Written by If you have been anywhere near Middleton lately, you have probably passed a Portillo’s. And if you have never been — or you have been and you are not sure what to order — this is your guide. Chicago-style street food, done right. (And yes, for anyone not from Chicago — this place is the real deal. Not a chain in the fast food sense. More like a Chicago institution that finally escaped the city.)
🌭 Start With What They’re Famous For
Never heard of Italian beef? Quick explainer: it’s thin-sliced roast beef slow-cooked in seasoned beef broth, piled onto a long Italian roll, then dunked (yes, dunked) in the drippings. It’s messy, juicy, and completely unlike anything else you’ll find in Central Florida. Order it wet.
- Italian Beef Sandwich — order it wet (the whole sandwich gets dipped in the jus) with hot giardiniera (spicy pickled veggie relish). This is non-negotiable. $7.59 reg / $9.59 big beef.
- Chicago-Style Hot Dog — yellow mustard, neon relish, diced onion, tomato slices, pickle spear, sport peppers, celery salt on a poppy seed bun. No ketchup. Ever. $3.89–$4.89.
- Italian Beef & Sausage Combo — both meats on the same sandwich. Can’t pick? Problem solved. $8.79–$11.69.
🍔 Burgers Worth Knowing
- Double Cheeseburger — char-broiled, American cheese, all the classics. The no-nonsense pick. ~$9.
- Bacon Cheeseburger — same charbroiled base, add bacon. ~$10.80.
- Rodeo Burger — BBQ sauce, onion rings, bacon, American cheese. For when you want to go a little wild. ~$11.85.
🍗 Chicken Worth Ordering
- Spicy Chicken Sandwich — crispy breaded chicken, giardiniera sauce, lettuce, tomato on a brioche bun. The sleeper hit. ~$9.80.
- Chicken Tenders — 4 or 6 piece. Dip them in the giardiniera sauce. Underrated choice. $5.29–$7.89.
🥗 The Chopped Salad (Seriously)
The Portillo’s Chopped Salad has a cult following for a reason — romaine, red cabbage, chicken, ditalini pasta, bacon, diced tomatoes, gorgonzola, and green onion. Get it tossed with the house dressing. $10.69. People drive out of their way specifically for this salad. Do not skip it.
🍟 Sides That Hit
- Crinkle-Cut Fries — classic. $2.89 small / $3.69 large.
- Cheese Fries — same price, better outcome.
- Onion Rings — consistently solid. $3.89–$4.79.
- Gravy Bread — French bread dunked in beef gravy. $2.29. Order this. It is exactly what it sounds like and it absolutely rules.
🍫 End Here: The Chocolate Cake Shake
Portillo’s has been famous for their chocolate cake since forever. Slices are ~$5. The Chocolate Cake Shake is a real slice of chocolate cake blended into a milkshake. It is a cultural experience. $4.69–$6.20 depending on size. Get it at least once. You will understand immediately.
🔓 Menu Hacks You Should Know
- Order the beef WET. Dry is fine. Wet is the experience. Ask for it dipped — the whole bun goes in the jus. It’s supposed to be a little soggy. That’s the point.
- Ask for extra giardiniera. It’s technically an add-on ($0.89) but it transforms every bite. Spicy, pickled, tangy. Get it on everything.
- Dip your fries in the cheese sauce AND the giardiniera sauce — mix them on the side. Trust.
- The Beef Bowl is the same Italian beef but served over bread in a bowl — great for lower-carb without fully going carb-free. ~$7.59–$7.99.
- Portillo’s Perks app — free to sign up, and they do BOGO Italian Beef deals for members. Download it before you go.
- Jumbo sizes (serves 5) — Jumbo Fries ($19.99), Jumbo Onion Rings ($22.99). Bring a crowd or a big appetite.
🌾 Gluten-Free + Dietary Notes
Portillo’s is not a dedicated GF kitchen, so always mention your needs when ordering. That said, here’s what works for different diets:
- Gluten-Free friendly options: The beef itself (without the bun) is GF — ask for it in a bowl. Cheese sauce, sweet/hot peppers, and side of gravy are GF. Fries and the garden side salad work too.
- Lower carb: Classic Beef Bowl or Chicago Combo Bowl — all the beef flavor, skip the bread.
- Vegetarian: The Garden Dog (plant-based hot dog) is available. Garden Side Salad, Cheese Fries, Onion Rings all work. The chopped salad can be ordered without chicken.
- Dairy-free: The Italian Beef, Chicago-style hot dog, and most proteins are dairy-free — skip the cheese sauce and croissant options.
- Allergen info: Full allergen menu available at portillos.com/allergens or ask at the counter.
🏆 The Quick Order Cheat Sheet
- First timer? → Italian Beef (wet, with hot giardiniera) + Cheese Fries + Chocolate Cake Shake
- Burger run? → Double Bacon Cheeseburger + Onion Rings
- Lighter day? → Chopped Salad with house dressing
- Gluten-free? → Classic Beef Bowl + Garden Side Salad
- Group order? → Jumbo Fries or Onion Rings for the table + a round of Italian Beefs
📍 Chicago-style comfort food | Open daily 10:30 AM | Middleton, FL
👇 Wet or dry on the beef? First time or longtime Portillo’s fan — drop your order in the comments!