Boston’s Best Chili Dishes

January 8, 2014 6:00 AM

Chili is one of those dishes that can be an appetizer or even a hearty meal. Packed with flavors and spices, veggies, meat and beans, no two recipes are the same since everywhere you go makes chili their own way. Served in a bowl and smothered in cheese with crispy chips for dipping or included as a topping to fries or even a hot dog, the following locations have options for enjoying chili the way you like it.
 Bostons Best Chili Dishes

Tasty Burger – All The Way Burger/Hot Dog with Chili (Credit, Michelle Levine)

Tasty Burger
1301 Boylston St.
Boston, MA 02215
(617) 425-4444

Just steps from Fenway Park, Tasty Burger takes chili and uses it in a few of its delicious dishes. You can order it up simply, in a bowl for just $3.95 with chopped onions, but the way to really enjoy it is on top of one of the burgers or hot dogs. For the ultimate experience, order the “All The Way” which includes a burger and a 1/2-pound hot dog with chili, cheese, bacon and onions on top, for $12. There is also a chili cheese dog with jalapeño cheese sauce or the Hubba Burger, which features chili, spicy cheese sauce and onions for $5.75. To eat alongside the burgers and dogs are fries, onion rings or salad, and to wash it down, over 30 kinds of canned beers, wine or milkshakes in unique flavors like creamsicle or Green Monster.

Sweet Caroline’s Restaurant & Bar
1260 Boylston St.
Boston, MA 02215
(617) 424-1260

Also near Fenway, but with much more of an upscale modern bar feel, is Sweet Caroline’s. This 4,000-square-foot multi-level restaurant features a menu filled with American comfort food favorites along with plenty of TVs for viewing all of the best local Boston sports teams. Start off a meal with a “Big Boy Bottle” of beer alongside a bowl of classic chili, available for $8. The spicy recipe features high-quality grass-fed beef with a Monterey jack and cheddar blend of cheeses on top, plus green onions to add a pop of flavor and texture to the mix, and then fresh cornbread for dunking. Other menu highlights include buffalo chicken Rangoon, fried oyster salad, lobster roll or stuffed mushroom sandwiches amongst the many choices.

Photo Credit: Fajitas & 'Ritas

Photo Credit: Fajitas & ‘Ritas

Fajitas & ‘Ritas
25 West St.
Boston, MA 02111
(617) 426-1222

Located in downtown Crossing is casual eatery Fajitas & ‘Ritas. Amongst the many options to eat, including fajitas with a variety of proteins, this spot also makes a mean cup or bowl of chili. Its meat- and bean-packed recipe can be served with cheese for under $6. One of the highlights on the menu is the tostada salad, which is a fried flour tortilla bowl filled up with crisp fresh veggies, drizzled with creamy cilantro lime dressing, guacamole and cheese. Add chili to it or go for steak, shrimp or one of the other available add-ons. The chili also makes a great addition to the cheesy nachos platter. To drink with the chili, you won’t want to miss out on the signature margarita menu with options like mango or raspberry, to name a few.

Related: Phantom Gourmet: Chili

nachos Bostons Best Chili Dishes

Grand Slam Nachos at Stadium (Credit, Michelle Levine)

Stadium Sports Bar & Grill
148 State St.
Boston, MA 02109
(857) 263-8262

Perfect for watching the big game or for after-work drinks is Stadium Sports Bar & Grill. Conveniently located in the Financial District and Faneuil Hall Marketplace, head here for appetizers perfect for sharing including the Grand Slam Nachos. For just $7.95, you get a skillet piled high with fresh corn tortillas, tomatoes, onions, jalapenos and melted cheese with sour cream and salsa. Then load up the nachos with your favorite toppings (for an extra few dollars) including the delicious chili, guacamole, chicken or steak. You can also choose from the same list of toppings for the loaded waffle fries. Or you can just order the Stadium chili as is, which features ground beef, veal and pork for a flavorful, spicy dish available in a cup or bowl, both for under $5.

Bean & Leaf Cafe
20 Custom House St.
Boston, MA 02110
(617) 261-4727

Also in Financial District is Bean & Leaf Café, a great place to pop in and get everything from a breakfast sandwich to a Middle Eastern roll-up. This spot is loved for its soups, chilis and comforting stews. All are made from scratch and come with pita or crackers to enjoy with it. Turkey chili, chicken chili, veggie chili, chicken stew and lemon chicken cilantro are just a few of the regular soup offerings available in 12- or 16-ounce sizes for under $6.

Related: Boston’s Best Chili

Michelle Levine is a creative energetic, young professional that is passionate about everything Boston has to offer. She loves to attend local events, dine out, and cook and wants to share her findings with you. Her work can be found on