The topic has been thrown around quite a bit in the past years. Low racer turnout, fields get combined, races up and get cancelled. This year we lost Team Intent's Tour of Glenn Ellyn and xXx Racing's Hillinois (formerly Tour of Galena). What's next?
When i began racing, it was organised under the old ABLofA, whose rules required all member clubs to hold at least one sanctioned event a year. At the time (early 70's) there were dozens of clubs in and around Chicago & NE Illinois, not to mention several clubs in Madison, Milwaukee, and Kenosha. There was at least one, and often two races every weekend from April through August within about 100 miles of Chicago. At the time a total prize list was about $300-$500, with prize list limits set under USOC/IOC rules concerning "amateurism." Most races were criteriums of 25-50 miles held in town squares, parks, and industrial parks. At one time, Illinois had more registered racers than any other state.
It eventually became too expensive for smaller clubs to organise and hold races and many of them folded. Most of the local groups were clubs, not teams, with open membership, and under the old rules sponsorship money was limited and basically restricted to about $500 and only one sponsor's name on a jersey (if indeed one got a jersey!) i don't remember how things came to be run under the USCF or USA Cycling. Prize lists ballooned when the "amateurism" rules went away, and several different racing organisations have arisen over the years.
Don't know what the solution is to increase the number of races. IMHO the infusion of Big Money prize lists and promotional hoopla has actually hurt the sport by reducing the number of small local, more accessible races. The bright spot is the increasing number of cyclocross races in the area.
Since i stunk as a roadie, i took to the velodrome -where i also stunk, but not as bad and the races were shorter- ideal for a working stiff. The big advantage of track is that one can race every week all summer. i highly recommend track for anyone who craves regular and local competition.
Road racing is hard, and it's a huge time commitment amidst competing priorities. We've got a short season in the Midwest and road racing is up against MTB, track, gravel, and 'cross. I know where my priorities lie, but maybe it's time to go to a road race and get stomped just to help the cause. It won't hurt my fitness, that's for sure. I'd like to see road make a comeback here.
HERE is the preliminary Illinois Cycling Association 2017 racing calendar. Clearly there are plenty of options here and this doesn't even account for those near-ish races in southern WI or NE IN.
Of these, here are the races within the Chicago city limits. Come race, come watch, bring a friend.
04/3/17-04/6/17 - Half Acre Cycling's - Skyway Classic Series - Evening races M-TH. Race after work!
(this is a beginner series aimed at bringing in new riders)
04/29/17 - xXx Racing's - Alderman James Cappleman’s 46th Ward Lincoln Park Criterium - (past editions of this race have featured the prologue of Fyxation bicycle's Fyxation Open fixed gear street crit)
05/06/17 - University of Chicago's Monster's of the Midway - Wide 1.1 mile loop crit raced on the Midway Plaisanace
And that's it for (road/crit) racing within the city. Obtaining permits from the city, competition with 'walk's and runs', etc. make it difficult in a city with plenty of things going on all the time.
I am not a fan of crits, personally, and there's not a lot of real road races around. For me personally it's a financial hurdle, but I at least try to promote and show up as a spectator because I do like that teams and organizers are putting in the work to make these options available for racers.