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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.
    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
      Wonderful! 4.9/5
      (80 reviews)
      avg/night
      • 3 BR
      • 2 BA
      • Separate Toilet
      • Sleeps 8
      Apartment #578762vb
      80
      Viewed 61 times in the last 48 hours
        Excellent! 4.3/5
        (12 reviews)
        avg/night
        • 2 BR
        • 2 BA
        • Sleeps 5
        Apartment #4047746
        12
        Viewed 56 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
            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
              Wonderful! 4.9/5
              (13 reviews)
              avg/night
              • 2 BR
              • 1 BA
              • Sleeps 4
              Apartment #780506vb
              13
              Viewed 25 times in the last 48 hours
                Excellent! 4.7/5
                (92 reviews)
                avg/night
                • 2 BR
                • 2 BA
                • Sleeps 4
                Condo #222038
                92
                Viewed 41 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
                    Wonderful! 4.8/5
                    (51 reviews)
                    avg/night
                    • 4 BR
                    • 4 BA
                    • Sleeps 12
                    Condo #679790vb
                    51
                    Viewed 37 times in the last 48 hours
                      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! 4.9/5
                        (39 reviews)
                        avg/night
                        • 3 BR
                        • 2 BA
                        • Sleeps 8
                        Condo #939473
                        39
                        Viewed 10 times in the last 48 hours
                          Wonderful! 4.9/5
                          (35 reviews)
                          avg/night
                          • 1 BR
                          • 1 BA
                          • Sleeps 4
                          Apartment #3790035
                          35
                          Viewed 20 times in the last 48 hours
                            Wonderful! 4.8/5
                            (45 reviews)
                            avg/night
                            • 3 BR
                            • 2 BA
                            • Sleeps 8
                            Condo #290256vb
                            45
                            Viewed 43 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
                                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! 4.7/5
                                  (15 reviews)
                                  avg/night
                                  • 1 BR
                                  • 1 BA
                                  • Sleeps 3
                                  Apartment #4146480
                                  15
                                  Viewed 58 times in the last 48 hours
                                    Wonderful! 4.9/5
                                    (53 reviews)
                                    avg/night
                                    • 2 BR
                                    • 2 BA
                                    • Sleeps 6
                                    Condo #3720918
                                    53
                                    Viewed 27 times in the last 48 hours
                                      • 2 BR
                                      • 1 BA
                                      • Sleeps 5
                                      Condo #3861165
                                      19
                                      Viewed 20 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
                                          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
                                            Excellent! 4.7/5
                                            (51 reviews)
                                            avg/night
                                            • 1 BR
                                            • 1 BA
                                            • Sleeps 4
                                            Apartment #415005vb
                                            51
                                            Viewed 19 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
                                                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
                                                  Wonderful! 4.8/5
                                                  (42 reviews)
                                                  avg/night
                                                  • 2 BR
                                                  • 1 BA
                                                  • Separate Toilet
                                                  • Sleeps 6
                                                  Apartment #271945
                                                  42
                                                  Viewed 21 times in the last 48 hours
                                                    Wonderful! 4.9/5
                                                    (56 reviews)
                                                    avg/night
                                                    • 4 BR
                                                    • 2 BA
                                                    • Sleeps 10
                                                    House #595328vb
                                                    56
                                                    Viewed 34 times in the last 48 hours
                                                      Exceptional! 5.0/5
                                                      (13 reviews)
                                                      avg/night
                                                      • 3 BR
                                                      • 2 BA
                                                      • Sleeps 6
                                                      Apartment #723132vb
                                                      13
                                                      Viewed 23 times in the last 48 hours
                                                        Wonderful! 4.9/5
                                                        (20 reviews)
                                                        avg/night
                                                        • 2 BR
                                                        • 2 BA
                                                        • Sleeps 6
                                                        Apartment #653828vb
                                                        20
                                                        Viewed 19 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
                                                            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
                                                              Wonderful! 4.8/5
                                                              (57 reviews)
                                                              avg/night
                                                              • 3 BR
                                                              • 2 BA
                                                              • Sleeps 12
                                                              House #376549vb
                                                              57
                                                              Viewed 22 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! 4.5/5
                                                                  (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
                                                                    (40 reviews)
                                                                    avg/night
                                                                    • 2 BR
                                                                    • 1 BA
                                                                    • Separate Toilet
                                                                    • Sleeps 8
                                                                    Apartment #3645846
                                                                    40
                                                                    Viewed 22 times in the last 48 hours
                                                                      Wonderful! 4.9/5
                                                                      (17 reviews)
                                                                      avg/night
                                                                      • 2 BR
                                                                      • 1 BA
                                                                      • Sleeps 7
                                                                      Apartment #792973vb
                                                                      17
                                                                      Viewed 15 times in the last 48 hours
                                                                        Wonderful! 4.9/5
                                                                        (74 reviews)
                                                                        avg/night
                                                                        • 2 BR
                                                                        • 2 BA
                                                                        • Sleeps 6
                                                                        Apartment #358020
                                                                        74
                                                                        Viewed 47 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
                                                                            (17 reviews)
                                                                            avg/night
                                                                            • 1 BR
                                                                            • 1 BA
                                                                            • Sleeps 5
                                                                            Apartment #784869vb
                                                                            17
                                                                            Viewed 5 times in the last 48 hours
                                                                              Wonderful! 4.8/5
                                                                              (22 reviews)
                                                                              avg/night
                                                                              • 2 BR
                                                                              • 2 BA
                                                                              • Sleeps 6
                                                                              Apartment #3795191
                                                                              22
                                                                              Viewed 13 times in the last 48 hours
                                                                                Wonderful! 4.8/5
                                                                                (17 reviews)
                                                                                avg/night
                                                                                • 2 BR
                                                                                • 2 BA
                                                                                • Sleeps 6
                                                                                Condo #735859vb
                                                                                17
                                                                                Viewed 28 times in the last 48 hours
                                                                                  Excellent! 4.7/5
                                                                                  (43 reviews)
                                                                                  avg/night
                                                                                  • 2 BR
                                                                                  • 1 BA
                                                                                  • Sleeps 4
                                                                                  Apartment #445608vb
                                                                                  43
                                                                                  Viewed 11 times in the last 48 hours
                                                                                    Exceptional! 5.0/5
                                                                                    (20 reviews)
                                                                                    avg/night
                                                                                    • 4 BR
                                                                                    • 1 BA
                                                                                    • Separate Toilets
                                                                                    • Sleeps 8
                                                                                    House #776608vb
                                                                                    20
                                                                                    Viewed 40 times in the last 48 hours
                                                                                      Wonderful! 4.9/5
                                                                                      (9 reviews)
                                                                                      avg/night
                                                                                      • 3 BR
                                                                                      • 2 BA
                                                                                      • Sleeps 6
                                                                                      Apartment #653830vb
                                                                                      9
                                                                                      Viewed 14 times in the last 48 hours
                                                                                        Excellent! 4.6/5
                                                                                        (31 reviews)
                                                                                        avg/night
                                                                                        • 4 BR
                                                                                        • 2 BA
                                                                                        • Sleeps 11
                                                                                        Condo #685840vb
                                                                                        31
                                                                                        Viewed 22 times in the last 48 hours
                                                                                          Exceptional! 5.0/5
                                                                                          (231 reviews)
                                                                                          avg/night
                                                                                          • 1 BR
                                                                                          • 1 BA
                                                                                          • Sleeps 4
                                                                                          Condo #65673vb
                                                                                          231
                                                                                          Viewed 26 times in the last 48 hours
                                                                                            Wonderful! 4.9/5
                                                                                            (30 reviews)
                                                                                            avg/night
                                                                                            • 2 BR
                                                                                            • 2 BA
                                                                                            • Sleeps 6
                                                                                            Condo #376149vb
                                                                                            30
                                                                                            Viewed 11 times in the last 48 hours
                                                                                              Wonderful! 4.9/5
                                                                                              (141 reviews)
                                                                                              avg/night
                                                                                              • 3 BR
                                                                                              • 2 BA
                                                                                              • Sleeps 8
                                                                                              Condo #7757vb
                                                                                              141
                                                                                              Viewed 48 times in the last 48 hours
                                                                                                Excellent! 4.5/5
                                                                                                (24 reviews)
                                                                                                avg/night
                                                                                                • 3 BR
                                                                                                • 2 BA
                                                                                                • Sleeps 8
                                                                                                Condo #622632vb
                                                                                                24
                                                                                                Viewed 15 times in the last 48 hours
                                                                                                  Wonderful! 4.8/5
                                                                                                  (62 reviews)
                                                                                                  avg/night
                                                                                                  • 2 BR
                                                                                                  • 1 BA
                                                                                                  • Sleeps 6
                                                                                                  Apartment #301852vb
                                                                                                  62
                                                                                                  Viewed 17 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
                                                                                                      • 1 BR
                                                                                                      • 1 BA
                                                                                                      • Sleeps 2
                                                                                                      Apartment #4005449
                                                                                                      2 Reviews
                                                                                                      • 1 - 50 of 300+