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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.
    Exceptional! 5.0/5
    (28 reviews)
    avg/night
    • 3 BR
    • 2 BA
    • Sleeps 8
    Condo #237914
    28
    Viewed 23 times in the last 48 hours
      Wonderful! 4.9/5
      (45 reviews)
      avg/night
      • 1 BR
      • 1 BA
      • Sleeps 4
      Condo #411255vb
      45
      Viewed 31 times in the last 48 hours
        Exceptional! 5.0/5
        (58 reviews)
        avg/night
        • 4 BR
        • 2 BA
        • Sleeps 10
        Apartment #627209vb
        58
        Viewed 48 times in the last 48 hours
          Wonderful! 4.9/5
          (11 reviews)
          avg/night
          • 5 BR
          • 5 BA
          • Sleeps 26
          Apartment #4087004
          11
          Viewed 53 times in the last 48 hours
            Excellent! 4.6/5
            (7 reviews)
            avg/night
            • 4 BR
            • 3 BA
            • Sleeps 10
            Apartment #845524vb
            7
            Viewed 37 times in the last 48 hours
              Wonderful! 4.9/5
              (14 reviews)
              avg/night
              • 2 BR
              • 1 BA
              • Sleeps 4
              Apartment #856957vb
              14
              Viewed 56 times in the last 48 hours
                Wonderful! 4.9/5
                (11 reviews)
                avg/night
                • 1 BR
                • 2 BA
                • Sleeps 2
                Apartment #864022vb
                11
                Viewed 109 times in the last 48 hours
                  Very Good! 4.2/5
                  (5 reviews)
                  avg/night
                  • 1 BR
                  • 1 BA
                  • Sleeps 2
                  Apartment #871119vb
                  5
                  Viewed 35 times in the last 48 hours
                    • 2 BR
                    • 2 BA
                    • Sleeps 4
                    Apartment #4257947
                    Viewed 7 times in the last 48 hours
                      avg/night
                      • 2 BR
                      • 2 BA
                      • Sleeps 6
                      Apartment #4291112
                      Viewed 64 times in the last 48 hours
                        avg/night
                        • 1 BR
                        • 1 BA
                        • Sleeps 2
                        Condo #4333389
                        Viewed 24 times in the last 48 hours
                          avg/night
                          • 2 BR
                          • 2 BA
                          • Sleeps 4
                          Apartment #4347568
                          Viewed 28 times in the last 48 hours
                            Exceptional! 5.0/5
                            (69 reviews)
                            avg/night
                            • 3 BR
                            • 3 BA
                            • Sleeps 8
                            Condo #109064vb
                            69
                            Viewed 35 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 95 times in the last 48 hours
                                Excellent! 4.5/5
                                (24 reviews)
                                avg/night
                                • 3 BR
                                • 2 BA
                                • Sleeps 8
                                Condo #622632vb
                                24
                                Viewed 20 times in the last 48 hours
                                  Excellent! 4.3/5
                                  (12 reviews)
                                  avg/night
                                  • 2 BR
                                  • 2 BA
                                  • Sleeps 5
                                  Apartment #4047746
                                  12
                                  Viewed 60 times in the last 48 hours
                                    Excellent! 4.5/5
                                    (12 reviews)
                                    avg/night
                                    • 3 BR
                                    • 1 BA
                                    • Sleeps 4
                                    Apartment #817492vb
                                    12
                                    Viewed 10 times in the last 48 hours
                                      Excellent! 4.3/5
                                      (12 reviews)
                                      avg/night
                                      • 1 BR
                                      • 1 BA
                                      • Sleeps 3
                                      Apartment #819227vb
                                      12
                                      Viewed 32 times in the last 48 hours
                                        avg/night
                                        • 3 BR
                                        • 2 BA
                                        • Sleeps 6
                                        Apartment #4196659
                                        3
                                        Viewed 16 times in the last 48 hours
                                          Very Good! 4.2/5
                                          (5 reviews)
                                          avg/night
                                          • 2 BR
                                          • 1 BA
                                          • Sleeps 4
                                          Apartment #4223517
                                          5
                                            avg/night
                                            • Studio
                                            • 1 BA
                                            • Sleeps 2
                                            Studio #4264320
                                            1
                                            Viewed 8 times in the last 48 hours
                                              Exceptional! 5.0/5
                                              (231 reviews)
                                              avg/night
                                              • 1 BR
                                              • 1 BA
                                              • Sleeps 4
                                              Condo #65673vb
                                              231
                                              Viewed 16 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 11 times in the last 48 hours
                                                  Wonderful! 4.9/5
                                                  (63 reviews)
                                                  avg/night
                                                  • 2 BR
                                                  • 2 BA
                                                  • Sleeps 6
                                                  Condo #374687
                                                  63
                                                  Viewed 19 times in the last 48 hours
                                                    Exceptional! 5.0/5
                                                    (28 reviews)
                                                    avg/night
                                                    • 3 BR
                                                    • 2 BA
                                                    • Sleeps 6
                                                    Apartment #470476vb
                                                    28
                                                    Viewed 25 times in the last 48 hours
                                                      Wonderful! 4.8/5
                                                      (41 reviews)
                                                      avg/night
                                                      • 4 BR
                                                      • 2 BA
                                                      • Sleeps 10
                                                      Apartment #3768288
                                                      41
                                                      Viewed 20 times in the last 48 hours
                                                        • 2 BR
                                                        • 1 BA
                                                        • Sleeps 5
                                                        Condo #3861165
                                                        19
                                                        Viewed 26 times in the last 48 hours
                                                          Wonderful! 4.8/5
                                                          (17 reviews)
                                                          avg/night
                                                          • 2 BR
                                                          • 2 BA
                                                          • Sleeps 6
                                                          Condo #4017105
                                                          17
                                                          Viewed 7 times in the last 48 hours
                                                            Excellent! 4.5/5
                                                            (6 reviews)
                                                            avg/night
                                                            • 1 BR
                                                            • 1 BA
                                                            • Sleeps 3
                                                            Apartment #836457vb
                                                            6
                                                            Viewed 22 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 78 times in the last 48 hours
                                                                avg/night
                                                                • 3 BR
                                                                • 2 BA
                                                                • Sleeps 7
                                                                Apartment #4172096
                                                                Viewed 20 times in the last 48 hours
                                                                  avg/night
                                                                  • 2 BR
                                                                  • 1 BA
                                                                  • Sleeps 6
                                                                  Apartment #888352vb
                                                                  3
                                                                  Viewed 14 times in the last 48 hours
                                                                    avg/night
                                                                    • 2 BR
                                                                    • 2 BA
                                                                    • Sleeps 7
                                                                    Apartment #4288358
                                                                    Viewed 6 times in the last 48 hours
                                                                      avg/night
                                                                      • 1 BR
                                                                      • 1 BA
                                                                      • Sleeps 3
                                                                      Apartment #4316570
                                                                      Viewed 12 times in the last 48 hours
                                                                        avg/night
                                                                        • 3 BR
                                                                        • 2 BA
                                                                        • Sleeps 10
                                                                        Townhome #4357835
                                                                        Viewed 38 times in the last 48 hours
                                                                          Excellent! 4.6/5
                                                                          (71 reviews)
                                                                          avg/night
                                                                          • 1 BR
                                                                          • 1 BA
                                                                          • Sleeps 4
                                                                          Apartment #179390vb
                                                                          71
                                                                          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 25 times in the last 48 hours
                                                                              Wonderful! 4.9/5
                                                                              (17 reviews)
                                                                              avg/night
                                                                              • 2 BR
                                                                              • 1 BA
                                                                              • Sleeps 7
                                                                              Apartment #792973vb
                                                                              17
                                                                              Viewed 18 times in the last 48 hours
                                                                                avg/night
                                                                                • 1 BR
                                                                                • 1 BA
                                                                                • Sleeps 2
                                                                                Apartment #4314311
                                                                                Viewed 12 times in the last 48 hours
                                                                                  Exceptional! 5.0/5
                                                                                  (114 reviews)
                                                                                  avg/night
                                                                                  • 2 BR
                                                                                  • 2 BA
                                                                                  • Sleeps 6
                                                                                  Condo #72685vb
                                                                                  114
                                                                                  Viewed 18 times in the last 48 hours
                                                                                    Excellent! 4.6/5
                                                                                    (83 reviews)
                                                                                    avg/night
                                                                                    • 2 BR
                                                                                    • 2 BA
                                                                                    • Sleeps 8
                                                                                    Apartment #179389vb
                                                                                    83
                                                                                    Viewed 60 times in the last 48 hours
                                                                                      Excellent! 4.4/5
                                                                                      (5 reviews)
                                                                                      avg/night
                                                                                      • 3 BR
                                                                                      • 2 BA
                                                                                      • Sleeps 10
                                                                                      House #3685036
                                                                                      5
                                                                                      Viewed 37 times in the last 48 hours
                                                                                        Excellent! 4.7/5
                                                                                        (21 reviews)
                                                                                        avg/night
                                                                                        • 2 BR
                                                                                        • 1 BA
                                                                                        • Sleeps 4
                                                                                        Apartment #588228vb
                                                                                        21
                                                                                        Viewed 17 times in the last 48 hours
                                                                                          Wonderful! 4.9/5
                                                                                          (56 reviews)
                                                                                          avg/night
                                                                                          • 4 BR
                                                                                          • 2 BA
                                                                                          • Sleeps 10
                                                                                          House #595328vb
                                                                                          56
                                                                                          Viewed 39 times in the last 48 hours
                                                                                            Exceptional! 5.0/5
                                                                                            (11 reviews)
                                                                                            avg/night
                                                                                            • 2 BR
                                                                                            • 1 BA
                                                                                            • Sleeps 4
                                                                                            Apartment #695418vb
                                                                                            11
                                                                                            Viewed 32 times in the last 48 hours
                                                                                              • 1 BR
                                                                                              • 1 BA
                                                                                              • Sleeps 4
                                                                                              Apartment #4155484
                                                                                              6
                                                                                                avg/night
                                                                                                • 3 BR
                                                                                                • 2 BA
                                                                                                • Separate Toilet
                                                                                                • Sleeps 6
                                                                                                Condo #4276593
                                                                                                1
                                                                                                Viewed 35 times in the last 48 hours
                                                                                                  avg/night
                                                                                                  • 5 BR
                                                                                                  • 2 BA
                                                                                                  • Sleeps 14
                                                                                                  Apartment #957831vb
                                                                                                  Viewed 23 times in the last 48 hours
                                                                                                    avg/night
                                                                                                    • 1 BR
                                                                                                    • 1 BA
                                                                                                    • Sleeps 4
                                                                                                    Apartment #374031vb
                                                                                                    2
                                                                                                    Viewed 5 times in the last 48 hours
                                                                                                      Excellent! 4.3/5
                                                                                                      (7 reviews)
                                                                                                      avg/night
                                                                                                      • 2 BR
                                                                                                      • 1 BA
                                                                                                      • Sleeps 4
                                                                                                      Apartment #748268vb
                                                                                                      7
                                                                                                      Viewed 11 times in the last 48 hours
                                                                                                      • 1 - 50 of 300+