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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.

    Excellent! 4.5/5
    (67 reviews)
    avg/night
    • 1 BR
    • 1 BA
    • Sleeps 4
    Apartment #690239vb
    67
    Viewed 128 times in the last 48 hours
      Excellent! 4.7/5
      (47 reviews)
      avg/night
      • 2 BR
      • 1 BA
      • Sleeps 4
      Apartment #445608vb
      47
      Viewed 38 times in the last 48 hours
        Wonderful! 4.8/5
        (101 reviews)
        avg/night
        • 3 BR
        • 2 BA
        • Separate Toilet
        • Sleeps 8
        Apartment #578762vb
        101
        Viewed 48 times in the last 48 hours
          Wonderful! 4.9/5
          (73 reviews)
          avg/night
          • 4 BR
          • 4 BA
          • Sleeps 12
          Condo #679790vb
          73
          Viewed 73 times in the last 48 hours
            Wonderful! 4.9/5
            (32 reviews)
            avg/night
            • 3 BR
            • 2 BA
            • Sleeps 6
            Townhome #3917584
            32
            Viewed 24 times in the last 48 hours
              Excellent! 4.7/5
              (18 reviews)
              avg/night
              • Studio
              • 1 BA
              • Sleeps 2
              Multiple rentals Apartment #4261388
              18
              Viewed 64 times in the last 48 hours
                Excellent! 4.7/5
                (106 reviews)
                avg/night
                • 2 BR
                • 2 BA
                • Sleeps 4
                Condo #222038
                106
                Viewed 57 times in the last 48 hours
                  Wonderful! 4.9/5
                  (36 reviews)
                  avg/night
                  • 1 BR
                  • 1 BA
                  • Sleeps 4
                  Apartment #3790035
                  36
                  Viewed 59 times in the last 48 hours
                    Wonderful! 4.8/5
                    (52 reviews)
                    avg/night
                    • 3 BR
                    • 2 BA
                    • Sleeps 8
                    Condo #290256vb
                    52
                    Viewed 71 times in the last 48 hours
                      Wonderful! 4.8/5
                      (53 reviews)
                      avg/night
                      • 4 BR
                      • 2 BA
                      • Sleeps 10
                      Apartment #3768288
                      53
                      Viewed 32 times in the last 48 hours
                        Wonderful! 4.8/5
                        (48 reviews)
                        avg/night
                        • 2 BR
                        • 2 BA
                        • Sleeps 6
                        Condo #265424vb
                        48
                        Viewed 96 times in the last 48 hours
                          Wonderful! 4.9/5
                          (31 reviews)
                          avg/night
                          • 2 BR
                          • 2 BA
                          • Sleeps 6
                          Condo #735859vb
                          31
                          Viewed 23 times in the last 48 hours
                            Wonderful! 4.8/5
                            (27 reviews)
                            avg/night
                            • 2 BR
                            • 2 BA
                            • Sleeps 6
                            Apartment #3795191
                            27
                            Viewed 46 times in the last 48 hours
                              Excellent! 4.4/5
                              (13 reviews)
                              avg/night
                              • 1 BR
                              • 1 BA
                              • Sleeps 3
                              Apartment #836457vb
                              13
                              Viewed 47 times in the last 48 hours
                                Exceptional! 5/5
                                (30 reviews)
                                avg/night
                                • 1 BR
                                • 2 BA
                                • Sleeps 2
                                Apartment #864022vb
                                30
                                Viewed 22 times in the last 48 hours
                                  Excellent! 4.7/5
                                  (41 reviews)
                                  avg/night
                                  • 1 BR
                                  • 1 BA
                                  • Sleeps 4
                                  Apartment #3751630
                                  41
                                  Viewed 49 times in the last 48 hours
                                    Excellent! 4.7/5
                                    (22 reviews)
                                    avg/night
                                    • 1 BR
                                    • 1 BA
                                    • Sleeps 3
                                    Apartment #4146480
                                    22
                                    Viewed 23 times in the last 48 hours
                                      Wonderful! 4.9/5
                                      (9 reviews)
                                      avg/night
                                      • 2 BR
                                      • 2 BA
                                      • Sleeps 6
                                      Apartment #4172462
                                      9
                                      Viewed 26 times in the last 48 hours
                                        Excellent! 4.6/5
                                        (44 reviews)
                                        avg/night
                                        • 2 BR
                                        • 1 BA
                                        • Sleeps 5
                                        Apartment #3833362
                                        44
                                        Viewed 16 times in the last 48 hours
                                          Excellent! 4.5/5
                                          (31 reviews)
                                          avg/night
                                          • 3 BR
                                          • 2 BA
                                          • Sleeps 8
                                          Condo #622632vb
                                          31
                                          Viewed 81 times in the last 48 hours
                                            Exceptional! 5/5
                                            (63 reviews)
                                            avg/night
                                            • 4 BR
                                            • 2 BA
                                            • Sleeps 10
                                            Apartment #627209vb
                                            63
                                            Viewed 30 times in the last 48 hours
                                              Excellent! 4.7/5
                                              (44 reviews)
                                              avg/night
                                              • 2 BR
                                              • 1 BA
                                              • Separate Toilet
                                              • Sleeps 8
                                              Apartment #3645846
                                              44
                                              Viewed 28 times in the last 48 hours
                                                Wonderful! 4.9/5
                                                (72 reviews)
                                                avg/night
                                                • 2 BR
                                                • 2 BA
                                                • Sleeps 6
                                                Apartment #358005
                                                72
                                                Viewed 21 times in the last 48 hours
                                                  Wonderful! 4.8/5
                                                  (71 reviews)
                                                  avg/night
                                                  • 2 BR
                                                  • 1 BA
                                                  • Sleeps 6
                                                  Apartment #301852vb
                                                  71
                                                  Viewed 19 times in the last 48 hours
                                                    Excellent! 4.6/5
                                                    (12 reviews)
                                                    avg/night
                                                    • 2 BR
                                                    • 2 BA
                                                    • Sleeps 6
                                                    Apartment #4172463
                                                    12
                                                    Viewed 55 times in the last 48 hours
                                                      Wonderful! 4.8/5
                                                      (55 reviews)
                                                      avg/night
                                                      • 3 BR
                                                      • 2 BA
                                                      • Sleeps 8
                                                      Condo #296798
                                                      55
                                                      Viewed 16 times in the last 48 hours
                                                        Wonderful! 4.9/5
                                                        (17 reviews)
                                                        avg/night
                                                        • 2 BR
                                                        • 1 BA
                                                        • Sleeps 4
                                                        Apartment #695418vb
                                                        17
                                                        Viewed 24 times in the last 48 hours
                                                          Wonderful! 4.9/5
                                                          (22 reviews)
                                                          avg/night
                                                          • 1 BR
                                                          • 1 BA
                                                          • Sleeps 4
                                                          Apartment #894129vb
                                                          22
                                                          Viewed 122 times in the last 48 hours
                                                            Excellent! 4.5/5
                                                            (82 reviews)
                                                            avg/night
                                                            • 2 BR
                                                            • 2 BA
                                                            • Sleeps 10
                                                            Condo #400905vb
                                                            82
                                                            Viewed 27 times in the last 48 hours
                                                              Wonderful! 4.9/5
                                                              (61 reviews)
                                                              avg/night
                                                              • 2 BR
                                                              • 2 BA
                                                              • Sleeps 6
                                                              Condo #3720918
                                                              61
                                                              Viewed 31 times in the last 48 hours
                                                                Excellent! 4.7/5
                                                                (42 reviews)
                                                                avg/night
                                                                • 3 BR
                                                                • 1 BA
                                                                • Sleeps 5
                                                                Apartment #600158vb
                                                                42
                                                                Viewed 16 times in the last 48 hours
                                                                  Wonderful! 4.8/5
                                                                  (24 reviews)
                                                                  avg/night
                                                                  • 1 BR
                                                                  • 1 BA
                                                                  • Sleeps 2
                                                                  Apartment #870495vb
                                                                  24
                                                                  Viewed 37 times in the last 48 hours
                                                                    Exceptional! 5/5
                                                                    (25 reviews)
                                                                    avg/night
                                                                    • 1 BR
                                                                    • 1 BA
                                                                    • Sleeps 4
                                                                    Apartment #870614vb
                                                                    25
                                                                    Viewed 29 times in the last 48 hours
                                                                      Excellent! 4.4/5
                                                                      (13 reviews)
                                                                      avg/night
                                                                      • 1 BR
                                                                      • 1 BA
                                                                      • Sleeps 2
                                                                      House #4280611
                                                                      13
                                                                      Viewed 30 times in the last 48 hours
                                                                        Excellent! 4.5/5
                                                                        (24 reviews)
                                                                        avg/night
                                                                        • Studio
                                                                        • 1 BA
                                                                        • Sleeps 2
                                                                        Apartment #742485vb
                                                                        24
                                                                        Viewed 26 times in the last 48 hours
                                                                          Wonderful! 4.9/5
                                                                          (52 reviews)
                                                                          avg/night
                                                                          • 2 BR
                                                                          • 2 BA
                                                                          • Sleeps 6
                                                                          Apartment #358013
                                                                          52
                                                                          Viewed 53 times in the last 48 hours
                                                                            Exceptional! 5/5
                                                                            (14 reviews)
                                                                            avg/night
                                                                            • 1 BR
                                                                            • 1 BA
                                                                            • Sleeps 2
                                                                            Apartment #871091vb
                                                                            14
                                                                            Viewed 13 times in the last 48 hours
                                                                              Wonderful! 4.9/5
                                                                              (76 reviews)
                                                                              avg/night
                                                                              • 2 BR
                                                                              • 2 BA
                                                                              • Sleeps 6
                                                                              Apartment #358020
                                                                              76
                                                                              Viewed 36 times in the last 48 hours
                                                                                Wonderful! 4.9/5
                                                                                (14 reviews)
                                                                                avg/night
                                                                                • 2 BR
                                                                                • 1 BA
                                                                                • Sleeps 4
                                                                                Apartment #780506vb
                                                                                14
                                                                                Viewed 13 times in the last 48 hours
                                                                                  Wonderful! 4.8/5
                                                                                  (45 reviews)
                                                                                  avg/night
                                                                                  • 2 BR
                                                                                  • 1 BA
                                                                                  • Separate Toilet
                                                                                  • Sleeps 6
                                                                                  Apartment #271945
                                                                                  45
                                                                                  Viewed 14 times in the last 48 hours
                                                                                    Wonderful! 4.9/5
                                                                                    (79 reviews)
                                                                                    avg/night
                                                                                    • 3 BR
                                                                                    • 1 BA
                                                                                    • Separate Toilet
                                                                                    • Sleeps 6
                                                                                    Apartment #225815
                                                                                    79
                                                                                    Viewed 11 times in the last 48 hours
                                                                                      • 3 BR
                                                                                      • 2 BA
                                                                                      • Sleeps 6
                                                                                      Apartment #890369vb
                                                                                      2
                                                                                      Viewed 23 times in the last 48 hours
                                                                                        Very Good! 4.1/5
                                                                                        (7 reviews)
                                                                                        avg/night
                                                                                        • 2 BR
                                                                                        • 2 BA
                                                                                        • Sleeps 4
                                                                                        Condo #159001vb
                                                                                        7
                                                                                        Viewed 168 times in the last 48 hours
                                                                                          avg/night
                                                                                          • 3 BR
                                                                                          • 2 BA
                                                                                          • Separate Toilet
                                                                                          • Sleeps 30
                                                                                          Condo #282940vb
                                                                                          2
                                                                                          Viewed 533 times in the last 48 hours
                                                                                            • 3 BR
                                                                                            • 2 BA
                                                                                            • Separate Toilet
                                                                                            • Sleeps 30
                                                                                            Condo #267014
                                                                                            2
                                                                                            Viewed 171 times in the last 48 hours
                                                                                              Very Good! 4/5
                                                                                              (7 reviews)
                                                                                              avg/night
                                                                                              • 3 BR
                                                                                              • 2 BA
                                                                                              • Separate Toilet
                                                                                              • Sleeps 6
                                                                                              Condo #267015
                                                                                              7
                                                                                              Viewed 441 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 168 times in the last 48 hours
                                                                                                  avg/night
                                                                                                  • 3 BR
                                                                                                  • 2 BA
                                                                                                  • Separate Toilet
                                                                                                  • Sleeps 6
                                                                                                  Condo #887767vb
                                                                                                  4
                                                                                                  Viewed 110 times in the last 48 hours
                                                                                                    Very Good! 4.2/5
                                                                                                    (20 reviews)
                                                                                                    avg/night
                                                                                                    • 1 BR
                                                                                                    • 1 BA
                                                                                                    • Sleeps 5
                                                                                                    Apartment #870916vb
                                                                                                    20
                                                                                                    Viewed 10 times in the last 48 hours
                                                                                                      Exceptional! 5/5
                                                                                                      (7 reviews)
                                                                                                      avg/night
                                                                                                      • 2 BR
                                                                                                      • 2 BA
                                                                                                      • Sleeps 6
                                                                                                      Condo #3645759
                                                                                                      7
                                                                                                      Viewed 11 times in the last 48 hours
                                                                                                      • 1 - 50 of 300+

                                                                                                      Chicago Holiday Apartments & Rentals (300+)

                                                                                                       

                                                                                                      Recent Reviews

                                                                                                      Fantastic location !!

                                                                                                      5 of 5
                                                                                                      We had the best stay here. It's so convenient for pubs, restaurants and shops. The station is also just a brief walk to downtown Chicago. Roe made sure we were taken care of and was helpful and informative from start to finish. Will be back for sure.
                                                                                                      • Review Submitted: Jun 03, 2017
                                                                                                      • Date of Stay: May 2017