Maybe you need to visit to check up on the state of affairs in the 'cool' era. I biked as primary transit in Minneapolis 2007-2014. The city is commonly ranked in the top ten for bike infrastructure in the U.S. (as you pointed out, admittedly a low bar).[1][2] I've been biking in Chicago for 5 years now and if you're going between any two points that don't happen to be connected by one of the non-deathtrap segments of lakefront, the cycle infrastructure here is at least a decade behind where Minneapolis is at. Most of it due to generally dismal road maintenance which impacts cyclists much harder than motorists, but lots of tremendously unsafe shared road conditions, too.

1. https://www.outsideonline.com/1930411/10-best-bike-cities-no...

2. https://www.travelchannel.com/interests/outdoors-and-adventu...