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

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.

  View Map Map
Additional service fee may apply.
    Excellent! 4.6/5
    (86 reviews)
    avg/night
    • 2 BR
    • 2 BA
    • Sleeps 8
    Apartment #179389vb
    86
    Viewed 86 times in the last 48 hours
      Excellent! 4.5/5
      (57 reviews)
      avg/night
      • 1 BR
      • 1 BA
      • Sleeps 4
      Apartment #690239vb
      57
      Viewed 77 times in the last 48 hours
        Wonderful! 4.9/5
        (35 reviews)
        avg/night
        • 1 BR
        • 1 BA
        • Sleeps 4
        Apartment #3790035
        35
        Viewed 62 times in the last 48 hours
          Excellent! 4.7/5
          (44 reviews)
          avg/night
          • 2 BR
          • 1 BA
          • Sleeps 4
          Apartment #445608vb
          44
          Viewed 54 times in the last 48 hours
            Excellent! 4.7/5
            (94 reviews)
            avg/night
            • 2 BR
            • 2 BA
            • Sleeps 4
            Condo #222038
            94
            Viewed 93 times in the last 48 hours
              Wonderful! 4.8/5
              (46 reviews)
              avg/night
              • 3 BR
              • 2 BA
              • Sleeps 8
              Condo #290256vb
              46
              Viewed 186 times in the last 48 hours
                Wonderful! 4.9/5
                (90 reviews)
                avg/night
                • 3 BR
                • 2 BA
                • Separate Toilet
                • Sleeps 8
                Apartment #578762vb
                90
                Viewed 99 times in the last 48 hours
                  Wonderful! 4.8/5
                  (60 reviews)
                  avg/night
                  • 4 BR
                  • 4 BA
                  • Sleeps 12
                  Condo #679790vb
                  60
                  Viewed 134 times in the last 48 hours
                    Excellent! 4.6/5
                    (17 reviews)
                    avg/night
                    • 1 BR
                    • 1 BA
                    • Sleeps 3
                    Apartment #4146480
                    17
                    Viewed 52 times in the last 48 hours
                      Wonderful! 4.9/5
                      (51 reviews)
                      avg/night
                      • 3 BR
                      • 2 BA
                      • Sleeps 8
                      Condo #296798
                      51
                      Viewed 42 times in the last 48 hours
                        Wonderful! 4.9/5
                        (19 reviews)
                        avg/night
                        • 1 BR
                        • 2 BA
                        • Sleeps 2
                        Apartment #864022vb
                        19
                        Viewed 106 times in the last 48 hours
                          Wonderful! 4.9/5
                          (14 reviews)
                          avg/night
                          • Studio
                          • 1 BA
                          • Sleeps 2
                          Apartment #742485vb
                          14
                          Viewed 77 times in the last 48 hours
                            Wonderful! 4.8/5
                            (42 reviews)
                            avg/night
                            • 4 BR
                            • 2 BA
                            • Sleeps 10
                            Apartment #3768288
                            42
                            Viewed 89 times in the last 48 hours
                              Excellent! 4.7/5
                              (16 reviews)
                              avg/night
                              • Studio
                              • 1 BA
                              • Sleeps 2
                              Multiple rentals Apartment #4261388
                              16
                              Viewed 97 times in the last 48 hours
                                Very Good! 4.2/5
                                (17 reviews)
                                avg/night
                                • 1 BR
                                • 1 BA
                                • Sleeps 3
                                Apartment #836462vb
                                17
                                Viewed 39 times in the last 48 hours
                                  Wonderful! 4.9/5
                                  (21 reviews)
                                  avg/night
                                  • 2 BR
                                  • 2 BA
                                  • Sleeps 6
                                  Condo #735859vb
                                  21
                                  Viewed 56 times in the last 48 hours
                                    Excellent! 4.7/5
                                    (67 reviews)
                                    avg/night
                                    • 1 BR
                                    • 1 BA
                                    • Sleeps 4
                                    Condo #177026vb
                                    67
                                    Viewed 25 times in the last 48 hours
                                      Wonderful! 4.9/5
                                      (40 reviews)
                                      avg/night
                                      • 3 BR
                                      • 2 BA
                                      • Sleeps 8
                                      Condo #939473
                                      40
                                      Viewed 40 times in the last 48 hours
                                        Wonderful! 4.8/5
                                        (23 reviews)
                                        avg/night
                                        • 2 BR
                                        • 2 BA
                                        • Sleeps 6
                                        Apartment #3795191
                                        23
                                        Viewed 77 times in the last 48 hours
                                          Wonderful! 4.8/5
                                          (44 reviews)
                                          avg/night
                                          • 2 BR
                                          • 2 BA
                                          • Sleeps 6
                                          Condo #265424vb
                                          44
                                          Viewed 82 times in the last 48 hours
                                            Exceptional! 5/5
                                            (22 reviews)
                                            avg/night
                                            • 5 BR
                                            • 1 BA
                                            • Separate Toilet
                                            • Sleeps 10
                                            Condo #776608vb
                                            22
                                            Viewed 153 times in the last 48 hours
                                              Wonderful! 4.9/5
                                              (54 reviews)
                                              avg/night
                                              • 2 BR
                                              • 2 BA
                                              • Sleeps 6
                                              Condo #3720918
                                              54
                                              Viewed 55 times in the last 48 hours
                                                Excellent! 4.7/5
                                                (51 reviews)
                                                avg/night
                                                • 1 BR
                                                • 1 BA
                                                • Sleeps 4
                                                Apartment #415005vb
                                                51
                                                Viewed 28 times in the last 48 hours
                                                  Wonderful! 4.9/5
                                                  (18 reviews)
                                                  avg/night
                                                  • 1 BR
                                                  • 1 BA
                                                  • Sleeps 5
                                                  Apartment #784869vb
                                                  18
                                                  Viewed 69 times in the last 48 hours
                                                    Exceptional! 5/5
                                                    (6 reviews)
                                                    avg/night
                                                    • 2 BR
                                                    • 2 BA
                                                    • Sleeps 6
                                                    Apartment #4172462
                                                    6
                                                    Viewed 95 times in the last 48 hours
                                                      Wonderful! 4.9/5
                                                      (75 reviews)
                                                      avg/night
                                                      • 2 BR
                                                      • 2 BA
                                                      • Sleeps 6
                                                      Apartment #358020
                                                      75
                                                      Viewed 63 times in the last 48 hours
                                                        Exceptional! 5/5
                                                        (59 reviews)
                                                        avg/night
                                                        • 4 BR
                                                        • 2 BA
                                                        • Sleeps 10
                                                        Apartment #627209vb
                                                        59
                                                        Viewed 55 times in the last 48 hours
                                                          Excellent! 4.5/5
                                                          (8 reviews)
                                                          avg/night
                                                          • 1 BR
                                                          • 1 BA
                                                          • Sleeps 3
                                                          Apartment #836457vb
                                                          8
                                                          Viewed 35 times in the last 48 hours
                                                            Wonderful! 4.9/5
                                                            (16 reviews)
                                                            avg/night
                                                            • 1 BR
                                                            • 1 BA
                                                            • Sleeps 4
                                                            Apartment #870614vb
                                                            16
                                                            Viewed 127 times in the last 48 hours
                                                              Excellent! 4.5/5
                                                              (76 reviews)
                                                              avg/night
                                                              • 2 BR
                                                              • 2 BA
                                                              • Sleeps 10
                                                              Condo #400905vb
                                                              76
                                                              Viewed 65 times in the last 48 hours
                                                                Excellent! 4.7/5
                                                                (39 reviews)
                                                                avg/night
                                                                • 3 BR
                                                                • 1 BA
                                                                • Sleeps 5
                                                                Apartment #600158vb
                                                                39
                                                                Viewed 46 times in the last 48 hours
                                                                  Excellent! 4.5/5
                                                                  (24 reviews)
                                                                  avg/night
                                                                  • 3 BR
                                                                  • 2 BA
                                                                  • Sleeps 8
                                                                  Condo #622632vb
                                                                  24
                                                                  Viewed 135 times in the last 48 hours
                                                                    Exceptional! 5/5
                                                                    (14 reviews)
                                                                    avg/night
                                                                    • 3 BR
                                                                    • 2 BA
                                                                    • Sleeps 6
                                                                    Apartment #723132vb
                                                                    14
                                                                    Viewed 48 times in the last 48 hours
                                                                      Excellent! 4.6/5
                                                                      (36 reviews)
                                                                      avg/night
                                                                      • 1 BR
                                                                      • 1 BA
                                                                      • Sleeps 4
                                                                      Apartment #3751630
                                                                      36
                                                                      Viewed 57 times in the last 48 hours
                                                                        Exceptional! 5/5
                                                                        (60 reviews)
                                                                        avg/night
                                                                        • 4 BR
                                                                        • 2 BA
                                                                        • Sleeps 11
                                                                        House #595328vb
                                                                        60
                                                                        Viewed 114 times in the last 48 hours
                                                                          Wonderful! 4.9/5
                                                                          (37 reviews)
                                                                          avg/night
                                                                          • 2 BR
                                                                          • 2 BA
                                                                          • Sleeps 6
                                                                          Apartment #408313vb
                                                                          37
                                                                          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 73 times in the last 48 hours
                                                                              Exceptional! 5/5
                                                                              (26 reviews)
                                                                              avg/night
                                                                              • 3 BR
                                                                              • 2 BA
                                                                              • Sleeps 6
                                                                              Townhome #3917584
                                                                              26
                                                                              Viewed 42 times in the last 48 hours
                                                                                Excellent! 4.7/5
                                                                                (22 reviews)
                                                                                avg/night
                                                                                • 2 BR
                                                                                • 1 BA
                                                                                • Sleeps 4
                                                                                Apartment #588228vb
                                                                                22
                                                                                Viewed 48 times in the last 48 hours
                                                                                  Wonderful! 4.9/5
                                                                                  (14 reviews)
                                                                                  avg/night
                                                                                  • 1 BR
                                                                                  • 1 BA
                                                                                  • Sleeps 4
                                                                                  Condo #4037980
                                                                                  14
                                                                                  Viewed 373 times in the last 48 hours
                                                                                    Excellent! 4.6/5
                                                                                    (8 reviews)
                                                                                    avg/night
                                                                                    • 2 BR
                                                                                    • 2 BA
                                                                                    • Sleeps 6
                                                                                    Apartment #4172463
                                                                                    8
                                                                                    Viewed 57 times in the last 48 hours
                                                                                      Wonderful! 4.8/5
                                                                                      (63 reviews)
                                                                                      avg/night
                                                                                      • 2 BR
                                                                                      • 1 BA
                                                                                      • Sleeps 6
                                                                                      Apartment #301852vb
                                                                                      63
                                                                                      Viewed 27 times in the last 48 hours
                                                                                        Wonderful! 4.9/5
                                                                                        (21 reviews)
                                                                                        avg/night
                                                                                        • 2 BR
                                                                                        • 2 BA
                                                                                        • Sleeps 6
                                                                                        Apartment #653828vb
                                                                                        21
                                                                                        Viewed 27 times in the last 48 hours
                                                                                          Wonderful! 4.9/5
                                                                                          (13 reviews)
                                                                                          avg/night
                                                                                          • 2 BR
                                                                                          • 1 BA
                                                                                          • Sleeps 4
                                                                                          Apartment #780506vb
                                                                                          13
                                                                                          Viewed 20 times in the last 48 hours
                                                                                            Wonderful! 4.9/5
                                                                                            (20 reviews)
                                                                                            avg/night
                                                                                            • 4 BR
                                                                                            • 2 BA
                                                                                            • Separate Toilet
                                                                                            • Sleeps 10
                                                                                            House #840552vb
                                                                                            20
                                                                                            Viewed 47 times in the last 48 hours
                                                                                              Exceptional! 5/5
                                                                                              (29 reviews)
                                                                                              avg/night
                                                                                              • 3 BR
                                                                                              • 2 BA
                                                                                              • Sleeps 6
                                                                                              Apartment #470476vb
                                                                                              29
                                                                                              Viewed 21 times in the last 48 hours
                                                                                                Wonderful! 4.9/5
                                                                                                (50 reviews)
                                                                                                avg/night
                                                                                                • 2 BR
                                                                                                • 2 BA
                                                                                                • Sleeps 6
                                                                                                Apartment #358013
                                                                                                50
                                                                                                Viewed 88 times in the last 48 hours
                                                                                                  Excellent! 4.6/5
                                                                                                  (71 reviews)
                                                                                                  avg/night
                                                                                                  • 1 BR
                                                                                                  • 1 BA
                                                                                                  • Sleeps 4
                                                                                                  Apartment #179390vb
                                                                                                  71
                                                                                                  Viewed 26 times in the last 48 hours
                                                                                                    Wonderful! 4.9/5
                                                                                                    (78 reviews)
                                                                                                    avg/night
                                                                                                    • 6 BR
                                                                                                    • 4 BA
                                                                                                    • Sleeps 18
                                                                                                    Condo #411142vb
                                                                                                    78
                                                                                                    Viewed 103 times in the last 48 hours
                                                                                                      Exceptional! 5/5
                                                                                                      (127 reviews)
                                                                                                      avg/night
                                                                                                      • 3 BR
                                                                                                      • 2 BA
                                                                                                      • Sleeps 8
                                                                                                      Apartment #422128vb
                                                                                                      127
                                                                                                      Viewed 27 times in the last 48 hours
                                                                                                      • 1 - 50 of 300+

                                                                                                      Chicago Holiday Apartments & Rentals (300+)