This week, Chicago turned sports stats into a tradable market, told its next class of lawyers to put AI away, and floated a half-billion-dollar plan to rebuild the Loop around culture. Plus Cloudflare and PostHog are in town next week for AI Tinkerers.

Here’s what’s happening in Chicago:

CME Group is turning sports stats into a financial market.

Last week they announced a partnership with Chicago-based startup FutureSports that converts league-approved play-by-play data into rules based indexes, and CME will list futures and options on the FutureSports Performance Indexes.

First monthly and quarterly cash-settled contracts are slated to begin trading this summer pending regulatory review.

FutureSports says the buyers are stadium owners / operators, sponsors, insurers, apparel makers, and broadcast partners looking to hedge exposure to a $650B global industry.

Starting this fall, UChicago Law is barring electronic devices in its required 1L core courses as part of a broader AI strategy: AI-resilient teaching, elevating the 'essential human' skills that distinguish good lawyers and teaching responsible use of the tech. The device rule is a pilot for the 2026-2027 year, and it applies to the foundational classes. Exams in those courses go in-class with no internet, files, or apps.

There are exceptions. Professors can name classroom "scribes" to take notes on devices and allow electronics for things like in-class polling, with disability accommodations preserved.

Legal writing is handled differently, with students drafting without AI as the foundation while using it for research, revision, and oral argument prep.

UChicago isn’t alone. Berkeley and UT Austin have moved in the same direction which makes this a real trend line worth tracking.

AI Tinkerers Chicago is back on Tuesday August 11th and this month we're joined by Cloudflare and PostHog for a night built around one of the hardest problems in AI right now: getting products from a working prototype to something that actually holds up in production.

We’re covering the full stack of shipping AI: edge infrastructure patterns for keeping things fast and reliable, the instrumentation and analytics that let teams iterate quickly, and how AI agents can automatically spot product issues, generate fixes, and even open pull requests for review.

Tuesday, August 11, 5:30 to 8:00 PM

Last week I sat down with Lou Raizin to talk through the Cultural Stadium, his $300 to $500M plan to rewire downtown Chicago around arts and culture.

Raizin runs Broadway in Chicago and helped bring Millennium Park to life, along with the Loop Theatre District.

The pitch is instead of one mega-development, we’d have a hundred smaller projects stitched together across the Loop.

Free museum access for every kid ages 3-13, a free residency program for up-and-coming artists, a floating farmers market on the river, alleys reborn as public art exhibits, a stretch of Lower Wacker converted into a concert hall, and a glass canopy connecting the buildings along LaSalle Street so the corridor works year round.

This is definitely the most ambitious downtown reinvention Chicago has floated in 20 years, and it sits right at the intersection of culture, real estate, and the foot-traffic problem every Loop employer is tracking.

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