Maxwell Street Style Pork Chop Sandwiches
Chicago Street Food, At Home
Maxwell Street Style Pork Chop Sandwiches are a twist on a Chicago hot dog stand classic with that backyard cookout flavor. Thin, juicy pork chops marinated in zesty Italian dressing, grilled hot and fast, are topped with slow-cooked sweet onions that are buttery, golden, and just a little tangy.
Mister Tipsy LOVES a good pork chop sandwich. If we go to a beef stand, and they have a pork chop sandwich, he will get a chop sandwich every single time over a beef.
I too love a good pork chop, but I am always tempted by the beef. That is why this past Monday I made these Maxwell Street Style Pork Chop Sandwiches at home.
After watching Mister devour these, I have a feeling they are going to be on the menu for a long time. He loved them and they were very easy to make.
What Is Maxwell Street?
If you are not familiar with what even is Maxwell Street in Chicago, let me tell you! A Maxwell Street sandwich in Chicago refers to a Polish sausage or bone-in pork chop served on a bun with grilled onions, yellow mustard, and sport peppers.
These come from the Maxwell Street Market area of Chicago. These sandwiches have specific toppings and poppy seed buns or white bun, and the signature flat-top griddle cooking style.
Maxwell Street is most famous for its iconic Polish Sausage Sandwich.
I did not want to have the bone in my sandwiches so I omitted the bone in chop for the boneless ones. I think it is a much better choice, especially if you are feeding children.
I also did mine on the grill and not a griddle.
The Marinade
The marinade is not classic to an actual Maxwell Street Style sandwich, but I knew I wanted to use it. I love the way zesty Italian dressing marinates chicken or pork.
I think it adds such great flavor so I use the whole bottle but you can use less if you like. I like the chops to be really soaking in the marinade overnight.
This is the same dressing I use to marinate the chicken for my Caesar Pasta Salad with Chicken.
Do Not Overmarinate
You can marinate these chops too long. Because the chops are thin, they can start to cure if they are left too long in the marinade.
Be sure to not leave them for more than 24 hours. If I had my way, twelve hours would be ideal but you can even get away with 6 to 8 hours if needed.
The Onions Take Time
The onions will take a long time to cook. Do not rush these.
I did include steps to make the onions in a slow cooker if you do not want to take the time to tend to the stove. The onions are the best part of this sandwich.
Give them the time they deserve!
Maxwell Street Style Pork Chop Sandwiches Recipe
A Chicago classic with that backyard cookout flavor. Thin, juicy pork chops marinated in zesty Italian dressing, grilled hot and fast, and topped with slow-cooked sweet onions that are buttery, golden, and just a little tangy. This one tastes like an old-school Chicago hot dog stand.
Ingredients
- 8–10 thinly cut boneless pork chops
- 1 bottle zesty Italian salad dressing (I like Wishbone brand) (16 ounce)
- 4–6 medium yellow or sweet onions, sliced thin
- 4 Tbsp butter
- 2 Tbsp brown sugar
- 2 Tbsp yellow mustard, plus more for topping
- 2 tsp soy sauce
- ½ tsp black pepper
- ½ tsp celery salt
- Pinch of paprika
- Soft hamburger buns of your choice
Instructions
- Marinate the Pork Chops. Pat the pork chops dry and place them in a shallow dish or large zip-top bag. Pour the entire bottle of Italian dressing over the chops, seal, and refrigerate up to 24 hours and no longer, or they’ll start to cure. Tip: If you need to wait another day, remove them from the marinade, pat dry, and refrigerate until ready to grill.
- Make the Onions. Slice onions thin and add them to a skillet with butter over low heat. Cook low and slow about 1 hour until they’re soft, golden, and caramelized. Add soy sauce, brown sugar, mustard, paprika, black pepper, and celery salt, then turn up the heat for 10 minutes to let everything get simmered in the seasonings.
- Grill the Pork Chops. Heat your grill to 450°F. Grill pork chops for about 3 minutes per side, adjusting for thickness. When done, cover with foil and rest for 5 minutes.
- Assemble the Sandwiches. Spread yellow mustard on your buns, layer on two chops, and top with as many onions as your heart desires.
- Slow Cooker Method: Sauté onions in butter on the stovetop for about 10 minutes until they just start to soften. Transfer them to your slow cooker. Add soy sauce, brown sugar, mustard, paprika, black pepper, celery salt, and ¼ cup beef broth. Cook on LOW for 6 hours until they’re tender, sweet, and golden.