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The Chicago Diner is probably the most famous and beloved vegetarian restaurant in the Chicago area, perhaps because they have been "meat free since '83."
The inside of the diner is really cute, decked out with red countertops and booths and chrome accents. Though it's a small restaurant, you don't get the feeling of being stuffed in or unable not to eavesdrop on your neighbors.
Our service was fast and friendly, which is exactly what you expect at a diner-style restaurant. The second time I visited was to pick up a take out order and head to a Chicago Cubs game (yes, you can bring in backpacks and outside food). We called ahead and the food was ready when we arrived, so we loaded our bag and headed to the game.
The only downside of the actual location is that parking is a real pain. You can park in their parking lot at night for free, and you can look for space on the street, but it's not easy to find. Even when I was just hovering in the area to wait for our carryout order, the owners of the lot stood outside glaring at me and then scurried to put up a "no parking" sign in the middle of the alleyway.
Their food is true diner heaven; burgers, fries, reubens, meatball subs, chicken salads, shakes, and brunch until 3 pm everyday. Not everything is vegan, but virtually everything can be made vegan.
Probably their most famous sandwich is the Radical Reuben, which is actually trademarked. It's on marbled rye bread, which my husband says is the foundation of a good Reuben sandwich. The bread is covered in the traditional fixings of Thousand Island dressing, sauerkraut, and grilled peppers and onions. It's then loaded with a very thick layer of seitan "corned beef"-- I'm talking like 2 inches of seitan.
In my non-vegan days I would never have ordered a Reuben sandwich, and I still have a very tough time enjoying fake meats, especially when they get extremely close to the real taste and texture.
So, my feelings about the Radical Reuben are mixed. But, if you ask someone who loves diner food, like my husband, he would say it's "the best vegan reuben he's ever had."
If you're a diner food fan bringing along a date like me, you could aim her for the salads. I had the Buffalo style Chickun Ranch Salad, and though it still had pieces of seitan, to me they didn't seem to imitate real meat and I loved them. They were perfectly spicy and had great texture, which paired really well with the cooling, dill-filled ranch dressing. You can also choose the same salad with BBQ seitan.
I've tried a few of The Chicago Diner's side items and all were really good. The sweet potato fries had nice crunch, which can be hard to pull off with a sweet potato base rather than white potatoes. The macaroni and cheese was amazing, and really, really reminded us of the non-vegan version, but not in a bad way. I've also had the ginger garlic flashed greens and I loved the flavor of them, I just wish they had been cooked for a little less time.
If you love a good sports bar style nachos platter, you should definitely try The Chicago Diner's Nachos unleashed. The plate is piled high with crunchy corn chips, and then just absolutely loaded with toppings like lettuce, tomatoes, onions, salsa, guacamole, jalapenos, black beans, and their seitan chorizo. It's enough to satisfy a table of four.
I would guess the vegan shakes are a diner fan favorite at The Chicago Diner. They're made with Chicago soy dairy vegan ice cream and are flavored with real fruit, using no artificial flavors.
milkBehind the cute retro diner bar complete with red booth chairs is a milkshake machine that they use to make every shake. When they come out, they're incredibly thick and sweet. I think they use about 4-5 scoops of ice cream to make each shake, so beware that it's probably a two man job to finish one.
The Chicago Diner also has a really popular bakery where you can order everything from a breakfast muffin to a vegan wedding cake. Their desserts always look amazing and are really well priced.
The only thing I've tried is the cinnamon bun, and it was really tasty. The bread itself is light and fluffy and only a tiny bit sweet, and it is filled with a nice cinnamon filling and topped with a thin layer of frosting. It's not over the top, and I like that.
Regardless of whether you love diner food, I think The Chicago Diner is a must-try when you're visiting. It's just such an institution that if you leave without eating a reuben, you'll regret it later when you hear people praising the sandwich.
If you're interested in trying to replicate some of their famous vegan diner food, check out their vegan cookbook.