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

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

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

Things to do on holiday to Chicago, USA

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

Places to visit on holiday to Chicago, USA

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

Weather in Chicago, USA

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

Travel to Chicago, USA

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

  • Showing 1-50 of 300+
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    Excellent! 4.6/5
    (86 reviews)
    avg/night
    • 2 BR
    • 2 BA
    • Sleeps 8
    Apartment #179389vb
    86
    Viewed 56 times in the last 48 hours
      Excellent! 4.5/5
      (57 reviews)
      avg/night
      • 1 BR
      • 1 BA
      • Sleeps 4
      Apartment #690239vb
      57
      Viewed 68 times in the last 48 hours
        Wonderful! 4.9/5
        (35 reviews)
        avg/night
        • 1 BR
        • 1 BA
        • Sleeps 4
        Apartment #3790035
        35
        Viewed 61 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
            Excellent! 4.7/5
            (94 reviews)
            avg/night
            • 2 BR
            • 2 BA
            • Sleeps 4
            Condo #222038
            94
            Viewed 74 times in the last 48 hours
              Wonderful! 4.9/5
              (89 reviews)
              avg/night
              • 3 BR
              • 2 BA
              • Separate Toilet
              • Sleeps 8
              Apartment #578762vb
              89
              Viewed 83 times in the last 48 hours
                Wonderful! 4.8/5
                (46 reviews)
                avg/night
                • 3 BR
                • 2 BA
                • Sleeps 8
                Condo #290256vb
                46
                Viewed 138 times in the last 48 hours
                  Excellent! 4.6/5
                  (17 reviews)
                  avg/night
                  • 1 BR
                  • 1 BA
                  • Sleeps 3
                  Apartment #4146480
                  17
                  Viewed 52 times in the last 48 hours
                    Wonderful! 4.8/5
                    (60 reviews)
                    avg/night
                    • 4 BR
                    • 4 BA
                    • Sleeps 12
                    Condo #679790vb
                    60
                    Viewed 108 times in the last 48 hours
                      Wonderful! 4.9/5
                      (51 reviews)
                      avg/night
                      • 3 BR
                      • 2 BA
                      • Sleeps 8
                      Condo #296798
                      51
                      Viewed 21 times in the last 48 hours
                        Wonderful! 4.9/5
                        (19 reviews)
                        avg/night
                        • 1 BR
                        • 2 BA
                        • Sleeps 2
                        Apartment #864022vb
                        19
                        Viewed 121 times in the last 48 hours
                          Wonderful! 4.9/5
                          (14 reviews)
                          avg/night
                          • Studio
                          • 1 BA
                          • Sleeps 2
                          Apartment #742485vb
                          14
                          Viewed 65 times in the last 48 hours
                            Wonderful! 4.8/5
                            (42 reviews)
                            avg/night
                            • 4 BR
                            • 2 BA
                            • Sleeps 10
                            Apartment #3768288
                            42
                            Viewed 83 times in the last 48 hours
                              Excellent! 4.7/5
                              (16 reviews)
                              avg/night
                              • Studio
                              • 1 BA
                              • Sleeps 2
                              Multiple rentals Apartment #4261388
                              16
                              Viewed 131 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 48 times in the last 48 hours
                                  Excellent! 4.6/5
                                  (41 reviews)
                                  avg/night
                                  • 2 BR
                                  • 1 BA
                                  • Sleeps 5
                                  Apartment #3833362
                                  41
                                  Viewed 57 times in the last 48 hours
                                    Wonderful! 4.9/5
                                    (21 reviews)
                                    avg/night
                                    • 2 BR
                                    • 2 BA
                                    • Sleeps 6
                                    Condo #735859vb
                                    21
                                    Viewed 51 times in the last 48 hours
                                      Wonderful! 4.9/5
                                      (40 reviews)
                                      avg/night
                                      • 3 BR
                                      • 2 BA
                                      • Sleeps 8
                                      Condo #939473
                                      40
                                      Viewed 23 times in the last 48 hours
                                        Wonderful! 4.8/5
                                        (23 reviews)
                                        avg/night
                                        • 2 BR
                                        • 2 BA
                                        • Sleeps 6
                                        Apartment #3795191
                                        23
                                        Viewed 69 times in the last 48 hours
                                          Excellent! 4.7/5
                                          (67 reviews)
                                          avg/night
                                          • 1 BR
                                          • 1 BA
                                          • Sleeps 4
                                          Condo #177026vb
                                          67
                                          Viewed 23 times in the last 48 hours
                                            Wonderful! 4.8/5
                                            (44 reviews)
                                            avg/night
                                            • 2 BR
                                            • 2 BA
                                            • Sleeps 6
                                            Condo #265424vb
                                            44
                                            Viewed 60 times in the last 48 hours
                                              Wonderful! 4.9/5
                                              (54 reviews)
                                              avg/night
                                              • 2 BR
                                              • 2 BA
                                              • Sleeps 6
                                              Condo #3720918
                                              54
                                              Viewed 48 times in the last 48 hours
                                                Wonderful! 4.9/5
                                                (75 reviews)
                                                avg/night
                                                • 2 BR
                                                • 2 BA
                                                • Sleeps 6
                                                Apartment #358020
                                                75
                                                Viewed 49 times in the last 48 hours
                                                  Excellent! 4.7/5
                                                  (51 reviews)
                                                  avg/night
                                                  • 1 BR
                                                  • 1 BA
                                                  • Sleeps 4
                                                  Apartment #415005vb
                                                  51
                                                  Viewed 24 times in the last 48 hours
                                                    Exceptional! 5/5
                                                    (6 reviews)
                                                    avg/night
                                                    • 2 BR
                                                    • 2 BA
                                                    • Sleeps 6
                                                    Apartment #4172462
                                                    6
                                                    Viewed 68 times in the last 48 hours
                                                      Exceptional! 5/5
                                                      (22 reviews)
                                                      avg/night
                                                      • 5 BR
                                                      • 1 BA
                                                      • Separate Toilet
                                                      • Sleeps 10
                                                      Condo #776608vb
                                                      22
                                                      Viewed 112 times in the last 48 hours
                                                        Exceptional! 5/5
                                                        (59 reviews)
                                                        avg/night
                                                        • 4 BR
                                                        • 2 BA
                                                        • Sleeps 10
                                                        Apartment #627209vb
                                                        59
                                                        Viewed 56 times in the last 48 hours
                                                          Wonderful! 4.9/5
                                                          (18 reviews)
                                                          avg/night
                                                          • 1 BR
                                                          • 1 BA
                                                          • Sleeps 5
                                                          Apartment #784869vb
                                                          18
                                                          Viewed 64 times in the last 48 hours
                                                            Excellent! 4.5/5
                                                            (8 reviews)
                                                            avg/night
                                                            • 1 BR
                                                            • 1 BA
                                                            • Sleeps 3
                                                            Apartment #836457vb
                                                            8
                                                            Viewed 37 times in the last 48 hours
                                                              Excellent! 4.7/5
                                                              (39 reviews)
                                                              avg/night
                                                              • 3 BR
                                                              • 1 BA
                                                              • Sleeps 5
                                                              Apartment #600158vb
                                                              39
                                                              Viewed 34 times in the last 48 hours
                                                                Excellent! 4.5/5
                                                                (76 reviews)
                                                                avg/night
                                                                • 2 BR
                                                                • 2 BA
                                                                • Sleeps 10
                                                                Condo #400905vb
                                                                76
                                                                Viewed 51 times in the last 48 hours
                                                                  Wonderful! 4.9/5
                                                                  (16 reviews)
                                                                  avg/night
                                                                  • 1 BR
                                                                  • 1 BA
                                                                  • Sleeps 4
                                                                  Apartment #870614vb
                                                                  16
                                                                  Viewed 123 times in the last 48 hours
                                                                    Exceptional! 5/5
                                                                    (14 reviews)
                                                                    avg/night
                                                                    • 3 BR
                                                                    • 2 BA
                                                                    • Sleeps 6
                                                                    Apartment #723132vb
                                                                    14
                                                                    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 52 times in the last 48 hours
                                                                        Exceptional! 5/5
                                                                        (60 reviews)
                                                                        avg/night
                                                                        • 4 BR
                                                                        • 2 BA
                                                                        • Sleeps 11
                                                                        House #595328vb
                                                                        60
                                                                        Viewed 115 times in the last 48 hours
                                                                          Excellent! 4.5/5
                                                                          (24 reviews)
                                                                          avg/night
                                                                          • 3 BR
                                                                          • 2 BA
                                                                          • Sleeps 8
                                                                          Condo #622632vb
                                                                          24
                                                                          Viewed 80 times in the last 48 hours
                                                                            Wonderful! 4.9/5
                                                                            (37 reviews)
                                                                            avg/night
                                                                            • 2 BR
                                                                            • 2 BA
                                                                            • Sleeps 6
                                                                            Apartment #408313vb
                                                                            37
                                                                            Viewed 36 times in the last 48 hours
                                                                              Exceptional! 5/5
                                                                              (6 reviews)
                                                                              avg/night
                                                                              • 1 BR
                                                                              • 1 BA
                                                                              • Sleeps 2
                                                                              Apartment #871091vb
                                                                              6
                                                                              Viewed 49 times in the last 48 hours
                                                                                Exceptional! 5/5
                                                                                (26 reviews)
                                                                                avg/night
                                                                                • 3 BR
                                                                                • 2 BA
                                                                                • Sleeps 6
                                                                                Townhome #3917584
                                                                                26
                                                                                Viewed 19 times in the last 48 hours
                                                                                  Wonderful! 4.9/5
                                                                                  (14 reviews)
                                                                                  avg/night
                                                                                  • 1 BR
                                                                                  • 1 BA
                                                                                  • Sleeps 4
                                                                                  Condo #4037980
                                                                                  14
                                                                                  Viewed 331 times in the last 48 hours
                                                                                    Excellent! 4.7/5
                                                                                    (22 reviews)
                                                                                    avg/night
                                                                                    • 2 BR
                                                                                    • 1 BA
                                                                                    • Sleeps 4
                                                                                    Apartment #588228vb
                                                                                    22
                                                                                    Viewed 36 times in the last 48 hours
                                                                                      Excellent! 4.6/5
                                                                                      (8 reviews)
                                                                                      avg/night
                                                                                      • 2 BR
                                                                                      • 2 BA
                                                                                      • Sleeps 6
                                                                                      Apartment #4172463
                                                                                      8
                                                                                      Viewed 46 times in the last 48 hours
                                                                                        Wonderful! 4.8/5
                                                                                        (62 reviews)
                                                                                        avg/night
                                                                                        • 2 BR
                                                                                        • 1 BA
                                                                                        • Sleeps 6
                                                                                        Apartment #301852vb
                                                                                        62
                                                                                        Viewed 39 times in the last 48 hours
                                                                                          Wonderful! 4.9/5
                                                                                          (21 reviews)
                                                                                          avg/night
                                                                                          • 2 BR
                                                                                          • 2 BA
                                                                                          • Sleeps 6
                                                                                          Apartment #653828vb
                                                                                          21
                                                                                          Viewed 24 times in the last 48 hours
                                                                                            Wonderful! 4.9/5
                                                                                            (13 reviews)
                                                                                            avg/night
                                                                                            • 2 BR
                                                                                            • 1 BA
                                                                                            • Sleeps 4
                                                                                            Apartment #780506vb
                                                                                            13
                                                                                            Viewed 30 times in the last 48 hours
                                                                                              Wonderful! 4.9/5
                                                                                              (20 reviews)
                                                                                              avg/night
                                                                                              • 4 BR
                                                                                              • 2 BA
                                                                                              • Separate Toilet
                                                                                              • Sleeps 10
                                                                                              House #840552vb
                                                                                              20
                                                                                              Viewed 74 times in the last 48 hours
                                                                                                Excellent! 4.7/5
                                                                                                (23 reviews)
                                                                                                avg/night
                                                                                                • 3 BR
                                                                                                • 1 BA
                                                                                                • Sleeps 8
                                                                                                Apartment #4016534
                                                                                                23
                                                                                                Viewed 56 times in the last 48 hours
                                                                                                  Excellent! 4.6/5
                                                                                                  (71 reviews)
                                                                                                  avg/night
                                                                                                  • 1 BR
                                                                                                  • 1 BA
                                                                                                  • Sleeps 4
                                                                                                  Apartment #179390vb
                                                                                                  71
                                                                                                  Viewed 28 times in the last 48 hours
                                                                                                    Wonderful! 4.9/5
                                                                                                    (50 reviews)
                                                                                                    avg/night
                                                                                                    • 2 BR
                                                                                                    • 2 BA
                                                                                                    • Sleeps 6
                                                                                                    Apartment #358013
                                                                                                    50
                                                                                                    Viewed 104 times in the last 48 hours
                                                                                                      Wonderful! 4.9/5
                                                                                                      (78 reviews)
                                                                                                      avg/night
                                                                                                      • 6 BR
                                                                                                      • 4 BA
                                                                                                      • Sleeps 18
                                                                                                      Condo #411142vb
                                                                                                      78
                                                                                                      Viewed 92 times in the last 48 hours
                                                                                                      • 1 - 50 of 300+

                                                                                                      Chicago Holiday Apartments & Rentals (300+)