Two major tenants have quietly started trimming their Loop footprints, a fresh sign that downtown Chicago’s office hangover is far from cured. Basis Technologies is shopping a big block at the historic Sullivan Center, while Lessen is pitching full floors in a LaSalle Street tower, underscoring how demand keeps gravitating to modern, amenity-heavy buildings as large chunks of older space sit idle.
As first reported by The Real Deal, Lessen has put just over 37,000 square feet on the 23rd floor, or roughly 39,000 square feet on the 22nd floor, up for sublease at 203 North LaSalle Street. Basis has listed its entire sixth-floor office at the Sullivan Center, 11 East Madison Street, totaling about 70,000 square feet. Both tenants are tied to their original deals for years to come. Basis’s lease runs through October 2030 and Lessen’s commitment stretches to February 2040, so these are long-dated blocks being quietly shopped to new occupants.
The move reflects evolving workplace habits as much as market conditions. “Basis is a remote first company. While we do utilize our office space, we do not fully utilize all of it daily,” Basis president Chris Hendricks told the outlet.
Market Backdrop
The timing of these subleases is no accident. Downtown vacancy remains stubbornly high, and landlords are still trying to figure out what to do with all the extra square footage. Data from CBRE pegs direct downtown vacancy near 27.0% in the first quarter of 2026, a level that leaves plenty of leverage with tenants that are willing to move.
Market analysis from JLL shows an increasingly split market, with top tier, fully amenitized “trophy” towers drawing the most interest while older, less competitive buildings lag behind. That classic flight to quality is pushing many tenants into newer or heavily upgraded properties and shunting secondary space onto the sublease market.
Thompson Center And The Trophy Chase
Developers and City Hall are banking on a handful of marquee projects to soak up at least some of the excess space. Google’s multi hundred million dollar overhaul of the Thompson Center has become the poster child for this strategy, turning a once unloved government complex into a would be trophy magnet.
One of the biggest gets on the wish list is Morningstar. The investment research firm has been in talks to take nearly 300,000 square feet in the revamped Thompson Center, according to Morningstar flirts with mega lease on Hoodline. The outlet notes that negotiations remain tentative, yet the potential deal highlights how demand could concentrate in a tight circle of refreshed Loop assets while older buildings keep scrambling for Plan B.
What Landlords And Tenants Will Do Next
For tenants, subleasing is a pressure valve. It lets companies shrink their day to day footprint without eating the full cost of a long term lease. For landlords, it buys time to rethink lobbies, add amenities and rework floor plans in hopes of luring higher quality occupants once the dust settles.
Lessen’s moves illustrate how fast the chessboard can change. The company only moved into 203 North LaSalle about a year ago and, according to reporting cited in the original coverage, exercised an option earlier this year to end a prior Prudential Plaza lease for $7.5 million. That payout is a reminder that big tenants are actively reshuffling their commitments across the city rather than simply riding out old deals.
Brokers expect the current wave of subleases to appeal most to firms that want turnkey, amenity rich space instead of costly build outs. Plug and play, full floor options like those at 203 North LaSalle and the Sullivan Center fit that bill, especially for companies that want a Loop address without a renovation headache.
More listings are likely as employers juggle long leases with smaller in office headcounts and as owners decide whether to upgrade, convert or simply wait out the market. For downtown Chicago, the big question is whether a few headline grabbing leases at trophy properties will spark a broader return to the Loop or simply speed up the conversion of aging office towers to something entirely different.
