Chicago with Kids – October 16-18, 2026

LS has been super into Pokemon for over a year, so when we saw that Japan’s Pokemon Fossil exhibit was coming to the Field Museum in Chicago, we knew we had to go. I had a couple of Suite Night upgrades at Accor (thanks to staying at all those Fairmonts last year!), so I booked a Junior Suite at the Swissotel Chicago for a long weekend in October during fall break at school.

Getting to Chicago was definitely the roughest part of the trip. Our flight was scheduled to leave at 9:36 am, but it was already delayed two hours as soon as we got to the airport around 7:45. So I looked for an earlier flight we could switch to and found one for 10:30. However, this meant that the seats I booked back in March weren’t available on this new flight and none of us were sitting together, so I had to visit a gate agent to at least get LS sitting next to one of us.

That flight was on time for boarding, but then there was a bit of a delay in taking off. The flight itself was short and uneventful, but upon arrival in Chicago, there was another plane broken down at our gate, so we sat on the tarmac for well over an hour before finally being let off the plane, roughly at the same time our original flight also unloaded. Of course.

We had also been forced to check our one bag, but at least baggage claim was quick. We hopped on the Blue Line train and were soon in the city.

We checked into our hotel, and our suite was amazing! We were on the 40th floor in a corner with a great view of both Navy Pier and the Chicago River. Soon after we arrived, the doorbell rang. The hotel surprised us with a complementary treat of a bread, jam, and cheese plate, as well as cookies and apple juice for LS. We were starving and didn’t have time for our planned pizza stop due to the plane delays, so we scarfed it down.

We headed over to Millennium Park to check out Cloud Gate (the Bean), which LS loved.

Then it was time for our scheduled architecture boat tour on the First Lady. It was a chilly evening, but not too bad as we started off. Our guide was great, telling us lots of interesting bits of info about the buildings and bridges along the river. As we started to head back, it began to rain. We decided to duck down inside and grabbed a hot cocoa before heading back up. There was a glorious rainbow!

After the boat tour, we decided to see how long the wait was at Lou Malnati’s, but it was an hour and a half, so we decided to save it for the next day and just grabbed a quick bite at Shake Shack instead since we hadn’t had an actual meal since breakfast.

The next day we took the bus over to the Field Museum. We explored many of the exhibits and checked out the Pokemon Fossil exhibit. It was a cool exhibit, and LS loved it, but it was smaller than I had expected. However, we liked how they combined the Pokemon with the actual real-life creatures they were based on. We bought a couple things at the gift shop, explored the museum a bit more, and then decided we were hungry.

We headed back to Lou Malnati’s (but the location closer to the museum) and were seated fairly quickly. Mr. Strange and I ordered a deep dish pepperoni, and we got a thin crust cheese for LS. LS thought her pizza was ok, so I asked if she wanted to try the deep dish. She said she did, so I took the pepperonis off a slice and gave it to her. SHE LOVED IT. Mr. Strange ended up giving her the rest of his portion of the deep dish and took her thin crust instead. We now have a Chicago pizza fan in the family! It was definitely good (love the sauce), though I tend to be partial to New York style myself.

Full of pizza, we headed over to the Wicker Park neighborhood. Mr. Strange went to check out some record shops, while LS and I did some window shopping and checked out Myopic Books.

We then returned to the hotel to relax before heading out after dark to ride the Ferris Wheel at Navy Pier.

We had breakfast at Wildberry Pancakes the next morning, which was delicious. We walked a bit down the River Walk, then checked out of the hotel, and took the train back to the airport. Our trip was too short, but we will be back!

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