Where to stay around Chicago?

Our 2018 accommodation listings offer a large selection of 1,025 holiday lettings near Chicago. From 563 apartments to 196 condos, find unique self catering accommodation for you to enjoy a memorable holiday or a weekend with your family and friends. The best place to stay near Chicago is on HomeAway.

What is the best area to stay when travelling to Chicago?

Whether you are travelling solo or with family and friends, here are the areas with the largest selection of holiday accommodations for a long holiday or just a weekend break in Chicago:

  • Chicago Loop: 159 holiday homes
  • Ukrainian Village: 71 holiday homes
  • Near West Side: 256 holiday homes
  • Roscoe Village: 98 holiday homes
  • Old Town: 132 holiday homes

For other neighbourhoods, please use our search bar to access the selection of holiday rentals available.

What are the most popular points of interest and landmarks to stay near when travelling to Chicago?

HomeAway offers a large selection of holiday accommodations near great places in Chicago. From HomeAway travellers, the most popular points of interest to stay near are:

  • Chicago 87th Street Station (Woodruff): 963 holiday lettings
  • Stage 773: 1,007 holiday lettings
  • Chicago 107th Street Station (Beverly Hills): 944 holiday lettings
  • Wrigley Field: 998 holiday lettings
  • Chicago Water Tower: 1,003 holiday lettings

But there are many other points of interest around Chicago listed on HomeAway where you can find your place to stay. Please use our search bar to access the selection of holiday rentals available near the point of interest of your choice.

Can I rent apartments in Chicago?

Yes, of course. HomeAway offers 563 apartments in Chicago. Our other popular types of Chicago holiday rentals include:

  • Condos: 196 self catering accommodations
  • Houses: 177 self catering accommodations
  • Bungalows: 3 self catering accommodations

But you can also enjoy a great stay in one of our other holiday rentals including cottages and more.

Can I find a holiday accommodation with pool in Chicago?

Yes, you can select your preferred holiday accommodation with pool among our 101 holiday homes with pool available in Chicago. Please use our search bar to access the selection of holiday rentals available.

    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.

    Sightseeing in and around Chicago

    Are you hoping to discover attractions to see in the area? Venture out of your holiday home and check out everything that makes Chicago a one-of-a-kind holiday spot. These are some of the major attractions to explore, all within 30 miles (48.2 km) of the city centre:

    • Skydeck Ledge (0.4 mi / 0.6 km)
    • Navy Pier (1.2 mi / 1.9 km)
    • John G. Shedd Aquarium (1.2 mi / 2 km)
    • Adler Planetarium and Astronomy Museum (1.5 mi / 2.4 km)
    • Lincoln Park Zoo (2.7 mi / 4.4 km)
    • Brookfield Zoo (11 mi / 17.7 km)

    Exploring the natural landscape of Chicago

    Whether you're an active traveller or just want to spend some time taking in the scenery, Chicago is a great place to get out in nature. These are a few of the area's noteworthy natural features, all within 30 miles (48.2 km) of the city centre:

    • Millennium Park (0.2 mi / 0.4 km)
    • Grant Park (0.7 mi / 1 km)
    • Lincoln Park (4.8 mi / 7.8 km)
    • Chicago Riverwalk (0.5 mi / 0.8 km)
    • Ohio Street Beach (1.2 mi / 1.9 km)
    • Northerly Island Park (1.5 mi / 2.4 km)