Where to stay around Oak Street, Chicago?

Our 2018 property listings offer a large selection of 988 vacation rentals near Oak Street. From 559 apartments to 185 condos, find a unique house rental for you to enjoy a memorable stay with your family and friends. The best places to stay near Oak Street for a holiday or a weekend are on VRBO.

What is the best area to stay near Oak Street?

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 near Oak Street:

  • Chicago Loop: 125 vacation rentals
  • Wrigleyville: 111 vacation rentals
  • Lakeview: 208 vacation rentals
  • Bronzeville: 44 vacation rentals
  • Wicker Park: 113 vacation rentals

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

Can I rent apartments near Oak Street?

Yes, of course. VRBO has 559 apartments near Oak Street. Our other popular types of vacation rentals near Oak Street include:

  • Condos: 185 rentals available
  • Houses: 163 rentals available
  • Townhomes: 18 rentals available

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

Can I find a vacation rental with online bookable near Oak Street?

Yes, you can select your prefered vacation rental with online bookable among our 979 vacation rentals with online bookable available near Oak Street. Please use our search bar to access the selection of vacation rentals available.