Casinos Across The Midwest: A Road Trip Full Of Hits, Stands, And Bad Beats

Living in Las Vegas, it almost feels wrong to board an airplane for the sole purpose of gambling. After spending the better part of four months confined to Clark County, however, I remembered something: My page is called “Casino Collective,” not “Las Vegas Collective.” Clearly, it was time to get back on the road. This time, I was headed to two of the Midwest’s finest cities — Detroit and Chicago — for a long weekend of casinos, hockey, and, hopefully, a little luck at the tables.

Stop No. 1: MotorCity Casino Hotel

My Detroit adventure got off to a promising start when I spotted my personal favorite table game: Spanish 21! I had no idea it was so prevalent in this part of the country. Naturally, there was only one thing to do: pull up a chair.

For anyone unfamiliar with Spanish 21, it's a blackjack variation played without the numbered 10s. The jacks, queens, and kings remain, but those missing 10s change the game considerably. What makes it fun are the unusual rules and payouts. An unsuited 6-7-8, for example, pays 3:2, and players can double down after doubling or even on three cards. It's a game with plenty of opportunities for some wild swings.

I am usually a devoted basic-strategy player at the blackjack table, but there is a part of me that wants to throw caution to the wind and play more aggressively. Hitting a 12 against a dealer's bust card? In traditional blackjack, absolutely not. In Spanish 21, however, the strategy changes enough that I finally have an excuse to make some of those plays. It's almost like the game was designed for me.

As is so often the case with my losing sessions, things started beautifully. I was drawing 20s and blackjacks, doubling down on my doubles, and even collecting those coveted 6-7-8 payouts. What could possibly go wrong?

Well, plenty, apparently. Just as I was closing in on my stopping goal, the wheels came off. I went on tilt, raised my bets to chase my losses, and proceeded to do just about everything a responsible gambler shouldn't. By the time I finally walked away, my chips had vanished. Final cash-out: $0.

Not exactly the grand opening I had envisioned for the trip, but what's a casino adventure without a little adversity?

Despite the rough session, MotorCity remains one of my favorite casinos in the area. Housed in a former Wonder Bread factory near downtown Detroit, the property has a ton of character and a personality all its own. Fortunately, it was also my home for the next couple of nights, so I had plenty of time to appreciate the place away from the blackjack table.

All in all, table minimums this evening at MotorCity included $5 triple-0 roulette; $10 continuously shuffled 6:5 blackjack, Chase the Flush (a High Card Flush variant), Three Card Poker (TCP), Ultimate Texas Hold’em (UTH), and Mississippi Stud (MS); $15 Spanish 21 and double-0 roulette; $25 eight-deck 3:2 blackjack, Fortune Pai Gow Poker (PGP), 5x odds craps, and baccarat; and $100 single-0 roulette and six-deck 3:2 blackjack.

Stop No. 2: Caesars Windsor

There were two major items on my Detroit itinerary: catch a Red Wings hockey game and finally exchange the Canadian cash left over from my February Seattle/Vancouver trip. Today, I would accomplish both. Not a bad way to spend a Friday!

I woke up relatively early — or, according to my body clock, at an absolutely unreasonable hour — and made my way through the tunnel into Windsor, Ontario. My destination was Caesars Windsor, one of my favorite casinos in the region, for a little morning blackjack.

I figured I was playing with house money, in a sense. Even if I lost everything but a single dollar, at least I would have finally put that colorful Canadian currency to use instead of letting it collect dust in my drawer for another eight months.

Unfortunately, Canadian Thanksgiving weekend had apparently brought everyone in Windsor to the same blackjack table. The lone open game was packed, and nobody looked remotely interested in giving up a seat. I wandered the casino for a while, stepped outside for a walk along the river separating the United States and Canada, and returned just in time to see a few more tables opening. Perfect timing!

I settled into a freshly opened table with a friendly Canadian dealer who sprinkled the occasional “eh” into conversation and discussed the weather in Celsius. It doesn't get much more Canadian than that! The first 20 minutes were a back-and-forth affair, but when a new dealer tapped in, everything changed. Suddenly, I couldn't seem to lose. I eventually cashed out with twice the Canadian money I had brought to the table. Now that is a currency exchange I can get behind!

Caesars Windsor is also one of my favorite casinos from a design standpoint. With its marble statues and unmistakable Roman styling, it feels like a close cousin of Caesars Palace in Las Vegas. The big difference? In my experience, the table game rules on this side of the border are considerably friendlier to the player.

Friday morning table minimums at Caesars Windsor included $15 UTH and I Luv Suits; $20 double-0 roulette, $25 eight-deck 3:2 blackjack, eight-deck 6:5 blackjack, Double Up blackjack, 5x odds craps, and baccarat; and $100 Face Up PGP. There were also Spanish 21, Double Down Madness, TCP, and MS tables that had not yet opened for the day.

Stop No. 3: MGM Grand Detroit

Back on American soil, I was carrying a fresh stack of U.S. cash from the Caesars Windsor currency exchange — although “fresh” might not be the right word. These were some of the oldest-looking $100 bills I had ever seen. In fact, at a later casino, a dealer actually called over the floorman to make sure they were acceptable! With my suspiciously vintage bankroll in hand, I headed to MGM Grand Detroit.

Unlike many gambling destinations where casinos sit on the outskirts of town, Detroit's three major casinos are all in or near downtown. MGM Grand feels the most urban of the bunch, with skyscrapers right next door and a parking garage shared with one of them. You certainly don't forget you're in a major city here.

Unfortunately, I had only a short window to explore before heading to Little Caesars Arena for the Red Wings game against the Seattle Kraken. That made MGM Grand one of only a couple casinos on this trip where I wouldn't actually sit down and play.

Of course, that's exactly when I found an open seat would be available at a Spanish 21 table. After the beating I took at MotorCity the previous night, the opportunity for redemption was practically calling my name. Sadly, hockey won this particular battle for my attention.

One thing I really appreciate about Detroit's casinos is that they're largely nonsmoking, setting aside separate smoking areas for many of the same games. I didn't fully appreciate that setup until I ventured into one of those smaller smoking sections to check the tables. The difference was immediate. I practically held my breath for the entire walk through it.

The Friday evening crowd was beginning to arrive, and I particularly liked the center bar near the table games. If I lived in Detroit, I could absolutely see myself grabbing a seat there to watch a game. It looked like a great place to spend an evening, even without a wager on the felt.

Friday evening table game minimums here consisted of $15 Let It Ride, Criss Cross Poker, MS, and TCP, Pontoon 21 (same as Spanish 21, it’s also what it is called at MGM National Harbor), 5x odds craps, UTH, and triple-0 roulette; $25 for six-deck 3:2 blackjack, Crapless craps, six-deck 3:2 Free Bet blackjack, double-0 roulette, Face Up PGP, and baccarat; and $100 single-0 roulette located in the high limits room.

MGM also offered 2-Way Monte, which I had never seen at any other casino, and Four Card Poker tables that had not opened for the evening.

Stop No. 4: Hollywood Casino at Greektown

Greektown is one of Detroit's liveliest entertainment districts, making it a natural home for a casino. As a regular at M Resort back in Las Vegas, I also had another reason to stop by: Hollywood Casino at Greektown is part of the Penn Entertainment family, meaning I could put my Penn Play card to work away from home.

The layout here is a little different from the other Detroit casinos. The main gaming floor, on the second level, allows smoking, while the much smaller non-smoking floor sits downstairs. Unless you know where to look, you could almost miss it entirely.

I found a seat at a $25 blackjack table alongside a couple who were betting what seemed like a small fortune on every hand. My session was fairly uneventful until a $5 chip I had won on blackjack found its way onto the Perfect Pair side bet. Just like that, my little red chip turned into five green $25 chips! That $125 payout ultimately saved the session, and despite a late slump, I walked away $100 ahead. I'll happily take that return on investment.

The place was absolutely buzzing. Red Wings jerseys were everywhere, suggesting plenty of fans had the same postgame idea I did. Almost every table was occupied, which made finding a relatively empty blackjack table feel like a small victory before I had even placed a bet.

With the casino planted in the middle of a bustling nightlife district, the crowd grew a little more rowdy as midnight approached. That was my cue to call it a night. Besides, I had an early alarm and a long drive ahead of me.

On a Friday night at Hollywood Casino at Greektown, table minimums included $10 MS, TCP, Four Card Poker, High Card Flush, & Criss Cross Poker; $15 eight-deck 3:2 blackjack (only one table was $15, located downstairs — the rest were $25 in the main pit), double-0 roulette, Double Down Madness, and UTH; $20 eight-deck 3:2 Free Bet blackjack, $25 Fortune PGP, 5x odds craps, and baccarat; $50 single-0 roulette; and $100 six-deck 3:2 blackjack.

Stop No. 5: Hollywood Casino Toledo

By day three in the Eastern Time Zone, my internal clock was still refusing to cooperate. The 7 a.m. alarm might as well have been going off at 4 o’clock. With a full day of driving ahead, my first stop was a gas station for an energy drink. Desperate times call for desperate measures.

It's becoming increasingly rare for me to visit a casino I've never seen before, especially in an area I've traveled through previously. Today, however, I had a new one to cross off the list: Hollywood Casino Toledo, another Penn Entertainment property, just across the state line in Ohio.

For a state with as many people as Ohio, I've always found its casino selection surprisingly limited, especially when it comes to properties offering live table games. Thankfully, Hollywood Toledo is one of them.

I arrived around 8:30 a.m., when the casino was still easing into the day and only a handful of tables were open. Can't say I was surprised.

My first impression was a good one. This property still has that older Hollywood Casino look, much like the Charles Town, West Virginia, location I enjoy visiting when work takes me near Washington, D.C. I have a soft spot for that style, especially as more Hollywood properties seem to be moving away from it — as my next two stops would demonstrate.

With Chicago still a long drive away, I decided to pass on gambling this morning. I did, however, manage to take a few photos for Instagram and help myself to a couple of free sodas from the self-serve machines. Not exactly a high-roller visit, but productive nonetheless.

Saturday morning table minimums at Hollywood Casino Toledo included $5 UTH, $10 six-deck 3:2 Free Bet blackjack and double-0 roulette; $15 eight-deck 3:2 blackjack; $25 baccarat; and $50 six-deck 3:2 blackjack in the high limits room. There were also 5x odds craps, High Card Flush, TCP, Crazy 4 Poker, MS, and Run ‘em Twice tables that had not opened yet for the day and had no posted limits.

Stop No. 6: Hollywood Casino Joliet

The last time I visited the Chicagoland area, Hollywood Casino Joliet was still operating out of a small riverboat on the Des Plaines River. Apparently, a lot can change between visits.

This time, I pulled up to an entirely new land-based casino, a complete transformation in size, style, and atmosphere. It reminded me of discovering Treasure Chest Casino's move ashore during my New Orleans trip over the summer. Another riverboat era had come to an end.

The casino was packed with weekend revelers and fans following the Chicago White Sox's memorable playoff run, which, unfortunately, was coming to an end in Cleveland that very night. The atmosphere was lively, even if the baseball results weren't going the home crowd's way.

Much like Greektown the previous evening, almost every table was full. Then a seat opened up just as I walked past, and nobody was there to claim it. Lucky me — or so I thought. What followed was one of the most frustrating blackjack sessions of the entire trip. Things got so bad that I didn't even feel comfortable holding a 20!

Back in Michigan and Ontario, I had apparently taken for granted the simple pleasure of winning two or three hands in a row. Here, that felt like an impossible dream.

After roughly an hour, I colored up with the grand total of $0. Illinois, the state where I was born, certainly wasn't rolling out the welcome mat for my return.

I have mixed feelings about the new Hollywood Joliet. On the positive side, everything is bright, fresh, and spotless. The purple-heavy design actually reminded me of Harrah's in Las Vegas, a big departure from the red tones of the old riverboat. On the other hand, it feels a bit like every other modern casino: one large rectangular room, tables in the middle, sportsbook off to the side, and not much of a distinctive theme. I miss some of the character, but I could still see myself visiting regularly if I lived nearby. There was no hotel operating during my visit, although it looked like one was being built next door.

Saturday night table limits at Hollywood Casino Joliet included $10 for eight-deck 3:2 blackjack (only one table with that limit, the rest were $15), TCP, & MS; $15 20x odds craps, double-0 roulette, and UTH; and $25 baccarat. The only game not open was single-0 roulette, which had no posted limits.

Stop No. 7: Hollywood Casino Aurora

I'm starting to notice a theme here. Four consecutive stops have now been at casinos flying the Hollywood banner. I'm not complaining, though. At this rate, my Penn Play card is getting more exercise than I am!

Just like Joliet, Hollywood Casino Aurora recently traded its former riverboat home for a shiny new land-based property. And when I say these two casinos look alike, I mean they look ALIKE. The exteriors have some differences — Aurora has an attached hotel, for one — but inside, the gaming floors are practically twins, right down to the layouts, games, and limits.

I do like these new Hollywood casinos, but the cookie-cutter design leaves me a little disappointed. My social media bio proudly declares, “No two casinos are the same.” Penn Entertainment seems determined to prove me wrong.

I sat down with one modest objective: break the losing streak and get back into the win column. After an hour of play, I can report with pleasure that I walked away exactly $10 ahead, even after tipping the dealer! After the disaster in Joliet, that felt like a major comeback.

I might have stayed longer, but a fellow player was growing increasingly irritated with everyone else's basic-strategy decisions, eventually drawing the attention of the floorman. At that hour, I had neither the energy nor the patience for blackjack-table drama. I took my $10 victory and made my exit.

Saturday night (into the early hours of Sunday morning) table minimums at Hollywood Casino Aurora included $10 MS; $15 six-deck 3:2 blackjack, 20x odds craps, UTH, and TCP; and $25 baccarat & double-0 roulette.

Stop No. 8: Horseshoe Hammond

At long last, my morning alarm felt somewhat normal. Naturally, that happened just in time for me to prepare to fly back to Pacific Time. Go figure.

But first, next up was Horseshoe Hammond in Hammond, Indiana — a city that had been floated as a future home for the Chicago Bears, for reasons I still can't quite wrap my head around. Unfortunately, the blackjack conditions at Horseshoe were among the least appealing I encountered all weekend.

Still, Horseshoe has a couple of things going for it. For starters, it's probably my favorite property in the Horseshoe family from a design standpoint. The classic interior makes it feel like an old-school gambling hall, and I love that atmosphere. Better yet, I spotted a Spanish 21 table. At last, another chance to avenge my MotorCity loss!

There was just one problem: The game used a continuous shuffling machine. Anyone who has read my previous reports knows how I feel about those contraptions. Let's just say the relationship is not a friendly one, and this session did absolutely nothing to improve it.

Even with the numbered 10s removed, the dealer seemed incapable of making anything other than 20. Meanwhile, the Spanish 21 strategy plays I normally enjoy — hitting 12s and 13s against seemingly any dealer upcard — kept sending me straight over 21. It was painful. Naturally, I made things worse by buying back in, apparently determined to experience the same misery twice. I finally walked away empty-handed.

And just like that, every dollar I had won in Michigan and Canada was gone. So much for the comeback tour.

Sunday morning table limits at Horseshoe Hammond included $5 UTH; $10 I Luv Suits; $15 Crapless craps, continuously shuffled 6:5 blackjack, continuously shuffled Spanish 21, double-0 roulette, and baccarat; and $25 six-deck 3:2 blackjack.

Horseshoe also offered TCP, MS, 100x odds craps, and Double Down Madness tables that had not yet opened this morning.

Stop No. 9: Ameristar East Chicago

On a map, Ameristar East Chicago is only a few miles from Horseshoe Hammond. In reality, the industrial maze of railroad crossings, winding roads, and inconvenient connections makes the journey feel like a small expedition. What should have been a quick hop took me about 15 minutes.

After what felt like a dozen 90-degree turns, I finally arrived at Ameristar, a property I hadn't visited in more than four years. It was good to be back — even if getting there required a minor navigation challenge.

Ameristar is one of the more unusual riverboat casinos I've visited. Instead of one massive barge or paddle-wheeler, the property feels like several smaller yachts stitched together. You can actually sense when you're leaving one section and entering another. The result is a wonderfully maze-like casino with multiple levels, winding corridors, and slot machines tucked into corners you'd never discover without exploring.

The table games are easier to find, gathered in one large room on the upper level, just beyond the escalators from the main entrance. I grabbed a seat at a blackjack table that was otherwise empty, apart from one gentleman who was simply sitting there watching the action without playing a hand himself.

He quickly appointed himself my personal cheerleader, although I began to wonder whether the casino had secretly hired him to promote side bets. He was especially enthusiastic about Trilux, making sure to point out every single time I would have won had I played it. Nothing quite like a running commentary on all the imaginary money you're leaving on the table.

After a couple of mostly solo shoes, I managed to turn things around with a few larger bets near the end and cashed out $25 ahead. Better yet, that was more than enough to cover the Portillo's lunch I'd been craving ever since moving away from Texas. Sometimes it's the little victories that matter most.

Table limits at Ameristar this morning were set at $10 for UTH, 20x odds craps, and double-0 roulette; and $15 for six-deck 3:2 blackjack and baccarat. Ameristar also offered High Card Flush and Spanish 21 tables that had not opened yet at the time of my visit.

Stop No. 10: Rivers Casino

My final casino stop of the long weekend brought me to Rivers Casino in Des Plaines, Illinois, conveniently located just a few miles from the rental-car return at O'Hare. With my flight only hours away, this was supposed to be a quick visit before heading home.

I had already made peace with my modest Ameristar win and wasn't planning to play again. Then I passed a blackjack table with only two players, and curiosity got the better of me. One last shot at taking a win back to Las Vegas? Why not?

It didn't take long to figure out why that table had so many empty seats.

I pride myself on playing perfect basic strategy, but I've never been one to scold other players for their decisions. Over the long run, their unusual plays can help you just as often as they hurt you. And the gentleman sitting next to me was about to provide a rather entertaining demonstration.

This guy seemed to know basic strategy well enough to do the exact opposite of it. He'd hit 15s and 16s against a dealer's 6, then stand on 12 against a 10. I couldn't make sense of it, but somehow his decisions kept working in my favor. He'd take the card that would have busted me, leaving me the little card I needed. It happened so often that I briefly considered tipping him for his services!

Eventually, our luck cooled off. With a rental car still needing gas and the security lines at O'Hare waiting for me, I decided not to push my luck. I colored up with a $10.50 profit — not exactly a fortune, but enough to end the trip on a winning note. This long weekend hadn't been particularly kind to my bankroll, but between the casinos, the hockey, and a few memorable characters along the way, it had certainly delivered some good stories. And if nothing else, at least I was heading home with a little momentum for my next session in Las Vegas!

All in all, on a Sunday afternoon at Rivers Casino, you can find $5 MS, TCP, and double-0 roulette; $10 UTH & 100x odds craps; $15 six-deck 3:2 blackjack, baccarat (face up), and Face Up Pai Gow Poker; and $25 baccarat (squeeze game).

Wrapping up another trip

In the past for me, boarding a plane headed to Las Vegas signified the beginning of a trip. This is the first time it’s meant the vacation is over and I am headed home.

This weekend in the upper Midwest, I visited 10 casinos and played blackjack (or Spanish 21) at eight of them. Won some, lost more, and had a great time overall. I was particularly impressed by the quality of the blackjack tables by and large, with 6:5 payouts rare. The only problem was that most of the games were using eight decks.