Wiseguys A Chicago Eatery

I pass this place everyday on my way to work. Today I finally decided to come in and lemme tell you… THIS PLACE IS THE BEEZ KNEES!!! My food was quick and fresh and HOT… sooo hot. Definitely coming back with some friends

Oh yeah!!! My belly is fullll. This place is da bomb. Being from the Chicago burbs, I’m pretty familiar with good Chicago eats and Wiseguys did not disappoint. I had the Italian beef with sweet peppers (HUGE), hubby had the Italian sausage. Both were so yummy. The French Fries are fresh, crispy and delicious. I has a little tear in my eye (not kidding) reminiscing about my childhood in this true Chicago feeling, Frank Sinatra playing homey diner (red checkerboard tableclothes and all). Loved every bit of it. Oh! I almost forgot… It’s $ 2.99 to «combo» your meal — add fries and a drink, BUT, if you come between 3:00 — 6:00pm it’s FREE to combo your meal… HAPPY HOUR (Hooch Hour).

Update: We ate there today, amazing that there Italian Combos can taste exactly like if you were eating in Chicago!
There décor is so home like.
I had commented that the bell peppers needed to be softer, this time there were cooked perfect, all of it was. I VERY highly recommend there food

Good value … messy food like the way it was meant to be. The Italian beef melts in your mouth if you get the sausage combo you get a different sandwich with each bite. I wanted to try their meatballs so I asked if I could order it a la carte and the cashier said «sure…» In an I’ll figure it out tone. He settled on the extra meat option on my sandwich and just told the kitchen that I wanted meatballs on the side. Which was genius… It also ended up being a bargain… But I always love it when I try a special request and they figure out how to make it happen. Vs… Franchises where they tell you no because they don’t have a button. Keep it local & keep it authentic… And yes … I ordered a meat & meat combo with a side of meat and they rose to the challenge most deliciously.

Been coming here since they first opened up & I am glad to say that they do not disappoint! I got the Gambino and it was delish don’t forget about hooch hour! Free drink and fries (3 – 6) will definitely keep coming here

We tried this place on a whim, and now it’s one of our favorite sandwich spots. The Philly Cheesesteaks are outstanding. The flavor is gorgeous, and the sandwiches are packed with meat, cheese, and other toppings. The other things we’ve tried (gyros, etc.) were also delicious and filling. I’m so glad this place opened up near us!
My only complaint is that the young guy taking orders seems rather clueless. If you ask him anything «off script», he freezes up and doesn’t know how to answer. I think he might just be new though, and all the rest of the servers/​management are very lovely.

I love hot dogs so this place was definitely on my list to try. I’ve been to the location before when it was another eatery that I liked. Knowing the area already, I was able to avoid the confusion surrounding the construction and got into the parking lot.
The place is well decked out with Chicago décor and gangster photos. Really cool to check out.
I had the Chicago dog, fries and a drink. Dog is meaty and on a poppy seed bun. A big plus if you like hot dogs. I’ll be coming back for more.

Chicago perfection in an out of the way location off 281 and Wurzbach Parkway. We stopped in after our monthly visit to see the Dr and wow– are we glad we did. Between 3 – 6 they have a special where you make any sandwich a combo with yummy house cut fries and a drink at no extra cost– what a deal!!!
Chicago dog is just perfect down to the sport peppers and the seeded roll.
Combo Italian Beef with a sausage underneath, barley wet– oh the deliciousness that came with every bite– even their gardieniera was brought in from Chicago — these folks do it right — very right. Stop in for a meal you wont forget– and we will be back — and back–

Wowzers! This place was awesome. Great food and friendly staff. We arrived about an hour before closing on a weekend night. It was very quiet, which was perfect for us (I’m sure it would be packed at lunch time and early dinner time).
Since it was our first time here (and we used the Unilocal deal) we got a few things to try, and we were not disappointed!
I ordered the chicken cheesesteak, my husband ordered the Chicago cheesesteak, and our son ordered the chili cheese dog. We also ordered fries, onion rings and stuffed jalapeños.
Every item we tried was good. I tried a bite of everything and by far my fav was the chicken cheesesteak with their spicy relish stuff on top followed by the delicious hand cut fries.
We will definitely be back again!
Give this place a try for a great sandwich, awesome service and a happy atmosphere!

This place is delicious! My husband and I ordered here for the first time tonight and everything we got was authentic and tasted amazing. We got a meatball sandwich, Philly cheese steak, mozzarella sticks and fried mushrooms. All great. The fried mushrooms were exceptional. I can’t wait to try the pizza!

I had the maxwell street polish with sauerkraut and it was awesome! The sausage itself had such an awesome flavor. My boyfriend for the Chicago cheese steak and he liked that too. We finished off with a cannoli and that was freaking delicious as well! ¹⁰⁄₁₀ would come again!

Yummm! The best Chicago food in San Antonio! We had the Italian Beef’s with fresh cut french fries and it was just like we used to get back home in Chicago where we grew up! We’re going back to try the gyros soon!

Wow, what a great place to eat!
It’s worth driving around the construction. I had a Philly Cheesesteak with a whole sausage buried in it.
Loved it! Thanks for suggesting it…
My buddy had a hamburger and it too was yummy.
Clean and a friendly staff…
We look forward to returning next week!
Since discovering WiseGuys, we’ve been retuning ever week and twice one week.
If you haven’t stopped by, you are missing out on some great food.
I’m hooked on Bonnie & Clyde a Philly Cheesesteak with an Italian Sausage.
OMG IT’S AWESOME

This is one of those instances where you’re glad SIRI screws you over and sends you nowhere towards the destination you requested. As I was getting quite hangry and was debating whether or not to be like the girl who eats seat cushion filler on My Strange Addiction. The hunger was real y’all.
Now I’ve heard about Wiseguys from a few Unilocalers and it was definitely put on my radar when I saw a UYE pop up on the Unilocal calendar. *Shout out to Steven G*
I decided to pull into the parking lot, give a loving finger to SIRI as a gift, and walk into Wiseguys. The back entrance was super cool and I was feeling like I was in the mob taking the back door instead of the main entrance. Has that bad ass feel to it, ya know.
The setup is clean and definitely ensures the main focus is all about their food. Very classic diner feel with the checkerboard table covers and dang the condiment bar was crazy. I’m a mustard fanatic so to see different styles of mustard was like being proposed to on the spot.
I opted for their chili cheese dogs and fries and damn were they good! I’ve actually gone back more than once since my first visit and have tried a few others and the toppings are great. They actually fly in their product to ensure the authenticity of Chicago style dogs! Pretty impressive and I love how much pride they take in their food.
One of the really cool things about Wiseguys is how they offer a Happy Hour that features free fries and a drink when you purchase the main entrée. Pretty solid in my opinion.
They also serve beer and are very family friendly. So you can bring the little ones to enjoy this establishment. I also noticed a back room which can be used for birthday parties or private events. I personally just want to host a Mob Meeting and have everyone walk in through the back but that’s just me.
The staff is very friendly and personable so don’t be afraid to have a story with them!

Still got it goin’ on! Today I had an Italian Beef, and instead of just getting the «BIG» portion, I created a new one that I call «The Double Barrel» with… yep…DOUBLE meat! Order it wet… for those who are uninitiated, «wet» means that they pour the au jus from the cooking process on the sandwich. You can order it «dry» if you want, but why bother? Don’t forget to top it off! Meaty, JUICY wet, and the Amoroso roll just makes this sandwich even better!
Now with two locations, Wiseguys has your Chicago fix down pat! Capone says to get ya can over dere and getcha some good grub!
***EDIT*** 4−28−16: I keep forgetting to mention about their specials and whatnot. Keep up with Wiseguys on Facebook, here on your FAVORITE site, Twitter, or whatever social medium/​platform of your choosing. Monday is Meatball Monday, where ya get a meatball sandwich, fries and drink for $ 7.49. Every Wednesday is Whacky Wednesday, where every 20^th customer gets their lunch on da house (dat’s FREE!). And they do have live entertainment with Rob Bernal, professional lounge lizard… er. crooner, who is there on Friday nights to sing for youse. And especially awesome is the NEW location located at Thousand Oaks @ Jones Maltsberger. Good stuff that even Capone hisself would appreciate!

This is my home away from home. We just moved to SA from Chicago and were homesick for the food. Well, this place definitely brings us back to Chicago without spending $$ on airfare. So far I’ve had the Chicago Dog and the Italian Beef (w/​mozzarella). Both were delicious! I definitely plan on exploring more of their menu. Atmosphere is enjoyable and they even have live music on occasion. A definite go-​to if you’re in the mood for REAL Chicago food!

Creative décor, happy owners and staff, outstanding fresh food, WiseGuys is now a new favorite! They even have entertainment tonight-​Deanatra. It was my first time to come in and it’s always a joy finding a new restaurant with a cool vibe and yummy food. I highly recommend the cheesesteak and fries!

WOW! It just keeps getting better than great!
Had the universally famous Chicago Vienna all-​BEEF hot dog (and NO, I did not put one single drop of ketchup on it). Clean, crisp SNAP, full of true Chicago flavor, and the celery salt and salad make this dog bark and BITE! Add the always fresh and delicious home fries and drink, and ya got a meal, palsie! The giardiniera… YUM!
Capone was definitely in da house today!
Thanks to everyone who came out for da UYE today! Definitely returning!

Pretty decent Chicago-​style food just off 281 at Nakoma. My father-​in-​law is from Chicago, so he’s pretty tough to please, and he and I have had many an Italian beef in his hometown. Wiseguys holds their own, however. The beef and fried we had were as close to original as you can get. I’m looking forward to going back for a Chicago-​style hot dog.

I absolutely love this place. Best Philly Cheesesteak sandwich in San Antonio. Best part is if you are watching your carbs they. will do any sandwich on lettuce, although passing up the bread is not easy because the bread is amazing. Highly recommend.

NOT the place it was when it first opened and we started going there.
We are from Chicago and used to enjoy going to watch the Bears games. But food had gone downhill and the prices uphill.
$ 4 for a plain hot dog-​fries extra?
Over $ 40 for 2 beef, 2 hot flogs, fries and a pizza puff?
The beef is not good at all, it used to be decent enough but it is NOT Vienna beef. Turano rolls are the only saving grace. Pity, we wish it had kept up the quality. We were there religiously during football season.
We won’t be gong there anymore.

My awesome coworker bought me a Marilyn Monroe w/​pickles and mustard! OMG this was definitely one of the best sandwiches I’ve had! The bun/​roll was obviously homemade (warm & chewy) and all the ingredients were fresh & the lettuce was crisp! The chicken was thinly sliced, juicy and seasoned perfectly. I don’t write reviews often but if you’re unsure about trying this place (like I was) then go asap!
Update: (Well a reply to you, my friend):
I had a bad experience at a Chicago pizza place and so I stereotyped Chicago eateries… Won’t be doing that again! You’ve brought me back to the good stuff: D BTW, the live music I’m listening to now while waiting for sandwich order #2 is awesome (bringing one home to the hubby)!!

I live in the neighborhood and frequent this place often. My go to is the John-​Gotti! Atmosphere is cool and relaxed. My college years were spent in Chicago so it was nice seeing all the memorabilia.
Stay away from the burgers! I tried the chili-​cheeseburger with fries for the first time today. Knowing that this was the only thing that came with it, I asked for tomatoes to be added. Apparently asking for tomatoes on a burger mean asking for literally ONE SMALL SLICE OF TOMATO!!! Come on! I mean really. My significant other and I were the only ones in there. My patty was thin, tasted like it was frozen and the chili was nothing short of canned chili my mom use to put on our hotdogs on the fourth of July. Disappointed. Ate a third before I realized my stomach is not going to like this when I got home.
I have always had a great experience here but had to knock my five stars down to three. Maybe it was a lazy cook or maybe he was told not to put too many fresh ingredients. Nonetheless, I will never, and please don’t, order the burger from here. Stick to a classic Chicago style sandwich.

I love all things Chicago and this place does not disappoint. I’ve been here several times, and each time I order the Chicago dog. My daughters and I love eating here and tell everyone we know how awesome it is. I also love all the Chicago memorabilia hanging around.

My friend recently brought me here and this is my kinda place. I always get the Chicago cheesesteak, it is the best one I have ever had hands down. I think it’s the bread that clinches it, so soft and fresh. They also have some great beers from Chicago and who doesn’t love that. I’m sold on this place

We really enjoy the food and music here. The staff is always friendly and the cheese steak is always yummy. The Chicago dogs are also delicious as are the fries! Want dessert? Don’t worry, they have that too! Oh yeah, don’t forget about hooch hour (3 – 6) free fries and drink with my sandwich… yes, please!

I wanted a really good burger. You might be surprised at the fantastic burgers you can get at a pizza/​sandwich shop. Not here. I ordered the Mushroom Burger «with everything «Apparently everything is the meat, cheese, mushrooms and onion. The patty was thin, likely frozen and I think I had 3 mushrooms. It came with «hand cut fries «that were more steamed than anything. So… if you do decide to come here, don’t get the burger. It’s average at best.
~~~~~In reply to Bill N.
you Clearly have me mistaken for someone else. I had NEVER been to Wise Guys before. I went in paid, tipped $ 2, DID NOT say anything to ANYONE other than Thank you to the girl who handed me my food. I did NOT sit down, I took my food and Left.
What was said above is MY opinion of what I received. For you to get so defensive is RUDE and unprofessional.

First timer here, and I am leaving satisfied. Chicago cheesteak was good and the gyro was pretty tasty, wifey was happy, as was the kiddos… We will be back!!!

This place has quickly become one of our favorites. The food is always great and the people are even better. We have ordered just about everything on the menu and have never been disappointed. It is really hard for me to pick a favorite here but you’ve got to try the french fries with Marana and meatballs. It’s not on the menu but they will happily make it for you. I promise, it will be GREAT! If you’re in the area, this place will not disappoint!

While visiting friends and family in San Antonio we decided to take a break from our usual Texmex that we were eating in the Alamo city and give this place a try. All I can say is wow. Every one in our party really enjoyed their food and we were impressed with their quality and quantity.
Having never been in this place I asked the guy at the counter what was the most popular dish and he referred me to the Italian beef sandwich. He said it was their best seller and their signature item. Boy I’m I glad I took his advice. This is one of the best sandwiches I’ve had in my life. I took it the Chicago way with spicy peppers and the entire sandwich dipped in au jus.
The place has a very relaxed casual feeling but was very clean. I only wish that I could have stayed a little longer so I could check out out their adult beverages and specials. I would highly recommend this place for anyone is looking for quality Chicago style food deep in the heart of Texas.

First time today. I came in during Hooch Hour (3−6pm) which allowed me to have a free side of fries and a drink for my Cheesesteak. Wow! It is absolutely delicious!

I’m not so sure what the appeal is here.
My husband and I both ordered a philly cheese steak. I was really underwhelmed with everything about it, I would have been just as happy at home with some steakums. It certainly wasn’t bad, I just can’t find a reason to try it again. Nothing about it screamed special.
We also shared a chili cheese fry. I hate to say that this completely underwhelmed me as well. Perhaps I’m wrong but the chili tasted canned and the cheese was the creamy liquid kind. At a place that specializes in dogs, I would have expected a higher quality chili cheese fry. Maybe some homemade chili and some real cheese?
Service was fine. You walk up to a counter to place your order, she brings it over to your table when it’s done.
Overall, a mediocre experience.

Normally not a fan of a sandwich shop but thems good groceries folks! I think it’s a little on the pricey side but still a good lunch destination.

Yummy Italian Beef! Hubby likes his completely submerged in Au Jus but they weren’t offended when I asked for mine on the side!
Perfect fried pickles and home style fries, too!
Fast, friendly service and TVs for Sunday football…

My wife & I tried Wiseguys this past Friday.
She had a gyros and I went with a Chicago Dog & Chile Cheese Dog.
Great food & staff.
Too bad they didn’t serve Old Style beer.
We’ll try the Roast Beef or Cheese Steak next time.

Came here after seeing it all the time, and have to say I really like it. Greeted immediately by the cashier, who was very friendly, intuitive of the menu, and helpful. I got a chicago beef sandwich while my gf got the cheesesteak and salad. Both sandwiches were amazing and delicious bread was nicely warmed without being overly toasted and the huge menu definitely make me wanna come back! Ill be back

Anytime you eat in one of those restaurants that features a cuisine or style of food from another part of the country, you’re taking a chance. It’s likely that your tastebuds will take you on a trip down memory lane to the last time you visited this faraway place, or you’ll be severely disappointed.
Wiseguys is a little oasis of Chicago in the middle of San Antonio. They have the prerequisite Chicago jerseys and mobster pictures on all the walls, as well as the prominent Vienna beef signs. The most commonly recognized Chicago food (other than deep dish pizza) is the hot dog, but I decided to go straight for the jugular and order the wet Italian Beef sandwich.
OK now, listen to this — Wiseguys prices their Italian Beef sandwich at $ 7.99, and their Italian Beef WITH sausage at $ 7.49. What?!? You’ll throw a sausage link into the middle of my Italian Beef sandwich and deduct 50 cents for the trouble? Yes please!
The moment of truth arrived when my sandwich was served just a couple minutes after I ordered it. Was it as good as Portillo’s in Chicago? No, it wasn’t. Was it pretty dang close? Yes, it was pretty dang close. The sausage wasn’t quite as spicy as I had hoped, but it had great texture and combined well with the Italian Beef. My sandwich had been dipped in exactly the right amount of au jus — not so much that it dripped all over me as I ate, but enough that every bite was perfectly covered and flavored.
One thing Wiseguys offers that Portillo’s doesn’t is homemade fries, and they were excellent. I’ve never understood why an owner would invest hundreds of thousands, and sometimes over a million dollars in a restaurant facility, and then serve fries that had been frozen in a bag in their freezer a few moments before reaching your table. It makes no sense to me. (My wife is seriously tired of listening to me complain about this at other restaurants.) The fries are a HUGE upgrade over standard fast food fare and an excellent compliment to the sandwiches and dogs.
Wiseguys also offers a good assortment of Italian pastries (although I haven’t had a chance to try them yet) and a fun tray of unusual condiments near the soda fountain.
The bottom line is that no, it isn’t Chicago, but it’s pretty stinkin’ good, and their only serious competition in town in my opinion in Jerry’s Hot Dogs downtown. So unless you’re willing to drive North about 1200 miles into the frozen tundra, Wiseguys is about as good as it gets.