Portillo’s Top Ten Dishes Ranked by Taste Testers

The Classic Italian Beef Holds the Crown

Megan Hageman visited Portillo’s in Chicago on August 9, 2026 to evaluate ten of the chain’s most talked‑about menu items. She sampled everything from the iconic Italian beef sandwich to the indulgent chocolate‑cake milkshake, rating each on flavor, texture, and overall satisfaction. The results offer a fresh look at what locals and tourists love most about the Chicago institution.

The tasting took place over a single afternoon, with Hageman ordering each item individually to avoid cross‑flavor contamination. She used a simple five‑point scale, noting standout ingredients, preparation methods, and how each dish compares to its street‑food counterparts. The ranking reflects both traditional favorites and newer experimental offerings that have appeared on the menu in recent years.

Portillo’s Italian beef sandwich secured the top spot, praised for its juicy, thinly sliced roast beef and perfectly seasoned gravy. Reviewers highlighted the crisped‑on‑the‑outside, soft‑inside roll that absorbs the savory broth without falling apart. „The beef is tender, the peppers add a subtle heat, and the cheese melts just right,” Hageman wrote. The sandwich’s popularity aligns with Chicago’s long‑standing love for this hearty street staple, confirming its status as a must‑try for any visitor.

Which Sweet Treat Surprises the Palate?

The chocolate‑cake milkshake earned a surprising third‑place ranking, beating out several savory items. Its rich, velvety texture combines real chocolate cake chunks with creamy vanilla ice cream, creating a dessert that feels both nostalgic and novel. „It’s like drinking a slice of cake,” Hageman noted, adding that the shake’s sweetness balances the menu’s predominantly savory focus. The drink’s success suggests Portillo’s ability to innovate beyond its classic fare while still honoring the indulgent cravings of its clientele.

Other notable entries included the Chicago‑style hot dog, praised for its snap of the all‑beef frank and bright relish, and the Polish sausage, which earned praise for its smoky flavor and generous mustard drizzle. The deep‑dish pizza, while a beloved Chicago icon, fell lower in the ranking due to a crust that some reviewers found overly dense compared to local pizzerias. Newer items like the jalapeño‑infused chicken sandwich and the caramel‑apple crumble pie each secured mid‑range spots, reflecting growing interest in diversified flavor profiles.

Overall, the ranking underscores Portillo’s continued relevance in a city famed for its street food culture. By blending time‑tested classics with inventive twists, the chain maintains a broad appeal that draws both repeat patrons and first‑time diners. As the menu evolves, future tastings may see items rise or fall, but the core emphasis on bold, comforting flavors appears set to endure.

Frequently Asked Questions

What criteria did the ranking use? Each dish was judged on taste, texture, authenticity to Chicago’s culinary traditions, and overall enjoyment, using a five‑point scoring system.

Is the chocolate‑cake milkshake a permanent menu item? Yes, the milkshake remains a regular offering, though its popularity may prompt Portillo’s to experiment with seasonal variations.

Will the ranking influence Portillo’s menu decisions? While the ranking is editorial, strong consumer response to top‑ranked items often guides the chain’s promotional focus and potential menu updates.