Family Travels: “Chicago” (Road to the Sweet-Up)


So I don’t know if you heard, but I took the family on a little trip to Chicago!

Of course, by “took” I mean dragged. And by “Chicago” I mean Woodridge, IL which is about a half hour from the city.

Aaaaaaaand by “I” I mean Wilton since they invited me over for their Sweet-Up and took care of the hotel accommodations.

What’s a Sweet-Up, you ask? Well I’ll get more into that in the next post. I figured it was a fairly long weekend for us and cramming it all in one post would surely have broken the entire Internet. So consider this part 1 of 2 of the longest 4 days ever.

When Wilton asked me to come to their Sweet-Up, I was humbled. They offered to take care of the flight and the hotel. Dinner for 2 nights, lunch, a car ride to and from the airport. All I needed to bring was me and my Hollywood superstar sunglasses while I signed autographs for my blog’s adoring fans.

Ha, I’m just kidding. I didn’t even know if my mom was going to be there.

But my guilt got the better of me. And it’s a guilt that most people would think is beyond silly, but I honestly can’t help it.

See, I’m a stay-at-home dad. Heavy emphasis on the stay-at-home. I go out with the kids or whatever, but I don’t do much of anything else. The wife, she works and brings home the bacon. And she works hard for that bacon. Up until a few days ago when she started working from home, she was busting her butt driving around everywhere for a job that didn’t give a piece of poo about her. Like me, she loves to travel and visit distant lands (like Florida). But because of her need to always work, we don’t get to take time off other than the long holiday weekends and few weeks of vacation a year.

So when Wilton asked me to travel to Chicago for a few days, I was reluctant. Of course, the wife was practically pushing me out the door, saying that I should go. But my guilty conscious felt bad if I was to go on this trip on my own and leave her at home with the kids. I felt like she works every day, and works hard, so it wouldn’t be fair if I – with my job of sitting on my butt and writing on my little website here – got to go on a trip to somewhere we’ve never been before. Get it? See, you think it’s silly!

So I asked Wilton if it would be cool for my family to join me in my hotel room. Of course, as cool as they are, they were down with the idea. And it was totally understandable that they couldn’t cover the flight cost, so that meant we had to drive.

Screenshot 2015-04-30 21.45.11_edited

Challenged accepted.

Sure, that 1 hour and 55 minutes on a plane was the easy route. But who wants easy?! Not this guy! Give me 12 hours in a car with a ticked off 2 year old and a 5 year old who’s deep into his “are we there yet?” phase.

In all seriousness, the drive was going to be long. But it’s a drive I’ve never done before, so I was kind of looking forward to it. I’ve driven from North Carolina to New York, from Florida to North Carolina, back and forth, forth and back, I know the east coast and I-95 rather well. But everything even remotely off course from that was new and exciting to me. Ohio?! Yes!


Indiana? Can’t wait!


I was taking pictures of road signs that said places like Cincinnati and Toledo as if I was from some foreign country and only read about these places in cheesy American romance novels.


In case you think I’m BS’ing you.

Plus, if the drive meant I was going with my fam, then it was a drive I was willing to take. I wouldn’t have been able to enjoy myself fully if they didn’t come. So I’m glad we took the trip.

How was it? Well let’s see…

We started at around 6pm on Wednesday. I needed to be at the hotel at 4:30pm on Thursday, so we thought it best to split the time on the road and sleep halfway. And we made it to the halfway point which turns out to be a little town called Washington Court House, Ohio. Yeah… that’s what it’s called. We didn’t make it till about 2 in the morning though and that sucked because we had to get up bright and early to get back on the road to get there by 4:30.

Sometime before midnight though, we encountered a bump in the road. Or, several…

See, we hardly ever carry cash. And we noticed the toll roads in West Virginia, but figured we’d just get off the highway and go around them like we always do toll roads. Shame on us, because as it turns out, that’s exactly how horror movies start…

We took this road which seemed ok at first. But then the GPS said turn right, and all I saw was a dirt road leading into the woods. I shit you not, I almost pooped my pants. I wish the wife was recording from the beginning because it was nuts. Crazy steep hills going up and down, insanely sharp 90° turns around corners that had broken tree trunks sticking out like booby traps, I wanted to just close my eyes and cry like a little girl. And that was BEFORE I turned the high beams on. And as SOON as I turned them on, I turned them RIGHT back off. The lights were just bright enough to accentuate the sheer creepiness of the road. I mean, it was already a manageable creepy. But now, after seeing everything lit up, I was ready for a change of underwear. The trees seemed to lean towards the car as if they were going to carry it away. The rail seemed to be the only thing protecting you from the seemingly infinite darkness of what appeared to be the edge of a cliff. The broken down wooden sheds on the edge of murky and lifeless bodies of water looked like the perfect place to keep old rusty machetes and chain saws. And I think that’s what I regret most about the video. How it didn’t capture everything. It captured my uneasiness and overall panic perfectly, but not the reason for it.

Anyway, we made it through the Forbidden Forest and drove on to good ol’ Washington Court House, Ohio.

We spent the night at our favorite place – a Holiday Inn Express. Why? Because we can use and build up rewards points, but most importantly, they have a pretty good free breakfast. And as you may recall, they have a machine that poops out pancakes! C’mon, if a place has a pancake pooping machine where you can just push a button and have as many pancakes as your happy little syrup loving butt desires, then how can you NOT want to stay there?! Exxaaaaaactly.


Of course, since we’re only staying in the room for a total of about 6 hours, we open the door to find one of the bigger, more cleaner hotel rooms we’ve stayed at in a long time. Figures. Whatever the case, we get in, sleep, eat pancakes, and get out.

Back on the road with daylight on our side, we were able to see the sights around us. And by sights, I mean trees, because there wasn’t much to look at otherwise. The wife warned me the farther you go west, the least stuff there is to see, as she recalled her family road trip as a kid from Florida to California.

But then, sometime before Illinois and after Indianapolis – which, hahaha, by the way to my surprise, turns out to not be a city in Minnesota – were these ridiculously awesome windmill farms.


I’m telling you, I never ventured this far west before. I knew these things existed but have never seen one in person. Their size is absolutely massive. As if that wasn’t enough, there are sooooooo many of them! As far as the eye can see there are windmills, all of them doing their dance on the side of the highway. I felt bad for Seb because he and Lucas had just fallen asleep. I didn’t want to stop and take good pictures because I knew I would’ve woken them up, so I figured I’d just take them on the way back. But while I’m there snapping pics with the cell phone without even looking, the wife asks if I know what they’re for. I looked at her with a defiant stare, as if I was appalled by her asking, seemingly questioning my knowledge and understanding of these mechanical marvels.


“They’re for generating wind. Duh.”

So we were reaching the border of Indiana and Illinois when something amazing happened… We time traveled! A mystical worm hole? Hermione apparated by with her Time-turner? TARDIS came swooping through the highway like it did that one time? Lightning strike the car as we were traveling 88mph?! …Don’t laugh at that one! Ask the wife – it’s seriously a fear of mine. I don’t worry about little things like paying the mortgage or my health. I worry about getting struck by lightning as I’m driving at a fast speed, and getting whisked away, back in time, unable to return to today. Aaaaaaanyway, as crazy as I may sound, it was neither of those things. It turned out to be a strange phenomenon known as “time zones”. So, so cray.

So we made it to Illinois an hour earlier than planned, and then shortly after, Chicago. From the city it was about a half hour or so to the hotel. We stayed in a town called Bolingbrook which appeared to be right in the middle of the suburbs. The Aloft Hotel was right smack in the center of a huge shopping center called The Promenade. Aside from the outdoor mall with tons of stores and restaurants we’ve never heard of, there was an Ikea and a Bass Pro Shop. Pfft! The wife and kids were SET. Those 2 stores alone would keep them busy for at least 32 hours. And 3/4 of those 32 hours is just trying to get out of Ikea!

I checked in and right away knew it was going to be a good stay. The staff at the front desk was awesome, friendly, and ready to help out with whatever I needed. Checked out the room and it was great. It wasn’t as kid friendly as I would’ve liked, but our 2 year old is like a monkey anyway so he’d find a way to get into everything regardless. They had no problem sending up a portable crib for the monkey though, and an air mattress for Seb. Overall I didn’t have any complaints and was looking forward to more than 4 hours of sleep.

I got ready for a night with Wilton where we talked trends (again, if you want to know more about that, check out the next post), and headed downstairs to meet up with the rest of the Sweet Treat Team. I found myself talking to the staff of the hotel again while I waited for the meet up time. They were asking stuff like what do I do and why I was there for Wilton. And I was asking them more important questions, like where can we order a good Chicago style pizza. I honestly could’ve sat there and talked to them more, they were that cool. But I met up with my Wilton peeps and we headed to HQ to talk trends. I texted my wife about the pizza recommendations and went about my evening.

And it was a great evening! Got to meet a lot of amazing people, got to listen to everything Wilton put together, had a nice dinner, it was awesome. (Follow to the next post if you want to hear more about that.) But when it was all over, I made it back to the room and found this sitting on the table.


Ooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooh, boy.

It put my entire night in perspective. I mean, yeah, I thought I was having a good night. But that box of heavenly goodness… It made it a million times better. It was what the staff recommended. A place called Rosati’s. I honestly was only going to have a bite. It was late, I was tired, I already had dinner, I had to wake up early. There were at least a hundred different factors giving me completely legitimate reasons to not eat this pizza.

Of course, this is all going through my head as I’m finishing my second slice and going for my third. It was so good! It was my first, real, authentic Chicago style pizza. And I have to admit, it made me question my love and blind patronage to New York style. My God, that almost sounds blasphemous coming out of my mouth, but it’s true! I think the best part was the sauce, I felt like that’s where the bulk of the flavor came from. But despite how good it was, when I was going for that third slice, that’s when I started talking sense into myself knowing that I really shouldn’t. And I think I scared my wife who was still awake because she heard me conversing with myself the way Gollum did in Lord of the Rings.

“We can has the pizza! It’s good, precious is hungry for it.”

“No! You already had more than what you should have. It’s late, you’re old, this won’t end well for us.”

“But, it’s so good. We needs it! Give its to us!”

[smacks own hand]

Wife: “What the f*$# are you doing?”

[realizes what was happening, puts pizza down]

“…I’m gonna get a shower.”

…It’s funny because it’s true.

The next day was full of fun and activities and surprisingly no regret! Guess I could’ve had that third slice… But while I was living it up at Wiltoncon (that’s what I called it with the wife, trying to fulfill my fantasy of attending a gaming convention), the wife had the entire day to herself and the kids. This was a reason why she wanted me to go on my own. Because even though we were all there, she wasn’t going to do anything worthwhile with just the kids. She took them around the shopping center and as it turns out, they (the kids) were huge fans of Bass Pro Shop!


They were climbing and pretending to drive the boats, checking out the fish, playing in the tents..


They probably could’ve spent the entire day in there. The wife though, is another story.
They continued their adventure throughout the day and so did I. I was scheduled to do Wilton stuff till 6, and then till 9 we had a dinner planned. I was all for it, but when I noticed some people skipping out on the dinner and heading back to the hotel, I figured I’d do the same thing. I was running on fumes and knew there was an exceptionally long day of driving starting in the morning. So I knew it was probably a better idea to try and get some rest rather than be out and about till after 9. Hahaha, I’m such an old man. 9 is so past my bed time.

So the good folks at Wilton ordered me an Uber! I asked “hey, can I skip out on the dinner?” And they were like “sure… Alright, you’re good to go! I ordered you an Uber and it should be here in 15 minutes.” Then I was like “whoa, sweet! You guys are so awesome, thank you! …….What’s an Uber, exactly?” Turns out it’s like a taxi service! And they’re just regular cars. Not the hovering, futuristic transportation vehicles that I pictured in my head when I heard the word Uber.

I made it to the hotel a few hours earlier than what the wife was expecting so I figured I’d surprise her! Hahaha, those of you who already processed that scenario in your head know that it was not the best of ideas… I unlocked the door and heard my wife ask Seb nervously “what was that?!” Then I opened the door which had the latch on it and she freaked. The hell. Out! “OH MY GOD, CLOSE THE DOOR, WHAT IS WRONG WITH YOU?!?!” Then Seb, “mommy, who is that?” … “I don’t know, but they’re going to hear it from me!” She opened the door to me trying to contain my hysterical laughter. After catching her breath she went on to tell me she saw my hair and thought for a second it was the guy from the front desk. And she was about to let him have it for scaring the crap out of her. Can you believe that? Such anger and hostility when I tried to surprise her by coming back early. The nerve!

Turns out they already had dinner and were about to get ready to relax before bed. What did they have? The leftover pizza! I almost wanted to leave again. Come back early, get screamed at, AND all the pizza is gone. What kind of a world is this?! So we had to venture out to get me something to eat.

But what? With so many new and exciting options I almost felt bad for being the only one trying something new. Then I remembered they ate all the pizza and I didn’t feel bad anymore.

What did I get? Something I’ve been wanting to try for a long, long time and never thought I’d get to – Portillo’s.


Let me tell you something… If you ever visit the Illinois area, and you ask someone “hey, what do you have to eat around here”, and they DON’T mention Portillo’s… Then they do not like you. And I mean, really don’t like you. In fact, they’re probably waiting for you to turn your back so they could call you names and make fun of you to their friends.

It was absolutely amazing. Glorious. When I took that hot dog out of the bag and unwrapped it, I swear, in the darkness of night, a heavenly light shone down and blessed my meal. Everything about it was so fantastic. The fries were irresistible, I ordered a chocolate cake and it was the moistess, most chocolaty cake I’ve had in a long time. The dog I ordered was a Char-Grilled Maxwell Street Style Polish. It comes with mustard and grilled onions, and extra love, on a steamed poppy seed bun. It was so crispy and charred that I had to use force to bite down on it. So perfect, just the way I love my hot dogs. Look, I’m missing like a thousand opportunities to make wiener jokes and I don’t care!


And the line at the drive thru was so insane! I’ve never seen a drive thru like that before. There were 2 lines and they both wrapped around the parking lot. THE PARKING LOT. This was a mini-mall, mind you. The lot was fairly big. They had a whole team of people just taking orders outside. They’d put a ticket on your car to keep track of you. You’d put your order in with one and then the next would take your money, and by the time you got to the window it was ready. It was a well oiled machine! I’ve always wanted to give them a try thanks to Greg Miller from I’ve been listening to his podcasts and content for yeeeeeeears and not a week passed where he didn’t mention Portillo’s in some way. Even named his wiener dog Portillo, and now I know why!

By the way, let me tell you about the serious lack of Portillo’s outside of Illinois. It’s just not right…

Screenshot 2015-05-01 07.44.58_edited

At this point I was making plans in my head to leave a little later in order to pick up a hot dog for the road and some pizza to bring home. But sadly, we had to leave in the morning. Early in the morning. And that we did. We were on the road at about 7:30am and this time we knew time travel was going to work against us. If it was any earlier, seeing this train in the middle of the highway would’ve freaked the hell out of me.


Even so, it was a pretty straight forward trip. Rather uneventful other than the constant rain we got all the way to Virginia! Man, it just wouldn’t let up. It totally messed up my plans of getting out to take proper pictures of the Windmill Farms. At least Seb got to see them this time though.

Oh! And we skipped that road. We didn’t have cash, but as it turns out they have kind of a pay later service. Only draw back is it adds $5. So instead of the regular $2 (which I totally guessed in that video up there), it came out to be $7. Which was alright with me because I could only imagine how that road would have been with the rain that was going on all day. I am glad we got to drive in the day time because most of the stuff we passed at night was pretty nice to look at.


I don’t know about you but I’m a sucker for mountains. I blame my 10 years of living in the flat lands of Florida. And I just love the way the roads moved with the land. It makes driving for hours on end a lot more exciting.


We had rain, and then crazy fog as we got out of West Virginia. You couldn’t even see the road ahead of you! The fog along with that creepy forest road, it’s almost like a sign telling me to never drive through that state again.


But after that it finally cleared up.


And I’m so glad it did because it gave us a really nice close to the trip.


And that’s that. The family trip to “Chicago” was mostly spent in the car and separate, but we had some memories that I’m sure we won’t forget any time soon. Seb got to sleep in a hotel (which he loves to do), Lucas got to see fish at Bass Pro Shop, the wife had some amazing chocolate cake, and I had my first out-of-body experience with a hot dog. Oh, and the pizza. You can’t forget about the pizza, because I know I won’t.

It was a great trip and I would honestly make it again to spend more time up there. There was a cool looking zoo I’m sure the kids would love to visit. As well as museums and the like, in addition to more pizza and Portillo’s (which I would try to have every day). And I’m not even counting the 4 or 5 friends of mine we drove by or were close to up there. I wouldn’t mind stopping to say hi to them, maybe go out for pizza and Portillo’s. There’s a lot to experience in another trip up there! And I hope we get to do it again soon. Because I’m telling you, I could really go for some more pizza and Portillo’s.


Here’s another reminder if you didn’t get the others: This trip was what the family and I did while in the Chicago area. I was there for the Wilton Sweet-Up and it was a blast! If you want to hear more about what happened there, head over to the post immediately following this one.



  1. Pingback: My Experience at the 2015 Wilton Sweet-Up! – The Man, The Chef, The Dad

  2. cphammer

    Great road trip chronicle. I like seeing the pics from state to state and road to road. Too bad you forgot to mention pizza and Portillo’s 😉 More sleep and more recreational stuff on the next visit, busy bee.

    1. What?! I didn’t mention pizza or Portillo’s?!? Let me go back and fix that!

      Definitely need to go back and explore more. Way too much to do and we didn’t even go to the city.

  3. Pingback: Humpday Update – New Logo, New Links, New Parks! – The Man, The Chef, The Dad

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