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.

  • Showing 1-50 of 300+
Additional service fee may apply.
  View Map Map
    Excellent! 4.6/5
    (86 reviews)
    avg/night
    • 2 BR
    • 2 BA
    • Sleeps 8
    Apartment #179389vb
    86
    Viewed 66 times in the last 48 hours
      Excellent! 4.7/5
      (44 reviews)
      avg/night
      • 2 BR
      • 1 BA
      • Sleeps 4
      Apartment #445608vb
      44
      Viewed 61 times in the last 48 hours
        Excellent! 4.5/5
        (57 reviews)
        avg/night
        • 1 BR
        • 1 BA
        • Sleeps 4
        Apartment #690239vb
        57
        Viewed 39 times in the last 48 hours
          Excellent! 4.7/5
          (93 reviews)
          avg/night
          • 2 BR
          • 2 BA
          • Sleeps 4
          Condo #222038
          93
          Viewed 72 times in the last 48 hours
            Wonderful! 4.9/5
            (89 reviews)
            avg/night
            • 3 BR
            • 2 BA
            • Separate Toilet
            • Sleeps 8
            Apartment #578762vb
            89
            Viewed 93 times in the last 48 hours
              Wonderful! 4.8/5
              (46 reviews)
              avg/night
              • 3 BR
              • 2 BA
              • Sleeps 8
              Condo #290256vb
              46
              Viewed 164 times in the last 48 hours
                Wonderful! 4.8/5
                (59 reviews)
                avg/night
                • 4 BR
                • 4 BA
                • Sleeps 12
                Condo #679790vb
                59
                Viewed 93 times in the last 48 hours
                  Excellent! 4.6/5
                  (17 reviews)
                  avg/night
                  • 1 BR
                  • 1 BA
                  • Sleeps 3
                  Apartment #4146480
                  17
                  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 47 times in the last 48 hours
                      Wonderful! 4.9/5
                      (18 reviews)
                      avg/night
                      • 1 BR
                      • 2 BA
                      • Sleeps 2
                      Apartment #864022vb
                      18
                      Viewed 64 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 57 times in the last 48 hours
                          Excellent! 4.4/5
                          (14 reviews)
                          avg/night
                          • 2 BR
                          • 2 BA
                          • Sleeps 5
                          Apartment #4047746
                          14
                          Viewed 137 times in the last 48 hours
                            Wonderful! 4.9/5
                            (14 reviews)
                            avg/night
                            • Studio
                            • 1 BA
                            • Sleeps 2
                            Apartment #742485vb
                            14
                            Viewed 99 times in the last 48 hours
                              Wonderful! 4.9/5
                              (40 reviews)
                              avg/night
                              • 3 BR
                              • 2 BA
                              • Sleeps 8
                              Condo #939473
                              40
                              Viewed 27 times in the last 48 hours
                                Wonderful! 4.8/5
                                (23 reviews)
                                avg/night
                                • 2 BR
                                • 2 BA
                                • Sleeps 6
                                Apartment #3795191
                                23
                                Viewed 85 times in the last 48 hours
                                  Wonderful! 4.9/5
                                  (35 reviews)
                                  avg/night
                                  • 1 BR
                                  • 1 BA
                                  • Sleeps 4
                                  Apartment #3790035
                                  35
                                  Viewed 42 times in the last 48 hours
                                    Wonderful! 4.9/5
                                    (21 reviews)
                                    avg/night
                                    • 2 BR
                                    • 2 BA
                                    • Sleeps 6
                                    Condo #735859vb
                                    21
                                    Viewed 45 times in the last 48 hours
                                      Wonderful! 4.8/5
                                      (42 reviews)
                                      avg/night
                                      • 4 BR
                                      • 2 BA
                                      • Sleeps 10
                                      Apartment #3768288
                                      42
                                      Viewed 41 times in the last 48 hours
                                        Wonderful! 4.9/5
                                        (74 reviews)
                                        avg/night
                                        • 2 BR
                                        • 2 BA
                                        • Sleeps 6
                                        Apartment #358020
                                        74
                                        Viewed 51 times in the last 48 hours
                                          Wonderful! 4.8/5
                                          (44 reviews)
                                          avg/night
                                          • 2 BR
                                          • 2 BA
                                          • Sleeps 6
                                          Condo #265424vb
                                          44
                                          Viewed 71 times in the last 48 hours
                                            Excellent! 4.6/5
                                            (36 reviews)
                                            avg/night
                                            • 1 BR
                                            • 1 BA
                                            • Sleeps 4
                                            Apartment #3751630
                                            36
                                            Viewed 35 times in the last 48 hours
                                              Wonderful! 4.9/5
                                              (54 reviews)
                                              avg/night
                                              • 2 BR
                                              • 2 BA
                                              • Sleeps 6
                                              Condo #3720918
                                              54
                                              Viewed 52 times in the last 48 hours
                                                Excellent! 4.6/5
                                                (41 reviews)
                                                avg/night
                                                • 2 BR
                                                • 1 BA
                                                • Sleeps 5
                                                Apartment #3833362
                                                41
                                                Viewed 32 times in the last 48 hours
                                                  Wonderful! 4.9/5
                                                  (18 reviews)
                                                  avg/night
                                                  • 1 BR
                                                  • 1 BA
                                                  • Sleeps 5
                                                  Apartment #784869vb
                                                  18
                                                  Viewed 29 times in the last 48 hours
                                                    Excellent! 4.7/5
                                                    (51 reviews)
                                                    avg/night
                                                    • 1 BR
                                                    • 1 BA
                                                    • Sleeps 4
                                                    Apartment #415005vb
                                                    51
                                                    Viewed 21 times in the last 48 hours
                                                      Excellent! 4.7/5
                                                      (67 reviews)
                                                      avg/night
                                                      • 1 BR
                                                      • 1 BA
                                                      • Sleeps 4
                                                      Condo #177026vb
                                                      67
                                                      Viewed 28 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
                                                          Wonderful! 4.9/5
                                                          (37 reviews)
                                                          avg/night
                                                          • 2 BR
                                                          • 2 BA
                                                          • Sleeps 6
                                                          Apartment #408313vb
                                                          37
                                                          Viewed 42 times in the last 48 hours
                                                            Exceptional! 5.0/5
                                                            (22 reviews)
                                                            avg/night
                                                            • 5 BR
                                                            • 1 BA
                                                            • Separate Toilet
                                                            • Sleeps 10
                                                            Condo #776608vb
                                                            22
                                                            Viewed 134 times in the last 48 hours
                                                              Wonderful! 4.9/5
                                                              (13 reviews)
                                                              avg/night
                                                              • 2 BR
                                                              • 1 BA
                                                              • Sleeps 4
                                                              Apartment #780506vb
                                                              13
                                                              Viewed 29 times in the last 48 hours
                                                                Exceptional! 5.0/5
                                                                (60 reviews)
                                                                avg/night
                                                                • 4 BR
                                                                • 2 BA
                                                                • Sleeps 11
                                                                House #595328vb
                                                                60
                                                                Viewed 74 times in the last 48 hours
                                                                  Excellent! 4.5/5
                                                                  (24 reviews)
                                                                  avg/night
                                                                  • 3 BR
                                                                  • 2 BA
                                                                  • Sleeps 8
                                                                  Condo #622632vb
                                                                  24
                                                                  Viewed 79 times in the last 48 hours
                                                                    Wonderful! 4.8/5
                                                                    (43 reviews)
                                                                    avg/night
                                                                    • 2 BR
                                                                    • 1 BA
                                                                    • Separate Toilet
                                                                    • Sleeps 6
                                                                    Apartment #271945
                                                                    43
                                                                    Viewed 44 times in the last 48 hours
                                                                      Excellent! 4.3/5
                                                                      (14 reviews)
                                                                      avg/night
                                                                      • 2 BR
                                                                      • 2 BA
                                                                      • Sleeps 6
                                                                      Apartment #593610vb
                                                                      14
                                                                      Viewed 32 times in the last 48 hours
                                                                        Wonderful! 4.9/5
                                                                        (76 reviews)
                                                                        avg/night
                                                                        • 3 BR
                                                                        • 1 BA
                                                                        • Separate Toilet
                                                                        • Sleeps 6
                                                                        Apartment #225815
                                                                        76
                                                                        Viewed 19 times in the last 48 hours
                                                                          Wonderful! 4.9/5
                                                                          (41 reviews)
                                                                          avg/night
                                                                          • 5 BR
                                                                          • 5 BA
                                                                          • Sleeps 14
                                                                          House #571144vb
                                                                          41
                                                                          Viewed 30 times in the last 48 hours
                                                                            Excellent! 4.3/5
                                                                            (28 reviews)
                                                                            avg/night
                                                                            • 3 BR
                                                                            • 2 BA
                                                                            • Sleeps 10
                                                                            House #3733046
                                                                            28
                                                                            Viewed 30 times in the last 48 hours
                                                                              Excellent! 4.6/5
                                                                              (32 reviews)
                                                                              avg/night
                                                                              • 6 BR
                                                                              • 5 BA
                                                                              • Sleeps 11
                                                                              Estate #289158vb
                                                                              32
                                                                              Viewed 78 times in the last 48 hours
                                                                                • 3 BR
                                                                                • 2 BA
                                                                                • Sleeps 6
                                                                                Apartment #890369vb
                                                                                1
                                                                                  Very Good! 4.0/5
                                                                                  (6 reviews)
                                                                                  avg/night
                                                                                  • 2 BR
                                                                                  • 2 BA
                                                                                  • Sleeps 4
                                                                                  Condo #159001vb
                                                                                  6
                                                                                  Viewed 115 times in the last 48 hours
                                                                                    avg/night
                                                                                    • 3 BR
                                                                                    • 2 BA
                                                                                    • Separate Toilet
                                                                                    • Sleeps 30
                                                                                    Condo #282940vb
                                                                                    2
                                                                                    Viewed 288 times in the last 48 hours
                                                                                      • 3 BR
                                                                                      • 2 BA
                                                                                      • Separate Toilet
                                                                                      • Sleeps 30
                                                                                      Condo #267014
                                                                                      2
                                                                                      Viewed 169 times in the last 48 hours
                                                                                        Very Good! 4.0/5
                                                                                        (5 reviews)
                                                                                        avg/night
                                                                                        • 3 BR
                                                                                        • 2 BA
                                                                                        • Separate Toilet
                                                                                        • Sleeps 6
                                                                                        Condo #267015
                                                                                        5
                                                                                        Viewed 267 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 117 times in the last 48 hours
                                                                                            avg/night
                                                                                            • 3 BR
                                                                                            • 2 BA
                                                                                            • Separate Toilet
                                                                                            • Sleeps 6
                                                                                            Condo #887767vb
                                                                                            2
                                                                                            Viewed 118 times in the last 48 hours
                                                                                              Exceptional! 5.0/5
                                                                                              (59 reviews)
                                                                                              avg/night
                                                                                              • 4 BR
                                                                                              • 2 BA
                                                                                              • Sleeps 10
                                                                                              Apartment #627209vb
                                                                                              59
                                                                                              Viewed 67 times in the last 48 hours
                                                                                                Excellent! 4.5/5
                                                                                                (8 reviews)
                                                                                                avg/night
                                                                                                • 1 BR
                                                                                                • 1 BA
                                                                                                • Sleeps 3
                                                                                                Apartment #836457vb
                                                                                                8
                                                                                                Viewed 55 times in the last 48 hours
                                                                                                  Exceptional! 5.0/5
                                                                                                  (14 reviews)
                                                                                                  avg/night
                                                                                                  • 3 BR
                                                                                                  • 2 BA
                                                                                                  • Sleeps 6
                                                                                                  Apartment #723132vb
                                                                                                  14
                                                                                                  Viewed 57 times in the last 48 hours
                                                                                                    Exceptional! 5.0/5
                                                                                                    (22 reviews)
                                                                                                    avg/night
                                                                                                    • 3 BR
                                                                                                    • 2 BA
                                                                                                    • Sleeps 8
                                                                                                    Condo #708413vb
                                                                                                    22
                                                                                                    Viewed 25 times in the last 48 hours
                                                                                                      • 1 BR
                                                                                                      • 1 BA
                                                                                                      • Separate Toilet
                                                                                                      • Sleeps 4
                                                                                                      Condo #735045vb
                                                                                                      3
                                                                                                      • 1 - 50 of 300+

                                                                                                      Chicago Holiday Apartments & Rentals (300+)