We’ve heard amazing things about two popular Tampa food venues – Portillos’s and Insomnia Cookies – for quite some time, and we decided it was finally time to try them ourselves! Portillo’s is a Chicago-style hot dog eatery that serves delicious dogs, Italian beef sandwiches, and more. Located nearby is a chain known for their scrumptious treats – Insomnia Cookies. What better combination for dinner and dessert? Join us as we try both of these locally praised restaurants and share what we think of each.


We were immediately impressed with the atmosphere of this venue upon walking inside – decked out with brick, vintage memorabilia, and neon signs, we felt as though we’d just stepped into an old-fashioned eatery in Chicago. Thankfully, there was not much of a crowd or wait, so we were able to get our food fairly quickly. We ordered the Maxwell Street Polish and the Italian Beef Sandwich. The Maxwell Street Polish was absolutely awesome, charred to perfection and full of flavor. We also really liked the Italian Beef Sandwich, and we’d recommend ordering it with all of the toppings and drenching it in gravy! Although we found everything to be slightly pricey, we really enjoyed our experience and thought it was worth trying. If you’re a hot dog lover, you’ll definitely want to check this place out.


This vendor is unique in that it offers a solution to your (very) late night cravings – they will deliver warm cookies to your door until three in the morning! This nighttime service obviously explains the business’s unusual name, but it’s not the only thing that it’s known for. The cookies here are remarkably huge and mouthwatering, which is another way they stand out among the competition. Some of the options here are very interesting, including Cereal N’ Milk cookies, as well an Everything Bagel cookie. The location itself is very small, so we took our cookies to go. We ended up ordering a Triple Chocolate Chunk, a Confetti Deluxe, a S’mores, and a White Chocolate and Macadamia Nut. They were very warm, soft, and fresh! While we thought each cookie was incredibly yummy, we thought some of them were so rich and sweet that we could only handle a few bites. Overall, we rank them as some of our favorite cookies of all time!