Our Story

About US

Samantha Lewis’s culinary journey began in her family’s kitchen, where she often helped prepare meals for gatherings. From 2013 to 2022, she worked at a childcare center as an assistant teacher. When her director needed someone to step in for a sick kitchen employee, Samantha took on the role, which was responsible for providing all daily meals and snacks to upwards of 50 children, a move that eventually led to her becoming the kitchen supervisor. In this capacity, she meticulously managed the kitchen operations, ensuring that meals met state standards and were tailored to the children’s dietary restrictions. In March 2022, Samantha transitioned to a school district position, providing her the summers off and giving her time to focus on the food truck season.

Samantha Lewis’s culinary journey started in her family’s kitchen, preparing meals for gatherings. From 2013 to 2022, she worked at a childcare center, initially as an assistant teacher, before stepping in to manage the kitchen. As kitchen supervisor, she ensured meals met state standards and catered to dietary restrictions. In March 2022, she moved to a school district position, allowing her summers off to focus on the food truck season.

Deshawn and Samantha with the Windy City Bites Team
DeShawn (DJ) Lewis and his signature traditional oxtail dinner

DaShawn Lewis, affectionately known as DJ, grew up in a family full of cooks, experiencing both the business and pleasure of the culinary world as his family owned multiple restaurants and bars during his childhood. As a teenager, DJ worked for Pizza Hut but later pursued finance and banking. After relocating to Sioux Falls, SD, DJ and Samantha opened Windy City Bites. DaShawn wanted to bring his Jamaican roots into the Chicago-based truck as he missed both Chicago food and his family’s cuisine from Spanish Town, Jamaica. Together, they created Windy City Bites’ ‘Chicago style with Caribbean soul.’ DJ enjoys cooking and uses family recipes, particularly for their Soul Food Sundays. He loves seeing customers’ excitement when he prepares dishes like oxtails and jerk chicken.

DaShawn “DJ” Lewis grew up in a family of cooks, experiencing both the business and pleasure of the culinary world. Despite working at Pizza Hut as a teenager and later pursuing finance, he always cherished his culinary roots. After moving to Sioux Falls, DJ and Samantha opened Windy City Bites, blending Chicago style with Caribbean soul. DJ loves cooking, especially family recipes for their Soul Food Sundays, delighting customers with dishes like oxtails and jerk chicken.

In October 2020, Samantha and DaShawn launched Windy City Bites from a large camper converted into a concessions trailer. By summer 2022, they upgraded to a smaller, more efficient trailer previously used as a corn dog stand at state fairs. Planning to keep the trailer active during summers and larger events, they also expanded with a brick-and-mortar location. Since February 2023, Windy City Bites Bar and Grill, located at 114 N. Indiana Ave., has featured a partial bar serving beer and wine. This 50-person capacity venue hosts various events, including comedy shows, birthday parties, group meetings, sip-and-paint sessions, live music, and wedding receptions. Samantha and DaShawn are committed to maintaining both locations and fostering connections with the Sioux Falls community and surrounding areas for years to come.

In October 2020, Samantha and DaShawn launched Windy City Bites from a converted camper. By summer 2022, they upgraded to a more efficient trailer and expanded with a brick-and-mortar location at 114 N. Indiana Ave. Since February 2023, Windy City Bites Bar and Grill, with a 50-person capacity and partial bar, has hosted events like comedy shows, birthday parties, and live music. Samantha and DaShawn are dedicated to maintaining both locations and fostering connections with the Sioux Falls community for years to come.

A photo of Windy City Bites' first food truck in Summer 2022 and their brick and mortar location which opened in February 2023.

Ways to Dine

Windy City Bites Indoor Dining Area

Dine In

Our truck and restaurant are more than just a place to grab a quick bite. Windy City Bites is the place you go when you wanna get away but can’t. Try some of our Caribbean and Chicago style foods. Be sure to visit us on Wing Wednesday’s to get our famous, full-sized chicken wings for only $1.00 each.

Our truck and restaurant offer more than just a quick bite. Windy City Bites is your escape, serving Caribbean and Chicago-style foods. Join us on Wing Wednesdays for our famous full-sized chicken wings at just $1.00 each.

Windy City Bites Food Delivery via DoorDash

Delivery

Need your Windy City Bites fix but can’t come in? We’ve got you covered with DoorDash! Get your favorite Chicago and Caribbean-inspired dishes delivered right to your doorstep. Just place your order on DoorDash and enjoy our mouth-watering flavors anywhere you are.

A plate of takeout food (tacos) from windy city bites

Take Out

Do you have a craving for our Chicago-style eats but can’t dine in? No problem! Windy City Bites offers convenient takeout options for all your favorite dishes. Whether you’re in the mood for our famous lemon pepper chicken wings or a classic Chicago dog, just place your order and pick it up at your convenience.

Windy City Bites Food Truck

Food Truck

Do you have a company picnic or other special event where you would like us to show up? Book our food truck! Our weekends tend to book up fast, so contact us in advance. We also take private bookings at our indoor location.

events

We take private bookings at our indoor location for a variety of events, including corporate meetings, baby showers, birthday celebrations, family reunions, anniversary parties, and holiday parties. Reach out to us today to plan your next event at Windy City Bites!

Our indoor space is perfect for events like corporate meetings, baby showers, birthday parties, family reunions, and holiday celebrations. Contact us to plan your next event at Windy City Bites!

Windy City Bites Catering Food

Catering

Windy City Bites offers catering services to make your gathering unforgettable! From corporate meetings to private parties, our flavorful dishes will impress your guests. Contact us today to customize your catering menu and bring the taste of Windy City Bites to your special occasion!