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Real Chicago-style dogs in Weymouth

At Windy City Eats. Just returned from a trip to Weymouth to try these, and we (including one genuine Chicagoan) weren't disappointed. The Chicago Dog is $2.49 and is the real deal: Vienna Beef hot dog, poppyseed bun, sport peppers,onions, mustard, celery salt, tomato slice, pickle spear, and neon green relish. Delish and perfectly done. Other menu items include a "Maxwell Street Polish": polish sausage deep fried to give it that perfect snap, with grilled onions and mustard for $3.49. They also serve hot and cold sandwiches, but we didn't try these. We also tried the sweet potato fries, onion rings,and a few corn dogs, which Grady hand dips himself. We didn't leave a crumb.

Owners Grady and Sen are super nice people- Grady is from Chicago and knows his stuff. They deliver (didn't ask for the delivery area b/c we came from Boston) and do catering. He quoted us a catering deal of 50 chicago dogs with the works for $119. We can't wait to have them cater our block party!

The space is very small, there is a small bar area where two people could stand and eat. In good weather, there is a lovely pond with a gazebo and benches just a few feet down the street where a 'hound could dine al fresco. We took an RV and gorged ourselves in there. Grady and Sen both came out to visit us in the RV, see how we liked our food, and just to chat.

This is the real deal folks, get on down there. It would be a crime if this place didn't survive.

Mon-Sat 11-8:30, Sun 12-7 (closed Labor Day Monday

Windy City Eats
407A Middle St, Weymouth, MA 02189

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  1. Powella, couldn't have written it better myself. I too have been down there a couple of times for a taste of home and have been very pleased. I've stuck to the dogs and polishs but need to try the italian beef next time I am there. Grady and Sen are very nice and should do well there. Speeds will still get all the hype on this board (Deservedly so) but Windy City Eats should always be mentioned in the same breath.

    1 Reply
    1. re: mats77

      Great eats! Great prices!! The Italian Beef and Grady's Steak Sandwich are definitely delicious--full of flavor and hit the spot when you're hungry and cruising for awesome grub. Finger licking good! Grady's special recipe corndogs are amazing as well. Add some sweet potato fries and a brownie .............was worth going to Weymouth from New Mexico!!

    2. This place is minutes from my house and I keep meaning to try them ever since I saw the sign first go up. Unfortunately, my summer's been a bit crazy and I haven't been able to make it yet.

      I am going to try to make it a point to go this week. No more procrastinating!

      1. Yeah this place rules!
        I work in the area and we've sent people out to get Chicago style 'dogs by the bagfull. They also have a frequent customer card where 12 hot dogs will get you a free one. It is very true to the Chicago style...though I'd prefer a thicker slice (or two) of tomato.

        1. I hope we can all do our part to spread the word on how terrific this place is and get another independent business up and successful over the long term. In a very convenient location, so it is easy to find. I was so happy to see a coupon in the mail for Chicago-style hot dogs, being a transplanted Chicagoan myself, that I could not have been happier to meet Grady and Sen and have one of my first Vienna hot dogs with that wonderfully steamed poppyseed bun in ages!
          I do my part, but I work in Boston so I only get there about once a week, two when I'm lucky. And I love that Grady and Sen are so friendly and remember my name, and we'll occasionally chat and you can tell the customer relationships mean a lot to them.

          1 Reply
          1. re: bagheera

            I'd have already gone there multiple times but don't have a car. Damn these places that like to open up in the burbs!

          2. I finally made it to Windy City Eats for lunch this weekend. It was worth the wait. The dog was juicy and snapped when I bit into it. It was a great, satisfying lunch for under $5.

            I agree with bagheera, the staff & owner are very friendly and chatty.

            I am definitely headed back sometime soon.

            jgg, the 222 bus from the Qunicy Center Redline stop goes to Middle Street in Weymouth.

            4 Replies
            1. re: mangorita

              The commuter rail also goes within a mile of it, but that's an awful hike to make for a dog. I'll probably do it at some point but stuff out in the burbs almost never gets any of my business.

              1. re: jgg13

                A brisk walk to get something good and tasty is never a problem. A mile certainly isn't a deterrent. The walk back is usually much slower.

                This place is def on the short list, maybe even this afternoon. Happy to see they have celery salt!

                1. re: Wursthof

                  It isn't the mile walk, it's the journey to get to the place where the mile walk starts ;) I will walk to things up to about 2 miles w/o really thinking about it. I'm just saying that pretty much no place is worth me spending a good chunk of my day to get to.

                  1. re: jgg13

                    jgg13, this is just the kind of dilemma that led us to sign up for zipcar. Much, much better than commuter rail, and you can make other stops en route should you wish....

            2. Saw this post and ran out for lunch to grab a coupla dogs. The OP is right, they are the real deal. I ordered a Chicago dog and a Polish Chicago Sausage. Both were very good. I ate the Polish first and was full after the first bite of the my hot dog.( those little sport peppers pack a punch and lend to the full feeling, I think.) A great deal; the dog and sausage only cost me $6.25. The menu is small, which I like, because what they do, they seem to do well. I'lll be back.

              1. Oh man. This is exciting. Is the italian beef the real deal, served wet?

                1 Reply
                1. re: celeriac

                  I asked if the Italian beef could be dipped and he said "of course". Haven't tried it yet though...I've only had the 'dogs.

                2. Powella, thank you for you post! I finally got to Windy City Eats today after seeing your post a few months ago and was in heaven! As a Chicago native, I have been craving Chicago Dogs and finally have a place to get my fix!!

                  Your post was very well written so no need for me to repeat. And as most have said, the owner Grady (didnt get a chance to meet his wife) was quite the gracious host.

                  I had a polish (and dare say I went and got a dog too after devouring the polish!) lol! They were so great!!

                  I tried Beezers this summer for Chicago hot dogs based on recommendations I saw on Chowhound, but it didnt make the grade for me.

                  Windy City Eats on the other hand, is something to rejoice over! lol! I definitely will be going back more often!!

                  And hopefully Grady wont be kicking me out for continually asking for ketchup to be added (Chicago people know what I mean). lol!

                  Am sure I will be seeing many of you there!

                  1. Wanted to pull up this old post. Went yesterday and had some Chilli Cheese fries and a Chicago dog. total was $5.50. Dog was good as always but I want to comment on the fries......They're GREAT. They're made to order, are thin and cripsy (think McD's) and have a great fri to chili to cheese ratio. The chilli is produced from the Vienna beef co., the same maker as the dogs, and it is far far better than i thought it'd be. The best part of all is the packaging they serve it in. They layer the fries, chili,and cheesse in a nice sturdy container that allows you to eat them with a fork and keep yourself free of chili stains.

                    2 Replies
                    1. re: cannedmilkandfruitypebbles

                      I ventured down to Weymouth after reading the original post and I'm afraid I was very disappointed.
                      The food was passable, but nothing we ordered was made from fresh ingredients.
                      By that I mean everything was frozen. I expected the potatoes to be at least hand cut and they were not.
                      Tried it once and won't be returning.

                      1. re: janzy

                        Don't get me wrong. It's not destination dining. But if you're in the area and have a craving for a Chicago dog, something you can not get anywhere else around here, it's worth a stop in. it's as fresh as a hotdog-stand-type-of-place in Weymouth can be in order to maintain financial existance. It's hotdog vendor. Nothing more, nothing less. You can get two dogs and a bag of chips for under $6. Try doing that at NE Hot Dog Co.

                    2. My prior Chicago Dog experience is from many trips to Chicago to the headquarters office of my company. Portillo's and others are required stops for lunch when I visit the team out there. I'm not quite the world's expert on the genre but lets just say I like to eat good food.

                      With the arrival of Windy City eats, I've become a regular, a devotee, an addict. Grady is very into the authenticity of the food he serves and it shows. I don't need to re-iterate many of the comments above. I've tried nearly everything on the menu. There's really not anything to criticize. My standard is the Maxwell Street Polish (Fried Polish Sausage), but I deviate from the menu and substitute sour kraut for the fried onions (It's the former New Yorker in me). Try the fries (comes with celery salt).

                      If your looking for some real food and some nice stop by Windy City Eats.


                      1. Stopped in last night for an Italian beef and maxwell Polish and couldn't have been happier. Combine that with my upcoming trip to see the Cubs take on the Yanks at the new Yankee Stadium and I'm enjoying a little Chicago-nirvana right now.

                        1. Wanted to give a shout out, finally made it down there via zip car. This place is amazing - it's probably a good thing htat it's not closer as i'd get far too fat :) The dog is certainly the real deal, ranking right at the top of the places I've been to in Chi-town. The italian beef was good, I've had better but it was still very tasty and I certainly haven't had anything better outside of chicago. :) The chili cheese fries were also quite tasty.

                          As others mentioned, the hosts were super nice, chatting us up, dealing wiht the regulars, etc. This is truly a great spot.

                          3 Replies
                          1. re: jgg13

                            Just returned from another happy visit to Windy City Eats. Grady and Sen have now added very nice (large and sturdy) picnic table seating. One table (covered with Vienna Beef umbrellas) was large enough to seat all 7 of us, comfortably. The food was, as usual, outstanding.

                            Grady also mentioned that he is frequently collaborating with a Weymouth pub (darn it, can't remember the name, maybe a Weymouth 'hound can help out here) that has a large number of fine beers on tap. Apparently, for certain special occasions (like July 3rd, coming up) Grady will do dogs at this pub. It sounded great to me... a nice beer would be the only way to improve the experience of eating Windy City Eats' dogs.

                            1. re: powella

                              I would bet the pub in Weymouth is Union Brewhouse, the only bar in the area with a good selection of craft beers.