
Longline Financial provided a $13.62 million senior acquisition loan secured by a 27,162 SF, four-story retail building with sub-grade space at 174 N. Michigan Avenue in Chicago—located along the North Michigan Avenue corridor between the Chicago River and Millennium Park.
174 N. Michigan Ave, Chicago — 27,162 SF retail building along the North Michigan Avenue corridor.

This transaction is structured to support a sponsor-led repositioning strategy designed to convert and modernize the asset for restaurant-oriented tenancy and active street-level retail use. The scope includes acquisition capital and funding for base-building improvements and tenant readiness—aligned to the practical sequencing and milestones that often define urban retail execution.
Urban retail transitions, especially in high-visibility corridors, can require coordinated diligence, fast decision making, and a clear path through design, permitting, and tenant-driven requirements. For 174 N.Michigan, Longline’s role was to align senior financing with an execution plan that includes building upgrades and leasing progress, supporting a timeline-sensitive acquisition and repositioning process.
The property sits in one of Chicago’s most recognizable retail corridors, benefiting from demand drivers that include tourism, residents, and the Loop workforce—a mix that supports daily foot traffic and multi-tenant retail visibility.
The borrower is The Windfall Group, formed in 2003, focused on acquiring and repositioning value-add opportunities and redeveloping underutilized assets. The sponsor’s platform includes experience across commercial projects nationally, with a track record of renovating and repositioning assets and executing tenant-driven strategies.
The sponsor’s tenant strategy focuses on a primarily Asian centric restaurant mix complemented by sub-grade retail. The future tenants will feature an Authentic Chinese restaurant, a Hot Pot restaurant,Japanese BBQ, a Japanese-themed gift shop, and a national taco chain.
Longline Management, LLC is an investment holding company based in Atlanta, GA. Founded in 2019, Longline invests in real estate and hard assets, related credit strategies and select operating companies. Longline invests nationally with a focus on the Southeast U.S. Since inception Longline has invested $500 million of equity across its platform on behalf of institutional and individual investors and for its own account.
Exploring retail or mixed-use financing?
Borrowers and brokers pursuing execution-focused senior mortgages for complex or time-sensitive situations are invited to connect with Longline Financial.