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.

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

Price Per Week

£ £

Sleeps

Bedrooms

Bathrooms

Payment Options

Property Type

Apartments
Condos
Cottages
Homes
Hotels
Villas
Barns
Boats
Bungalows
Cabins
Castles
Chalets
Chateau
Farmhouses
Lodges
Yachts

Popular Searches

Facilities

Themes

Local Area

Property Details

Cancel Clear Filters Apply Filters
Use filters to narrow your search results!

Chicago Holiday Apartments & Rentals(298)

298 Results
Book Now!
2 night minimum stay
  • 2 BR,
  • 2 BA,
  • Sleeps 8
    (61)
    Book Now!
    2 - 4 night minimum stay
    • 3 BR,
    • 1 BA,
    • 1 Separate Toilet,
    • Sleeps 6
      (56)
      Book Now!
      3 - 7 night minimum stay
      • 2 BR,
      • 2 BA,
      • Sleeps 6
        (56)
        Book Now!
        3 - 7 night minimum stay
        • 2 BR,
        • 2 BA,
        • Sleeps 6
          (58)
          Book Now!
          3 - 7 night minimum stay
          • 2 BR,
          • 2 BA,
          • Sleeps 6
            (55)
            Book Now!
            3 - 7 night minimum stay
            • 2 BR,
            • 2 BA,
            • Sleeps 6
              (35)
              Book Now!
              2 - 5 night minimum stay
              • 3 BR,
              • 2 BA,
              • Sleeps 8
                (26)
                Book Now!
                4 night minimum stay
                • 2 BR,
                • 1 BA,
                • Sleeps 4
                  (42)
                  Book Now!
                  3 - 7 night minimum stay
                  • 2 BR,
                  • 2 BA,
                  • Sleeps 6
                    (18)
                    Book Now!
                    2 - 5 night minimum stay
                    • 2 BR,
                    • 2 BA,
                    • Sleeps 6
                      (21)
                      2 - 3 night minimum stay
                      • 6 BR,
                      • 5 BA,
                      • Sleeps 11
                        (20)
                        Book Now!
                        3 - 7 night minimum stay
                        • 2 BR,
                        • 2 BA,
                        • Sleeps 6
                          (4)
                          Book Now!
                          3 - 7 night minimum stay
                          • 2 BR,
                          • 2 BA,
                          • Sleeps 6
                            (4)
                            Book Now!
                            2 - 3 night minimum stay
                            • 7 BR,
                            • 6 BA,
                            • 1 Separate Toilet,
                            • Sleeps 24
                              (14)
                              Book Now!
                              3 - 5 night minimum stay
                              • 2 BR,
                              • 2 BA,
                              • Sleeps 4
                                (3)
                                Book Now!
                                3 - 4 night minimum stay
                                • 1 BR,
                                • 1 BA,
                                • Sleeps 2
                                  Book Now!
                                  3 - 7 night minimum stay
                                  • 2 BR,
                                  • 2 BA,
                                  • Sleeps 6
                                    1 Review
                                    Book Now!
                                    3 - 7 night minimum stay
                                    • 2 BR,
                                    • 2 BA,
                                    • Sleeps 6
                                      Book Now!
                                      3 - 4 night minimum stay
                                      • 5 BR,
                                      • 5 BA,
                                      • Sleeps 14
                                        4 night minimum stay
                                        • 4 BR,
                                        • 2 BA,
                                        • Sleeps 10
                                          (28)
                                          • 2 BR,
                                          • 2 BA,
                                          • Sleeps 6
                                            (17)
                                            3 night minimum stay
                                            • 4 BR,
                                            • 2 BA,
                                            • Sleeps 10
                                              (12)
                                              2 night minimum stay
                                              • 2 BR,
                                              • 2 BA,
                                              • Sleeps 6
                                                2 - 3 night minimum stay
                                                • 2 BR,
                                                • 1 BA,
                                                • Sleeps 7
                                                  (128)
                                                  Book Now!
                                                  2 night minimum stay
                                                  • 3 BR,
                                                  • 2 BA,
                                                  • 1 Separate Toilet,
                                                  • Sleeps 8
                                                    (4)
                                                    3 night minimum stay
                                                    • 4 BR,
                                                    • 2 BA,
                                                    • Sleeps 8
                                                      (8)
                                                      30 night minimum stay
                                                      • 4 BR,
                                                      • 2 BA,
                                                      • Sleeps 10
                                                        (10)
                                                        • 2 BR,
                                                        • 2 BA,
                                                        • Sleeps 6
                                                          (12)
                                                          2 night minimum stay
                                                          • 3 BR,
                                                          • 2 BA,
                                                          • 1 Separate Toilet,
                                                          • Sleeps 30
                                                            1 Review
                                                            2 night minimum stay
                                                            • 3 BR,
                                                            • 2 BA,
                                                            • Sleeps 6
                                                              2 Reviews
                                                              Advertisement