New to STR market in Northwest Indiana

Chicago, Illinois
Short-Term & Vacation Rental Discussions
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New to STR market in Northwest Indiana

Jason KiolbasaPro Member
Member since 2021 · 5 posts · 1 vote

Hello! My wife and I own a long term investment property in the suburbs of Chicago. We're considering making a purchase in the Northwest Indiana vacation market (Michigan City, IN specifically) and starting our first STR. Are there any other investors in this market in the forum? The area looks like it's getting competitive and we're worried about saturation. We'd love to glean any tips, tricks, or things you wish you would've known when you started out specifically relating to property amenities and maximizing the shoulder seasons. We've utilized AirDNA to run comps but are looking for a little human mentorship from an experienced investor in the area.

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Mike GrudzienPro Member
Lender · Eugene, OR · Member since 2019 · 2k+ posts · 1k+ votes
2mo

It's very common for a newbie to jump on a national forum for the entire country seeking info about a single select market.  

The best suggestion is to network locally, in the local market that you are seeking local market intel on. Try Facebook Host groups. Try a local chapter of REIA (Real Estate Investment Association) Try connecting with a local real estate agent that works with investors.

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  • Mike GrudzienPro Member
    Lender · Eugene, OR · Member since 2019 · 2k+ posts · 1k+ votes
    2mo

    It's very common for a newbie to jump on a national forum for the entire country seeking info about a single select market.  

    The best suggestion is to network locally, in the local market that you are seeking local market intel on. Try Facebook Host groups. Try a local chapter of REIA (Real Estate Investment Association) Try connecting with a local real estate agent that works with investors.

    3Reply
    • John UnderwoodPro Member
      Investor · Greer, SC · Member since 2014 · 13k+ posts · 17k+ votes
      2mo
      Quote from @Mike Grudzien:

      It's very common for a newbie to jump on a national forum for the entire country seeking info about a single select market.  

      The best suggestion is to network locally, in the local market that you are seeking local market intel on. Try Facebook Host groups. Try a local chapter of REIA (Real Estate Investment Association) Try connecting with a local real estate agent that works with investors.


       All Great advice from Mike.

      Also do a bit more digging on Vrbo and Airbnb to see what a similar property to what you want to buy is doing. Look at nightly rates and occupancy levels. Find the most successful properties and see if you could duplicate what they offer such as amenities and location.

      1Reply
  • Andrew SteffensBusiness Member
    Tampa, FL · Member since 2022 · 3k+ posts · 3k+ votes
    2mo

    I agree with @Mike Grudzien

    I dont want to sound ignorant, but there's a vacation market in Indiana?

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  • Robert Leach
    Contractor · Romeoville, IL · Member since 2015 · 198 posts · 137 votes
    2mo

    I am pretty familiar with that market. Location is especially important in proximity to the beaches and the closer to New Buffalo the better. That area has and will always be a hot STR market. I have been in Osleka's marina since the 1980s as a kid and have never seen it slow down. Pay attention to the outdoor space. If you DM me I can expand.

    1Reply
  • Victor SoBusiness Member
    Real Estate Agent · Chicago, IL · Member since 2017 · 322 posts · 192 votes
    1mo
    Quote from @Jason Kiolbasa:

    Hello! My wife and I own a long term investment property in the suburbs of Chicago. We're considering making a purchase in the Northwest Indiana vacation market (Michigan City, IN specifically) and starting our first STR. Are there any other investors in this market in the forum? The area looks like it's getting competitive and we're worried about saturation. We'd love to glean any tips, tricks, or things you wish you would've known when you started out specifically relating to property amenities and maximizing the shoulder seasons. We've utilized AirDNA to run comps but are looking for a little human mentorship from an experienced investor in the area.

    Just throwing this out there but my friend Jason Wagner has a podcast called The Real Investing podcast and this week’s guest invests in Michigan City. DM me and I can connect you to Jason 
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  • Jason KiolbasaPro Member
    OP
    Member since 2021 · 5 posts · 1 vote
    1mo

    Thank you! I just talked to Jason last week! Appreciate the connection. 

    0Reply
  • Jason KiolbasaPro Member
    OP
    Member since 2021 · 5 posts · 1 vote
    1mo

    Thanks, John. 

    0Reply
  • Jason KiolbasaPro Member
    OP
    Member since 2021 · 5 posts · 1 vote
    1mo

    Thanks, Mike. 

    0Reply
  • Angela Venger
    Member since 2026 · 47 posts · 21 votes
    1mo

    Jason, on saturation I'd stop worrying about it. Almost every market looks saturated nowadays. Restaurants prove saturation doesn't decide anything, there are twenty on one street and the good ones still have a line. What decides it is whether you're the obvious pick inside your comp set, and true comps means same layout, same guest count, same amenities, not just whatever is nearby on AirDNA. On amenities I run every purchase through one filter, does it raise ROI or does it generate 5 star reviews, and one yes is enough.

    I feel like every business is saturated in every market, think of coffee shops, restaurants, plumbing companies, roofing companies, bakeries, I mean I can keep naming businesses that are saturated. My main point is when you start any business, you need to ask yourself how can I be that "purple cow", so people will remember me or catch their attention?

    0Reply
  • Alexis Engelking
    Member since 2026 · 5 posts · 0 votes
    1mo

    Start with the property facts, not the market debate. Write down the real inventory: exact sleeping arrangements and bed sizes, bathroom setup, kitchen appliances and supplies, Wi-Fi/workspace, parking and arrival constraints, stairs/accessibility, noise and shared-space realities, and what your house rules actually are (occupancy, visitors, quiet hours, pets, smoking). Draft a listing that opens with a one-sentence factual summary, then the three strongest specific benefits, room-by-room detail, location context, honest limitations, rules, and check-in/check-out basics. Verify every claim against your photos before publishing. Then do a practice guest journey yourself - book flow, directions, entry, Wi-Fi, checkout - and fix what breaks. Market saturation chatter matters less than whether your listing is accurate and your basics work; you can only adjust pricing/positioning after the fundamentals are solid.

    0Reply
  • Vijay FriedmanBusiness Member
    Miami, FL · Member since 2026 · 766 posts · 121 votes
    1mo
    Quote from @Jason Kiolbasa:

    Hello! My wife and I own a long term investment property in the suburbs of Chicago. We're considering making a purchase in the Northwest Indiana vacation market (Michigan City, IN specifically) and starting our first STR. Are there any other investors in this market in the forum? The area looks like it's getting competitive and we're worried about saturation. We'd love to glean any tips, tricks, or things you wish you would've known when you started out specifically relating to property amenities and maximizing the shoulder seasons. We've utilized AirDNA to run comps but are looking for a little human mentorship from an experienced investor in the area.

    @Jason Kiolbasa
    It sounds like you're taking a smart approach by combining AirDNA data with local investor feedback. One thing I'd pay close attention to is seasonality and local regulations, since those can have a big impact on occupancy and cash flow. Talking with a few local property managers can also give you a much better feel for guest demand than the data alone.

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  • Bryce Fairburn
    Lender · Lake City, MI · Member since 2019 · 118 posts · 42 votes
    3w

    Michigan City is an interesting STR market, especially with the Chicago proximity. I work with investors on STR/DSCR financing and would be happy to connect. I can also share what I'm seeing from a financing and underwriting standpoint as you evaluate properties. Happy to compare notes.

    0Reply
  • Matthew Tregoning
    Real Estate Consultant · Melbourne, FL · Member since 2019 · 174 posts · 103 votes
    3w

    AirDNA is a starting point, but I would not let a market level occupancy number answer the saturation question. Pull 20 to 30 listings that truly match what you would buy and track their open dates, review velocity, rates and minimum stays through the shoulder season. Then call local cleaners and property managers. Buy only if the deal works with conservative shoulder season demand, not the top comp.

    0Reply
  • Amber Stout
    Lender · Tampa/Saint Petersburg, FL · Member since 2014 · 356 posts · 148 votes
    3w

    Great advice from @Matthew Tregoning

    To add, a lot of areas are getting competitive. I would look to connect with options in that particular area and hear first hand what's working/not working. Also definitely pay attention to local STR regulations and any HOA restrictions. I've seen people find a deal they love and then realize the property or financing doesn't work the way they expected.

    Once you identify a specific area, one thing I’d look into once especially since this will be your first STR is the financing side. I’m a mortgage broker and work with lenders specifically for STRs that can actually use AirDNA projections to qualify the property upfront. It can be really helpful when you’re trying to figure out what properties make sense before getting too far into a deal.

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