Skip to main content


Straight Up Chicago Investor Podcast Episode 208: Going Deep In Bucktown And Wicker Park With Jason Stratton

Straight Up Chicago Investor Podcast Episode 208: Going Deep In Bucktown And Wicker Park With Jason Stratton

Investing in Chicago’s Hot Neighborhoods with Jason Stratton

Are you interested in investing in Chicago’s popular Bucktown neighborhood but worried you may have missed the opportunity? Not to worry, according to Jason Stratton, a realtor, investor, and Bucktown resident, there are still deals to be found.

In this episode of Straight Up Chicago Investor, Jason shares what first attracted him to Bucktown and how he found his first successful deal in the neighborhood. He defines the boundaries of Bucktown and describes the amazing attributes like walkability, dining, nightlife, and architecture that make it such a desirable place to live. While the neighborhood has appreciated greatly over the years, Jason explains how he is still finding deals for investors today.

The adjacent Wicker Park neighborhood is also discussed, including how owning a landmark property there can be an opportunity. Jason shares his perspective on other up-and-coming Chicago neighborhoods he’s bullish on and why.

Jason closes with an inspiring message about the strength of the Chicago real estate market and the mindset investors need to be successful. If you’re looking for an insider’s take on investing in Chicago’s hottest neighborhoods, you won’t want to miss this episode!

Watch Straight Up Chicago Investor Podcast Episode 208 in Full Here

Questions We Answer In this Show:

Q. Should I invest in Wicker Park or Bucktown

  1. Video

Q. Exploring the Real Estate Market in Bucktown, Chicago


  1. Video

Q. Real Estate Investing: Leveraging Assets and Maximizing Returns

  1. Video

Show Notes:

  • 03:00 Housing Provider Tip: Leverage keyless entry locks to make access easier! 

  • 05:12 Intro to our guest, Jason Stratton! 

  • 09:58 Jason discusses his first real estate deal!

  • 17:30 What are the borders of Bucktown?

  • 19:19 How is Jason finding deals in the small neighborhood of Bucktown?

  • 23:25 Jason talks about Wicker Park!

  • 30:21 Other North Side Neighborhoods with a ton of potential!

  • 35:52 Jason gives his outlook on the Chicago Real Estate Market.

  • 38:22 What is Jason's competitive advantage? 

  • 38:48 One piece of advice for new investors.

  • 39:48 What do you do for fun?

  • 41:57 Good book, podcast, or self development activity that you would recommend? 

  • 43:43 Local Network Recommendation?

  • 44:46 How can the listeners learn more about you and provide value to you?

Guest Name: Jason Stratton

Guest Company: The KlopasStratton Team

Guest Link:

Other Links for show notes:

Extreme Ownership (Book Recommendation)

Seth Kaplan (Attorney)

Jeff Swanberg (Inspector)

KlopasStratton Podcast

Hillside Lumber (Lumber Vendor)

Chicago Investor Resources Shared

Want extra Hacks & Tricks? Follow us on Facebook & Youtube!

Looking for a breakthrough in your career? Join Our Team!

SUBSCRIBE on to our podcast on iTunes | Spotify | Stitcher | TuneIn Radio