Where to stay around Chicago?

Our 2018 accommodation listings offer a large selection of 59 holiday lettings near Chicago. From 50 Houses to 3 Townhouses, find unique self catering accommodation for you to enjoy a memorable stay with your family and friends. The best place to stay near Chicago for a long holiday or a weekend break 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:

  • Dundee-Happy Hollow Historic District: 18 holiday homes
  • West Omaha: 17 holiday homes
  • South Central Omaha: 32 holiday homes
  • North Omaha: 19 holiday homes
  • Millard: 16 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:

  • Sempeck's Bowling and Entertainment: 116 holiday lettings
  • Sacred Heart Parish Church: 118 holiday lettings
  • Kenefick Park: 119 holiday lettings
  • Strategic Air and Space Museum: 29 holiday lettings
  • Tregaron Golf Course: 116 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 Houses in Chicago?

Yes, of course. HomeAway offers 50 Houses in Chicago. Our other popular types of Chicago holiday rentals include:

  • Townhouses: 3 self catering accommodations
  • Flats: 3 self catering accommodations
  • Studios: 2 self catering accommodations

Can I find a holiday accommodation with pool in Chicago?

Yes, you can select your preferred holiday accommodation with pool among our 7 holiday homes with pool available in Chicago. Please use our search bar to access the selection of holiday rentals available.