Have Toddler, Will Travel

Health permitting, we head to the Windy City for the weekend. Not gonna lie, I’m a little nervous about taking Wesley with us, who is just about 19 months old. Our late summer vacation to Hilton Head Island was perfect, but it was 85 degrees, we had access to both the beach and a pool, we had a condo for a full week, and he was just over a year old.

This mini vacation consists of a) big city traffic/lights/sound/wind, b) FRIGID COLD TEMPS, c) no car (we’re taking the train) and d) a picky eater. That’s right, it’s going to be 24 degrees in Chicago while we’re there. Don’t get me wrong, I’m stoked, but also fairly certain that this could be a bad idea.

Why are we going? We both need a break. We have gone to Chicago a few times, and it usually seems to be around this year. Wait. I should clarify. We went to Chicago in Feb. 2010 and had plans to go again in Feb. 2011, but Steven got terribly sick the day before so we had to cancel the trip. Boo. The hotel rates in February are fantastic, and I happened to score $75 nights at the Hyatt Regency Chicago, right off Magnificent Mile.

(Here’s :60 of our last trip to Chicago.)

Why are we taking Wes? Well, for one, he’s our kid. I think he’ll love all the sights and sounds, museums and pizza. He enjoys excursions and seeing new things. He even is pretty good at spending the night in a hotel. Annnd, I think if he didn’t come with us, we’d miss him like crazy cakes.


  • Our hotel doesn’t offer complimentary breakfast (FAIL). Wes demands milk FIRST THING each morning. I assume there is a fridge in our room, but can we be certain?
  • The in-room snacks in a 4-star hotel are priced to the max. We gotta create a distraction.
  • The weather will be coooold.
  • I have no idea if there are rules about kids in taxis or city buses. Do we have to walk everywhere?
  • We’re taking the train into the city. Gotta keep our stuff minimal as we’ll have to walk to the hotel.

d24a9375-2168-4c57-8a2d-5626b8dfb6dfSo. To alleviate my concerns about snacks and milk, of course, I made a mad Target run today. I’m pretty proud of my finds. Hey, did you know that milk boxes don’t have to be refrigerated?! Score. I stocked up on these for the morning cravings, specifically. I figured I should probably get snacks that were both healthy and provided portability, so I also grabbed some applesauce packets (Wes’ fave), fruit/veggie chews and some Annie’s yumminess. I really doubt Wes will eat or like the freeze dried peas and corn, but it’s worth a shot.

We’re planning to visit a couple museums and perhaps the Willis Tower to stay indoors as much as possible. But, I really want to check out Polar Adventure Day at Northerly Island, so I’m planning to bring lots of layers for the 3 of us. I fully expect to battle colds when we return; let’s hope they are worth it.

Contrary to my plans to bring layers, I’m challenged to pack light. We aren’t bringing the pack n play; instead, we’re borrowing a crib from the hotel. Of course, I’ll have to find room for Wes’ lovie, “Dee Dee,” and his two preferred blankets. Also, diapers, wipes, pjs, clothes… It can be done, right? The hope is to fit everything in two backpacks plus a small diaper bag, my purse and the umbrella stroller. That way we can cram everything into lockers at a museum on the way out of the city to avoid having to go back to the hotel.

I really have no idea about big city public transportation etiquette. I mean, people use taxis to get around everywhere, right? But I assume they have to follow car seat laws, so maybe we’re best going the bus route. “Children in open strollers are welcome on CTA…” Whew. (I guess I knew this, but I didn’t have a kid before!) 

It will be a fun weekend. I’m sure of it. Now, if we could just get over this new stomach bug that Wes caught, we’re in good shape. I would hate to have written this ridiculous post in vain if we have to cancel the whole trip.

Oh, and I just found that taxis and commercial vehicles don’t have to follow car seat laws. So put that in your back pocket.

What are your toddler travel secrets?

Posted: February 12th, 2013
Categories: Leah
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