HomeAway uses cookies to improve your site experience. Learn more. By continuing, you consent to our use of cookies.
HomeAway uses cookies to improve your site experience. Learn more. By continuing, you consent to our use of cookies.
Verified Review icon check navigate-up navigate-left navigate-right expand mail svg-lightning svg-24hr svg-house svg-sleeps svg-bedrooms svg-bathrooms svg-stay svg-toilet calendar svg-report-flag pet-dog svg-multiunit Default Owner Icon

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+
  View Map Map
Additional service fee may apply.
    Excellent! 4.6/5
    (17 reviews)
    avg/night
    • 1 BR
    • 1 BA
    • Sleeps 3
    Apartment #4146480
    17
    Viewed 55 times in the last 48 hours
      Excellent! 4.7/5
      (95 reviews)
      avg/night
      • 2 BR
      • 2 BA
      • Sleeps 4
      Condo #222038
      95
      Viewed 119 times in the last 48 hours
        Excellent! 4.6/5
        (86 reviews)
        avg/night
        • 2 BR
        • 2 BA
        • Sleeps 8
        Apartment #179389vb
        86
        Viewed 80 times in the last 48 hours
          Excellent! 4.5/5
          (57 reviews)
          avg/night
          • 1 BR
          • 1 BA
          • Sleeps 4
          Apartment #690239vb
          57
          Viewed 81 times in the last 48 hours
            Wonderful! 4.8/5
            (46 reviews)
            avg/night
            • 3 BR
            • 2 BA
            • Sleeps 8
            Condo #290256vb
            46
            Viewed 150 times in the last 48 hours
              Wonderful! 4.9/5
              (35 reviews)
              avg/night
              • 1 BR
              • 1 BA
              • Sleeps 4
              Apartment #3790035
              35
              Viewed 55 times in the last 48 hours
                Excellent! 4.7/5
                (44 reviews)
                avg/night
                • 2 BR
                • 1 BA
                • Sleeps 4
                Apartment #445608vb
                44
                Viewed 36 times in the last 48 hours
                  Wonderful! 4.9/5
                  (91 reviews)
                  avg/night
                  • 3 BR
                  • 2 BA
                  • Separate Toilet
                  • Sleeps 8
                  Apartment #578762vb
                  91
                  Viewed 71 times in the last 48 hours
                    Wonderful! 4.8/5
                    (62 reviews)
                    avg/night
                    • 4 BR
                    • 4 BA
                    • Sleeps 12
                    Condo #679790vb
                    62
                    Viewed 94 times in the last 48 hours
                      Exceptional! 5/5
                      (21 reviews)
                      avg/night
                      • 1 BR
                      • 2 BA
                      • Sleeps 2
                      Apartment #864022vb
                      21
                      Viewed 41 times in the last 48 hours
                        Wonderful! 4.9/5
                        (51 reviews)
                        avg/night
                        • 3 BR
                        • 2 BA
                        • Sleeps 8
                        Condo #296798
                        51
                        Viewed 23 times in the last 48 hours
                          Wonderful! 4.8/5
                          (45 reviews)
                          avg/night
                          • 4 BR
                          • 2 BA
                          • Sleeps 10
                          Apartment #3768288
                          45
                          Viewed 38 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 84 times in the last 48 hours
                              Wonderful! 4.9/5
                              (18 reviews)
                              avg/night
                              • 1 BR
                              • 1 BA
                              • Sleeps 4
                              Apartment #870614vb
                              18
                              Viewed 37 times in the last 48 hours
                                Wonderful! 4.9/5
                                (23 reviews)
                                avg/night
                                • 2 BR
                                • 2 BA
                                • Sleeps 6
                                Condo #735859vb
                                23
                                Viewed 62 times in the last 48 hours
                                  Wonderful! 4.8/5
                                  (16 reviews)
                                  avg/night
                                  • Studio
                                  • 1 BA
                                  • Sleeps 2
                                  Apartment #742485vb
                                  16
                                  Viewed 27 times in the last 48 hours
                                    Exceptional! 5/5
                                    (23 reviews)
                                    avg/night
                                    • 5 BR
                                    • 1 BA
                                    • Separate Toilet
                                    • Sleeps 10
                                    Condo #776608vb
                                    23
                                    Viewed 137 times in the last 48 hours
                                      Wonderful! 4.8/5
                                      (44 reviews)
                                      avg/night
                                      • 2 BR
                                      • 2 BA
                                      • Sleeps 6
                                      Condo #265424vb
                                      44
                                      Viewed 86 times in the last 48 hours
                                        Wonderful! 4.8/5
                                        (24 reviews)
                                        avg/night
                                        • 2 BR
                                        • 2 BA
                                        • Sleeps 6
                                        Apartment #3795191
                                        24
                                        Viewed 62 times in the last 48 hours
                                          Wonderful! 4.9/5
                                          (8 reviews)
                                          avg/night
                                          • 2 BR
                                          • 2 BA
                                          • Sleeps 6
                                          Apartment #4172462
                                          8
                                          Viewed 91 times in the last 48 hours
                                            Excellent! 4.7/5
                                            (67 reviews)
                                            avg/night
                                            • 1 BR
                                            • 1 BA
                                            • Sleeps 4
                                            Condo #177026vb
                                            67
                                            Viewed 33 times in the last 48 hours
                                              Excellent! 4.7/5
                                              (39 reviews)
                                              avg/night
                                              • 3 BR
                                              • 1 BA
                                              • Sleeps 5
                                              Apartment #600158vb
                                              39
                                              Viewed 30 times in the last 48 hours
                                                Wonderful! 4.9/5
                                                (19 reviews)
                                                avg/night
                                                • 1 BR
                                                • 1 BA
                                                • Sleeps 5
                                                Apartment #784869vb
                                                19
                                                Viewed 30 times in the last 48 hours
                                                  Wonderful! 4.9/5
                                                  (42 reviews)
                                                  avg/night
                                                  • 3 BR
                                                  • 2 BA
                                                  • Sleeps 8
                                                  Condo #939473
                                                  42
                                                  Viewed 28 times in the last 48 hours
                                                    Exceptional! 5/5
                                                    (6 reviews)
                                                    avg/night
                                                    • 1 BR
                                                    • 1 BA
                                                    • Sleeps 2
                                                    Apartment #871091vb
                                                    6
                                                    Viewed 22 times in the last 48 hours
                                                      Exceptional! 5/5
                                                      (27 reviews)
                                                      avg/night
                                                      • 3 BR
                                                      • 2 BA
                                                      • Sleeps 6
                                                      Townhome #3917584
                                                      27
                                                      Viewed 45 times in the last 48 hours
                                                        Excellent! 4.5/5
                                                        (76 reviews)
                                                        avg/night
                                                        • 2 BR
                                                        • 2 BA
                                                        • Sleeps 10
                                                        Condo #400905vb
                                                        76
                                                        Viewed 49 times in the last 48 hours
                                                          Wonderful! 4.9/5
                                                          (75 reviews)
                                                          avg/night
                                                          • 2 BR
                                                          • 2 BA
                                                          • Sleeps 6
                                                          Apartment #358020
                                                          75
                                                          Viewed 59 times in the last 48 hours
                                                            Excellent! 4.5/5
                                                            (8 reviews)
                                                            avg/night
                                                            • 1 BR
                                                            • 1 BA
                                                            • Sleeps 3
                                                            Apartment #836457vb
                                                            8
                                                            Viewed 30 times in the last 48 hours
                                                              Wonderful! 4.9/5
                                                              (56 reviews)
                                                              avg/night
                                                              • 2 BR
                                                              • 2 BA
                                                              • Sleeps 6
                                                              Condo #3720918
                                                              56
                                                              Viewed 46 times in the last 48 hours
                                                                Excellent! 4.6/5
                                                                (36 reviews)
                                                                avg/night
                                                                • 1 BR
                                                                • 1 BA
                                                                • Sleeps 4
                                                                Apartment #3751630
                                                                36
                                                                Viewed 51 times in the last 48 hours
                                                                  Excellent! 4.6/5
                                                                  (42 reviews)
                                                                  avg/night
                                                                  • 2 BR
                                                                  • 1 BA
                                                                  • Sleeps 5
                                                                  Apartment #3833362
                                                                  42
                                                                  Viewed 17 times in the last 48 hours
                                                                    Excellent! 4.7/5
                                                                    (10 reviews)
                                                                    avg/night
                                                                    • 2 BR
                                                                    • 2 BA
                                                                    • Sleeps 6
                                                                    Apartment #4172463
                                                                    10
                                                                    Viewed 19 times in the last 48 hours
                                                                      Excellent! 4.5/5
                                                                      (25 reviews)
                                                                      avg/night
                                                                      • 3 BR
                                                                      • 2 BA
                                                                      • Sleeps 8
                                                                      Condo #622632vb
                                                                      25
                                                                      Viewed 75 times in the last 48 hours
                                                                        Excellent! 4.7/5
                                                                        (51 reviews)
                                                                        avg/night
                                                                        • 1 BR
                                                                        • 1 BA
                                                                        • Sleeps 4
                                                                        Apartment #415005vb
                                                                        51
                                                                        Viewed 18 times in the last 48 hours
                                                                          Wonderful! 4.9/5
                                                                          (50 reviews)
                                                                          avg/night
                                                                          • 2 BR
                                                                          • 2 BA
                                                                          • Sleeps 6
                                                                          Apartment #358013
                                                                          50
                                                                          Viewed 52 times in the last 48 hours
                                                                            Exceptional! 5/5
                                                                            (12 reviews)
                                                                            avg/night
                                                                            • 2 BR
                                                                            • 1 BA
                                                                            • Sleeps 4
                                                                            Apartment #695418vb
                                                                            12
                                                                            Viewed 49 times in the last 48 hours
                                                                              Wonderful! 4.8/5
                                                                              (64 reviews)
                                                                              avg/night
                                                                              • 2 BR
                                                                              • 1 BA
                                                                              • Sleeps 6
                                                                              Apartment #301852vb
                                                                              64
                                                                              Viewed 45 times in the last 48 hours
                                                                                Wonderful! 4.9/5
                                                                                (13 reviews)
                                                                                avg/night
                                                                                • 2 BR
                                                                                • 1 BA
                                                                                • Sleeps 4
                                                                                Apartment #780506vb
                                                                                13
                                                                                Viewed 36 times in the last 48 hours
                                                                                  Excellent! 4.7/5
                                                                                  (42 reviews)
                                                                                  avg/night
                                                                                  • 2 BR
                                                                                  • 1 BA
                                                                                  • Separate Toilet
                                                                                  • Sleeps 8
                                                                                  Apartment #3645846
                                                                                  42
                                                                                  Viewed 60 times in the last 48 hours
                                                                                    Wonderful! 4.9/5
                                                                                    (22 reviews)
                                                                                    avg/night
                                                                                    • 4 BR
                                                                                    • 2 BA
                                                                                    • Separate Toilet
                                                                                    • Sleeps 10
                                                                                    House #840552vb
                                                                                    22
                                                                                    Viewed 51 times in the last 48 hours
                                                                                      Exceptional! 5/5
                                                                                      (61 reviews)
                                                                                      avg/night
                                                                                      • 4 BR
                                                                                      • 2 BA
                                                                                      • Sleeps 10
                                                                                      Apartment #627209vb
                                                                                      61
                                                                                      Viewed 34 times in the last 48 hours
                                                                                        Excellent! 4.7/5
                                                                                        (22 reviews)
                                                                                        avg/night
                                                                                        • 2 BR
                                                                                        • 1 BA
                                                                                        • Sleeps 4
                                                                                        Apartment #588228vb
                                                                                        22
                                                                                        Viewed 19 times in the last 48 hours
                                                                                          Wonderful! 4.9/5
                                                                                          (38 reviews)
                                                                                          avg/night
                                                                                          • 2 BR
                                                                                          • 2 BA
                                                                                          • Sleeps 6
                                                                                          Apartment #408313vb
                                                                                          38
                                                                                          Viewed 44 times in the last 48 hours
                                                                                            Excellent! 4.5/5
                                                                                            (11 reviews)
                                                                                            avg/night
                                                                                            • 1 BR
                                                                                            • 1 BA
                                                                                            • Sleeps 2
                                                                                            Apartment #871119vb
                                                                                            11
                                                                                            Viewed 23 times in the last 48 hours
                                                                                              Wonderful! 4.8/5
                                                                                              (18 reviews)
                                                                                              avg/night
                                                                                              • 1 BR
                                                                                              • 1 BA
                                                                                              • Sleeps 2
                                                                                              Apartment #870495vb
                                                                                              18
                                                                                              Viewed 9 times in the last 48 hours
                                                                                                Excellent! 4.6/5
                                                                                                (71 reviews)
                                                                                                avg/night
                                                                                                • 1 BR
                                                                                                • 1 BA
                                                                                                • Sleeps 4
                                                                                                Apartment #179390vb
                                                                                                71
                                                                                                Viewed 35 times in the last 48 hours
                                                                                                  Wonderful! 4.9/5
                                                                                                  (70 reviews)
                                                                                                  avg/night
                                                                                                  • 2 BR
                                                                                                  • 2 BA
                                                                                                  • Sleeps 6
                                                                                                  Apartment #358005
                                                                                                  70
                                                                                                  Viewed 29 times in the last 48 hours
                                                                                                    Excellent! 4.7/5
                                                                                                    (15 reviews)
                                                                                                    avg/night
                                                                                                    • 1 BR
                                                                                                    • 1 BA
                                                                                                    • Sleeps 4
                                                                                                    Condo #4037980
                                                                                                    15
                                                                                                    Viewed 441 times in the last 48 hours
                                                                                                      Wonderful! 4.9/5
                                                                                                      (21 reviews)
                                                                                                      avg/night
                                                                                                      • 2 BR
                                                                                                      • 2 BA
                                                                                                      • Sleeps 6
                                                                                                      Apartment #653828vb
                                                                                                      21
                                                                                                      Viewed 67 times in the last 48 hours
                                                                                                      • 1 - 50 of 300+

                                                                                                      Chicago Holiday Apartments & Rentals (300+)