Where to stay around Downtown Chicago?

Our 2018 accommodation listings offer a large selection of 962 holiday lettings near Downtown Chicago. From 752 Flats to 580 Studios, 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 Downtown Chicago is on HomeAway.

What are the most popular destinations to visit in Downtown Chicago?

There are many lovely places to stay for a long holiday or just a weekend break in Downtown Chicago. From HomeAway travellers, the popular destinations to visit are:

  • Greektown: 23 holiday homes
  • Lake Michigan: 10,491 holiday homes
  • Indiana: 1,426 holiday homes
  • Ukrainian Village: 249 holiday homes
  • Magnificent Mile: 301 holiday homes

HomeAway offers you the possibility to discover many other popular destinations in Downtown Chicago! Please use our search bar to access the selection of self catering accommodations available in other popular destinations.

What are the main cities to discover in Downtown Chicago?

Whether you are travelling solo or with family and friends, here are the cities in Downtown Chicago with the largest selection of holiday lettings for a perfect city break:

  • Evanston: 821 holiday lettings
  • South Englewood: 247 holiday lettings
  • Winnetka: 180 holiday lettings
  • Oak Park: 985 holiday lettings
  • Countryside: 62 holiday lettings

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

What are the most popular points of interest and landmarks to stay near in Downtown Chicago?

HomeAway offers a large selection of holiday lettings near great places to visit in Downtown Chicago. From HomeAway travellers, the top popular points of interest to stay for a holiday trip or just for a weekend are:

  • Chicago 87th Street Station (Woodruff): 1,098 holiday rentals
  • Stage 773: 1,138 holiday rentals
  • Chicago 107th Street Station (Beverly Hills): 1,056 holiday rentals
  • Wrigley Field: 1,122 holiday rentals
  • Chicago Water Tower: 1,117 holiday rentals

But there are many other points of interest around Downtown Chicago listed on HomeAway where you can find your place to stay. Just write your wanted destination in our search bar and have a look at our selection of holiday accommodations.

Explore destinations around Downtown Chicago

821 holiday rentals
South Englewood
247 holiday rentals
180 holiday rentals
Oak Park
985 holiday rentals
62 holiday rentals
526 holiday rentals
135 holiday rentals
82 holiday rentals
Des Plaines
162 holiday rentals
372 holiday rentals
544 holiday rentals
66 holiday rentals
122 holiday rentals
41 holiday rentals
892 holiday rentals
Forest Park
905 holiday rentals
La Grange
73 holiday rentals
River Forest
947 holiday rentals
299 holiday rentals
Oak Lawn
142 holiday rentals