When it comes to air shows, the Midwest doesn't just watch—it performs. The Chicago Air & Water Show is the largest free outdoor air and water show in the United States, drawing over 2M spectators to the Lake Michigan shoreline each August, a tradition stretching back to 1959. Cleveland's National Air Show has been a Labor Day weekend staple at Burke Lakefront Airport for decades, set against one of the more dramatic urban backdrops in the country with the skyline and Lake Erie framing every pass. Milwaukee joins the lakefront action with its own Air & Water Show returning July 25–26 along the waterfront, and Dayton—a city with aviation in its bones thanks to the Wright Brothers—hosts the CenterPoint Energy Dayton Air Show June 13–14, this year featuring the U.S. Navy Blue Angels. Down in Indianapolis, pilots from the 175th Fighter Squadron flew over the Indy 500 and the race's iconic pace lap draws a couple of Blackhawk helicopters tracking the field from above. It’s one of the few sporting events where the air show is baked right into the main event. From the Great Lakes shoreline to the birthplace of aviation, the Midwest's skies are about to get very loud, very fast and very worth looking up for.

The Midwest's startup engines are cleared for takeoff. Pittsburgh is pulling double duty with Gray Swan closing a $40M round—its AI red-teaming platform stress-tests the biggest models in the game—and Hellbender adding $12.5M in seed funding for AI hardware. Ann Arbor is having yet another moment too, with Utilidata landing a $40M Series C for its grid intelligence platform and Volt Harbor publicly launching with a $2M seed. Chicago keeps stacking: Trajektory raised $8M for its sponsorship intelligence platform, Oath closed a $6.6M seed bringing automation to audit and accounting, Benji raised $6.25M for loyalty partnership infrastructure and Kosmos pulled in $5M from Norwest for enterprise IT intelligence. Ohio's decision to pause data center tax breaks after costs blew past projections is worth a read too. See all the latest deals + news below.

Have any insights into the Midwest ecosystem or a funding announcement to share? Want to share your favorite type of airplane? Send us an email: [email protected]

Exits

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Have exciting news to share? If you're announcing a funding round, exit or other milestone, send your press release to [email protected] to be featured. While we can’t share everything, we love to feature great stories from across the region.

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