Here's where to bear down on Chicago flavor on the streets of Sarasota

Some families pass down recipes; ours handed down a deep, unwavering love for Chicago and more specifically, the Chicago Bears. 

My dad was in his 30s when the Bears won the Super Bowl (cue "The Super Bowl Shuffle" on repeat). When I was growing up, that era felt larger than life to me — untouchable, frozen in time like the Windy City itself.

Photo by Emma Burke

Fast-forward to the present. After watching the Ice Man himself, quarterback Caleb Williams, Coach of the Year (in my heart) Ben Johnson and the entire Bears organization (including emotionally invested fans like me) finally take down the Green Bay Packers earlier this month, I felt like I was having my own Super Bowl victory in my 30s. I think it's Dad's way of saying, "I pulled some strings and this one's for you, kid."

Part of me hesitates to write this while the Bears are in the playoffs because it feels a little like tempting fate. But my love for Chicago, not only its sports teams, but its comforting cuisine, is something I can no longer gatekeep. So instead of hopping a flight to O’Hare, I did what any devoted foodie and Bears fan would do, I took a tour of Chicago right here in Sarasota — one bite, one memory and one hopeful season at a time.

Tony’s Chicago Beef

6569 Superior Ave, Sarasota; 941-555-1234; 1856 S. Tamiami Trail, No. 3136, Venice; 941-497-1611; TonysChicagoBeef.com

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Bear Down & Chow Down: A true Chicago-style hot dog isn’t just a hot dog, it’s a rulebook. One all-beef frank, a steamed poppyseed bun, kosher pickle spear, yellow mustard (no ketchup), chopped onions, neon-green relish, sport peppers, a dash of celery salt and, for some, slices of tomato (respectfully optional in my world). Tony’s gets it right with their no-frills dawg. At $6.39, it’s proof that perfection doesn’t need dressing up. 'Nuff said.

Grate (the cheeseheads) Bites: Snag an Italian Beef ($8.89) served on French bread with sweet peppers to ensure the full Chicago style eatery experience.

Joey D's Chicago Style Eatery & Pizzeria

6401 Manatee Ave., W., Bradenton; 941-378-8900; 3811 Kenny Drive, Sarasota; 941-378-8900; 945 10th St. E., Palmetto; 941-417-2106; 750 U.S. 41 Bypass North, Venice; 941-786-1300; JoeyDsFL.com

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Bear Down & Chow Down: Chicago deep dish pizza: you either love it or hate it. But if it's the latter, you're wrong. Thick, buttery crust built to hold mountains of gooey cheese, then crowned with a rich, tangy tomato sauce that somehow manages to steal the show. Good things take time, so allow 25 minutes for this masterpiece to come out piping hot (ranging from $15.99-$27.99). This is a pie that proves deep dish is not just a meal, it’s a Chicago ritual. 

Grate (the cheeseheads) Bites: Established in October 1994, the name honors Joseph “Joey D,” born in 1967. Joey D was born with a rare genetic disease with an average life expectancy of just 12 years. He defied every expectation, living to be 32 years old, the longest-known case of its kind.

Piccolo Deli Italian Market

6518 Gateway Ave., Sarasota; 941-923-2202; PiccoloMarket.com

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Bear Down & Chow Down: There’s something about a proper Italian Beef that makes you pause and remember why Chicago is Chicago. Piccolo's version ($9.80 and up) is full of roast beef dripping in rich au jus, layered with provolone and finished with a kick of hot giardiniera. One bite and it's an immediate taste of Soldier Field that somehow makes you feel like you’re watching the Bears battle it out on the gridiron.

Grate (the cheeseheads) Bites: Because this is a love letter to all things Chicago, I can’t help but pay tribute to my dad. Ordering a sandwich named for his favorite musician, The Frank Sinatra ($12.50 and up), practically raises the glass itself. Chicken cutlet, prosciutto, mozzarella, roasted reds and a drizzle of balsamic: chef's kiss!

Remy's on Main

8139 Lakewood Ranch Main St., Lakewood Ranch; 941-355-9391; RemysonMain.com 

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Bear Down & Chow Down: There are multiple origin stories of the Old Fashioned cocktail, but Chicago has long claimed a special place in that tale. It’s the kind of cocktail that feels like Chicago itself — classic, confident and unpretentious, yet full of character. So I headed to Remy's to sip on their version of the classic: smoked Old Fashioned ($15) made with Four Roses bourbon, smoked, with filthy cherry and orange.

Grate (the cheeseheads) Bites: Raise another glass to Chicago with the Oaxaca Old Fashioned ($14). Made with Cazadores Reposado, smoky Del Maguey mezcal and a filthy cherry, it's perfect for celebrating a Bears win or just pretending you’re cheering from the 50-yard line.

Siesta Key Oyster Bar

5238 Ocean Blvd., Siesta Key; 941-346-5443; SKOB.com

Most Valuable Player: When owner Jill Pedigo made the move from Naperville, Illinois, to Osprey, she brought her loyalty to the 1985 Super Bowl champs with her. During that first season on Florida's Gulf Coast, Jill and her dad headed to a local sports bar to catch a Bears game. As mid-game frustration set in, her dad joked, “We should get our own bar so we can get a good spot.” Turns out, he wasn’t kidding. Whether you’re a lifelong Chicago loyalist or just want to watch the game surrounded by people who get it, SKOB is where Bears fans come to Bear Down.