Big Bill’s Sandwich Shop and Coffee Bar

What do you get when you mix an 18-year-old with big ideas, no experience and a passion to succeed in the restaurant business? The answer is Big Bill’s Sandwich Shop and Coffee Bar in Galena.

Jack Dieter, the aforementioned go-getter, now 23, had a dream in college to open a restaurant. He studied entrepreneurship and wanted to run his own business – it just happened faster than he expected.

His family, originally from Oak Park, has owned the historic brick building on the north end of Main Street in downtown Galena for 11 years. They previously rented the space to other businesses, and it provided the perfect spot for Jack to launch his dream.

Jack’s original vision was to offer cold gourmet deli sandwiches and coffee. That idea ended up expanding into a place with comfortable seating, a dining area and a coffee bar, thanks to help from previous manager, Constance Chambers, who also helped him come up with ideas for his sandwiches. 

The building has exposed brick walls, large windows that look out onto busy Main Street, and you can’t miss the aroma of freshly ground coffee as you enter. 

Besides the typical tables and chairs, there are large comfortable sofas and armchairs that give the place a cozy “Friends” vibe. It seats 65-75; Jack would like to add more tables but doesn’t want to lose its current atmosphere.

Big Bill’s opened in October 2015, on Country Faire weekend, which is a busy festival weekend in Galena. “It was an absolutely insane time to open because of the crowds,” says Dieter. “It was definitely baptism by fire. The first thing they should teach in business school is if you go by the book and do A you get B, but you sometimes get Z!”

He learned quickly to adjust to the circumstances.

When Big Bill’s opened, Jack purchased coffee beans from another company. Over time, he became interested in coffee roasting, purchased a roaster and started making his own blend. He watched YouTube videos and talked to others about the process and came up with Big Bill’s Coffee, which is available by the pound.

Eventually, he was able to purchase more equipment for the restaurant, including flat-top grills and ovens, and ventured into hot sandwiches—and later, breakfast.

Jack credits frequent customer Jim Post with giving him the impetus to start making hot sandwiches.

“Jim is here a lot, and he brought me this Reuben sandwich and said, ‘you just have to try this,’” says Jack. “I tasted it and knew I had to do something like it. More than the Reuben itself, it just gave me the idea that I really needed to do hot sandwiches. So, now we have Jim Post’s Reuben. We don’t use Thousand Island on ours. Instead, we have a house-made sauce which gives it a different flavor.”

Beefy Roman Sandwich
The Beefy Roman is a favorite.

Big Bill’s menu occasionally changes, but four sandwiches are always available – the Beefy Roman, corned beef and Swiss, Jacked-Up turkey and the Black Forest pretzel.

The Beefy Roman, named one of the top sandwiches in Illinois, is made with natural hormone-free roast beef with fresh mozzarella cheese, roasted red peppers and baby spinach with basil pesto and a balsamic vinaigrette on an artisanal bun.

The Black Forest pretzel is a pretzel roll piled high with Black Forest ham and smoked Gouda cheese topped with a mustard slaw.

Sandwiches range in price from $7.95 to $13.95 and come with house-made chips and a pickle.

Santa Fe Chicken Soup
Santa Fe Chicken Soup

Soups include the creamy Santa Fe Chicken, and a variety of salads are offered, such as the honey sriracha superfood or the cranberry chicken, available as a salad or sandwich.

Breakfast is served until 11 a.m. and includes a variety of egg dishes, including Ireland’s hash, a combination of chopped corned beef with green peppers, onions, potatoes and mixed with cheddar cheese—and topped with two sunny side up eggs.

According to Jack, they don’t run “specials” per se, but one popular dish, when available, is the jalapeno cheddar biscuits with sausage gravy.

Breakfast is served until 11 a.m.

Big Bill’s was named after Jack’s grandfather. He explains, “Grandpa was always teaching my dad and me. At a young age, he had me running a table saw, and I still have all my fingers, so he must have done a good job! He was a mechanical engineer and taught me how to figure things out. He came down here when we first opened and helped us. We figured it was only appropriate to name it after him because he’s just special.”

The lessons learned from his grandfather have helped him to roll with the punches when things break down or the unexpected happens.

“Every day is a challenge,” Jack says. “Things break. We got hacked once. If something goes wrong, it’s figuring out a workaround without the customers knowing we are having issues.”

He credits his mother’s help at the restaurant for its success. “Mom has had my back through the entire thing,” he says. “She’s helped me find a work/life balance and be able to step away from the business for a break.”

Big Bill’s has a set of regulars who can be found sitting at one of the tables having coffee or breakfast. It’s become a local meeting spot. “I didn’t know anyone when I came out here,” says Jack. “Everyone in Galena has really accepted me. I’ve enjoyed getting to know the community and talking to our customers.”

When in Galena, be sure to venture north to find Big Bill’s at the corner of Franklin and Main. Whether you grab a cup of coffee and relax on one of the couches or take time for breakfast or lunch, it’s a place worth visiting.

There’s more!

Jack’s big plans haven’t ended with the restaurant. An upstairs renovation by Jack and his father has recently been completed after more than a year of working nights and weekends. The two completely gutted the upstairs to expose the original brick walls and hardwood floors. The building now includes six loft apartments available for rent through Airbnb.

Let’s EAT!

Map_GalenaBig Bill’s Sandwich Shop and Coffee Bar
301 N. Main St., Galena, Illinois
(815) 777-6979
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  • Closed Tuesdays
  • Monday, Wednesday-Friday 7 a.m.-3 p.m.
  • Saturday 8 a.m.-4 p.m.
  • Sunday 9 a.m.-3 p.m.