The Ugly Truth: A Disastrous Day in Chicago’s River North & Magnificent Mile

Most of the time, this blog depicts a rosy picture of traveling with a little one: smiling faces on sunny days in beautiful places.

Those stories of course do exist. But there’s also an ugly truth behind traveling with kids. A truth that doesn’t get shown very often, not because I’m trying to hide anything, but because it’s usually not very fun or exciting to write about (and definitely not worth photographing!)

Sometimes when you’re traveling with little ones, things don’t go as planned. There are tantrums and food throwing and overtired babies who don’t want to nap. Just like at home, there are good days and there are bad days, and I think it’s important to share those “off” days too. Because it’s unrealistic to think it’ll be all rosy and perfect when you’re traveling with a child.

The Ugly Truth of Travel with Kids: a day gone wrong in {Chicago}'s River North & Magnificent Mile | ournextadventure.co

I try to be as prepared as possible before a trip to avoid these mishaps. Sure it’s not so spontaneous, but I plan our adventures down to the minute, with time penciled in for snacks, naps and downtime to relax. Just about everything we do is pre-booked with a reservation attached, so we can keep things running smoothly with little wasted time and patience.

The thing is, kids don’t really care about all that planning. Sometimes they just want to stay at home, watch cartoons and eat hot dogs.

As such was our experience on our last day in Chicago. We had planned to have lunch in Chicago’s River North neighborhood, followed by a walk along Michigan Avenue (the “Magnificent Mile”). Nothing too strenuous; a pretty slow-paced day actually.

The Ugly Truth of Travel with Kids: a day gone wrong in {Chicago}'s River North & Magnificent Mile | ournextadventure.co

It started out fine. We had a late start getting out of the house since we decided to give Evelyn an extra morning nap. She was a little cranky and we wanted to make sure she was in her best mood. By 11 AM we were out the door and feeling great.

We stopped on the La Salle Bridge to snap a few pictures. It was shaping up to be a beautiful day, and we were on our way to our lunch reservation at Rick Bayless’ Frontera Grill.

The Ugly Truth of Travel with Kids: a day gone wrong in {Chicago}'s River North & Magnificent Mile | ournextadventure.co

The Ugly Truth of Travel with Kids: a day gone wrong in {Chicago}'s River North & Magnificent Mile | ournextadventure.co

As we walked down Clark Street, we passed patio after patio, each a little different and looking so inviting. Were it not for the 1 year old we were pushing, I would have gladly stopped for a drink (or two, or three).

The Ugly Truth of Travel with Kids: a day gone wrong in {Chicago}'s River North & Magnificent Mile | ournextadventure.co

The Ugly Truth of Travel with Kids: a day gone wrong in {Chicago}'s River North & Magnificent Mile | ournextadventure.co

We arrived at Frontera Grill about 20 minutes early, but I thought “what the heck, let’s just see if they’ll seat us now”. As I reached down to take Evelyn out of the stroller, something was missing.  “Did you take her glasses off?” I asked.

“No??” Matt snapped back.

I lifted Evelyn out of the stroller, looking in every nook and cranny. Surely they had to be here somewhere? But the more I searched, the more I realized the glasses were gone.

WHAT THE HELL, EVELYN?!

“She must have taken them off and thrown them out of the stroller!” I panicked.

I handed Matt the baby and hurried back along our path, sure that I would see them laying somewhere close by. I had only hoped they weren’t dropped in the crosswalk and run over by a car. This had to have just happened.

My stomach sank further with every passing city block until I reached the glasses’ last known whereabouts at the CVS 3 blocks away. I frantically searched the aisles and asked the cashier if anyone had turned them in. Nada.

So I headed back towards Frontera Grill, searching every patio we had just admired, stopping into every bar and restaurant (6 or 7 of them, to be exact) to see if anyone had turned them in. None. Nada. No one had them.

The Ugly Truth of Travel with Kids: a day gone wrong in {Chicago}'s River North & Magnificent Mile | ournextadventure.co

“These aren’t hard to spot,” I told myself. “We’re talking about pink plastic baby glasses.”

I met back up with Matt across the street. “They’re gone. It doesn’t make any sense. How could they just disappear??”

We gave into defeat. We didn’t have a spare pair for Evelyn, and she would be without glasses for at least a week and a half until we could order a new pair. I felt absolutely sick, but there was nothing more we could do. “I guess we’ll go get lunch then?”

As we crossed back over the street to the corner where the whole debacle began, I spotted a tiny pink pair of glasses sitting perfectly in the middle of the sidewalk. “OH MY GOD!” I shouted as I ran to pick them up. I couldn’t believe it.

I don’t know where those glasses came from, or how on earth we could have missed them with each of us walking the area at least 4 times. But I didn’t question it. I’m convinced it was nothing short of divine intervention.

The Ugly Truth of Travel with Kids: a day gone wrong in {Chicago}'s River North & Magnificent Mile | ournextadventure.co

Finally seated at Frontera, we ordered a pair of margaritas without hesitation. We’d certainly earned ourselves a drink.

The Ugly Truth of Travel with Kids: a day gone wrong in {Chicago}'s River North & Magnificent Mile | ournextadventure.co
“Oh, did I do something bad?”

We enjoyed our lunch and Evelyn was actually fairly calm during the meal. I think she was feeling bad about what she’d just done. I thought we might salvage the day, until Evelyn flung her head backwards, banging it on the wall behind her. I paid the check while Matt consoled a crying Evelyn outside.

I was ready to give up on the day. But with Matt’s encouragement, we trudged forward towards the Mag Mile. We had come so far and been through so much already, we couldn’t give up now! There were really only 2 stops I wanted to make: Eataly and the Crate&Barrel flagship store. Anything more than that would be a bonus.

The Ugly Truth of Travel with Kids: a day gone wrong in {Chicago}'s River North & Magnificent Mile | ournextadventure.co
“Why are we here Dad? You know I just want to go home and play.”

A few blocks away we stopped into Eataly, a giant Italian food hall/market with locations all around the world. After a harried experience in New York, I wanted a re-do in Chicago. Evelyn made it pretty clear that she was not interested though, trying to squirm out of her stroller every 2 minutes.

The Ugly Truth of Travel with Kids: a day gone wrong in {Chicago}'s River North & Magnificent Mile | ournextadventure.co

The Ugly Truth of Travel with Kids: a day gone wrong in {Chicago}'s River North & Magnificent Mile | ournextadventure.co

The Ugly Truth of Travel with Kids: a day gone wrong in {Chicago}'s River North & Magnificent Mile | ournextadventure.co

That didn’t stop me from ogling at the beautifully fresh market counters. I was surprised by how much more open the Chicago store was. Next time, it’d make for a nice casual lunch stop.

The Ugly Truth of Travel with Kids: a day gone wrong in {Chicago}'s River North & Magnificent Mile | ournextadventure.co

We pushed forward to Michigan Avenue and stopped at the 4-story Crate&Barrel flagship, but I couldn’t focus on anything but our wiggling whiny baby. Then on our way to the subway (against my better judgement) I thought we should pop into Zara quick to see if we could find a cute new outfit for Evelyn. Bad idea. Another meltdown ensued and that was the last straw. It was time to call it a day.

The Ugly Truth of Travel with Kids: a day gone wrong in {Chicago}'s River North & Magnificent Mile | ournextadventure.co
This is my “if you don’t get me out of here right now, I’ll scream” face. She meant it too.

Our day 3 in Chicago was definitely not what we’d hoped for, but honestly, I can’t say that I’d have done anything different. The truth is, there will always be those days when kids just don’t want to cooperate. Children don’t discriminate on where their tantrums will occur and sometimes there’s no amount of preparation you can do to avoid it.

The key, though, is how you will respond to it. Will you roll with the punches? Or give up and stay home? I’m glad we decided to push forward and make the best of it, even if we didn’t quite get to see everything we’d wanted. Looking back, although the day seemed awful then, it really wasn’t so terrible in the grand scheme of the entire trip.

Plus, now we’ll always be able to tell Evelyn the story of how she almost threw away a $200 pair of glasses in downtown Chicago. 🙂

Happy Travels!

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