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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 87 times in the last 48 hours
      Excellent! 4.7/5
      (44 reviews)
      avg/night
      • 2 BR
      • 1 BA
      • Sleeps 4
      Apartment #445608vb
      44
      Viewed 66 times in the last 48 hours
        Excellent! 4.5/5
        (57 reviews)
        avg/night
        • 1 BR
        • 1 BA
        • Sleeps 4
        Apartment #690239vb
        57
        Viewed 60 times in the last 48 hours
          Excellent! 4.7/5
          (93 reviews)
          avg/night
          • 2 BR
          • 2 BA
          • Sleeps 4
          Condo #222038
          93
          Viewed 82 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 93 times in the last 48 hours
              Wonderful! 4.8/5
              (46 reviews)
              avg/night
              • 3 BR
              • 2 BA
              • Sleeps 8
              Condo #290256vb
              46
              Viewed 183 times in the last 48 hours
                Wonderful! 4.8/5
                (59 reviews)
                avg/night
                • 4 BR
                • 4 BA
                • Sleeps 12
                Condo #679790vb
                59
                Viewed 113 times in the last 48 hours
                  Excellent! 4.6/5
                  (17 reviews)
                  avg/night
                  • 1 BR
                  • 1 BA
                  • Sleeps 3
                  Apartment #4146480
                  17
                  Viewed 43 times in the last 48 hours
                    Wonderful! 4.9/5
                    (51 reviews)
                    avg/night
                    • 3 BR
                    • 2 BA
                    • Sleeps 8
                    Condo #296798
                    51
                    Viewed 85 times in the last 48 hours
                      Wonderful! 4.9/5
                      (18 reviews)
                      avg/night
                      • 1 BR
                      • 2 BA
                      • Sleeps 2
                      Apartment #864022vb
                      18
                      Viewed 68 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 75 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 48 times in the last 48 hours
                            Wonderful! 4.9/5
                            (14 reviews)
                            avg/night
                            • Studio
                            • 1 BA
                            • Sleeps 2
                            Apartment #742485vb
                            14
                            Viewed 88 times in the last 48 hours
                              Excellent! 4.4/5
                              (14 reviews)
                              avg/night
                              • 2 BR
                              • 2 BA
                              • Sleeps 5
                              Apartment #4047746
                              14
                              Viewed 144 times in the last 48 hours
                                Wonderful! 4.9/5
                                (40 reviews)
                                avg/night
                                • 3 BR
                                • 2 BA
                                • Sleeps 8
                                Condo #939473
                                40
                                Viewed 31 times in the last 48 hours
                                  Wonderful! 4.8/5
                                  (23 reviews)
                                  avg/night
                                  • 2 BR
                                  • 2 BA
                                  • Sleeps 6
                                  Apartment #3795191
                                  23
                                  Viewed 90 times in the last 48 hours
                                    Wonderful! 4.9/5
                                    (35 reviews)
                                    avg/night
                                    • 1 BR
                                    • 1 BA
                                    • Sleeps 4
                                    Apartment #3790035
                                    35
                                    Viewed 60 times in the last 48 hours
                                      Wonderful! 4.9/5
                                      (21 reviews)
                                      avg/night
                                      • 2 BR
                                      • 2 BA
                                      • Sleeps 6
                                      Condo #735859vb
                                      21
                                      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 89 times in the last 48 hours
                                          Wonderful! 4.9/5
                                          (74 reviews)
                                          avg/night
                                          • 2 BR
                                          • 2 BA
                                          • Sleeps 6
                                          Apartment #358020
                                          74
                                          Viewed 54 times in the last 48 hours
                                            Excellent! 4.6/5
                                            (41 reviews)
                                            avg/night
                                            • 2 BR
                                            • 1 BA
                                            • Sleeps 5
                                            Apartment #3833362
                                            41
                                            Viewed 50 times in the last 48 hours
                                              Wonderful! 4.8/5
                                              (44 reviews)
                                              avg/night
                                              • 2 BR
                                              • 2 BA
                                              • Sleeps 6
                                              Condo #265424vb
                                              44
                                              Viewed 116 times in the last 48 hours
                                                Exceptional! 5/5
                                                (59 reviews)
                                                avg/night
                                                • 4 BR
                                                • 2 BA
                                                • Sleeps 10
                                                Apartment #627209vb
                                                59
                                                Viewed 81 times in the last 48 hours
                                                  Wonderful! 4.9/5
                                                  (54 reviews)
                                                  avg/night
                                                  • 2 BR
                                                  • 2 BA
                                                  • Sleeps 6
                                                  Condo #3720918
                                                  54
                                                  Viewed 61 times in the last 48 hours
                                                    Wonderful! 4.9/5
                                                    (18 reviews)
                                                    avg/night
                                                    • 1 BR
                                                    • 1 BA
                                                    • Sleeps 5
                                                    Apartment #784869vb
                                                    18
                                                    Viewed 37 times in the last 48 hours
                                                      Excellent! 4.7/5
                                                      (51 reviews)
                                                      avg/night
                                                      • 1 BR
                                                      • 1 BA
                                                      • Sleeps 4
                                                      Apartment #415005vb
                                                      51
                                                      Viewed 15 times in the last 48 hours
                                                        Excellent! 4.7/5
                                                        (67 reviews)
                                                        avg/night
                                                        • 1 BR
                                                        • 1 BA
                                                        • Sleeps 4
                                                        Condo #177026vb
                                                        67
                                                        Viewed 36 times in the last 48 hours
                                                          Excellent! 4.6/5
                                                          (36 reviews)
                                                          avg/night
                                                          • 1 BR
                                                          • 1 BA
                                                          • Sleeps 4
                                                          Apartment #3751630
                                                          36
                                                          Viewed 57 times in the last 48 hours
                                                            Excellent! 4.5/5
                                                            (76 reviews)
                                                            avg/night
                                                            • 2 BR
                                                            • 2 BA
                                                            • Sleeps 10
                                                            Condo #400905vb
                                                            76
                                                            Viewed 66 times in the last 48 hours
                                                              Wonderful! 4.9/5
                                                              (37 reviews)
                                                              avg/night
                                                              • 2 BR
                                                              • 2 BA
                                                              • Sleeps 6
                                                              Apartment #408313vb
                                                              37
                                                              Viewed 49 times in the last 48 hours
                                                                Excellent! 4.5/5
                                                                (24 reviews)
                                                                avg/night
                                                                • 3 BR
                                                                • 2 BA
                                                                • Sleeps 8
                                                                Condo #622632vb
                                                                24
                                                                Viewed 121 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 48 times in the last 48 hours
                                                                    Excellent! 4.3/5
                                                                    (14 reviews)
                                                                    avg/night
                                                                    • 2 BR
                                                                    • 2 BA
                                                                    • Sleeps 6
                                                                    Apartment #593610vb
                                                                    14
                                                                    Viewed 49 times in the last 48 hours
                                                                      Wonderful! 4.9/5
                                                                      (76 reviews)
                                                                      avg/night
                                                                      • 3 BR
                                                                      • 1 BA
                                                                      • Separate Toilet
                                                                      • Sleeps 6
                                                                      Apartment #225815
                                                                      76
                                                                      Viewed 32 times in the last 48 hours
                                                                        Wonderful! 4.9/5
                                                                        (41 reviews)
                                                                        avg/night
                                                                        • 5 BR
                                                                        • 5 BA
                                                                        • Sleeps 14
                                                                        House #571144vb
                                                                        41
                                                                        Viewed 54 times in the last 48 hours
                                                                          Excellent! 4.3/5
                                                                          (28 reviews)
                                                                          avg/night
                                                                          • 3 BR
                                                                          • 2 BA
                                                                          • Sleeps 10
                                                                          House #3733046
                                                                          28
                                                                          Viewed 39 times in the last 48 hours
                                                                            Excellent! 4.6/5
                                                                            (32 reviews)
                                                                            avg/night
                                                                            • 6 BR
                                                                            • 5 BA
                                                                            • Sleeps 11
                                                                            Estate #289158vb
                                                                            32
                                                                            Viewed 78 times in the last 48 hours
                                                                              • 3 BR
                                                                              • 2 BA
                                                                              • Sleeps 6
                                                                              Apartment #890369vb
                                                                              1
                                                                                avg/night
                                                                                • 3 BR
                                                                                • 2 BA
                                                                                • Separate Toilet
                                                                                • Sleeps 6
                                                                                Condo #887767vb
                                                                                2
                                                                                Viewed 150 times in the last 48 hours
                                                                                  avg/night
                                                                                  • 3 BR
                                                                                  • 2 BA
                                                                                  • Separate Toilet
                                                                                  • Sleeps 30
                                                                                  Condo #282940vb
                                                                                  2
                                                                                  Viewed 393 times in the last 48 hours
                                                                                    • 3 BR
                                                                                    • 2 BA
                                                                                    • Separate Toilet
                                                                                    • Sleeps 30
                                                                                    Condo #267014
                                                                                    2
                                                                                    Viewed 246 times in the last 48 hours
                                                                                      Very Good! 4/5
                                                                                      (5 reviews)
                                                                                      avg/night
                                                                                      • 3 BR
                                                                                      • 2 BA
                                                                                      • Separate Toilet
                                                                                      • Sleeps 6
                                                                                      Condo #267015
                                                                                      5
                                                                                      Viewed 326 times in the last 48 hours
                                                                                        Very Good! 4/5
                                                                                        (6 reviews)
                                                                                        avg/night
                                                                                        • 2 BR
                                                                                        • 2 BA
                                                                                        • Sleeps 4
                                                                                        Condo #159001vb
                                                                                        6
                                                                                        Viewed 157 times in the last 48 hours
                                                                                          Very Good! 4.2/5
                                                                                          (5 reviews)
                                                                                          avg/night
                                                                                          • 3 BR
                                                                                          • 2 BA
                                                                                          • Sleeps 6
                                                                                          Condo #318483vb
                                                                                          5
                                                                                          Viewed 124 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 173 times in the last 48 hours
                                                                                              Wonderful! 4.9/5
                                                                                              (13 reviews)
                                                                                              avg/night
                                                                                              • 2 BR
                                                                                              • 1 BA
                                                                                              • Sleeps 4
                                                                                              Apartment #780506vb
                                                                                              13
                                                                                              Viewed 43 times in the last 48 hours
                                                                                                Exceptional! 5/5
                                                                                                (60 reviews)
                                                                                                avg/night
                                                                                                • 4 BR
                                                                                                • 2 BA
                                                                                                • Sleeps 11
                                                                                                House #595328vb
                                                                                                60
                                                                                                Viewed 77 times in the last 48 hours
                                                                                                  Exceptional! 5/5
                                                                                                  (22 reviews)
                                                                                                  avg/night
                                                                                                  • 3 BR
                                                                                                  • 2 BA
                                                                                                  • Sleeps 8
                                                                                                  Condo #708413vb
                                                                                                  22
                                                                                                  Viewed 41 times in the last 48 hours
                                                                                                    • 1 BR
                                                                                                    • 1 BA
                                                                                                    • Separate Toilet
                                                                                                    • Sleeps 4
                                                                                                    Condo #735045vb
                                                                                                    3
                                                                                                      Excellent! 4.5/5
                                                                                                      (8 reviews)
                                                                                                      avg/night
                                                                                                      • 1 BR
                                                                                                      • 1 BA
                                                                                                      • Sleeps 3
                                                                                                      Apartment #836457vb
                                                                                                      8
                                                                                                      Viewed 39 times in the last 48 hours
                                                                                                      • 1 - 50 of 300+

                                                                                                      Chicago Holiday Apartments & Rentals (300+)