                                                                                                      3
                                                                                                      Viewed 9 times in the last 48 hours
                                                                                                      • 1 - 50 of 300+