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 heart-filled

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.

Cancel Clear Filters Apply Filters
More Filters

Price Per Night

£ £

Bedrooms

Bathrooms

Payment Options

Popular Searches

Facilities

Location Type

Local Area

Property Details

Clear Filters
Use filters to narrow your search results!
Favorite
    Viewed 43 times in the last 48 hours
    avg/night
    Favorite
      Viewed 96 times in the last 48 hours
      Wonderful! 4.8/5
      (55 reviews)
      avg/night
      55
      Favorite
        Viewed 75 times in the last 48 hours
        Wonderful! 4.8/5
        (57 reviews)
        avg/night
        57
        Favorite
          Viewed 112 times in the last 48 hours
          Exceptional! 5/5
          (8 reviews)
          avg/night
          8
          Favorite
            Viewed 40 times in the last 48 hours
            avg/night
            2
            Favorite
              Viewed 60 times in the last 48 hours
              Wonderful! 4.8/5
              (46 reviews)
              avg/night
              46
              Favorite
                Viewed 20 times in the last 48 hours
                Wonderful! 4.8/5
                (67 reviews)
                avg/night
                67
                Favorite
                  Viewed 31 times in the last 48 hours
                  Wonderful! 4.9/5
                  (53 reviews)
                  avg/night
                  53
                  Favorite
                    Viewed 30 times in the last 48 hours
                    Excellent! 4.6/5
                    (43 reviews)
                    avg/night
                    43
                    Favorite
                      Viewed 30 times in the last 48 hours
                      Excellent! 4.7/5
                      (49 reviews)
                      avg/night
                      49
                      Favorite
                        Viewed 34 times in the last 48 hours
                        Excellent! 4.5/5
                        (12 reviews)
                        avg/night
                        12
                        Favorite
                          Viewed 46 times in the last 48 hours
                          Wonderful! 4.8/5
                          (113 reviews)
                          avg/night
                          113
                          Favorite
                            Viewed 66 times in the last 48 hours
                            Wonderful! 4.9/5
                            (61 reviews)
                            avg/night
                            61
                            Favorite
                              Viewed 47 times in the last 48 hours
                              Excellent! 4.3/5
                              (18 reviews)
                              avg/night
                              18
                              Favorite
                                Viewed 88 times in the last 48 hours
                                Wonderful! 4.9/5
                                (81 reviews)
                                avg/night
                                81
                                Favorite
                                  Viewed 19 times in the last 48 hours
                                  Wonderful! 4.9/5
                                  (58 reviews)
                                  avg/night
                                  58
                                  Favorite
                                    Viewed 52 times in the last 48 hours
                                    Wonderful! 4.8/5
                                    (27 reviews)
                                    avg/night
                                    27
                                    Favorite
                                      Viewed 18 times in the last 48 hours
                                      Wonderful! 4.9/5
                                      (12 reviews)
                                      avg/night
                                      12
                                      Favorite
                                        Viewed 32 times in the last 48 hours
                                        Wonderful! 4.9/5
                                        (74 reviews)
                                        avg/night
                                        74
                                        Favorite
                                          Viewed 33 times in the last 48 hours
                                          Exceptional! 5/5
                                          (72 reviews)
                                          avg/night
                                          72
                                          Favorite
                                            Viewed 52 times in the last 48 hours
                                            Wonderful! 4.9/5
                                            (21 reviews)
                                            avg/night
                                            21
                                            Favorite
                                              Viewed 37 times in the last 48 hours
                                              Excellent! 4.7/5
                                              (49 reviews)
                                              avg/night
                                              49
                                              Favorite
                                                Exceptional! 5/5
                                                (8 reviews)
                                                avg/night
                                                8
                                                Favorite
                                                  Viewed 23 times in the last 48 hours
                                                  Exceptional! 5/5
                                                  (10 reviews)
                                                  avg/night
                                                  10
                                                  Favorite
                                                    Viewed 41 times in the last 48 hours
                                                    Excellent! 4.4/5
                                                    (16 reviews)
                                                    avg/night
                                                    16
                                                    Favorite
                                                      Viewed 25 times in the last 48 hours
                                                      Wonderful! 4.9/5
                                                      (75 reviews)
                                                      avg/night
                                                      75
                                                      Favorite
                                                        Viewed 22 times in the last 48 hours
                                                        Excellent! 4.6/5
                                                        (26 reviews)
                                                        avg/night
                                                        26
                                                        Favorite
                                                          Viewed 65 times in the last 48 hours
                                                          Exceptional! 5/5
                                                          (43 reviews)
                                                          avg/night
                                                          43
                                                          Favorite
                                                            Viewed 25 times in the last 48 hours
                                                            Exceptional! 5/5
                                                            (24 reviews)
                                                            avg/night
                                                            24
                                                            Favorite
                                                              Viewed 32 times in the last 48 hours
                                                              Exceptional! 5/5
                                                              (24 reviews)
                                                              avg/night
                                                              24
                                                              Favorite
                                                                Viewed 35 times in the last 48 hours
                                                                Exceptional! 5/5
                                                                (19 reviews)
                                                                avg/night
                                                                19
                                                                Favorite
                                                                  Viewed 22 times in the last 48 hours
                                                                  Wonderful! 4.9/5
                                                                  (77 reviews)
                                                                  avg/night
                                                                  77
                                                                  Favorite
                                                                    Viewed 18 times in the last 48 hours
                                                                    Exceptional! 5/5
                                                                    (17 reviews)
                                                                    avg/night
                                                                    17
                                                                    Favorite
                                                                      Viewed 24 times in the last 48 hours
                                                                      Wonderful! 4.8/5
                                                                      (36 reviews)
                                                                      avg/night
                                                                      36
                                                                      Favorite
                                                                        Viewed 15 times in the last 48 hours
                                                                        Wonderful! 4.9/5
                                                                        (90 reviews)
                                                                        avg/night
                                                                        90
                                                                        Favorite
                                                                          Viewed 15 times in the last 48 hours
                                                                          Wonderful! 4.9/5
                                                                          (56 reviews)
                                                                          avg/night
                                                                          56
                                                                          Favorite
                                                                            Viewed 87 times in the last 48 hours
                                                                            Very Good! 4.1/5
                                                                            (7 reviews)
                                                                            avg/night
                                                                            7
                                                                            Favorite
                                                                              Viewed 27 times in the last 48 hours
                                                                              Wonderful! 4.8/5
                                                                              (134 reviews)
                                                                              avg/night
                                                                              134
                                                                              Favorite
                                                                                Viewed 25 times in the last 48 hours
                                                                                Wonderful! 4.9/5
                                                                                (25 reviews)
                                                                                avg/night
                                                                                25
                                                                                Favorite
                                                                                  Viewed 16 times in the last 48 hours
                                                                                  Good! 3.8/5
                                                                                  (19 reviews)
                                                                                  avg/night
                                                                                  19
                                                                                  Favorite
                                                                                    Viewed 29 times in the last 48 hours
                                                                                    Excellent! 4.4/5
                                                                                    (12 reviews)
                                                                                    avg/night
                                                                                    12
                                                                                    Favorite
                                                                                      Viewed 21 times in the last 48 hours
                                                                                      Wonderful! 4.8/5
                                                                                      (82 reviews)
                                                                                      avg/night
                                                                                      82
                                                                                      Favorite
                                                                                        Viewed 23 times in the last 48 hours
                                                                                        Wonderful! 4.9/5
                                                                                        (49 reviews)
                                                                                        avg/night
                                                                                        49
                                                                                        Favorite
                                                                                          Viewed 34 times in the last 48 hours
                                                                                          Good! 3.7/5
                                                                                          (23 reviews)
                                                                                          avg/night
                                                                                          23
                                                                                          Favorite
                                                                                            Viewed 30 times in the last 48 hours
                                                                                            Wonderful! 4.8/5
                                                                                            (18 reviews)
                                                                                            avg/night
                                                                                            18
                                                                                            Favorite
                                                                                              Viewed 9 times in the last 48 hours
                                                                                              Exceptional! 5/5
                                                                                              (134 reviews)
                                                                                              avg/night
                                                                                              134
                                                                                              Favorite
                                                                                                Viewed 26 times in the last 48 hours
                                                                                                Excellent! 4.3/5
                                                                                                (19 reviews)
                                                                                                avg/night
                                                                                                19
                                                                                                Favorite
                                                                                                  Viewed 31 times in the last 48 hours
                                                                                                  Wonderful! 4.9/5
                                                                                                  (38 reviews)
                                                                                                  avg/night
                                                                                                  38
                                                                                                  Favorite
                                                                                                    Viewed 40 times in the last 48 hours
                                                                                                    Very Good! 4.2/5
                                                                                                    (26 reviews)
                                                                                                    avg/night
                                                                                                    26
                                                                                                    Favorite
                                                                                                      Viewed 17 times in the last 48 hours
                                                                                                      Wonderful! 4.9/5
                                                                                                      (25 reviews)
                                                                                                      avg/night
                                                                                                      25

                                                                                                      Chicago Holiday Apartments & Rentals (300+)