Traveling with a Terrible Two Year Old. Travelogue: Chicago and Milwaukee 2018

This is the story of the trip that has ended long-distance travel with our toddler.


We recently traveled to the Midwest with my family to celebrate my parents' 60th birthdays and to visit my brother who moved out there. 

Our son's been pretty good until now. We took him to New York for 6 nights on a business trip with me when he was only 3 months old. He's flown over 10 times in just two years. We love traveling with him, but now that we're in the thick of the terrible twos/threes, I think we're going to take a pause. 

The first leg of our trip to Chicago was fine. He watched some videos, I got some reading in. But on our lay-over, he threw a fit because he didn't want people to get off the plane. Then he didn't want me to go to the bathroom. Then he didn't want to put on his seatbelt. The plane couldn't take off again until he did, so everyone sat on the plane listening to our screaming child. In the midst of the tantrum he said he needed to pee, so we begged for a cup, and were eventually allowed to go to the bathroom while everyone waited for us. He collapsed into his seat afterwards and immediately fell asleep and we were able to take off. Ironically, the book I brought with me on the trip, Mindful Discipline, gives great advice about approaching discipline with mindfulness, meeting the underlying needs of your child, and helping them develop resilience and self-regulating mechanisms. "Underlying all acts of misbehaviors are needs, so we must meet misbehavior by meeting the need. When we meet our children's needs, their nervous systems are emptied of the tension driving them toward gratification." Clearly, this child was over-tired and cold during our entire trip, which resulted in lots of big, dramatic misbehavior. Staying kind and mindful through all of this proved to be extremely difficult. 


But we had a great time with my family! After all the larger purpose of this trip was to get quality family time. We got to experience the joys and pains of toddler life together. If anything, Harlem helps keep things real. 

We stayed in a historic 4-bedroom condo in Chicago's Little Italy neighborhood.

For our first evening, we ordered take-out from Lou Malnati's. The butter crust on this pizza was delicious and the slab of sausage patty in the middle was interesting. We talked about going out to a tiki bar after Harlem went to sleep, but ended up just staying in and catching up. 

We opted not to bring a stroller and just our car seat and travel cartThis Go-Go Babyz Travelmate is great for the airport, but it was a little hard to get around the city. Harlem is going through a clingy phase and insists on being carried, exclusively by me when he's upset. I've had lower back issues since my pregnancy so carrying this 40-pound kid around is really hard on me. 

We visited Millennium Park and the Cloud Gate bean. Harlem was more interested by chasing the pigeons around the park. There was also a melt-down here. 

My sister expertly planned our whole trip with a master excel sheet, naps planned in, and all meals reserved. Normally, I love to plan trips like this but I've been so busy that it was such a relief to have her handle the details. Thank you Eurie, you're the best! 


Also my brother Eugene is one of Harlem's favorite people.

The next day we went to Willis Tower (previously known as Sears Tower) and up to the Skydeck 103 stories up. They have ledge glass boxes where you can stand and get views at 1,353 feet in the air.  

You wouldn't be able to tell from these photos, but Harlem was pretty unhappy here and threw a large tantrum in front of the elevators while several dozen people watched with bemusement. I had to haul his flailing body away and let him cry it out in a less visible corner. 

We had lunch at a small Cuban deli downtown and then headed out of Chicago for Milwaukee. On our way, we stopped at Mars Cheese Castle, a "cheese landmark." We picked up some curds and cured meats for some pre-dinner appetizers at our AirBNB in Milwaukee. 

Milwaukee was even colder than Chicago and it rained most of the time we were there. We didn't do much besides visit my brother's apartment and eat. My parents were craving Korean food so we skeptically went to the Korean restaurant in downtown Milwaukee. The service was slow but the food was decent. 

We picked up dessert from the Milwaukee Public Market and went back there again the next day for lunch. 

Harlem had mint chocolate chip ice cream and another tantrum when he realized there was no cone. He then refused to put on a jacket so I let him go outside in to the wintry mix storm without it and figure out for himself that he really needed that jacket. He got a good long nap at my brother's place, then we said bye to Eugene and headed back home. 

The flight went much more smoothly this time on Harlem's part, but there were mechanical and weather delays. Harlem fell asleep the last half hour of the flight. By the time we got home it was past midnight Pacific time, 2 AM Central Time. Russell and I successfully transferred Harlem to bed, then agreed not to do this again for a while. 


I love Chicago and wish we could've explored more. But ultimately, it's not a super kid-friendly place and we went during a particularly difficult phase in Harlem's development. Thanks again to my sister for planning and my family for bearing with us. And happy birthdays, Mom and Dad! 






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