Welcome to Chicago, also known as the Windy City! Or, if you’re a competitive eater, the City of Unlimited Possibilities. Feel like doing a food challenge? Or two or three? One must only type in their location into the foodchallenges.com search bar, and the map will light up with more food challenges than would ever be possible for one person to complete in a single weekend. At least this is what I found out during my weekend in Chicago earlier this summer, along with a few of my closest friends; Kyle, Mansour, and Cody.
What are you in the mood for? Pizza? (Don’t forget to try the deep dish!) Burgers? Frozen yogurt? An absolutely ridiculous amount of ice cream? Or do you want to be extra brave and try some of the spiciest wings (or ramen!) that you’ve ever tasted? Whatever you might be craving, Chicago has it, and if you’re lucky (and hungry), you may even get it for free. And don’t forget about the free T-shirts!
As you can probably tell, it was hard for us to decide what challenges we wanted to do over the next three days, but with some spontaneous planning and a fair amount of walking, we were able to throw together a weekend that was not only fun but successful.
While waiting for our appetites to build, we decided to check out some of the amazing views at Chicago’s historical Navy Pier. The beautiful skyline looks best when viewed from 200 feet in the air, which was easily accomplished with a ride on the historical Centennial Wheel.
Only a couple of us are afraid of heights, me being one of them, but fortunately, we made it out alive. And it would have been silly to miss out on the relaxing Shoreline Cruise of Lake Michigan, which we also enjoyed before taking on the first challenge.
Finally ready to tackle our first food challenge, we only needed to take a 15-minute walk down to Timothy O’Toole’s, home to the “Big Timmy Burger Challenge,” made famous by Man v. Food. This is a fairly simple challenge, consisting mainly of a 1.5-pound burger alongside a 1-pound serving of loaded “Irish” french fries. Even better, it’s a one-sitting time limit, and we were able to score our first free T-shirts of the weekend, with all of us finishing in 15 minutes or less!
Still craving more and feeling a bit brave, we then took a 10-minute walk to Jake Melnick’s Corner Tap, where daring souls can take on their “XXX Hot Wing Challenge,” consisting of 8 wings drenched in a sauce that includes Trinidad Scorpion, Carolina Reaper, and Ghost Pepper. This was another one-sitting time limit, but we all finished in less than 13 minutes, meaning that we had just won our second food challenge in less than an hour AND were now the proud owners of yet another super cool T-shirt.
At this point, all we wanted was to find a place to recover for the night because unless we had stomachs of steel, we weren’t going to be feeling too hot. So, after booking it to the nearest hotel, we tried to figure out where we were all going to sleep. (Somehow, Cody ended up with a bed all to himself, while Kyle settled for the noisiest air mattress in the entire world, and I was stuck in a bed in-between a snoring Mansour and my 9-year-old son, Dexter.)
After a long night of barely any sleep, we were ready to tackle another challenging day in Chicago. For our first challenge of the morning, and technically breakfast for most of us, we headed on over to Di Nico’s Pizza to attempt their World’s Largest Pizza Slice challenge, consisting of two giant slices of pizza weighing over 3 pounds, with a 30-minute time limit!
With so much time on our hands until our next challenge, we decided to head back to the Pier, where we once again enjoyed the Centennial Wheel, rode on the swings, and enjoyed some SpongeBob pops! (Dexter dropped his on the ground, but when you’re surrounded by competitive eaters, no food goes to waste.)
Finally, it was time for our next challenge, which was a VERY delicious ice cream sundae/banana split. Although it was another one-sitting time limit, we made short work of this one, finishing in less than 7 minutes. When it was gone, I wished I would have ordered two!
Still hungry, we drove to another restaurant, but unfortunately, their challenge had been discontinued, so back to the hotel, we went. Tomorrow would hopefully contain more eating feats, so we wanted to get some rest and digest as the sun went down on another challenge-filled day in the City by the Lake. (Of course, we didn’t go right to sleep; we watched a little bit of Blade first, because why not?)
Even with as much planning that goes into specific food challenge attempts, sometimes things just don’t work out as you had hoped. After checking out of the hotel, we discovered that our first two challenges were either one, only offered during a specific month, or two, came with a ridiculous price tag regardless of winning or losing.
So, Cody and Kyle instead decided to attempt one of the most insane ice cream challenges I’ve ever seen, Lindy’s 18-Scoop “Beast” Sundae Challenge! I chose to sit this one out because I am well aware of my strengths and weaknesses, and this thing would have definitely been a weakness. Just look at the size of it in the photo below!
Although I chose not to attempt the challenge myself, it was so much fun getting to watch two of my best friends tackle this thing with all the speed and willpower they could muster. They didn’t come out with W’s, but that just means they get to try it again next time!
Finally, our weekend of challenges was over, and we all went our separate ways. Cody and Kyle headed home, while Dexter, Mansour, and I stopped at a super interesting golf course we had spotted during our drive - a hidden gem called Haunted Trails Family Entertainment Center.
I’m not sure if trips like this are common within the competitive eating world, but I’m glad that they are for us. I’ve been doing this for a little over a year now, and I can say with one hundred percent certainty that these dorks are my friends for life, and without competitive eating, I never would have met them! (And honestly, at this point I can’t even imagine a life without Kyle sending me songs every day or talking to Cody about his girl problems.) In only a few more days, I have another food challenge trip coming up, and I’m sure I’ll be telling you all about it. So, until next time, stay hungry!
Article by Cherish "5 Pounds" Brown