Chessie's Restaurant - Barrington, Illinois

Debbie W.

Fun place. Just an "old fashioned" restaurant. Our bartender was busy, but super nice. Made a great drink. Next time I will get the club sandwich. I watched as the servers delivered it to several tables and I realized that I missed the mark when I ordered the fish fry. It was good, but next time for sure I will get the club. My husband ordered the New England Clam Chowder and he is still raving about it. He also got the chopped salad. It was super good, but too big and too expensive. Hard to eat a leftover dressed salad. We will for sure be back!

Steve J.

First time back in many years. It's still as cool and delicious as I remember. The food was very good. The atmosphere is relaxed and a little elegant. Can't wait to come back during the day to see the stores and brewery.

Alexis R.

It’s beautiful, one of a kind, and the atmosphere is spectacular. It’s definitely a place to make memories, be with family, be with friends. There has been wedding rehearsals, graduation functions, promotion parties, even retirement celebrations. This is a hub any occasion for such as those and there’s even been speed dating events. So, with all sincerity I can tell you it’s a place where love is in the air and it always prevails, and at times can be mysterious, not to mention exciting.

Elisabeth T.

If you're looking for a dining experience that transcends the ordinary, then look no further than Chessie’s—a culinary paradise that redefines what it means to dine out. From the moment you step inside, you’re greeted not just by a hostess, but by an atmosphere so warm and inviting, it feels like being wrapped in a luxurious culinary embrace.

The interior itself is nothing short of awe-inspiring—think elegant chandeliers that seem to shimmer with promise, and a real train over a hundred years old. But, of course, it’s the food that truly steals the show.

Every dish at Chessie’s is a masterpiece, an immaculate fusion of flavors that takes your taste buds on an unforgettable journey. The appetizers are not mere starters—they are the prelude to a symphony of tastes. Imagine crispy crab cakes with a delicate, yet bold, remoulade sauce that dances on your tongue. Or a caprese salad that’s as vibrant as it is indulgent, with every bite a perfect harmony of tangy and earthy notes.

The main courses? Oh, where do I even begin! The prime rib, cooked to a flawless medium-rare, arrives on your plate with the precision of a fine-tuned orchestra—tender, juicy, and complemented by a decadent truffle butter sauce that you’ll want to bathe in. And don’t get me started on the sweet potato salmon its buttery sweetness and melt-in-your-mouth texture elevating the entire dining experience to something bordering on divine.

But, wait—Chessie’s isn’t just about the food; it’s the whole sensory experience. The service is unparalleled—attentive without being intrusive, knowledgeable without sounding rehearsed. The staff here seems to possess a near-telepathic understanding of what you need before you even know it yourself. Molly was the most impecable server.

And, for those lucky enough to indulge in dessert, the chocolate moose tower is nothing short of a religious experience.

The cherry on top of this unforgettable evening? The cocktail list. Each drink is a bespoke creation, artfully crafted with the finest ingredients, and presented with the kind of flair that makes you feel like you’ve stepped into a world where everything is just a little bit more magical.

In short, Chessie’s is not just a restaurant—it’s a celebration of everything food should be: bold, beautiful, and utterly unforgettable. Don’t just go here; immerse yourself in an experience that will leave you counting the days until you can return. A 10 out of 10, with no hesitation. Simply put: Chessie’s is perfection on a plate.

Deplorable R.

Been wanting to try this place for over a year, finally made it in this past July and was pleased with this venue.

Started out taking pics outside before heading in and a Latina lady who I presume was the hostess asked if I wanted a brief tour and I gladly agreed.

I knew Chessie's was formerly a train station but had no idea it was more than a century old, amazing! She was very kind and informative and I was starving so couldn't wait to be seated.

Unfortunately all window tables were reserved and if I wanted a window seat then it would have to be by the bar but I wanted to dine in the car so settled for a table at the very end, no biggie.

The feeling of dining in this museum piece was definitely a memorable experience. Not too often my family and I do something like this so of course you gotta cherish the moment.

Good food at reasonable prices bolstered by great service in a clean/sanitized landmark atmosphere. I could easily come back here, Barrington is lucky to have this remarkable piece of Americana.

josh L. W.

I love railroads and trains so this Place hit the spot in my stomach & curiosity 😁 highly recommend and see you soon ✌🏼

Mary P.

OH MY GOSH! I didn't realize Chessies was still around. I used to go there a LONG TIME ago. It is still adorable with the rail road dining car atmosphere.

I have been back a few times recently and love the food and atmosphere. They have an amazing reuben sandwich and their fries are delish. I had the roast beef and brie sandwich the other day! YUM YUM YUM!

Their menu is varied and nicely priced. Sorry, I forgot to take pictures.
The mousse tower for dessert is "to die for"

I'm glad I have rediscovered Chessie's Restaurant

James J.

Dining in a railroad car brought back very early childhood memories. I ordered the steak sandwich that is served open-faced, and it was one of the best steak sandwiches I've ever had. Surprisingly affordable, the atmosphere of the dining area had a certain understated Elegance to it.