Is Chicago the Gambling Capital of the Midwest?

Once a den for gambling rings and scandals (Al Capone, anyone?), Chicago has come a long way in recent years. We’ve got Vegas to the west and Atlantic City to the east. Nestled between them is the midwestern metropolis of Chicago, which is putting the “win” in WINdy City and swiftly becoming the Midwest’s top gambling hub. 

Let’s look at Chicago’s recent gambling renaissance, including new casinos, riverboats turned landlubbers, and more, all from me, a lifelong Chicagoan. 

The Downtown Crown: Bally’s Casino

Bally’s is poised to spearhead Chicago’s ongoing gambling growth as it constructs a massive casino, hotel, and entertainment complex on the former site of the Chicago Tribune. The property is slated to open early next year with 3,400 slots, 170 table games, 500 hotel rooms, and a 3,000-seat theater. 

In the meantime, Bally’s has already planted roots in Chitown. The company opened its temporary casino at the historic Medinah Temple in River North. The three-level casino is a sight to behold, preserving stained glass windows that gave the original temple its architectural identity and giving you the feeling that you’re on the up and up as you ride the escalator in search of new games. 

If you’re in downtown Chicago and want to place a few bets, the Bally’s temporary casino is an excellent stop right downtown, surrounded by restaurants, shopping, and nightlife. 

And soon enough, Chicago will open the $1.7 billion River West Bally’s property, further cementing the city’s status as a gambling hub.  

A Major Score for the Suburbs

While downtown grabs the headlines, the South Suburbs have quietly claimed a massive piece of the regional pie. If you drive about 25 miles south of the Loop down I-80, you’ll hit Wind Creek Chicago Southland.

Straddling the border of East Hazel Crest and Homewood, this $529 million, 70,000-square-foot facility fundamentally changed the Chicago gambling market. Owned by Wind Creek Hospitality (an arm of the Poarch Band of Creek Indians), the casino floor features 1,400 slot machines and 56 live table games. The venue features a luxury AAA Four Diamond hotel tower, a rooftop lounge with skyline views, and a high-end sports bar. It brings a legitimate, full-scale tribal resort experience directly to Chicago's southern gates, ensuring that top-tier gaming isn't just a north-side or downtown luxury.

Digital Betting In Illinois

Illinois was among the early wave of states to legalize mobile sports betting following the federal downfall of PASPA in 2018. However, the initial rollout included a serious catch -- and trust me -- that catch put a lot of miles on my car.

When the state's sports betting market first launched, you were legally required to visit a sportsbook’s physical, partnered casino in person just to complete your mobile registration. If you lived hours away from the nearest retail sportsbook, that first hurdle was an absolute pain.

Thankfully, Illinois lawmakers eventually did away with that rule, opening the floodgates for remote sign-ups. Today, the state is flush with top-tier digital sportsbooks, including DraftKings, FanDuel, BetMGM, and Caesars.

The digital ecosystem doesn't stop at sports. Illinois players have widespread access to promotional sweepstakes casinos, alongside a robust online lottery platform that lets you buy Powerball or Mega Millions tickets and play instant, scratch-off-style games directly from your phone. The bottom line? Visitors and residents don’t even need to set foot inside a brick-and-mortar casino to get a taste of what the city's gambling scene has to offer.

Groceries, Gas, and Gambling: VGTs are (almost) Everywhere

If you're exploring greater Chicagoland, you’ll eventually notice something uniquely fascinating when you stop for gas, grab groceries, or head into a local pub. Are those slot machines next to the cash register?

Well, yes and no. The machines you see embedded in local businesses across the suburbs and select areas are Video Gaming Terminals (VGTs). These machines are a massive economic engine, funneling critical tax revenue back into the local bars, restaurants, and truck stops that host them.

While they look, sound, and feel exactly like a classic casino slot machine, allowing you to sit down and choose from dozens of slot-style games, they operate differently under the hood. Instead of relying on a standard casino slot Random Number Generator (RNG), VGTs run on a centralized lottery model where outcomes are determined by electronic drawings. For the casual player, the experience feels nearly identical to a slot game, so there’s always action to be had in and around Chicago. 

Greater Chicagoland’s Evolving Gambling Landscape

To truly appreciate where Chicagoland gaming is going, you have to look at where it started. For decades, Illinois law strictly confined suburban casinos to navigable waterways, which birthed the "riverboat casino" era. But floating on a river has its limits, and the state's modern gaming laws have finally allowed these legacy properties to ditch the water and move entirely onto dry land.

PENN Entertainment is spearheading this land-based revolution with two massive suburban overhauls:

• Hollywood Casino Joliet: Ditched its long-standing riverboat setup for a completely new, easily accessible land-based casino right off I-80. It’s already up and running.
• Hollywood Casino Aurora: Swapped its old floating home on the Fox River for a $360 million land-based resort next to the Chicago Premium Outlets mall off I-88. The venue is under construction and will feature a hotel, a massive retail sportsbook, and a celebrity-chef dining lineup featuring concepts like Sorella by Giada (from Giada De Laurentiis).

By moving to land, these properties are shedding the cramped, multi-level layouts of old vessels and building expansive, single-level gaming floors with modern amenities that rival anything you'd find on the Vegas Strip. Others may follow suit. We might see Harrah’s Joliet or Grand Victoria in Elgin move toward land next. 

Conclusion: Chitown Is Winning Big

Thanks to a friendly political environment for gambling operators and an ongoing legislative willingness to evolve beyond archaic stipulations, Chicago has already found its role as the Midwest’s premier gambling hub. The next few years will only shape this reputation further as the Bally’s casino opens its permanent location and suburban destinations head ashore.