Chili's Grill & Bar
33 Crystal Run Crossing, Middletown
(845) 692-4478
Customers' Favorites
Chicken Bacon Ranch Quesadillas
Crispy Chicken Crispers Combos
Chili's Secret Sauce Burger
Chili's House Mar-Go-Rita
Bottomless Chips & Salsa
Grilled Chicken Fajitas
Bottomless Tostada Chips
Alex's Santa Fe Burger
Molten Chocolate Cake
Southwestern Eggrolls
Featured items
Triple Dipper™
Select three appetizers and enjoy! Served with dipping sauces.
Honey-Chipotle Chicken Crispers® Combo
Chicken tenders tossed in our famous honey-chipotle sauce, served with NEW white cheddar mac & cheese (270 cal), fries (420 cal) & house-made ranch (170 cal).
Chicken Bacon Ranch Quesadillas
Chicken, shredded cheese, chile spices, bacon, house-made ranch. Served with pico, sour cream, ranch.
Crispy Chicken Crispers® Combo
Chicken tenders served with NEW white cheddar mac & cheese (270 cal), fries (420 cal), house-made ranch (170 cal) and 2 dipping sauces.
Nashville Hot Chicken Crispers® Combo
Chicken tenders tossed in our NEW Nashville Hot sauce, served with NEW white cheddar mac & cheese (270 cal), fries (420 cal) & house-made ranch (170 cal).
Ultimate Smokehouse Combo
Our famous Baby Back Ribs, Crispy Chicken Crispers® and Jalapeño-Cheddar Smoked Sausage. Served with roasted street corn, fries & garlic toast.
Skillet Chocolate Chip Cookie
Topped with vanilla ice cream, hot fudge.
Big Mouth Crispy Chicken Sandwich
Hand-breaded crispy chicken, lettuce, tomato, and our secret sauce on a brioche bun.
Full Order of Ribs
A full order of Baby Back Ribs slow-cooked and smoked in-house in your choice of two flavors. Served with fries & white-cheddar mac & cheese.
Chipotle Bowl
Your choice of grilled chicken, shrimp or Ancho salmon, pico, field greens, Mexican rice, corn salsa, avocado, shredded cheese, tortilla strips, cilantro, chipotle pesto, house-made ranch.
Big Mouth® Bites
4 mini burgers with bacon, American cheese, sauteed onions, house-made ranch.
Oldtimer® w/Cheese*
The original burger. Pickles, lettuce, tomato, red onion, mustard, cheddar cheese.
Classic Sirloin* - 10oz
Seasoned & topped with garlic butter. Served with loaded mashed potatoes (add 350 cal), and steamed broccoli (add 40 cal).
Bacon Rancher Burger*
Two beef patties, six slices of bacon, house-made ranch, American cheese, sauteed onions, pickles.
Fajita Trio
Margarita Grilled Chicken
Pico, tortilla strips, Mexican rice, black beans.
Santa Fe Crispers® Salad
Hand-battered Chicken Crispers, pico, avocado, cilantro, tortilla strips, house-made ranch & a drizzle of spicy Santa Fe sauce.
Just Bacon Burger*
Layered with slices of bacon, cheddar cheese, pickles, lettuce, red onion, tomato, mayo.
Mix & Match Fajitas
Appetizers
Triple Dipper™
Select three appetizers and enjoy! Served with dipping sauces.
Fried Mozzarella
Served with Marinara sauce.
Boneless Wings
Crispy boneless wings hand-tossed in up to 2 flavors with 2 sides of house-made ranch. Choose the count that fits your game day appetite!
Bone-In Wings
Our classic, crispy wings are hand-tossed with your choice of 2 flavors and 2 sides of house-made ranch. Now serving all NEW counts!
Texas Cheese Fries - Half
Shredded cheese, bacon, jalapeños, green onions. Served with house-made ranch.
Southwestern Eggrolls
Crispy flour tortillas, chicken, black beans, corn, jalapeño Jack cheese, red peppers, spinach. Served with avocado-ranch.
Chicken Bacon Ranch Quesadillas
Chicken, shredded cheese, chile spices, bacon, house-made ranch. Served with pico, sour cream, ranch.
Brisket Quesadillas
Shredded cheese, slow-smoked pulled brisket, jalapeños, house BBQ. Served with pico, sour cream & ranch.
Texas Cheese Fries - Full
Shredded cheese, bacon, jalapeños, green onions. Served with house-made ranch.
Fresh Guacamole
Made fresh daily. Served with corn-tostada chips & fresh salsa.
Chips & Salsa
Corn tostada chips made fresh daily. Served with fresh salsa.
Dip Trio
Choose any three. Skillet queso, white queso, fresh salsa, fresh guacamole or house-made ranch. Served with corn tostada chips.
White Skillet Queso
Served with corn tostada chips & fresh salsa.
Skillet Queso
Original queso with beef. Served with chips & fresh salsa.
Fajitas
Fajita Trio
Chicken Fajitas
Mix & Match Fajitas
Steak Fajitas
Shrimp Fajitas
Big Mouth Burgers®
Big Mouth® Bites
4 mini burgers with bacon, American cheese, sauteed onions, house-made ranch.
Just Bacon Burger*
Layered with slices of bacon, cheddar cheese, pickles, lettuce, red onion, tomato, mayo.
Secret Sauce Burger*
Secret sauce, American cheese, lettuce, sauteed onions.
Oldtimer® w/Cheese*
The original burger. Pickles, lettuce, tomato, red onion, mustard, cheddar cheese.
BBQ Brisket Burger*
Pulled brisket, house BBQ, cheddar cheese, pickles.
Bacon Rancher Burger*
Two beef patties, six slices of bacon, house-made ranch, American cheese, sauteed onions, pickles.
Mushroom Swiss Burger*
Sauteed onions, mushrooms, Swiss cheese, lettuce, tomato, mayo.
Double Old Timer w/Cheese*
NEW! Two juicy beef patties, cheddar cheese, pickles, lettuce, tomato, red onion, mustard.
Alex's Santa Fe Burger*
Avocado, pepper Jack, red onion, jalapeños, tomato, pickles, cilantro, spicy Santa Fe sauce.
Chicken Crisper® Combos
Honey-Chipotle Chicken Crispers® Combo
Chicken tenders tossed in our famous honey-chipotle sauce, served with NEW white cheddar mac & cheese (270 cal), fries (420 cal) & house-made ranch (170 cal).
Crispy Chicken Crispers® Combo
Chicken tenders served with NEW white cheddar mac & cheese (270 cal), fries (420 cal), house-made ranch (170 cal) and 2 dipping sauces.
Nashville Hot Chicken Crispers® Combo
Chicken tenders tossed in our NEW Nashville Hot sauce, served with NEW white cheddar mac & cheese (270 cal), fries (420 cal) & house-made ranch (170 cal).
Steaks & Ribs
Full Order of Ribs
A full order of Baby Back Ribs slow-cooked and smoked in-house in your choice of two flavors. Served with fries & white-cheddar mac & cheese.
Classic Sirloin* - 6oz
Seasoned & topped with garlic butter. Served with loaded mashed potatoes (add 350 cal), and steamed broccoli (add 40 cal).
Classic Ribeye*
Marbled, thick-cut steak topped with garlic butter. Served with loaded mashed potatoes (add 350 cal), and steamed broccoli (add 40 cal).
Half Order of Ribs
A half order of Baby Back Ribs slow-cooked and smoked in-house in your choice of flavor. Served with fries & white-cheddar mac & cheese.
Surf & Turf Ribeye*
Marbled, thick-cut steak topped with garlic butter and a dozen shrimp. Served with loaded mashed potatoes (add 350 cal) & steamed broccoli (add 40 cal).
Surf & Turf Sirloin* - 10oz
Seasoned & topped with garlic butter and a dozen shrimp. Served with loaded mashed potatoes (add 350 cal) & steamed broccoli (add 40 cal).
Classic Sirloin* - 10oz
Seasoned & topped with garlic butter. Served with loaded mashed potatoes (add 350 cal), and steamed broccoli (add 40 cal).
Classic Sirloin* with Avocado - 10oz
Seasoned and topped with cilantro pesto, avocado slices, cilantro, pico. Served with roasted asparagus.
Classic Sirloin* with Avocado - 6oz
Seasoned and topped with cilantro pesto, avocado slices, cilantro, pico. Served with roasted asparagus.
Smokehouse Combos
Ultimate Smokehouse Combo
Our famous Baby Back Ribs, Crispy Chicken Crispers® and Jalapeño-Cheddar Smoked Sausage. Served with roasted street corn, fries & garlic toast.
Smokehouse Combo
Our famous Baby Back Ribs and Crispy Chicken Crispers®. Served with roasted street corn, fries & garlic toast.
Chicken & Seafood
Ultimate Cajun Pasta
NEW! Grilled chicken, shrimp, penne in Alfredo sauce, topped with chile spices, shredded Parmesan, tomatoes, green onions. Served with garlic toast.
Chipotle Bowl
Your choice of grilled chicken, shrimp or Ancho salmon, pico, field greens, Mexican rice, corn salsa, avocado, shredded cheese, tortilla strips, cilantro, chipotle pesto, house-made ranch.
Margarita Grilled Chicken
Pico, tortilla strips, Mexican rice, black beans.
Ancho Salmon
Seared chile-rubbed Atlantic salmon, cilantro pesto, cilantro, queso fresco. Served with Mexican rice & steamed broccoli.
Cajun Pasta
Your choice of grilled chicken or shrimp with penne in Alfredo sauce, topped with chile spices, Parmesan, tomatoes, green onions. Served with garlic toast.
Guiltless Grill
Margarita Grilled Chicken
Pico, tortilla strips, Mexican rice, black beans.
Ancho Salmon
Seared chile-rubbed Atlantic salmon, cilantro pesto, cilantro, queso fresco. Served with Mexican rice & steamed broccoli.
Santa Fe Salad
Your choice of protein, pico, avocado, cilantro, tortilla strips, house-made ranch & a drizzle of spicy Santa Fe sauce.
Classic Sirloin* with Avocado - 10oz
Seasoned and topped with cilantro pesto, avocado slices, cilantro, pico. Served with roasted asparagus.
Classic Sirloin* with Avocado - 6oz
Seasoned and topped with cilantro pesto, avocado slices, cilantro, pico. Served with roasted asparagus.
Bowls & Quesadillas
Chipotle Bowl
Your choice of grilled chicken, shrimp or Ancho salmon, pico, field greens, Mexican rice, corn salsa, avocado, shredded cheese, tortilla strips, cilantro, chipotle pesto, house-made ranch.
Chicken Bacon Ranch Quesadillas
Chicken, shredded cheese, chile spices, bacon, house-made ranch. Served with pico, sour cream, ranch.
Brisket Quesadillas
Shredded cheese, slow-smoked pulled brisket, jalapeños, house BBQ. Served with pico, sour cream & ranch.
Sandwiches
Big Mouth Crispy Chicken Sandwich
Hand-breaded crispy chicken, lettuce, tomato, and our secret sauce on a brioche bun.
Chili's Philly
NEW! Our take on a Philly Cheesesteak. Premium thinly sliced steak, grilled bell peppers & onions, jalapeños, white queso on a toasted buttery roll.
Bacon Avocado Grilled Chicken Sandwich
Grilled chicken, bacon, Swiss cheese, avocado, sauteed onions, lettuce, tomato, mayo on a toasted buttery roll.
Buffalo Chicken Ranch Sandwich
Hand-breaded crispy chicken with spicy Buffalo sauce, tomato, lettuce, house-made ranch on a brioche bun.
Lunch Specials
Lunch Combo - Half Order Bacon Ranch Chicken Quesadillas
Chicken, bacon, shredded cheese, chile spices & house-made ranch. Served with chips & salsa.
Lunch Combo - Chipotle Chicken Fresh Mex Bowl
Grilled chicken, pico, field greens, Mexican rice, corn salsa, avocado, shredded cheese, tortilla strips, cilantro, chipotle pesto, house-made ranch.
Lunch Combo - Boneless Wings
Hand-tossed in your choice of sauce: House BBQ, Honey-Chipotle, or Buffalo. Served with fries.
Lunch Combo - Double Burger
Two grilled patties, American cheese, lettuce, tomato & mustard. Served with fries.
Mini Chocolate Molten
Mini version of our Molten Chocolate Cake. Chocolate cake with a melted chocolate center, topped with vanilla ice cream in a chocolate shell with caramel drizzle.
Lunch Combo - Bacon Avocado Grilled Chicken Sandwich
Half sandwich with grilled chicken, bacon, swiss, avocado, sauteed onions, lettuce, tomato, mayo on a toasted buttery roll. Served with fries.
Salads, Soups & Chili
Bowl of Soup
Quesadilla Explosion Crispers® Salad
Hand-battered Chicken Crispers, cheese, tomatoes, corn salsa, tortilla strips, cilantro with citrus-balsamic. Topped with our cheese quesadillas. Dressing served on the side.
Santa Fe Crispers® Salad
Hand-battered Chicken Crispers, pico, avocado, cilantro, tortilla strips, house-made ranch & a drizzle of spicy Santa Fe sauce.
Soup & Caesar Salad
A delicious bowl of Soup with a side Caesar Salad. Dressing served on the side.
Quesadilla Explosion Salad
Your choice of protein, cheese, tomatoes, corn salsa, tortilla strips, cilantro with citrus-balsamic. Topped with our cheese quesadillas. Dressing served on the side.
Chili & Caesar Salad
A delicious bowl of the Original Chili with a side Caesar Salad. Dressing served on the side.
Side Caesar Salad
Greens, Parmesan, croutons & Caesar dressing. Dressing served on the side.
Side House Salad
Tomatoes, red onions, cucumbers, shredded cheese, garlic croutons with your choice of dressing.
Cup of the Original Chili
Our original recipe with beef, onions & signature blend of spices. Topped with cheese & tortilla strips.
Cup of Soup
Soup & House Salad
A delicious bowl of Soup with a side House Salad. Dressing served on the side.
Bowl of the Original Chili
Our original recipe with beef, onions & signature blend of spices. Topped with cheese & tortilla strips.
Chili & House Salad
A delicious bowl of the Original Chili with a side House Salad. Dressing served on the side.
Santa Fe Salad
Your choice of protein, pico, avocado, cilantro, tortilla strips, house-made ranch & a drizzle of spicy Santa Fe sauce.
Desserts
Skillet Chocolate Chip Cookie
Topped with vanilla ice cream, hot fudge.
Molten Chocolate Cake
Chocolate cake with a molten chocolate center, topped with vanilla ice cream in a chocolate shell with caramel drizzle.
Cheesecake
Served over strawberry puree.
Sides & Sauces
Sides
Choose from several mouth-watering choices.
Sauce Options (4oz)
Kids Menu
Mini Chocolate Molten
Mini version of our Molten Chocolate Cake. Moist chocolate cake with a melted chocolate center. Topped with vanilla ice cream & a thin chocolate shell.
Pepper Pals® Crispy Crispers®
Crispy Chicken Crispers® served with choice of side and a drink.
Pepper Pals® Cheese Burger Bites
Cheeseburger bites made with all-natural beef and served with choice of side and a drink.
Kraft® Macaroni & Cheese
Kraft® Macaroni & Cheese served with choice of side and a drink.
Pepper Pals® Cheese Quesadilla
Cheese Quesadilla served with choice of side and a drink.
Pepper Pals® Cheesy Chicken Pasta
Cheesy chicken pasta served with choice of side and a drink.
Pepper Pals® Cheese Pizza
6" Cheese Pizza served with choice of side and a drink.
Pepper Pals® Grilled Chicken Dippers
Grilled Chicken Dippers served with choice of side and a drink.
Pepper Pals® Pepperoni Pizza
6" Pepperoni Pizza served with choice of side and a drink.
Pepper Pals® Burger Bites
Burger bites made with all-natural beef and served with choice of side and a drink.
Pepper Pals® Grilled Chicken Bites
Grilled Chicken Sandwich Bites served with choice of side and a drink.
Beverages
Beverages
Brewed tea, lemonade and fountain drinks
Gallon of Strawberry Lemonade
Blackberry Iced Tea
Our fresh-brewed iced tea has a delightful hint of blackberry to tickle your taste buds
Strawberry Lemonade
Cold, bold and thirst-quenching lemonade juiced up with real strawberries.
NEW! Wildberry Tea
Mango Iced Tea
Adding sweet mango flavor to our fresh-brewed iced tea makes it delicious.
NEW! Wildberry Lemonade
Photos
+46 photos
+45 photos
Add a photo
Recent Reviews
So we usually come to this Chillis every other weekend or at minimum once a month. We notice the manager Maruk hopefully I got his name right he's always walking around making sure the customers are good. We were here yesterday with a party of 7. So far the largest party we have come with to this Chillis. Well our serve Quentin was great always checking up on us and making sure if we needed anything or any refills. Unfortunately the soup I planned to order was going to take...
August 2025
Our server Louie was phenomenal, super attentive and really took care of me and my family. Always made sure we didn’t have to ask for refills and was constantly tidying up our table to prepare us for the next course. I highly recommend dining here. Definitely will be asking for him again.
August 2025
My daughter wanted to go to Applebees for her 5.5 birthday. But we’ve been to Applebees three times in the last 2 weeks. That’s too much. I don’t even really like Applebees. So we settled on Chilis, southwestern Applebees. And it was actually great. All three things on my sampler were exactly what I wanted. And my beer was cold. First round of kiddie fries were messed up due to a flake of pepper making its way onto one single fry. But they were good to replace the whole...
July 2025
You May Also Like
It's Just Wings - 33 Crystal Run Crossing
![]()
Chicken Wings
D lux Diner - 14 Crystal Run Crossing
![]()
Diner, American, Vegetarian
Dunkin' - 2 Ben Gilman Wy
![]()
Coffee Shops, Coffee & Tea, Donuts, Coffee