Reinventing Downtown Chicago by Repositioning and Converting Vacant Offices

This article is originally from officeinsight published January 19, 2026 by Sophie Bidek.

In Chicago’s iconic Loop, many once-bustling office towers now stand underused, their halls quieted by hybrid work patterns that have reshaped the demand for office space. However, a growing back-to-work trend is prompting owners to invest in existing office properties at the same time that the city has leaned into a plan to convert outmoded office inventory into housing.

While vacancy in Chicago’s Central Business District remains elevated, with year-to-date leasing at just under 5.4 million square feet, sublease availability has declined for two-consecutive quarters, to 5.3 million square feet. Meanwhile, leasing volumes are at their highest since the pandemic, availability is trending lower and the best-located buildings are drawing more tenant interest.

It appears that the new market cycle is beginning to unfold, and renewed office-to-office investment is expected in many existing buildings. Like New York City and other top markets, Chicago is poised for reinvestment by existing owners, and by new owners with capital to strategically refresh and reposition newly acquired properties. This provides enormous opportunity for thoughtful, targeted improvements.

As investors begin to consider office repositioning, Chicago is embracing an ambitious strategy to transform non-viable corporate spaces into desperately needed housing. This approach tackles two urban challenges at once: filling vacant towers with life and addressing an affordable housing shortfall of roughly 100,000 homes in the city.

At the heart of Chicago’s strategy is the LaSalle Street corridor, the one time financial canyon now poised for a residential renaissance. Under the city’s “LaSalle Street Reimagined” initiative, six major office-to-residential projects are moving forward, channeling roughly $900 million in private investment, backed by about $250–$300 million in city incentives.

In April 2024, City Hall announced support for four large conversions on or near LaSalle Street, including more than 1,000 new apartments of mixed-income housing, with over 300 affordable units. That’s nearly a 1,000% increase in affordable homes in the Loop, which previously had only 32. By turning vacant offices into homes, Chicago expects to repurpose 1.3 million square feet of empty space and cut LaSalle’s commercial vacancy by more than 25%.

Several LaSalle Street conversions are already under construction: the Rector Building is being reworked into apartments, 30 N. LaSalle into hundreds of homes, 111 W. Monroe into mixed residential use, and the landmark Field Building into a major adaptive-reuse program. Together they represent a first wave that will restore round-the-clock life to blocks that once emptied after 6 p.m.

Execution accelerated in 2025. City committees advanced $65 million in subsidies this spring, while new landmark incentives pushed the 135 S. LaSalle conversion forward with 386 mixed-income units across 1.3 million square feet.

From a practice standpoint, office-to-residential conversion requires careful engineering, creative space planning and sensitivity to history, all balanced with marketability, cost and livability. Amenity selectivity and ROI-driven design are key. Owners now focus on features that affect leasing and quality of life, including multifunctional spaces and daily-use amenities rather than flashy, underused extras. Designing for adaptability is equally important. Large gathering rooms can host a 120-person event one night, a lounge another and small-group activities by day. Smart scheduling and support spaces keep amenities in constant use, improving returns and user experience.

Conversions often mean carving new light wells, rethinking elevator cores and overhauling building systems. In Chicago, codes around natural light and ventilation have been a challenge with the deeper building depths of the historic offices, but collaboration between designers, engineers and officials is helping adapt standards for conversion realities. Conversions also preserve architectural heritage. Reusing landmark facades and interiors is both an economic and cultural win: incentives like tax credits make projects viable while residents gain homes with a sense of place.

Vocon has deep experience nationally with office repositioning and adaptive-reuse projects, bringing creative thinking and technical rigor to help transform buildings. On the corporate side, we’ve helped owners rethink offices with hospitality-inspired amenities and targeted upgrades that make older buildings competitive again.

A 21-story office tower is currently undergoing a full modernization including an expanded lobby, new windows and storefronts, upgraded elevators and redesigned mechanical systems to improve comfort and efficiency. The comprehensive transformation, paired with flexible floor plates and a new conference and social center, is repositioning the property as a contemporary workplace destination with elevated tenant experience and strong appeal for major occupiers.

Similarly, we recently completed a careful repositioning of a 900,000-square-foot office property originally designed by a renowned mid-century architect. To bring the building into line with current tenant requirements, we refreshed the lobbies, enhanced interiors and added a new amenity suite that blends original materials with modern design. Additional upgrades include all-new elevators and a restored elevator bay, conference facilities and a rooftop garden, collectively repositioning the property as a sophisticated, hospitality-driven workplace that honors its architectural legacy while aligning with modern tenant expectations.

Additional work that I led before joining Vocon includes contributing to the adaptive reuse of a late-19th-century landmark structure, transforming a former private club into a hospitality destination with guestrooms, event spaces and a contemporary rooftop addition. Additionally, my experience includes supporting a mid-century modern tower through the local landmark designation process and developing early repositioning concepts featuring an activated, amenity-rich ground floor, integrated food and beverage offerings, a rooftop lounge and a multi-level wellness component.

Past work within the Fulton–Randolph Historic District contributed to the adaptive reuse of more than a dozen existing structures as the area evolved into what is now known as Fulton Market. These projects involved transforming former warehouses, meat-packing facilities and cold-storage buildings into modern workplaces, thereby reinforcing the district’s distinctive character and demonstrating the catalytic impact of reuse within historic urban contexts.

These buildings already had good bones. Today, the convergence of a return-to-office push, office-to-residential conversions and asset repositioning is shaping the Loop’s next chapter. Through updates and additions, owners can restore relevance, attract tenants and residents and reinvigorate the district’s streets and skyline. Work like this will drive near-term recovery and long-term vitality.