Where to stay around Downtown Chicago?

Our 2018 accommodation listings offer a large selection of 941 holiday lettings near Downtown Chicago. From 540 apartments to 187 condos, find the best place to stay with your family and friends to discover Downtown Chicago area.

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: 16 holiday homes
  • Lake Michigan: 10,062 holiday homes
  • Indiana: 1,427 holiday homes
  • Near North: 963 holiday homes
  • Ukrainian Village: 71 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: 753 holiday lettings
  • South Englewood: 215 holiday lettings
  • Winnetka: 135 holiday lettings
  • Oak Park: 930 holiday lettings
  • Countryside: 56 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): 968 holiday rentals
  • Stage 773: 1,007 holiday rentals
  • Chicago 107th Street Station (Beverly Hills): 944 holiday rentals
  • Wrigley Field: 1,006 holiday rentals
  • Chicago Water Tower: 1,003 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.