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Leona's demolition and third Ashland apartment proposal add 115 homes on Chicago's Far North Side

Leona's demolition and third Ashland apartment proposal add 115 homes on Chicago's Far North Side

Built World Chicago, IL local

Rogers Park site cleared for 80 units; Andersonville developer proposes 35 more with seven affordable

Today: Leona's site cleared for 80 apartments

Overview

Updated 1 hour ago

The Leona's restaurant site in Rogers Park is now a cleared lot. On the same day, a developer proposed a third apartment building on North Ashland Avenue in Andersonville.

The two projects would add 115 apartments: 80 at the Leona's site and 35 on Ashland. The Andersonville project needs a zoning change from Ald. Andre Vasquez before it can go to the City Council.

Why it matters

The projects test whether Chicago's Far North Side can add housing on vacant and former commercial sites while meeting affordable-unit rules.

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Key Indicators

115
Total apartments
Combined units in the two projects.
80
Rogers Park units
Planned for the former Leona's site.
35
Andersonville units
Proposed at 5036-44 N. Ashland Ave.
7
Affordable units
Set aside in the Andersonville project under city guidelines.

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People Involved

James Fox
James Fox
Developer, Mackinaw Development, LLC
Seeking zoning change for 35-unit Ashland project
MM
Mike Maresso
Architect
Designing third Ashland Avenue project
 Andre Vasquez
Andre Vasquez
Alderman, Chicago 40th Ward
Reviewing zoning change request
MH
Maria Hadden
Alderman, Chicago 49th Ward
Not directly involved in current proposals

Organizations Involved

MD
Mackinaw Development, LLC
Developer
Proposing 35-unit Ashland Avenue project

Chicago developer behind the proposed five-story apartment building at 5036-44 N. Ashland Ave.
Chicago City Council
Chicago City Council
Municipal legislature
Final approval authority for zoning changes

The City Council gives final approval to zoning changes.
CZ
Committee on Zoning, Landmarks and Building Standards
City Council committee
Reviews zoning change requests

Chicago City Council committee that reviews zoning, landmark and building standard changes.

Timeline

2019 November 2026

4 events Latest: Today
Tap a bar to jump to that date

  1. Leona's site cleared for 80 apartments

    Today Development

    Demolition reported; five-story building with ground-floor commercial space planned.

  2. Third Ashland apartment proposal reported

    Today Development

    Mackinaw Development proposes 35 units at 5036-44 N. Ashland Ave.

  3. Developers present Ashland project at community meeting

    Community meeting

    Mackinaw Development outlines 35-unit building with seven affordable units.

  4. Leona's closes in Rogers Park

    Closure

    The restaurant closed after decades in the neighborhood.

Scenarios

1

Vasquez backs Ashland zoning change, project advances

Possible Resolves by Q2 2027

Discussed by: Block Club Chicago reporting; developer statements

Ald. Andre Vasquez approves the zoning change for the 35-unit building at 5036-44 N. Ashland Ave. The proposal then goes to the Committee on Zoning, Landmarks and Building Standards and the full City Council. The developer has said he would not seek more zoning changes for a while if this project is approved.

2

City Council approves both Far North Side projects

Possible Resolves by End of 2027

Discussed by: Block Club Chicago reporting

The 80-unit Leona's site project and the 35-unit Ashland Avenue project both receive the approvals needed to build. Together they add 115 apartments. The Leona's project already has a planned five-story building with ground-floor commercial space.

3

Andersonville project stalls after aldermanic hold

Unlikely Resolves by Q2 2027

Discussed by: Block Club Chicago reporting

Ald. Andre Vasquez declines to advance the zoning change, or the developer withdraws the 35-unit proposal. The Leona's site project may still proceed, but the Ashland Avenue project does not. The article says the developer has already built two projects on Ashland with the same architect.

Historical Context

3 moments from history that rhyme with this story — and how they unfolded.

2019

Leona's closure in Rogers Park (2019)

Leona's, a restaurant that had been a neighborhood gathering place for decades, closed in Rogers Park in 2019. The site later drew reuse proposals, including a Zen Leaf dispensary that was rejected over zoning issues.

Then

The building sat vacant and became a candidate for redevelopment.

Now

The site is now cleared for an 80-unit apartment building with ground-floor commercial space.

Why this matters now

Shows how a failed commercial reuse can become housing in a tight market.

Before 2026

Zen Leaf dispensary rejection at Leona's site

A proposed Zen Leaf dispensary at the former Leona's site was rejected by Ald. Maria Hadden because of zoning issues.

Then

The dispensary did not open.

Now

The site remained available for a different project.

Why this matters now

Explains why the Leona's site went to housing instead of retail.

2020s

Mackinaw Development's prior Ashland projects

James Fox of Mackinaw Development and architect Mike Maresso completed two previous apartment projects along Ashland Avenue.

Then

The projects advanced through the local zoning process.

Now

The team is now proposing a third building on the same street.

Why this matters now

Shows the developer has a track record in the area.

Sources

(2)
Block Club Chicago Illini Current