Milwaukee's Best Cheesesteak [Updated 2025]

Having devoured countless sandwiches in search of that perfect bite, I’ve scoured twelve of the top spots in the city, each one a contender for the cheesesteak crown. Trust me, I’ve tasted enough gooey cheese and tender steak to know what makes a cheesesteak truly stand out.

Whether you’re a lifelong fan of this Philly classic or just curious about what makes these sandwiches so special, I promise you’ll find some mouthwatering gems here. So grab a napkin and get ready—your taste buds are about to embark on a delicious adventure through Milwaukee’s cheesesteak scene!

Riley's Sandwich Co.

Highlights
Indoor dining with pets
Friendly and helpful staff
Unique menu options
Delicious sauces available
Community-recommended

Riley's Sandwich Co. is a gem tucked into Milwaukee’s vibrant food scene, and let me tell you, it’s a true cheesesteak haven! As I walked in, I was instantly charmed by the relaxed atmosphere, where even pets are welcome to join their humans at the tables. It created such a warm, inviting vibe!

The staff at Riley’s were not only friendly but also incredibly helpful, guiding me through their menu with enthusiasm. With a selection of unique options, I felt a rush of excitement as I made my choice. Their cheesesteak is, without a doubt, a must-try! The steak was cooked to perfection, with savory flavors that paired beautifully with the delicious sauces available. Each bite was a delightful explosion of taste that transported me straight to cheesesteak nirvana.

What truly sets Riley's apart is the community support it has garnered, with locals consistently recommending it as a top spot for sandwiches. If you're hunting for the best cheesesteak in Milwaukee, don’t miss out on this culinary treasure. Riley’s Sandwich Co. has officially earned a place in my heart—and stomach!

You might also want to check out the best breakfast in Milwaukee.

Who's on Third | A Cream City Concepts Destination

Highlights
Friendly and attentive staff
Great bar burger experience
Varied and tasty drink options
Reasonable lunch pricing
Quick food service

When I strolled into Who's on Third, I was instantly greeted by the friendly and attentive staff who made me feel right at home. Not only do they serve up a fantastic cheesesteak, but they also boast a great bar burger experience that has become the talk of the town.

As I settled in to enjoy my meal, I appreciated the varied and tasty drink options available. A good drink can elevate any meal, and their selection definitely complements the food well. The cheesesteak itself was a delightful surprise—boasting a perfectly toasted hoagie roll stuffed with generous portions of tender beef, perfectly melted cheese, and just the right amount of seasoning.

What truly impressed me was how reasonable the lunch pricing was. With such quality on offer, I expected at least a little bit of sticker shock, but I found it pleasantly surprising. To top it all off, my food was served quickly, allowing me to savor every bite without the long wait.

In the quest for the best cheesesteak in Milwaukee, I can confidently say Who's on Third is a strong contender. It's definitely a place I’ll be revisiting!

You might also want to check out the best restaurants in West Allis.

Oak Barrel Public House

Highlights
Spectacular food options
Great for large groups
Attentive and friendly staff
Spacious and comfortable atmosphere
Convenient downtown location

Review of Oak Barrel Public House:

Nestled conveniently in the heart of downtown Milwaukee, Oak Barrel Public House is a true gem for cheesesteak lovers. Right from the moment I stepped through the door, I was captivated by the spacious and comfortable atmosphere—perfect for striking up a conversation with friends or diving into a game on TV.

Now, let's talk cheesesteaks! The moment I took a bite of their creation, I knew I was in for a treat. The flavors were bold, with perfectly seasoned steak layered under gooey cheese, all enveloped in a warm, toasty roll. It’s a glorious blend that dances on the palate.

What’s more, the attentive and friendly staff added to the overall experience. They were eager to share recommendations and made sure our drinks were never empty. If you're looking to enjoy a meal with friends, Oak Barrel excels at accommodating large groups, making it a great spot for gatherings.

In summary, if you're searching for the ultimate cheesesteak experience in Milwaukee, Oak Barrel Public House deserves a top spot on your list. This is a must-try destination for anyone craving that perfect bite!

You might also want to check out the best coffee shops in Milwaukee.

Milwaukee Brat House

Milwaukee Brat House brings a delightful twist to the classic cheesesteak experience. Nestled in the heart of the city, this gem serves up a cheesesteak that is as comforting as it is satisfying. The tender, juicy cuts of steak are perfectly complemented by a melty blend of cheese whiz that adds a touch of indulgence. Each bite is a celebration of flavors, with fresh, crusty bread that holds it all together. The inviting atmosphere and friendly staff make it a top choice for a relaxed meal. If you’re in search of a cheesesteak that feels like a warm hug, look no further!

You might also want to check out the best pizza in Waukesha.

Chubby’s Cheesesteaks West Milwaukee

My visit to Chubby’s Cheesesteaks West Milwaukee was an adventure in every bite! The mouthwatering aroma wafting from the grill had me salivating before I even placed my order. Upon trying their signature cheesesteak, I was delighted by the perfect balance of tender steak, melted cheese, and just the right amount of sautéed onions. The hoagie roll was freshly baked, adding an inviting crunch that contrasted beautifully with the savory filling. The friendly staff made the experience even more enjoyable, proving that Chubby's is a place where cheesesteak dreams come true! A must-try for any enthusiast!

You might also want to check out the best cafes in Milwaukee.

The Goodway Grille

At The Goodway Grille, I was greeted by the intoxicating aroma of grilled meat and sizzling onions. Their cheesesteak features tender slices of beef, perfectly paired with gooey provolone, all nestled in a freshly baked roll that held up against the delicious mess. Each bite was a harmonious blend of savory and cheesy goodness, with just the right amount of seasoning leaving me wanting more. The cozy atmosphere added to the charm, making this place a delightful stop for any cheesesteak enthusiast. If you’re on a quest for the best, The Goodway Grille is definitely one to consider!

You might also want to check out the best soup in Milwaukee.

Sinbad’s grill

Sinbad's Grill offers a delightful twist on the classic cheesesteak that left me longing for more! The tender beef is generously piled high, enveloped in melted cheese that stretches with every bite. What sets it apart is the house-made whiz—a creamy indulgence that elevates this sandwich to heavenly status. Nestled in a warm, toasted roll, each mouthful bursts with flavors true to the tradition while adding a dash of Sinbad's flair. The friendly atmosphere makes dining here a pleasure, enhancing the overall experience. For a fun and delicious cheesesteak adventure, Sinbad's Grill is a must-visit!

You might also want to check out the best pizza in Milwaukee.

Daddy Subz & More

Daddy Subz & More is a hidden gem that decidedly packs a punch with their cheesesteak! As I sank my teeth into the warm, toasted hoagie, the juicy ribeye melted perfectly alongside a generous heap of grilled onions and peppers. Each bite was a delightful symphony of flavors, topped off with their house-made cheese sauce that brought everything together. The portion size is nothing short of generous, making it great for sharing—or not! A cozy vibe and friendly staff complete the experience. If you’re hunting for the ultimate cheesesteak in Milwaukee, this place should definitely be on your list!

You might also want to check out the best ramen in Milwaukee.

Crispy and Grill

At Crispy and Grill, I was greeted with the tantalizing aroma of sizzling beef and gooey cheese that instantly made my mouth water. Their cheesesteak is a delightful symphony of flavors, featuring perfectly seasoned steak, melted provolone, and a generous helping of fresh veggies, all nestled in an incredibly soft hoagie roll. The balance of textures and flavors left me craving more with each bite! The friendly staff added a personal touch, making the atmosphere feel inviting. If you’re on the hunt for a cheesesteak that truly satisfies, look no further than Crispy and Grill—it’s a flavor-packed adventure!

You might also want to check out the best hibachi in Milwaukee.

North Ave Grill

Upon stepping into North Ave Grill, I was greeted by an inviting atmosphere that hinted at deliciousness. The cheesesteak I ordered was an absolute delight—tender, flavorful meat enveloped in a perfectly toasted hoagie. The onions were grilled to perfection, adding a subtle sweetness that complemented the savory steak beautifully. I appreciated their generous use of gooey cheese, which created a delightful melty goodness in every bite. Each mouthful was a joyful dance of flavors. If you're hunting for a cheesesteak that’s both hearty and satisfying, North Ave Grill is undoubtedly a must-try destination in Milwaukee!

You might also want to check out the best chicken wings in Milwaukee.

Chubby’s Cheesesteaks East Side

Chubby’s Cheesesteaks East Side is an absolute delight for any cheesesteak aficionado! The moment I sank my teeth into their juicy, well-seasoned steak, I was transported to flavor heaven. The toasted hoagie bun held everything together beautifully, while the melted provolone added a creamy richness that perfectly complemented the savory beef. What truly sets Chubby’s apart is the generous heap of fresh toppings, creating a fantastic crunch with each bite. Their friendly service radiates warmth, making it feel like home. If you’re looking for a cheesesteak that’s big on taste and even bigger on heart, Chubby’s is a must-visit!

You might also want to check out the best hot wings in Milwaukee.

Chubbys Cheesesteaks Brookfield

At Chubbys Cheesesteaks Brookfield, I discovered a flavor explosion that had my taste buds dancing. The generously stuffed rolls brim with perfectly seasoned steak, and each bite encapsulates a delightful blend of cheesy goodness. The bread was fresh and crispy, providing the ideal vessel for this culinary masterpiece. The option to customize with toppings is a delightful touch, elevating the experience even further. The welcoming ambiance and friendly staff made my visit even more enjoyable. If you're on the hunt for the ultimate cheesesteak in Milwaukee, Chubbys is undoubtedly a top contender for your appetite's affections!

You might also want to check out the best prime rib in Milwaukee.