Received $15 Cadillac Cash or $15 Match Play, complimentary beverages while actively gaming, complimentary entry into the Red Eye Slot Tournament on a Monday, BOGO beverages, 15% off food at the Wagers Sportbook & Grille plus several other discounts with our stay at Marriott Springhill Suites. The casino staff and waiters were very friendly. Food was priced reasonably. This casino is relatively small and on the first floor of at least 3 hotels. A ramp connects the Marriott Springhill Suites hotel with Cadillac Jack. Plenty of parking including handicap spaces. Families seemed to like having food choices and a large pool and hot tub at the Marriott. read more

Tried this place again for gambling. I have been coming to Deadwood for over 20 years and live here and will tell you I have NEVER won here. It is the worst casino for gambling in Deadwood. The place sucks donkey dick. read more

We had a fun time, my wife did a little gambling on the slot machines. I would love to see some of the older style slot machines . We loved the Halloween decorations, took lots of pics with them! read more

Cadillac Jack's Gaming Resort - My wife winning some money - Casinos Near Me - Deadwood, South Dakota

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My plane got in late which made me have a really late check-in and the female working the front desk was so friendly. She explained everything to me and it was so appreciated. This place is spotless and the rooms are huge and welcoming. I am in town for a football game and seeing how awesome this place is, is an added bonus. I will definitely stay here again when in town. read more

The cowardly ownership of this casino only welcomes the uneducated, inept, and those with no knowledge or skill. Just a tourist trap with an awful food court, 2 star restaurant and modest rooms. Spare yourself the trouble and go elsewhere. read more

This place has lost its sparkle. The last time I came was before Covid and it was a positive experience with positive employees. Now I get more of a I'm here because I have to and I don't care about customer service. The food is not very good and considering there isn't much around that speaks volumes, you charge high prices for trash. We came on a holiday this time so maybe that changes the experience but overall I truly feel this place has gone down hill. read more

Not impressed with this place. There were only a few games that I liked and the drink that I was served came in a dirty glass. Although we stayed at a hotel that was attached to this place I did not spend my time there. I will say though that it smelled nice and the service was pretty fast. read more

Machines are very temperamental. Had issues which required gaming official to fix. Too much effort for results

No mask requirements Or plexiglass and they kick you out if you think about your hand for more than 5 seconds read more

Cadillac Jack's Gaming Resort - Worst poker room in history - Casinos Near Me - Deadwood, South Dakota

I've stayed at this hotel/casino 4 to 6 times through the years. My father passed away last week and my sister and her husband are in town for the funeral and we decided to go to deadwood for a night to have a little fun. I'm literally standing there looking at the blackjack tables after dropping $200 on roulette plus $100 on slots and some dude walks up to me and says I won't be served anymore so I asked why? I've never been kicked out of anywhere. I'm 43 years old and I asked what did I do? They said you're obviously too drunk. I said I'm just standing here. So I went back up to my room on the 3rd floor to grab my cigarettes then went back down to the ground floor and came out of the elevator and a man approached me and said I'm not allowed on the floor. I said I'm going outside to smoke. I asked what did I do wrong? He said you've been cut off and you're not allowed on the floor. I'm so confused at this point so I went outside to smoke and some dude brought out bottles of water and I told him, dude I'll leave. I'm feeling super disrespected right now and if you don't want me here I'll go. Just refund me my money for my room and I'll gladly go elsewhere, all the while asking him what the hell did I even do. Dude , I travel all over the country and have for the last 20 years. I'm going to Norway this fall. I just spent a week in Los Angeles. I've never felt more disrespected in my whole life. I recommended Cadillac jacks to my sister and brother in law and booked this room and I'm pissed off. I will never come here again. read more

We stayed at the Lodge but unless you want to enjoy the ride into town on a Harley then I suggest stay here. Historic places have their charm but this is THEE Vegas style casino in Deadwood with craps & all the tables games and a nice food court etc. plus we made out like bandits! read more

Cadillac Jack's Gaming Resort - Buddy hit the Mega Grand Jackpot on Green Machine! - Casinos Near Me - Deadwood, South Dakota

Stayed for the night in the Double tree. Room was great. Nice and clean. Nice shower and comfortable bed. Had a good time gambling. We won a little and lost a little but that's why it's called gambling! Food selection was great and the Mexican restaurant was delicious. All of our staff experience was very friendly and professional. Even the housekeeper as we checked in went out of her way to make sure we had a good experience. I've stayed a lot of places in Deadwood and while it's easy to complain when you don't hit on machines or have a good night on the tables, I'd rather go in knowing I'm willing to lose what I brought to gamble with and have a good dining and hospitality experience then get upset that my betting didn't pay off. If you were guaranteed to get money for being here you would have a name tag and a job title. I recommend Cadillac Jacks! Great time! read more

Im from Vegas, this place does everything Vegas style. I dont understand the tons of rotten reviews, the GF and I stayed at the Doubletree for 5 days for New Years and I have to say, everything was wonderful. 0 complaints. I dont like that they charge for parking, but they make it up to you with more than the cost of parking discounts everywhere. Would stay here again. read more

Totally FUN place! Great gaming, good drinks, and great restaurant to dine. Loved the atmosphere and people!

I have been a loyal Cadilac Jack's customer for years. I have stayed at the various properties 3-4 times a year for the past 15 years. I have always really enjoyed the customer service, restaurants, excitement, and the pool at this resort. I live in Denver Colorado but most of my family lives in the Black Hills. I am extremely disappointed with the level of service that I received my most recent stay at the Tru hotel. I arrived and printed my $50 off hotel room coupon like I always do when I arrive. I gave it to the girl at the check in counter and she said she would take off the $50. When I went to check out I noticed that they had not taken the coupon off, and offered me no explanation as to why. The girl at the checkout said she would look into the matter. I attended my grandmother's funeral, which was extremely sad and emotional. After the funeral I went back and asked about the coupon, the girl said she would have hotel manager give me a call. I went and walked around for a little, and never received a call. I went back to the hotel and the receptionist was very aggressive with me. At this point she told me I had booked the room from a 3rd party site and there was nothing they could do. I pushed back a little explaining that they had accepted the coupon, and noone ever told me about the incorrect way of booking. I asked if there was anything they could do. She was extremely rude, and called the Casino manager Warner. I began to tell her it was ok, and she began to get in the elevator to go down to the casino. I followed her. When we arrived to the players desk she began talking to Warner. At this point I was getting annoyed by spending so much time arguing about $50. This is when Warned walked over and said that it was not protocol but he could offer me $50 in free play. I said how annoyed I was, told him that I was having a bad day. I asked him "this is how you treat customers who have been coming here for over 15 years?" I wish that someone would have explained to me the situation, so I wouldn't have wasted so much time arguing with the staff. I told him that the hotel staff lied to me, they never called me back, and they were hoping I just wouldn't notice the charge. This is when Warner called me an asshole. I was so taken back I couldn't believe the customer service and how this man treats people. I had an emotional day and was honestly about to cry when he told me this. I said this is how you treat people after years of loyalty. He called me an asshole again, and told me to find another casino to play at. He also stated that he was having the bar cut me off, which was an insult because I had been at a funeral all day. I can't believe the way he acted. As a high school and middle school teacher I have dealt with disrespect, but nothing like what Warner did. After about 2 months at home I received offers front he casino, for comp room nights. I called and talked to a manager, but he defended Warner and was unapologetic. I would steer clear of Cadilac Jack's. They do not treat their customers with respect, and have shady business practices. I have never been so loyal to an establishment and been treated so poorly. Warner you are a horrible human, shame on you for treating people so horribly. read more

We travel to Deadwood South Dakota for our anniversary and stayed at the DoubleTree by Hilton Cadillac Jack's. The casino was beautiful. The dealers were very friendly and fun to play cards with. Our room was very nice. The Casino Host: Warren was great. He was the best host we have ever dealt with.He was so friendly and comp some of our nights and offered us great advice on places to go and visit. The head lady in the gift shop was also wonderful. I brought several shirts and she gave me 2 stuff bears to bring home to my grand-babies. We played a little in most of the Casinos in Deadwood. But Cadilac Jacks is by for the nicest and were we won the most $. Thank you Warren for making our trip great. We will come back to visit. read more

Cadillac Jack's Gaming Resort - Casinos Near Me - Deadwood, South Dakota

Nice enough rooms at the doubletree BUT what a rip off! Over priced drinks over priced food. Horribly tight machines no variations of types of machines. The whole towns that way! No free parking anywhere downtown. Never again not worth it at all!! read more

Small but very nice casino. Good selection of slot machines and didn't find them to be too "tight". We had dinner at FLYT...a bacon wrapped filet mignon, baked potato, Texas toast, and a wedge salad with yummy homemade ranch dressing for $15.95. Living in the SF Bay Area, we weren't expecting much for $16...boy were we pleasantly surprised! The steak tender and perfectly cooked. The wedge salad was large and crisp, and the salad dressing was very good. The service was excellent. The server was friendly and attentive. We were very pleasantly surprised and will be back for more adventures in South Dakota! read more

Had an excellent stay here, fun in the casino and the Doubletree had large clean rooms. Easy parking. They welcomed our dogs, provide doggy bags, and there is lots of area to walk them with sidewalks and a crosswalk to access more paths across the road. We walked to the downtown area and found it to be an easy safe walk, less than a mile. Knocked off one star for atrocious low quality food. The only halfway decent food we got there after staying four nights was a chicken parm and filet mignon at Flyt one evening. Definitely recommend finding food elsewhere. But overall we had a great time and will be back! read more

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Professional dealers that create excitement at the game. I worked in the casino business for a lot of years so when I visit a casino my biggest critique is about dealers. All of the casinos that have tables in this town are very small, which surprised me, but a lot of things about the town surprised me. Cadillac's jacks is well lit, clean and very modern. Dealers made craps and the card games a good time. I'll gladly visit again. read more

Cadillac Jack's is my favorite hotel/casino in downtown Deadwood. Planning a five night family get-together next month. Can't wait! Terrific beverage bar and gorgeous pool await! read more

Sorely disappointed. The casino was small and tight. The room was ample size but was lacking bed side tables. The shower was apparently trying to be a water saver. There was no water pressure and the amount that came out was limited. I generally take a 3 minute shower with regular pressure. It took over twice as long to wash my hair with the limited water. The bed was soft. read more

I have generally always enjoyed this venue but this weekend sucked. Maybe the vid has changed things but I found the staff and gaming support condescending and rude. craps attendant didn't want to take my money and play, told me I could only play from a certain point on the table and then told me I only could walk around the table a certain way. Reported it to a "manager" but got no acceptable response. I have stayed and played here every time I have come to deadwood - never again. I know it is difficult to find good employees in this environment but this resort obviously settles for bodies rather than people with a service mentality. Extremely disappointing! read more

I had been here before for the Rally and thought it was just another casino, but it has recently been renovated. The place is gorgeous now. Fun staff, new restaurants including Flyt by the owners of Alpine (Hill City) We ate at Flyt twice while in town, and it becomes a nightclub at night. The whole complex has a fun energy and feel. It is located right under the TRU hotel in this three hotel complex in downtown Deadwood. Definitely the place to stay and play. We will be back next year for sure. read more

Cadillac Jack's Gaming Resort - Casinos Near Me - Deadwood, South Dakota

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Stayed here for 2 nights. The rooms are clean and staff is friendly. I used the atm and didn't check the receipt until the next morning and realized that I was charged $300 more than I took out, the floor manager was so helpful he took the time to go through the atm and searched all transactions from the night before just to realize I took the receipt from the person before me. The floor manager was very good and would definitely go back my only complaint was it was very limited for blackjack seats I would have gambled a little before I left, but there was only 1 blackjack table that was taken and since I'm not a big gambler I just left instead waiting. read more

The pit bosses at this place are awesome. Tyler is by far the coolest pit boss I have come across. He is very professional and personable. The staff is the main reason I choose to lose my money at this casino. It's newly updated and classy. You wont be disappointed read more

decent casino until you win any reasonable amount. I only play slot machines, which are programmed to make the house money no matter what and they permanently banned me for winning too much after about a year of good luck. I'm not the only person to know of that this has happened to. I spent like 2k at their coffee shop and about 1000 on hotel rooms and it means nothing, they consider my wins to make me "not profitable." No other casino in town has reacted to my winnings this way, they're sore losers, greedy, and track your activity exhaustively always ready to 86 you. Don't come here if you want to be viewed as a person and not a dollar sign. I have had no issues at other deadwood casinos, including tin lizzie's which is under the same ownership. One member of the management is after winning slot players from what I understand. read more

It's a casino, with not so good management. Lots of time spent standing around waiting for a table to be opened... never did so we left and went to another establishment. read more

Typical casino, tight machines and slow service. I'm not a casino buff, but this one seemed really dead to me and my money seemed to disappear very fast. I did like the feature that came with your players card that allowed you to electronically order drinks from your slot machine. read more

Hands down the most unfriendly, inhospitable employees I've ever seen in a gaming establishment. From cocktails, bartenders, cashier's, employees of the dining establishments. Extremely disappointing read more

Not a bad place to stay but we got home and seen that this place charged us for smoking in the room when 100% we didn't, I don't know what else to say but it's borderline CRIMINAL! Crooked management? Would not recommend. read more

We stayed here on April 7 and 8 2021. The casino has 3 hotels and we stayed in the Doubletree which was wonderful. It was immaculate and had large rooms. We reserved it through Travelocity at an amazing rate as it was during the slow season. The beds were comfortable and the accessible room was great. I am marking it down because of the dining options were not good. There is a Marcos pizza that is food but the Sandwiches in the restaurant were not good. The "steak" house has only two steaks a chicken and some small plates of things to add to your plate. I would hardly call it a steak house. Guadalajara's was the worst. There was only one server on duty trying to handle 10 tables. The only good thing we had were their refried beans. We ordered shredded beef taco and a shredded beef chimichanga. The server said the chimi came with cheese in it and it had none. Both when served were filled with ground beef that was very oily and unseasoned. I couldn't eat it. I also had a chili relleno which tasted good but they obviously used a canned chili pepper. I highly recommend giving this a pass and going to one of the other restaurants in town for dinner. We enjoyed playing slot machines in the small casino. If we return to Deadwood I would definitely choose to eat somewhere else but would probably stay at this hotel as it was the star of the vacation read more

Poor service all throughout the casino, waitress had a bad attitude because we didn't want an alcoholic beverage. We ate at Marcos pizza, the food was a decent slice of pizza, staff was poor. Cashed out and went down the road where they appreciate customers spending money in their casino. read more

wouldn't let slot lady livestream could especially see she wasnt counting cards since she lost half her stack and everytime she up bet she would lose the hand will never ever come here unless she is comped rooms food free play the whole nine yards ridicoulous read more

This is the worst place to go in Deadwood. Originally it was mediocre, but after coming back I will say I have filed a complaint with the state. Piss poor employees. Not all but quite a few. To be fair there are some really good ones but not worth coming back. read more