Chicago IL and greater midwest vacation rentals!

[Philip Wrigley]

Hey everyone, I’m Phil based out of Chicago. I originally got into real estate through short term rentals almost by accident after buying one property that snowballed into a full time business over the years. Most of my experience is in vacation rentals, renovations, guest experience, and figuring things out as I go like most of us probably are. My first attempt at a hello got deleted as I made the rookie mistake of adding the name of my business! :P I’ve spent a long time lurking on BiggerPockets so figured it was time to finally introduce myself. Looking forward to connecting with other investors, especially anyone in the Chicago, Galena, or Southwest Michigan areas.

[Ryan Flanagan]

If you're looking for STR investing, Miller Beach is often overlooked because of the Gary address (it actually used to be a separate city that was annexed decades ago). It's a little enclave nestled in the Indiana Dunes National Park... thank you Mike Pence for this designation. It's highly seasonal business, but deals can be profitable if done right.
There are $1M+ houses on the beach but if you go a few blocks out, prices come down considerably. The Miller STR market has become much more saturated in recent years, probably because other cities that overlap with the Indiana Dunes don't allow STR.

For BRRRR investing Hammond and East Chicago are great but you need to vet tenants carefully (really this is true anywhere, but especially so here). These are B- to C neighborhoods depending on location with great rent to price ratios (esp if renovating). I have some buy and holds in Crown Point and Cedar Lake as well. These are considered more desirable neighborhoods with good schools and nicer downtown areas.