Chicago has a proud history of gambling, from Capone opening up parlors in the Roaring Twenties, to Cutler opening up the field into triple-coverage. Continuing that tradition, Rivers Casino.
Located in Des Plaines, just a short jaunt up the Kennedy from downtown (with planned shuttles from the Loop & Blue Line for the driving-averse), RC's a sprawling temple of risk and revelry that's the first casino in the nation to apply for LEED certification, which should be in the bag given how much of your green they'll be taking. Speaking of which, the 44000sqft gaming floor includes more than 1000 slots (from Star Wars to Wheel of Fortune), and 48 tables spanning craps, baccarat, and blackjack, which rolls as high as 50k per hand in the VIP area (though if she could have gotten 50k per hand, Pam Anderson never would have to do VIP in the first place). Breaks in the action can be filled at Lotus, a 360-degree cocktail lounge in the center of the floor, while adjacent sustenance options range from aged prime steaks at Hugo's Frog Bar & Chop House, to steaming bowls of ramen at the Asian noodlery MianBar, to fresh-packed burgers and shakes at FLIPT, a trippy, '50s-style diner whose color-changing lights are reminiscent of old-timey hair dryers, though that doesn't mean the FOOD blows.
Those seeking even more epic distractions can hit Cube, a multi-level, patio-equipped entertainment complex that transitions seamlessly from nightclub, to concert venue, to flatscreen-studded sports bar, meaning you can watch triple-coverage of Cutler's next gamble.