News | Historic Chicago office tower trades for fraction of former price

Why this matters

Office continues to trade in two distinct markets: trophy assets in walkable submarkets that are leasing at or near record rents, and commodity Class B and C buildings where the basis is still resetting. Underwriting on the latter has moved toward replacement-cost-minus, with credit underwriting now leaning on tenant covenant and remaining lease term rather than mark-to-market expectations. Chicago capital flow has been concentrated in industrial along the I-55 and I-80 corridors and in the most select downtown trophy office submarkets. Multifamily transaction volume has moved up in the Near North and West Loop. For LP-positioned capital, the read-through is that the bifurcation is now a structural feature of the sector, not a cycle to wait out.

Editorial analysis · Real Estate Trail Editorial

On the RET wire

• The 33rd Chicago story tracked on the wire in November 2026. All Chicago coverage →
• Disclosed office deal value tracked in November 2026: $6.2B across 32 reported transactions. All Office coverage →

Computed from Real Estate Trail’s own tracked coverage

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