Best Month to Buy a Multifamily in Chicago

Chicago, Illinois
Multi-Family and Apartment Investing
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Best Month to Buy a Multifamily in Chicago

Rochelle Fernando
Member since 2025 · 14 posts · 8 votes

I’m looking to purchase a multifamily property in Chicago and want to choose the best month to buy so I can rent out the units quickly. I’m considering December, January, or February—which month typically allows for faster tenant placement?

For neighborhoods, I’m thinking about Logan Square, Bucktown, and Wicker Park, but I’m not interested in the South Side. Are there other areas with high rental yields, low eviction rates, and reasonable starting prices for multifamily homes that you would recommend? Thank you!

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Eudith VacioPro Member
Real Estate Agent · Chicago & NWI · Member since 2015 · 860 posts · 521 votes
1y

Hey @Rochelle Fernando 👋🏽

Yes, those are the BEST months to buy! I personally begin my search around August to start looking and understanding where the market is at and then try going under contract Dec - January. I had to a property in the market in January this year and it did not do too well. I got more activity towards the end of January into February, so spring time starting in March is way better if you can wait that long or maybe do some renovations before renting it out. 


Focus on class A / B areas for low eviction rates, high rental yields but overall low cash flow unless you are putting a hefty down payment. 

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  • Aaron ZimmermanBusiness Member
    Accountant · Chicago, IL · Member since 2018 · 2k+ posts · 1k+ votes
    1y

    @Syed Ahmed is spot on. I'd be looking to get under contract in December/January and close in January/february. You may have some holding costs but you should be able to fill up your unit by end of March/April at the latest. I would encourage you to think long term about tenant placement. You don't want to take on the first potential resident especially if they're marginal. You can also have a longer lease term too so the next lease ends during a more peak month to rent

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  • Jack Matthias
    Lender · Chicago · Member since 2023 · 176 posts · 70 votes
    1y

    Hi Rochelle,

    You are definitely picking good areas and a timeline to get into a place. The biggest thing will be beating the spring market which usually starts in the end of February, this past year with the weather it seemed to start even earlier. I would be in the same boat with Aaron and plan on being under contract in December or January at the latest. Otherwise your going to get to many multiple offer scenarios. If you need an agent referral I work with several agents that specialize exactly what you're looking for. 

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  • Paul De Luca
    Real Estate Agent · Chicago, IL · Member since 2018 · 1k+ posts · 1k+ votes
    1y

    @Rochelle Fernando

    For buying & selling, if you're looking to get the "best deal", then it makes sense to buy during months when there is lower demand/less competition. Usually that's the fall and winter months.

    In general you will get higher demand for your rental listings in the spring and summer since that's when the most amount of people are looking to move.

    What do you consider a "reasonable starting price for multi-family homes"? The areas that you mentioned are A class, so be prepared to pay higher prices compared to other neighborhoods but you will also benefit from higher rents. 

    Start with your budget and then reverse engineer what neighborhoods make sense for your buying criteria.

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  • Allan C.
    Rental Property Investor · Member since 2018 · 826 posts · 810 votes
    1y

    I don't see buy timing related to tenant placement for multi families. Do you plan on getting the unit delivered vacant? If you aren't renovating, then perform strong tenant due diligence and keep them in place. The key is to walk the units and get a feel for how the tenants treat the place.   

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  • Eudith VacioPro Member
    Real Estate Agent · Chicago & NWI · Member since 2015 · 860 posts · 521 votes
    1y

    Hey @Rochelle Fernando 👋🏽

    Yes, those are the BEST months to buy! I personally begin my search around August to start looking and understanding where the market is at and then try going under contract Dec - January. I had to a property in the market in January this year and it did not do too well. I got more activity towards the end of January into February, so spring time starting in March is way better if you can wait that long or maybe do some renovations before renting it out. 


    Focus on class A / B areas for low eviction rates, high rental yields but overall low cash flow unless you are putting a hefty down payment. 

    2Reply
  • Rochelle Fernando
    OP
    Member since 2025 · 14 posts · 8 votes
    1y

    Thank you all for the insights. When evaluating properties, what key factors should I focus on? Given current interest rates and my plan to put down the minimum, achieving positive cash flow in Chicago neighborhoods is challenging. I’m considering covering some expenses out of pocket while living in the property, aiming to break even once I move out in a year or two.

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  • Rochelle Fernando
    OP
    Member since 2025 · 14 posts · 8 votes
    1y
    Quote from @Syed Ahmed:

    timing your purchase with rental demand can definitely make a difference. In Chicago, the spring and summer months April through August, tend to have the strongest rental activity since most tenants prefer to move when the weather is better. Winter deals Dec–Feb can sometimes come with lower purchase prices, but filling units quickly in those months is tougher.As for neighborhoods, Logan Square, Bucktown, and Wicker Park are all solid choices with strong tenant demand. You might also look into Avondale, Irving Park, or even parts of Humboldt Park where you can still find multifamily properties with decent starting prices and steady rental demand. Each area has its own tenant base, so it’s worth comparing vacancy rates and turnover trends before deciding.Feel free to connect if you’d like to talk through more ideas.


     

    Thank you so much! I’m looking to choose a neighborhood with low entry prices, strong rental demand, and low eviction rates. Do you have any other suggestions?

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  • Henry Lazerow
    Real Estate Agent · Chicago, IL · Member since 2017 · 2k+ posts · 2k+ votes
    1y

    I have been telling clients this for a while the best time to buy in chicago is August to January. The fall is really slow and sellers are more motivated. 

    Those ares you mention are great. Also check out Avondale we have been getting $2300 now on 2/1s there. The price point to buy is lower then Logan but the rents for units if you renovate them is very similar so more net cashflow. Old irving park and portage park solid growth bets too little lower rents but growing. I also like Albany Park and Irving Park still some good 4 unit deals there. All these areas will be 680+ credit tenants and close to 0 vacancy rates. I have a 4 unit in Rogers Park and only had 3 months of one unit at a time vacancy in 8 years, I try always have someone move in same day a tenant leaves and market in advance. 

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    • Rochelle Fernando
      OP
      Member since 2025 · 14 posts · 8 votes
      1y
      Quote from @Henry Lazerow:

      I have been telling clients this for a while the best time to buy in chicago is August to January. The fall is really slow and sellers are more motivated. 

      Those ares you mention are great. Also check out Avondale we have been getting $2300 now on 2/1s there. The price point to buy is lower then Logan but the rents for units if you renovate them is very similar so more net cashflow. Old irving park and portage park solid growth bets too little lower rents but growing. I also like Albany Park and Irving Park still some good 4 unit deals there. All these areas will be 680+ credit tenants and close to 0 vacancy rates. I have a 4 unit in Rogers Park and only had 3 months of one unit at a time vacancy in 8 years, I try always have someone move in same day a tenant leaves and market in advance. 


       Thank you so much!

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  • Jonathan KlemmBusiness Member
    Moderator
    Contractor · Chicago, IL · Member since 2016 · 4k+ posts · 2k+ votes
    1y

    Hi there @Rochelle Fernando!  What's a reasonable starting price?

    I love all those Chicago neighborhoods you suggested and would also add Hermosa, Belmont Gardens, Irving Park, Humboldt Park, Little Village, McKinley Park, Brighton Park, etc.  

    Are you planning on buying something that needs renovation?  Will you be living in one of the units?

    Best time to buy for a good deal is in the winter.

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    • Rochelle Fernando
      OP
      Member since 2025 · 14 posts · 8 votes
      1y
      Quote from @Jonathan Klemm:

      Hi there @Rochelle Fernando!  What's a reasonable starting price?

      I love all those Chicago neighborhoods you suggested and would also add Hermosa, Belmont Gardens, Irving Park, Humboldt Park, Little Village, McKinley Park, Brighton Park, etc.  

      Are you planning on buying something that needs renovation?  Will you be living in one of the units?

      Best time to buy for a good deal is in the winter.


       

      Thanks for the information. I’m planning to house hack, but since this will be my first property, I’d prefer to avoid renovations. 

      1Reply
  • Henry Lazerow
    Real Estate Agent · Chicago, IL · Member since 2017 · 2k+ posts · 2k+ votes
    1y

    @Jonathan Klemm forgot about Little Village nice suggestion. I recently sold my own flip there and we got $2000 for the 3/2 and $1700 the 3/1 rents are flying in that area as well as next door neighborhood Brighton Park. The 4 units and even many 3 units still have high cash flow at low down payments. 

    1Reply
  • John Clark
    Member since 2018 · 1k+ posts · 1k+ votes
    1y
    Quote from @Rochelle Fernando:

    I’m looking to purchase a multifamily property in Chicago and want to choose the best month to buy so I can rent out the units quickly. I’m considering December, January, or February—which month typically allows for faster tenant placement?

    For neighborhoods, I’m thinking about Logan Square, Bucktown, and Wicker Park, but I’m not interested in the South Side. Are there other areas with high rental yields, low eviction rates, and reasonable starting prices for multifamily homes that you would recommend? Thank you!

    Why are you not interested in the South side?

    Southwest side following the orange line to midway is great.
    1Reply
  • Eudith VacioPro Member
    Real Estate Agent · Chicago & NWI · Member since 2015 · 860 posts · 521 votes
    1y

    Totally agree with @John Clark

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  • Jonathan KlemmBusiness Member
    Moderator
    Contractor · Chicago, IL · Member since 2016 · 4k+ posts · 2k+ votes
    1y

    Excellent call on those SW Neighborhoods - I still think those are sleepers for most Chicago investors @Henry Lazerow!  That's pretty much surfing along the Orange line like @John Clark and @Eudith Vacio mentioned.

    Most important thing is once you get your tenants is to screen them well! @Rochelle Fernando

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  • Jonathan KlemmBusiness Member
    Moderator
    Contractor · Chicago, IL · Member since 2016 · 4k+ posts · 2k+ votes
    1y

    That makes total sense @Rochelle Fernando!  I actually envy your intelligence for avoiding a renovation on the first property!

    I took the opposite approach and did a live and flip for my first property, and there is OF COURSE stress that comes along with a renovation.

    What's the top of your purchase price?  And desired number of units?  That will help determine which Chicago neighborhoods you can buy in.

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  • Rochelle Fernando
    OP
    Member since 2025 · 14 posts · 8 votes
    1y

    $800,000 to 900,000 with 3 to 4 units.

    1Reply
    • Jack Matthias
      Lender · Chicago · Member since 2023 · 176 posts · 70 votes
      1y
      Quote from @Rochelle Fernando:

      $800,000 to 900,000 with 3 to 4 units.


       You should be able to find something that fits your location range with this price point! Send a DM if you ever want to look at numbers on something like this. Don't forget that you will need 6 months worth of reserves

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