Find the best place to stay — Chicago

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

Whether you're traveling with family or friends, here are the areas with the largest selection of vacation rentals for a holiday trip or just for a weekend in Chicago:

  • Chicago Loop: 167 vacation rentals
  • Heart of Chicago: 20 vacation rentals
  • Wrigleyville: 88 vacation rentals
  • South Loop: 84 vacation rentals
  • Wicker Park: 101 vacation rentals

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

What are the popular point of interests near where I can stay when traveling to Chicago?

VRBO offers a large selection of vacation rentals near lovely places in Chicago. From VRBO travelers, the top 5 most popular points of interest to stay for a holiday trip or just for a weekend are:

  • Grant Park: 882 vacation rentals
  • McCormick Place: 879 vacation rentals
  • Chicago Water Tower: 882 vacation rentals
  • Chicago History Museum: 882 vacation rentals
  • Navy Pier: 879 vacation rentals

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

Can I find a vacation rental with suitable for kids in Chicago?

Yes, you can select your prefered vacation rental with suitable for kids among our 690 vacation rentals with suitable for kids available in Chicago. Please use our search bar to access the selection of vacation rentals available.