Chicago Multifamily · Since 2021
Chicago's apartment buildings, handled like legacy assets.
We advise owners and buyers of 10- to 99-unit apartment buildings across Chicago, from South Shore courtyard buildings to North Side walk-ups.
What we do
Advisory for Chicago apartment buildings
Sell
Positioning, marketing and negotiating the sale of your building to qualified buyers, including 1031 exchange buyers.
Buy
Finding and underwriting buildings for investors, including off-market opportunities.
Value
A confidential broker opinion of value for your building.
1031 & Legacy Planning
Coordinating with your attorney, CPA and qualified intermediary on exchanges and generational plans. We don't give legal or tax advice.
How a closing moves
From your building to closed, in five moves.
Say you own a 24-unit courtyard building in South Shore and you're weighing a sale. We bring it straight to buyers and lenders we already work with, so it moves without sitting on the open market. When it closes, you have your proceeds and a clean path into a 1031 exchange if that's the plan.
- 01
Your building
A courtyard or walk-up you own or want to own.
- 02
A local agent
Us — on your block, not in a call center.
- 03
Buyer, lender or resident
Someone already in our network.
- 04
Capital moving
Terms negotiated, financing lined up.
- 05
Closed
Proceeds to you — and a 1031 path if you want one.
More than 1,800 KW Commercial agents across the U.S. and Canada (KW Commercial, Sept 2026).
Keller Williams, No. 1 real estate franchise in the U.S. by agent count: 136,511 U.S. agents and 796,658 transaction sides in 2025 (T3 Sixty, Apr 2026).
Selected closings
A few of our recent transactions
Presidential Library Portfolio
South Shore
6 buildings · 237 units
5451–5461 S. Everett
Hyde Park
31 units
The Fairfax
Chicago
Selected closing
St. Edmund's Village
Chicago
Selected closing
Neighborhoods
Where we work in Chicago
South Shore
Historic courtyard buildings along the lakefront.
Hyde Park
University-adjacent walk-ups and mid-size rentals.
Washington Park
Grand brick apartment courts and value-add stock.
North Side
Walk-ups and boutique multifamily along transit.
Dolton
South-suburban townhome and small-portfolio trades.
Bronzeville
Restoration-era courtyards and repositioning plays.
This site launched in 2021 as Multifamily Investment Advisors – Chicagoland. Back then it was tracking apartment buildings across Chicagoland. Today it's the Chicago multifamily home of Midwest Investment Advisors | Powered by KW Commercial.
Off-market opportunities
We have a few off-market opportunities where the seller has indicated they will sell but isn't quite ready to list yet. We completely understand, and we share those opportunities with our preferred clients. Let's talk about getting you on that list so you get early looks at opportunities.
Join the preferred client listLed by Tony Hardy, J.D., founder and president of Midwest Investment Advisors.