Perhaps it’s all due to America’s “second city”, but attitudes on betting in Illinois are pretty darn libertarian. Prevailing gambling law has generally been quite flexible if the right legislators, politicos and prosecutors are ameliorated, that is – as daily fantasy sports providers are continuing to learn, three years into continuous court battles.

Betting in Illinois

Sure, lots of the action in the Roaring Twenties was centered on illegal booze in the face of national prohibition. But with such a stranglehold on a variety of, off-the-beaten-path business interests in Chicago, you can bet (so to speak) that Illinois was home to some of the United States’ largest gambling operations.

Mobsters such as James O’Leary and Mont Tennes had built financial empires on betting games well before Al Capone’s serious power grabs began in 1919. Going into the 20s, an illegal gambling house was keep alive via bribery and providing blackjack, roulette, craps and faro and/or poker tables. Betting on horse racing was also the purview of the gangster until the early 30s when Illinois followed most of the country’s trend to standardizing and legalizing pari-mutuel betting at horse tracks. Even so, by the time of the Great Depression, the illegal joints were so well-entrenched as to draw more bets than the legitimate tracks straight through the mid-1940s.

High-profile hits of key Mafiosi, usually centered on the Chicago Outfit, continued to be regular occurrences in Chicago straight through the 1950s. And illegal gambling flourished. Ultimately, by 1990, Illinois lawmakers had apparently adopted an if-you-can’t-beat-’em attitude, allowing the licensure of riverboat gambling on the state’s waterways. Ten years later, land-based casinos were allowed as well. The cynic could remark that certain, likesay, non-traditional lobbyists may have been involved in such legislature – and such a reality might be reflected in the attitude of state politicians who are oddly righteous about DFS, whose major providers are 100% mob-free…

In late December 2016, Illinois attorney general Lisa Madigan offered a legal opinion which concluded that “the daily fantasy sports contests offered by FanDuel and DraftKings clearly constitute gambling.” The Fantasy Contests Act, a bill that would provide provisions for DFS betting in Illinois, was heard by the Illinois legislature early in ’17 and was tabled shortly thereafter. As of 13 months later, no further moves have been made on the bill.

Football in Illinois

Let’s face it: For the outsider, football can be summed up in those two words promulgated on a highly overrated era of Saturday Night Live. So who are who to disillusion football fans? So if a picture’s worth 1,000 words, here’s at least 3,000 worth about Chicago Bears history…

Hey, did you know the Bears have nine NFL titles? Of course, eight of those came before the Super Bowl existed and seven were before 1947. Chicago can certainly take credit for the grandest demolition of an NFL team ever in the 1940 NFL championship game.

On the way to finishing off arguably the greatest single season in the Super Bowl era, the 1985 Bears produced one the top 10 songs of the 1980s.

And a few years afterward came the Bears’ last significant addition to greater pop culture. NFLbets bets you can’t sit through the below clip in its entirety without hating yourself.

Betting on Football in Illinois

As it stands here in 2018, betting even on daily fantasy football is technically illegal in Illinois, but police are hardly rounding DraftDuel players on a regular basis (or at all). Given the state’s long history with laxity on crime in the areas of vice, we reckon that state authorities will simply look the other way on sports betting for years to come yet.

Betting on football may not become 100% legal for some time in Illinois, but as know, there’s a pretty significant gray area in which to play to your heart’s content.