I just wanted to share how disappointed I was with dining at this establishment this Thanksgiving. I spent over well over 20 minutes in line to get to the buffet and then food trays were empty which resulted in even more waiting. My family barely sat together, everyone was in line at one point or another, since we needed to stagger going up the buffet due to accommodate children and elderly in our party. We've attended Thanksgiving at this establishment in years past with positive experiences, but after our experience this year we will not be returning. We payed far too much of a price to have such a disappointing dinning experience. The drinks were flat, the dessert table was in constant need of restocking. Beyond disappointing experience. I reached out to the business owner to share my experience via email, but have received no reply. Want to warn others of this experience so they don't have an expensively disappointing thanksgiving experience as well. read more

The service here was amazing! Great food and a great staff. We had my best friends wedding rehearsal dinner here and one bartender in particular, Holly, was especially attentive. She was extremely friendly and went above and beyond in so many ways. She really made the night special for us and feel personalized. We highly recommend coming here. read more

Wife and I stopped in on a Friday night. Jazz band was playing. Quiet, pleasant atmosphere. Food was tasty and priced reasonably (for Barrington) Beer was cold. No problem in accommodations for 2 but 4+ we would have needed a reservation. Overall a nice experience. read more

Stopped in for a drink and snack. We sat at the bar and received no service...didn't even get a greeting! Used to be a nice place. They doubled the length of the bar for no good reason that I could see. The bartender couldn't handle what she had! read more

The Christmas decorations are the best, the servers are nice, but that's all Chessies has to offer. The food is awful. I ordered Pena pasta with veggies. The pasta was so over cooked it was turning into mush, what few veggies were there were soggy, and discolored. I had to send it back and ate a salad. Cheesie has been in Barrington for years. It has certainly seen better days for their food. read more

Food was ok, my husband got a steak sandwich that was far from a "sandwich" (it was slab of meat on one piece of bread) but rest was ok. Hostess wasn't very friendly at all and a bit rude. read more

I was at Chessie's today for lunch. The french onion soup is awesome. The strawberry salmon salad was excellent. The prime rib french dip was perfect. The key lime pie was out of this world. Best of all, Holly (our server) was top shelf. She was very personable, knowledgeable, and professional. I will ask for her when I go back, I suggest that you do the same. And yes, do eat in the dining car, an experience you won't soon forget. read more

Took my kids there today to have the Tuesday special which is listed on their website menu as a $5 Angus burger. We got seated and on the menu it stated the burger was $7 plus you are required to purchase a drink to get the special. I asked the waiter about it and she said that the price increased in September. I said it's still showing on your webpage in November as $5 and there is absolutely no mention of needing to purchase a drink to get the special. She didn't care. The hostess didn't care. I walked out of the restaurant with my kids never to return. It is false advertising to list a special and then charge almost twice as much for it. I guess they figure they can shame customers into paying it once they are already seated. read more

Chessies is an old Barrington village spot that has recommitted to providing a great experience. Great food, great atmosphere, and wonderful time. Try the baked Brie for starters. Most entrees decent to great, but stay for dessert and the mousse tower. You'll be glad you did. Ask for Monica as your server. She made the evening special. read more

I had a great experience here as always, love the train car, it is so old-fashioned and great atmosphere. the food and drinks were delicious! highly recommend ! read more

So so. Had a salad and a glass of wine. Overpriced. Salad was watery. Bacon bits obviously fake. Waiter was amateur. The ambience was lovely. read more

NOT kids-friendly!! Hostess gave us attitude as soon as we got there. My friend and I had 2 kids each to see the Easter Bunny in Ice House Mall. And we decided to try having lunch here since some friends went to have lunch with their little ones after taking photos with the bunny also. We started getting attitude from the hostess as soon as we arrived. We were not the only ones with kids. My kids were not eating and getting cranky. I got them up & out to benches just outside the restaurant when they started crying. I was just signing the check when I overheard the hostess & our waitress complaining about us saying "why can't she take them to the car already?!" Seriously?! My kids were not the only kids there and not the only ones being loud. The hostess should look for another job. You can't have a bad attitude when you deal w customers on a daily basis like that. read more

My wife and I had Valentine's dinner here tonight, our first visit to Chessie's. It was awesome! I had the prime rib, cooked to perfection! My wife had the New York strip, also cooked to perfection! We dined in the train car. The only thing this place is missing is their own brewery. Hint, hint. So if you're in the Barrington area, it is worth a trip. read more

Just wanted to say that we have been to Chessies several times and the food has always been great. I wanted to express a few concerns on our last visit. First off the mixed drinks that were ordered from the bar were very weak with hardly any liquor in them.The second concern was the mini plate salad we received at dinner compared to the regular salad plate size we received in the past.The third concern was the peppermint sundae we always get there around the holidays.This is usually served in a schooner with peppermint ice cream, real hot fudge, whip cream and a cherry.This year a small scoop of ice cream in a small dish with chocolate sauce and a little whipped cream and no cherry for $5.50!! I understand everyone has to make cuts to survive in the restaurant business but do not like the direction that this established restaurant is going read more

Lunched with friends and had a delightful time. Hostess was very friendly, server did a good job, and fish tacos tasty. Will go again.

We just enjoyed a delicious early dinner for 10 people at Chessie's prior to our daughter's high school graduation. Our server, Sarah, was AMAZING. She did not even skip a beat when my husband emphasized a little too firmly that he and our daughter had to leave in 30 minutes and needed their food quickly. Their food came quickly and then the rest of us were able to enjoy a leisurely meal together. The food and dessert were wonderful. The ambiance was very nice. We had a lovely round table for the 10 of us, which we really liked better than a long, rectangular table. We were seated in a quiet corner with our family. Overall, we could not have been happier with first our Chessie's experience. We will definitely return. Good food, great service! Well worth the time and money that we spent :-) read more

Went to Chessie's for dinner last night and while dinning in the train car is always a good experience sorry to say their fish fry was a big disappointment. The fish was dry, not flaky at all and not meaty, but thin little pieces, the outer layer was limp and wet feeling, not a crispy crunch in the lot. I almost think our dinners might have been zapped in a microwave. My husband got the potato pancakes and they were over cooked and dry and I got the house cut chips, very dried out and cooked to such a dark fry that they tasted burnt. My husband said the soup was tasty but just warm, not hot, my salad was ok, chopped up so small it was hard to eat with a fork. Sorry to see the cloth napkins gone, now they serve paper napkins. Was surprised that a restaurant that serves $90.00 a bottle wine no longer has cloth napkins. When we were leaving the train car there was a waitress scolding, rather loudly, a busboy. Very embarrassing to say the least. The last couple of times we've gone to Chessie's we felt the food was just not what it used to be and the service very choppy, just doesn't run smoothly. We will probably give it one more chance. read more

Do not order the chicken parmigiana. It was one of 3 menu items offered on a pre-planned bus trip for our seniors from church. I have had this entrée several times over the years at different restaurants. Always has been served with a breaded chicken breast over pasta with some type of spaghetti sauce. Chessie's version of this was a cooked chicken breast on top of spaghetti with some tasteless red sauce. Ugh. The bread and ice cream were pretty good! read more

I had seen some intriguing pictures of the place in ads recently (especially the train car!), so I convinced my family to go here for our family Sunday night out dinner. We arrived around 5pm, and while the parking lot was relatively full, the place itself seemed mostly empty. When we walked up to the host stand, I could see numerous empty tables inside the train car. We had 2 kids in our party but they are good eaters and request adult menus instead of kid menus. But they're kids, so I figured they would seat us in the train car. Instead, the hostess walked us aaaaaaalllll they way down the bar to the very end, and sat us in a booth directly below a huge big screen television. So much for intrigue and ambiance! After she left we moved over a booth so as not to have that giant screen in our faces, and all the tables around us were empty anyway (she later sat the only other group to arrive while we dined in that same table, now right next to us). The service was okay but not great. Once they refilled my husband's water glass with some other clear liquid that definitely was not water (weird!). My son ordered the chicken tenders meal, and when our orders arrived I noticed that he did not get nearly as much food as my husband's similar dish, and did they perhaps give him the kid's meal? My husband pointed out that no, he had clearly ordered from the adult menu, so it should have been the adult portion. Our food came out very soon after ordering, which always makes us suspicious for made-to-order food. I had the red snapper special, and it was anything but. It was rather overcooked and definitely not special. Everyone agreed that their food was mediocre at best. We were indeed charged the kids' meal price for my son's chicken tender meal, but that meant he finished the whole thing since it was too small, and he didn't get any leftovers for school lunch the next day. Throughout the dinner I was frustrated that I had made a big deal about this place to my family in order to convince them to try it over other new places or our tried and true favorites. I guess I should have requested to sit in the train car, but I still can't figure out why they wouldn't have at least asked us if we wanted to sit there. When we left, shortly after 6pm, the parking lot was almost empty. We commented that the place must be catering to a much older crowd than families like us, and the place even smelled "blue-haired" at the entrance. On the drive home my family agreed that that was not a place we needed to go to again - mediocre food, average service, and little to no atmosphere. Perhaps it would have been more fun if we had gotten to sit in the train car, but with so many other cool restaurants to try instead, we won't bother to go back and find out. read more

Been enjoying this place for decades with family and friends. Would definitely have given five stars, except for the fact that the manager is bringing this place down. Have witnessed him screaming at several employees, acting unprofessional and just bringing a negative vibe to this once steadfast gem of Barrington. Great food, awesome bartender on Fridays, and still a cool old fashion style restaurant and lounge with great music Friday nights.. I hope the current manager situation changes and the atmosphere goes back to the classy, remarkable gem Barrington deserves!!! Ohhhhhh... read more

First time at Chessie's and NOT impressed. Upscale prices - low scale food. Friday fish fry was extremely bland among other things. Beer was over a month old. Service slow and not pleasant. Had to move our seats in the overflow area as we had water dripping on us from the ceiling. Will not return. read more

Although I've been here several times over the years this last time was not a great experience. Priced are high but not outrageous. Booked for dinner at 7pm in the train car and were seated promptly. Dining car was half empty so service was prompt but not particularly friendly or attentive. Ordered medium Filet which was cooked correctly with average presentation. Vegetables were cold, I mean cold! so I requested them to reheat. Meal was return after a long wait and was replated but the Filet now overcooked. Seems like it was under different management. Not much interested in returning. read more

I have been dining at Chessie's for awhile now and really enjoy the $5 Burger Tuesday Night. However, over the past few months, the "vibe" of the restaurant has totally changed. I have witnessed the manager pour himself beer in to go cups, witnessed him speak to the servers in a disrespectful manner, and at times yell at them, all in front of customers. I am not sure if the management has recently change in the past few months, however six months ago the atmosphere within the restaurant was completely different, more relaxed, laid back and very professional. Overall all the food and wait staff is extremely good, read more

Easter Brunch was awful..eggs were dry...sausage was greasy....fruit was not ripe......I can go on and on. Two hostesses were taking selfie and showing each other rather than paying attention to the customers. Bus boy took plates away while we were still eating.....will not return read more