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Chili cheeseburgers in Florida

A cheeseburger that holds its own against a bowl of chili without being overshadowed by the spice.

Based on 604 Opinions
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Updated May 2026
01
Wayback Burgers image 1
Wayback Burgers image 2
Wayback Burgers image 3
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Hamburger restaurant

Small but spacious hamburger restaurant offers comfy booths and open kitchen views. Calm, welcoming atmosphere features oldies music from the 70s, 80s, and 90s. Seating suits families and friends with indoor and outdoor options.

High quality chili pairs well with chili cheese fries that are consistently mouthwatering and top notch.

Burgers feature fresh, flavorful patties cooked well and never dry. The inverted bun adds a crunchy texture, and options like the double bacon cheeseburger offer classic, quality ingredients with lots of flavor.

People are saying

"I found the food here to be fresh and amazing."

"This cheeseburger was cooked perfectly with fresh, flavorful ingredients."

"The chili cheese fries here are delicious and mouthwatering."

Good to know

1

Wayback Burgers has a gluten-free dedicated fryer for chips.

2

The restaurant maintains a high standard of cleanliness.

3

Expect good value for the price of meals.

02
Pee-Pa's Garage Craft Brewery image 1

Converted auto body shop offers a large AstroTurf patio, axe throwing pits, and vintage car decor creating a rustic, family-friendly vibe. Outdoor games and live music add to the lively, social atmosphere. Food trucks and well-regarded craft beers complement the engaging setting.

Chili comes with thick bacon chunks that add rich flavor. The menu includes a Chili with Bacon and Chili Tots with Bacon on top, offering hearty, meaty options.

Cheeseburgers come with bacon and cheese in solid, satisfying forms like The Slab and the Gatewood burger. The food truck serves options that fill hunger well and offer a good way to wind down.

People are saying

"They have a huge selection of delicious craft beers."

"I thought the cheeseburgers were outstanding and the best in town."

"Jason's chili is delicious and made by hand."

Good to know

1

Trivia night happens every Thursday at 8pm with a $5 entry fee.

2

The brewery hosts a farmers market on the first Sunday of every month.

3

Live music occurs every Friday night starting at 9pm.

03
Jack's Old Fashion Hamburger House image 1

Small hamburger joint with retro Americana decor and a vintage jukebox sets a nostalgic 1950s-60s vibe. Atmosphere stays clean and quiet, attracting locals who appreciate old-fashioned burgers and a simple, classic setting.

Chili here comes in a house-made sauce that tops both fries and hot dogs. The chili cheese fries feature a sloppy Joe style meat that stands out, and the chili cheese dogs offer a flavor close to classic coney sauce.

Classic flavor defines the cheeseburger here, served hot and fresh with a 1/3 pound patty cooked well done. It comes quickly and pairs well with chili cheese fries, though it can be a bit messy.

People are saying

"I thought these burgers were the best I ever had."

"I stepped back in time to an old school burger joint."

"This old-school spot serves a delicious, classic cheeseburger."

Good to know

1

Two burgers and fries cost around $39, while a smaller meal is $30.

2

Jackโ€™s has been serving burgers for over 50 years, ensuring quality.

3

They offer jalapenos at the self-service area for added flavor.

04
Portillo's Orlando Palm Pkwy image 1
Fast food restaurant

50s diner style with vintage art and rockabilly vibe creates an upbeat atmosphere. Spacious seating includes indoor and outdoor patios, welcoming families and pets. Staff announce orders with rhymes, adding a unique touch to the lively environment.

Homemade chili tops the Chicago Chili Cheese Dog with a taste that recalls Villa Park originals. The chili is well balanced, not over seasoned, and pairs well with the large Chili Cheese Dog and fries.

Burgers come hot and fresh with a Double Patty Bacon Cheeseburger standing out for its flavor. Combos offer a good variety of cheeses and generous portions that appeal to all ages.

People are saying

"The food here is fresh, hot, and delicious."

"I found the chili cheese dog to be very good."

"I found the cheeseburger here to be great every time."

Good to know

1

They offer a Wednesday special hot dog for $1 with any order.

2

Each meal includes a $1 Chicago Dog on Wednesdays.

3

The menu features a variety of options, including Italian beef sandwiches.

05
Jack's Old Fashion Hamburger image 1
Hamburger restaurant

Old school burger joint with a nostalgic 70s vibe and cozy atmosphere. Central condiment bar invites self-service, complemented by a Wurlitzer jukebox playing retro tunes. Walls display vintage photos, enhancing the classic, unassuming charm.

Chili here stays true to tradition with no cinnamon, allspice, or beans. The chili cheese fries and chili hot dogs stand out, especially with the fixings bar that lets you customize your toppings.

Original recipe cheeseburgers stay true to their classic taste. The 1/4 pound size matches the flavor remembered from decades ago. These cheeseburgers deliver a phenomenal, old-fashioned experience.

People are saying

"I thought the burgers here were the best I've ever had."

"This old school cheeseburger is exactly what I remembered from years ago."

"You've gotta try the chili fries; they're the best I ever had."

Good to know

1

Prices for burgers have increased significantly, averaging around $30 for a meal.

2

The condiment station closes early, so check availability before ordering.

3

Grilled onions and other toppings incur extra charges.

06
Portillo's Waterford Lakes image 1
Fast food restaurant

Retro diner design with 50's Americana dรฉcor and a giant alligator mural creates a nostalgic, upbeat vibe. Bright, spacious interior combines natural light with vintage signs and checkered floors. Busy, lively atmosphere fills with friendly energy and casual outdoor seating.

Chili stands out for its meaty texture and rich flavor. It complements dishes like chili dogs and chili cheese hot dogs well.

Double cheeseburgers come with fresh ingredients and a classic taste. Fries are crispy and the cheeseburger pairs well with a drink or shake.

People are saying

"The beef sandwich is stuffed with meat and peppers."

"I found the cheeseburger delicious and outstanding."

"The chili here is so meaty and flavorful."

Good to know

1

The restroom is very clean and well-maintained.

2

There is plenty of space to park and sit.

3

Expect gridlock in both drive-through lanes during peak hours.

07
Babe's Meat & Counter image 1

Small butcher shop with limited seating and a clean, inviting atmosphere. Offers high-quality meats and award-winning burgers that attract a steady crowd. Outdoor bistro tables provide a casual spot to enjoy simple, well-crafted sandwiches.

Chili fries stand out as a popular choice, often paired with craft beer and sodas. The chili dog tends to be soggy with the bread falling off.

The cheeseburger stands out as a favorite lunch choice and sometimes replaces other sandwiches by mistake. It pairs well with hearty sides like the breakfast hash.

People are saying

"I considered this one of the best burgers I've ever had."

"This cheeseburger's brilliance sneaks up on you with its simple craft."

"I thought the chili here was just about the best ever."

Good to know

1

There is parking right outside the shop.

2

Ordering online ahead is recommended to avoid long wait times.

3

Seating is limited, so plan accordingly.

08
Carolina Jax image 1
American restaurant

Small, crowded restaurant with cozy, tight space and fun pig decor creates a relaxed, family-friendly vibe despite a loud, bustling atmosphere. Sidewalk seating offers an alternative to the cramped interior. Walls display art and history, adding unique character to the old building setting.

Chili cheese fries stand out with rich, flavorful chili and melted cheese. The chili cheese dog offers a hearty, satisfying topping. Both dishes pair well with burgers for a filling meal.

Bacon cheeseburgers come with perfect seasoning and all the trimmings. Lunch specials include an Angus beef cheeseburger with Cajun fries and a drink for $13.

People are saying

"The food here is amazing and always seasoned perfectly."

"The chili cheese fries here are to die for."

"I had the best cheeseburger I have ever eaten."

Good to know

1

Parking is limited, so expect to walk if you canโ€™t find a spot.

2

Dining during lunchtime on Fridays is nearly impossible due to long lines.

3

Expect about 15 minutes in line to order and another 30 minutes for food.

09
Portillo's St. Petersburg image 1
Fast food restaurant

Fast food restaurant with 50s-style retro decor and nostalgic diner vibe creates a fun, lively atmosphere. Spacious interior offers interesting visual details and outdoor seating. Known for authentic Chicago hot dogs and a selection of beer on tap.

Chili dogs come with a great spice and kick and keep the bun from getting soggy. The chili cheese dogs stand out as exceptional and pair well with sides like onion rings and fries.

Cheeseburgers have a flavorful taste similar to Burger King but with more depth. They come as single patties and pair well with cheese fries and a drink from the drive-thru.

People are saying

"You have to try the American Food hot dogs; they have a fantastic snap and flavor."

"The chili dogs here are satisfying and flavorful."

"I thought the cheeseburger was great and more flavorful."

Good to know

1

Hot dogs are $1 with any sandwich purchase on Wednesdays.

2

The drive-thru only accepts card payments.

3

The restaurant maintains a clean environment.

10
Kappy's Subs image 1
Cheesesteak restaurant

Old-school diner with 1960s setup and classic stools and countertops creates a strong sense of nostalgia. Busy and lively atmosphere with limited seating inside and shaded outdoor picnic tables outside. Background music adds to the friendly, vintage vibe.

Chili cheese burger and chili cheese hot dog come with rich, flavorful chili. The Carolina Dog features chili with mustard, ketchup, onions, and slaw for a classic taste.

The cheeseburgers come with seasoned fries or waffle fries and include options like the Chili Cheeseburger. A combo with a cheeseburger, fries, and a chocolate shake costs around $42.

People are saying

"It's got that classic old school diner vibe."

"I found the chili dog to be generous and delicious."

"Javi made the best cheeseburger I ever had."

Good to know

1

Kappy's closed several weeks ago due to a leasing issue with the land owner.

2

The parking situation was horrible.

11
Culverโ€™s image 1
American restaurant

Restaurant offers a modern interior design with a clean and comfortable dining area. Atmosphere feels welcoming and relaxing, with a unique parking spot food delivery system. Energy is generally quiet and calm, attracting those who appreciate a peaceful meal.

Chili stands out for its rich flavor and pairs well with cheese fries. It includes fat kidney beans and offers a hearty, satisfying taste.

Fresh, hot cheeseburgers come out looking just like the photos. The double cheeseburger and double bacon cheeseburger both taste great and pair well with fries.

People are saying

"The food here is always fresh and amazing."

"I thought the chili was amazing."

"I had a fantastic, fresh, and hot cheeseburger."

Good to know

1

Culver's food is cooked when ordered, ensuring freshness.

2

Parking can be congested due to a new policy requiring waiting for food.

3

Prices are higher compared to other fast food chains.

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