The long drive to Chicago was much more exciting for us than for the other competitors because we had just pulled off a win in the Twin Cities. Coming down off our Spam Challenge high, Adam, Shawn and I were all feeling pretty good. But we also got serious and discussed how Chicago would be a challenge…

I mentioned before that the bigger cities are the ones that give everyone problems. Trucks tend to go unnoticed amongst the hustle bustle, unlike the attention we get from the small towns. When we arrived in Chicago, the weather turned on us, hail pounding the car for a good 3 to 4 minutes. The forecast said we would be getting some bad weather that week, which is never good news. Unless of course, you own a farm and are in the middle of a drought.

As we made our way into the city, I’m happy to say we did more homework on Chicago than any other location so far. Our coconut wireless technique was strong, but the city was so big, finding the right location seemed to be much harder than before. The heavy foot traffic spots such as The Magnificent Mile or the Wrigley Field neighborhood areas were out of the question. And they didn’t allow parking on any of the streets, nor on any of the beaches near the lakes. Everyone and their MOMS kept telling us to park in places that we soon found out were not allowed. There was a disconnect… what to do, what to do…

After long days of driving, the producers always give us a day off to rest. Of course on that ‘day of rest’ though, you’re doing everything BUT resting! There’s no way anyone would be foolish enough to do nothing. This is really your only time to figure out what in the hell you are going to do. It’s when you meet the locals, scout the foot traffic and hone in on your parking area. I got a text early that morning from an unknown Chicago number saying, “Lanai, call me when you have a chance, I think I have a place for you to park the truck.” Talk about relieving some stress and lowering the blood pressure!

After a few hours passes, I realize that the text turned out to be multiple texts from different people in the Chicago area code, all with the same message: “Join us at our Kamehameha Day Celebration!” JACK POT. The network of Hawaiians in Chicago had come to life, and again the Aloha Spirit was with us. The best part was that the Kamehameha Day Celebration did not include food, so Aloha Plate pretty much became the caterers of the event. Winna!

However, the day didn’t start like we wanted it to. We got stuck in a Puerto Rican parade for 2 hours. I don’t think there has been any frustration-free weekend. It just goes to show, nothing was going to be easy in this race. When we arrived, it was as if they had all been waiting for a rock star to show up! 200+ people were standing in line, cheering and throwing shakas. Wow, I just couldn’t believe it. But were they happy to see us because we finally arrived? Or because they had just waited 2 hours for food and were starving? Either way, half of me wanted to cry and the other half was feeling the overwhelming stress of needing to feed this group of people.

The day could not have finished any nicer. We had a trio of Hawaiian singers, ladies were dancing hula and the sun came out like we were back home on the beach in Hawaii. Kamehameha’s people were with us that day, and this celebration just so happened to be in Chicago, right next to the ice hockey arena where the Black Hawks were playing for a championship. Tons of people and lots of excitement.

Day two was much different for Aloha Plate, as Tyler threw a Truck Stop at us- It was time to make a deep dish Chicago pan pizza in 2 hours. Adam can make some great Italian food, but he had never made a deep dish before. So here we go! I was very impressed with not only how tasty it was and how traditional Chicago style he made it, but how calm and cool he stayed throughout the cooking process.

My brother’s thought process is very much like our grandfather’s. He keeps it simple. And like my grandpa always said, “Don’t think too much, you’ll make yourself stupid.”

We didn’t win the challenge, as the Mayor of Chicago was supposedly looking for something new, not traditional. But we were still feeling okay, because we knew our sales would keep us in the game. When Tyler said he was going to drop a bombshell on us, he really did something that’s never been done before in the race…

As you saw, all three of us are now in the finals! At first I didn’t know if I liked that method, because now you had to look out for 2 teams instead of just 1 more. Regardless, we didn’t even have time to think about it or be happy because we had some catching up to do with Tika Tika Taco in the money department.

On the final day in Chicago, Tyler threw another challenge at us. To sell Ditka Dogs. The winner got a 5-hour start to the next city, and it was crucial for us not to let Tika win this challenge. If they did, they would have the head start and the 1k in there- which would really put us in a hole.

We decided to post up in Whicker Park, one of the busiest shopping places in Chicago during weekends. When we arrived, we had about 75 people in line, but it wasn’t quite what we needed for the challenge. People who came to our truck simply weren’t interested in hot dogs. They wanted to sample something from Hawaii. What to do, what to do…

We ran out of time eventually and had to head over to Ditka’s to find out who actually made the challenge. All we could hope for was that the Philly Boys got this challenge, and not Tika.

Walking up to the 2nd floor to see Tyler and find out how we did was one of those exciting-not-so-exciting moments. I mean, we were going to get the news that someone else won, but at the same time Mike Ditka was sitting there with Tyler, so it was impossible to not get excited. Tika had a great weekend in Chicago with the taste challenge and now the 5-hour head start. We have to hand it to them- they did good and we can’t take that away from them. No. We just have to step it up in the next city.

We made some new friends in Chi town and we can’t thank all the Hawaiians enough. Aloha was alive and well in Chicago and we were very flattered to receive all the support. It’s week 6 and we still feel so overwhelmed with all the support we’ve been getting. Driving to the next city, we feel some pressure because we’re getting closer to the hometowns of The Philly Boys and Tika Tika Taco. Let’s just hope we can find some Hawaiians.