Smith & Wollensky - Chicago — Restaurant in Chicago

I came here during St. Patrick's Day 2025 with my family (party of 9). Surprisingly, we were able to be seated immediately, which was about the extent of the positive experience we had. This place is regal inside and you feel like you're walking into a high quality establishment just based on the decor. I think you'd assume that too, based off the menu, but that turned out to be an illusion of superiority.

Now, to be expected, the service was a bit slow, but it took almost 30 mins before we were able to order any food. The waitress never asked us about splitting our bill which naturally lead to issues down the line with a nearly $1,200 bill.

My wife and I both tried to order the 14oz Wagyu NY Strip ($150) and were told they were out. We tried going up to the next highest steak which was a 18oz Long Bone Wagyu Filet ($158) which was also sold out. So we went up again to the 38oz Wagyu Porthouse for Two ($270). We also tried the Smoked Salmon Tartare ($26), the Truffled Mac & Cheese ($20), the Caramelized Onion & Potato Hash ($13), and as enhancements for the steak we opted for the Gorgonzola Crusted ($10) and the Roasted Bone Marrow ($12). We also ordered 3 Ginger Peach Sparklers ($19 ea) and 3 Blackberry Lavender Lemonades ($19). All in the bill was around $470 for the 2 of us.

Once the food finally came out, it do so on comically-large plates. There wasn't enough room at the end of the table for all our plates. I can only imagine if the rest of my group had ordered full meals as we had, where everything would've fit.

The Smoked Salmon Tartare was amazing. Strong smoked taste, great texture, and came with house made chips which broke easily and were terrible for scooping up the heavy and sticky tartare. They did, however, taste good, so despite a little mess and the most outrageously sized plate I've seen at a restaurant, very little complaints.

The steak was a dud. Again, I assumed with this being a place known for steak and ordering a cut at nearly $300, it wouldn't be terrible. We ordered medium rare but instead were presented with something that looked like it was medium rare when taken off the flame, and continued to cook to a medium-to-medium-well. I believe it's because they not only pre-sliced the entire steak for us, but they left the steak in the same stainless steel pan it looked to have been fried in. A Porterhouse isn't as nice as a NY Strip, so I knew going into it the steak would be a bit tougher, but man... the overcooking combined with the presentation just ruined this steak. The steak itself was mildly seasoned, nothing to write home about. Far from worth $270; I've had $50-60 steaks that yielded less gristle and tasted better. The enhancements were also pointless; the gorgonzola came out in a small pot—so it wasn't crusted on anything and was basically like dippable queso at a Mexican resturant—and the roasted bone marrow was tasty but yielded around 2 tablespoons of marrow.

As for the sides, the truffled mac and cheese was amazing. Zero complaints and the portion size was large. The caramelized potatoes were bland and boring. The potatoes came with a mole sauce that was inedible with a strong bitter earthy taste that made the potatoes taste even worse (like anti seasoning).

As we wound things down, the new waiter who switched out halfway through our meal brought the check over to me, requiring me to have to break out each of the items on the receipt to each sub-group. This process added another 10 mins onto our time, so we spent close to 45-50 mins at this restaurant just waiting to order or figuring out the bill (that's not including the time we waited for food).

Overall, when I go to a restaurant and spend $500, I expect a food experience that I remember fondly. I've felt this way at many eating establishments around Chicago, but Wollensky's Grill will be remembered as an overpriced restaurant that can't live up to its own name as a steakhouse. I have no plans to return here and would implore any serious foodie to...

I made reservations in advance and requested a seat with a view. We are from out of town and chose this restaurant due to its proximity to The River. The hostess was pleasant, but her idea of a seat with “a view” was quite the opposite of ours. We could not see anything except the back of our booth seat. It was obvious that they left the panoramic views for customers that were there to spend hundreds of dollars on alcohol. After our waiter came to our table and took our order, he was never to be seen again. We expressed that we only wanted fountain drinks, so I believe that was when he lost interest in us. He came out once more to check on how we liked our food when we were done with it. Of course he was constantly checking on the table behind us, as they were ordering copious amounts of the finest alcohol and dishes. We felt very disappointed that the service at this restaurant depended on how big of a spender you were. Our waiter slammed our check down at the table, because he was upset to give us back our change. He stood around for 30 minutes hoping that we would leave and he would get to keep our change (a 30%+ tip.) The food was great and the prices were reasonable. Forget hospitality unless you are ordering their most expensive steak, appetizers, $100 bottles of wine, and a...

We read great reviews about the Grill (which is the more casual and "cheaper" option to Wollensky's upstairs). Much of the seating faces the river and the river walk. So fun to see the boats going by and to people watch. Restaurant has their own menu but you can also order from the menu upstairs as well. Great selection of steaks, seafood, salads, etc. Good bar menu. But it's expensive! Just warning you --- And we had our kids with us and nothing really appealed. We cobbled together a couple of things but for the price, not the best place to bring kids. Lesson learned. Our servers were friendly, attentive and accommodating. Our food was delicious but rich. They brought the dessert menu and wow! It was hard to walk away from it but we were stuffed. If you are in the River North part of the city, consider this for...