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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 110 times in the last 48 hours
      Excellent! 4.6/5
      (86 reviews)
      avg/night
      • 2 BR
      • 2 BA
      • Sleeps 8
      Apartment #179389vb
      86
      Viewed 118 times in the last 48 hours
        Excellent! 4.3/5
        (12 reviews)
        avg/night
        • 2 BR
        • 2 BA
        • Sleeps 5
        Apartment #4047746
        12
        Viewed 181 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 48 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 147 times in the last 48 hours
              Excellent! 4.7/5
              (93 reviews)
              avg/night
              • 2 BR
              • 2 BA
              • Sleeps 4
              Condo #222038
              93
              Viewed 98 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! 4.7/5
                  (44 reviews)
                  avg/night
                  • 2 BR
                  • 1 BA
                  • Sleeps 4
                  Apartment #445608vb
                  44
                  Viewed 58 times in the last 48 hours
                    Wonderful! 4.8/5
                    (59 reviews)
                    avg/night
                    • 4 BR
                    • 4 BA
                    • Sleeps 12
                    Condo #679790vb
                    59
                    Viewed 225 times in the last 48 hours
                      Excellent! 4.6/5
                      (16 reviews)
                      avg/night
                      • 1 BR
                      • 1 BA
                      • Sleeps 3
                      Apartment #4146480
                      16
                      Viewed 61 times in the last 48 hours
                        Wonderful! 4.9/5
                        (51 reviews)
                        avg/night
                        • 3 BR
                        • 2 BA
                        • Sleeps 8
                        Condo #296798
                        51
                        Viewed 42 times in the last 48 hours
                          Excellent! 4.7/5
                          (40 reviews)
                          avg/night
                          • 2 BR
                          • 1 BA
                          • Sleeps 5
                          Apartment #3833362
                          40
                          Viewed 67 times in the last 48 hours
                            Wonderful! 4.9/5
                            (35 reviews)
                            avg/night
                            • 1 BR
                            • 1 BA
                            • Sleeps 4
                            Apartment #3790035
                            35
                            Viewed 50 times in the last 48 hours
                              Excellent! 4.6/5
                              (36 reviews)
                              avg/night
                              • 1 BR
                              • 1 BA
                              • Sleeps 4
                              Apartment #3751630
                              36
                              Viewed 47 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 80 times in the last 48 hours
                                  Wonderful! 4.9/5
                                  (53 reviews)
                                  avg/night
                                  • 2 BR
                                  • 2 BA
                                  • Sleeps 6
                                  Condo #3720918
                                  53
                                  Viewed 69 times in the last 48 hours
                                    Wonderful! 4.8/5
                                    (46 reviews)
                                    avg/night
                                    • 3 BR
                                    • 2 BA
                                    • Sleeps 8
                                    Condo #290256vb
                                    46
                                    Viewed 234 times in the last 48 hours
                                      Excellent! 4.7/5
                                      (51 reviews)
                                      avg/night
                                      • 1 BR
                                      • 1 BA
                                      • Sleeps 4
                                      Apartment #415005vb
                                      51
                                      Viewed 20 times in the last 48 hours
                                        Wonderful! 4.8/5
                                        (12 reviews)
                                        avg/night
                                        • 1 BR
                                        • 1 BA
                                        • Sleeps 3
                                        Apartment #4146120
                                        12
                                        Viewed 72 times in the last 48 hours
                                          Wonderful! 4.9/5
                                          (37 reviews)
                                          avg/night
                                          • 2 BR
                                          • 2 BA
                                          • Sleeps 6
                                          Apartment #408313vb
                                          37
                                          Viewed 53 times in the last 48 hours
                                            Wonderful! 4.9/5
                                            (39 reviews)
                                            avg/night
                                            • 3 BR
                                            • 2 BA
                                            • Sleeps 8
                                            Condo #939473
                                            39
                                            Viewed 33 times in the last 48 hours
                                              Wonderful! 4.9/5
                                              (16 reviews)
                                              avg/night
                                              • 1 BR
                                              • 2 BA
                                              • Sleeps 2
                                              Apartment #864022vb
                                              16
                                              Viewed 141 times in the last 48 hours
                                                Wonderful! 4.9/5
                                                (74 reviews)
                                                avg/night
                                                • 2 BR
                                                • 2 BA
                                                • Sleeps 6
                                                Apartment #358020
                                                74
                                                Viewed 127 times in the last 48 hours
                                                  Wonderful! 4.9/5
                                                  (14 reviews)
                                                  avg/night
                                                  • Studio
                                                  • 1 BA
                                                  • Sleeps 2
                                                  Apartment #742485vb
                                                  14
                                                  Viewed 102 times in the last 48 hours
                                                    Exceptional! 5.0/5
                                                    (59 reviews)
                                                    avg/night
                                                    • 4 BR
                                                    • 2 BA
                                                    • Sleeps 10
                                                    Apartment #627209vb
                                                    59
                                                    Viewed 79 times in the last 48 hours
                                                      Wonderful! 4.9/5
                                                      (58 reviews)
                                                      avg/night
                                                      • 4 BR
                                                      • 2 BA
                                                      • Sleeps 11
                                                      House #595328vb
                                                      58
                                                      Viewed 170 times in the last 48 hours
                                                        Exceptional! 5.0/5
                                                        (13 reviews)
                                                        avg/night
                                                        • 3 BR
                                                        • 2 BA
                                                        • Sleeps 6
                                                        Apartment #723132vb
                                                        13
                                                        Viewed 86 times in the last 48 hours
                                                          Wonderful! 4.8/5
                                                          (19 reviews)
                                                          avg/night
                                                          • 2 BR
                                                          • 2 BA
                                                          • Sleeps 6
                                                          Condo #735859vb
                                                          19
                                                          Viewed 97 times in the last 48 hours
                                                            Excellent! 4.7/5
                                                            (22 reviews)
                                                            avg/night
                                                            • 2 BR
                                                            • 1 BA
                                                            • Sleeps 4
                                                            Apartment #588228vb
                                                            22
                                                            Viewed 72 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
                                                                Exceptional! 5.0/5
                                                                (22 reviews)
                                                                avg/night
                                                                • 5 BR
                                                                • 1 BA
                                                                • Separate Toilet
                                                                • Sleeps 10
                                                                Condo #776608vb
                                                                22
                                                                Viewed 206 times in the last 48 hours
                                                                  Exceptional! 5.0/5
                                                                  (127 reviews)
                                                                  avg/night
                                                                  • 3 BR
                                                                  • 2 BA
                                                                  • Sleeps 8
                                                                  Apartment #422128vb
                                                                  127
                                                                  Viewed 67 times in the last 48 hours
                                                                    Wonderful! 4.9/5
                                                                    (21 reviews)
                                                                    avg/night
                                                                    • 2 BR
                                                                    • 2 BA
                                                                    • Sleeps 6
                                                                    Apartment #653828vb
                                                                    21
                                                                    Viewed 46 times in the last 48 hours
                                                                      Wonderful! 4.9/5
                                                                      (18 reviews)
                                                                      avg/night
                                                                      • 1 BR
                                                                      • 1 BA
                                                                      • Sleeps 5
                                                                      Apartment #784869vb
                                                                      18
                                                                      Viewed 41 times in the last 48 hours
                                                                        Excellent! 4.7/5
                                                                        (66 reviews)
                                                                        avg/night
                                                                        • 1 BR
                                                                        • 1 BA
                                                                        • Sleeps 4
                                                                        Condo #177026vb
                                                                        66
                                                                        Viewed 52 times in the last 48 hours
                                                                          Exceptional! 5.0/5
                                                                          (25 reviews)
                                                                          avg/night
                                                                          • 3 BR
                                                                          • 2 BA
                                                                          • Sleeps 6
                                                                          Townhome #3917584
                                                                          25
                                                                          Viewed 41 times in the last 48 hours
                                                                            Excellent! 4.5/5
                                                                            (76 reviews)
                                                                            avg/night
                                                                            • 2 BR
                                                                            • 2 BA
                                                                            • Sleeps 10
                                                                            Condo #400905vb
                                                                            76
                                                                            Viewed 107 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 44 times in the last 48 hours
                                                                                Wonderful! 4.8/5
                                                                                (59 reviews)
                                                                                avg/night
                                                                                • 3 BR
                                                                                • 2 BA
                                                                                • Sleeps 12
                                                                                House #376549vb
                                                                                59
                                                                                Viewed 87 times in the last 48 hours
                                                                                  Wonderful! 4.8/5
                                                                                  (49 reviews)
                                                                                  avg/night
                                                                                  • 6 BR
                                                                                  • 3 BA
                                                                                  • Sleeps 18
                                                                                  Condo #682966vb
                                                                                  49
                                                                                  Viewed 73 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
                                                                                      Wonderful! 4.9/5
                                                                                      (12 reviews)
                                                                                      avg/night
                                                                                      • 3 BR
                                                                                      • 2 BA
                                                                                      • Sleeps 6
                                                                                      Apartment #653830vb
                                                                                      12
                                                                                      Viewed 19 times in the last 48 hours
                                                                                        Excellent! 4.3/5
                                                                                        (14 reviews)
                                                                                        avg/night
                                                                                        • 2 BR
                                                                                        • 2 BA
                                                                                        • Sleeps 6
                                                                                        Apartment #593610vb
                                                                                        14
                                                                                        Viewed 61 times in the last 48 hours
                                                                                          Wonderful! 4.9/5
                                                                                          (13 reviews)
                                                                                          avg/night
                                                                                          • 1 BR
                                                                                          • 1 BA
                                                                                          • Sleeps 4
                                                                                          Condo #4037980
                                                                                          13
                                                                                          Viewed 251 times in the last 48 hours
                                                                                            Excellent! 4.7/5
                                                                                            (38 reviews)
                                                                                            avg/night
                                                                                            • 3 BR
                                                                                            • 1 BA
                                                                                            • Sleeps 5
                                                                                            Apartment #600158vb
                                                                                            38
                                                                                            Viewed 38 times in the last 48 hours
                                                                                              Wonderful! 4.8/5
                                                                                              (42 reviews)
                                                                                              avg/night
                                                                                              • 4 BR
                                                                                              • 2 BA
                                                                                              • Sleeps 10
                                                                                              Apartment #3768288
                                                                                              42
                                                                                              Viewed 55 times in the last 48 hours
                                                                                                Wonderful! 4.8/5
                                                                                                (62 reviews)
                                                                                                avg/night
                                                                                                • 2 BR
                                                                                                • 1 BA
                                                                                                • Sleeps 6
                                                                                                Apartment #301852vb
                                                                                                62
                                                                                                Viewed 36 times in the last 48 hours
                                                                                                  Wonderful! 4.9/5
                                                                                                  (19 reviews)
                                                                                                  avg/night
                                                                                                  • 2 BR
                                                                                                  • 1 BA
                                                                                                  • Sleeps 7
                                                                                                  Apartment #792973vb
                                                                                                  19
                                                                                                  Viewed 87 times in the last 48 hours
                                                                                                    Excellent! 4.7/5
                                                                                                    (23 reviews)
                                                                                                    avg/night
                                                                                                    • 3 BR
                                                                                                    • 1 BA
                                                                                                    • Sleeps 8
                                                                                                    Apartment #4016534
                                                                                                    23
                                                                                                    Viewed 40 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 41 times in the last 48 hours
                                                                                                      • 1 - 50 of 300+

                                                                                                      Chicago Holiday Apartments & Rentals (300+)