We left the cornfields of Iowa bright and early… well, vacation early (9am)… so we could maximize our time in Chicago and see all the Windy City, or at least what you see in 12 hours. Challenge accepted!

Coming into the city, we started seeing the skyline, and the traffic

Definitely different than we are used to seeing the last 2 weeks.

The boys liked this parking garage. They said it looked like their old Hot Wheels parking garage.

We were all amazed with Chicago. It really is a beautiful city, although there have been a lot of changes since my last visit 20 years ago, and not necessarily in a good way. But the city itself was still beautiful to see.

Chicago Must-Do #1: Deep Dish Pizza. Why not go right to the best, Pizzeria Uno? Of my goodness, it was delicious!

Bellies full (again), we did some exploring through the city.

Next Chicago Must-Do #2: Navy Pier.

The Pier has changed quite a bit. They’ve built a mall on top floor, as well as giant ferris wheel. The boys and I decided to take a spin to get the full city view. (Mike kept his feet on the ground.) Considering they now charge $30-$40 to go to the top of the tallest buildings, it wasn’t a bad deal. And the views were great!

This stage was the funniest to watch. It is open to anyone to “perform.” I think “perform” must be a fluid term in Chicago because some of these people were… brave. (Whew. I was afraid I couldn’t think of a kind word.) Michael said it best: “this is what happens when everyone has gotten a participation trophy for their whole like.” Yep, he’s definitely our child 🤣

We stopped by the hotel to drop off our leftover pizza, and I think if I had left these three alone, they would have enjoyed some time relaxing. Oh No! We have got to Clark Griswold this City and we’re burning daylight!

Next, Chicago Must-Do #3: The Miracle Mile. We headed back out in the City to hit the Miracle Mile of Michigan Avenue.

We went in and out of a few stores… Nike, Under Armor and Vans, and then we found it! Diplomatic, Inc. The greatest shoe store in all of Chicago… or at least this face sure thinks so!

Leo was in absolutely heaven. To the rest of us, it was a little weird. All the shoes were shrink wrapped? (Leo says it’s because people come in with dirty hands and touch the shoes. Um hello? They’re shoes the go on your feet… on the ground?!?!) There was even a case with the really expensive shoes (over $1,000… for shoes) under lock and key. And they had their own armed security guard… this is serious bug business! We stayed for at least 20+ minutes while Leo looked at every shoe, and we sat in awe that this is a place 🤪.

We are staying in the Intercontinental in Chicago (don’t worry it’s part of the Holiday Inn family 😉). The hotel is older, and the pool was gorgeous. With all we were trying to see, we really didn’t know if we could squeeze in a swim. But we ended up with 22 minutes to spare when we left the shoe store, so let’s make it happen 😍 From these smiles, it was totally worth it.

We scooted back to the room for boys to change, and ran downstairs to catch a cab and head to Chicago Must-Do #4: Baseball Game. We aren’t necessarily baseball people, so it didn’t matter to us whether we saw the Cubs or the Sox. It was cheaper to see the Sox and much better seats. So, off we went.

We had an official ballpark dinner – hot dog and peanuts (which i think could be counted as Chicago Must-Do #4a: Baseball Stadium Food.) The game was a little dull in the beginning. The A’s scored 2 runs early and then it was scoreless until bottom of the 7th when the Sox scored 2 on a homerun. Of course, that was the moment that the boys and I went to get souvenir hats and ice cream 🤦🏻‍♀️

When we came back, it was a whole new game. And finally in the bottom of 9th, with a wild pitch, the Sox scored the winning run and won the game! We yelled and screamed with everyone as if we had been Sox fans for life.

We scooted out to beat the traffic and caught a few more landmarks on the way home. Chicago Must-Do #5: Landmarks!

We made it back in time for another 20 minutes of swimming before the pool closed… nothing like staying until the very end and you’re the last ones in the pool.

So to recap:

Deep Dish Pizza: ✔️

Navy Pier: ✔️

Miracle Mile: ✔️

Baseball game: ✔️

Landmarks: ✔️

Yea, I think we did a great job of seeing Chicago. Imagine what we could do with a whole day?

Tomorrow we head home from an amazing trip. We are exhausted and ready to be home but wouldn’t trade this time and these giggles for the world. I’ll probably start doing a little pre-planning for our next Adventure on the plane!