Hey, everyone! Finally, I am getting out this long overdue Chicago post. It’s 445 AM, I have a hot cup of frothy Nespresso in hand and oatmeal on board, so let’s dive in! We decided to go to Chicago over Father’s Day weekend since it’s a relatively short trip, and we were itching to travel! The evening of June 16th we hit the road.

Quinnie was less amused by the construction getup photo-op at a rest stop than I was 😅.

It was a rough trip. Quinn’s a light sleeper and would wake up with every bump in the road 😣. We realized gone are the days of driving through the night. Day trips are going to be the way we roll for now!

We arrived in Chicago around 1130 pm central time. We took in the fantastic views of the city before eagerly catching some 💤s.

Quinn has started pointing at everything, and it was adorable how she eagerly pointed out the window when we woke up.

“Mom, look! It’s Chicagahhhhh!”

I was feeling the cobwebs in the morning and needed to get caffeine on board ASAP. Once we got ready, we headed out to breakfast around 830 AM.

We went to brunch at a restaurant called Terrace 16 that promised the best views in the city. It did not disappoint!

DJ and I started with mimosas, and I didn’t turn down the opportunity for another cup of coffee. We didn’t realize the only option for mimosas was bottomless, and the guy looked at us funny when we said we were good after one- when we got the bill we understood why 🫠.

Time for food! I ordered their vegetable frittata with asparagus, wild mushrooms, spinach and Gruyère. Every bite was spectacular!

For Quinn I ordered a parfait bowl with berries that she didn’t touch, but DJ and I happily enjoyed some.

Deej had their Croque Madame. I had a bite and woah, so good. A great savory option.

Whoopsies another portrait mode fail lol.

After brunch, we decided we better change since it was getting warmer out. We also applied a bunch of sunscreen and then headed out to explore the Windy City!

I made a mistake with the spray sunscreen- I tried to apply it to my hair part, but sprayed too heavily and it turned my hair white. Good times, haha.

I love being among the hustle and bustle of a big city. The energy of Chicago was electric on that Saturday morning. Many people were exercising in various forms- running, bicycling or doing yoga in the big green space of Millennium Park. I tried to catch the names of coffee shops displayed on paper cups of people we passed “just in case” I needed another ;). Tourists fought for a spot around The Bean and various street artists performed beautiful melodies, a soundtrack to accompany the gorgeous day.

We then ventured over to Maggie Daley park to explore the three acre play garden for kids. This place is epic. I can’t wait to bring Quinn back here when she’s a bit older. That day we just enjoyed the sights and the bucket swings :).

While walking back to the hotel, we saw a surprising amount of people sporting Orioles gear. DJ is a huge Orioles fan (I am a fan now too by proxy, except when they’re playing the Guardians 😜). We checked to see if they were in town, and sure enough they were! We didn’t have a strict agenda that day and decided it’d be fun to take Quinn to her first baseball game!! I just happened to have an Orioles hat on me and one of DJ’s old Orioles shirts I wear as a night shirt I lent back to him- so we were accidentally prepared 😄. I should have just played this off like I planned it as a Father’s Day gift haha!

Parking was a bear (pun intended), but we made it to the stadium with plenty of time to spare.

I was thrilled at the opportunity to go to Wrigley Field!

Is there anything better than a baseball game in the summer?!

Quinn fell asleep on the walk over to the game and grabbed some snoozes in my carrier while we waited for the game to start.

We haven’t been to a game in ages, and I was impressed with the QR core option to have food and drinks delivered to your seat!

Chillin’ on her Dad’s lap enjoying the game! DJ was in heaven I’m pretty sure.

Early into the first inning, DJ goes, “oh noooo”. I look at him frantically as a litany of scenarios run through my mind in a second- what’s wrong?! Is she choking?! No, ok phew. Did she lick the seat? Spit up on the people in front of us? Lose a shoe? Did DJ order food to the wrong seat?!!!! He pointed to Quinn’s hat and, I realized it had a little bear cub on it. It was worse than I thought. The betrayal by your own daughter… hard to put into words 😭. I thought we raised her better!

Anywho- back to the food! I don’t know if I’ve actually ever tried Cracker Jacks, but they’re pretty good.

I was also craving a cheeseburger and got a soft pretzel to share with Quinn after we walked around the stadium for a while. She enjoyed the cheeseburger most!

Family pic 🥰.

After the game, we navigated the traffic, parked our car and then headed on foot to Navy pier.

Navy pier is much more of a little amusement park than I expected! It’s adorable and has fantastic food options too.

She fell asleep as we walked around the pier.

We walked along the river and then decided ice cream sounded like a great appetizer before dinner.

We saw a Ghirardelli store and a rush of amazing memories flooded back from San Francisco ☺️.

We were even greeted by a Painted Ladies photo while waiting in line.

Seriously some of the best!!!

We put an order in at Lou Malnati’s, a famed deep dish pizza joint in Chicago. I have had Giordano’s in the past (the other famous deep dish), but I didn’t love it. That was over 10 years ago though. I’ve heard from others that don’t love Giordano’s that Lou’s is where it’s at. Do people call it Lou’s? Some local Chicagoan is probably rolling their eyes at this whole paragraph, hah!

The line for the restaurant seating was crazy long, so we just ordered food to go. We still had a 30/40 minute wait for pickup, so we killed time running around with Quinn in the area outside the restaurant. She was having a ball, pointing at the tall statue nearby, waving, making friends. It was golden hour, a violinist was playing nearby, and people seemed to have an extra pep in their step. At the end of the trip DJ asked me my favorite part, and for some reason this simple memory stood out 💕.

Food’s ready!!

We went back to the hotel to eat. I ordered Quinn chicken tenders and fries – she didn’t eat much of the chicken, but fries are this girl’s jam.

Pizza pizza pizza! 🍕 DJ ordered their deep dish Malnati classic with sausage, mozzarella, vine-ripened tomato sauce all on their trademarked buttecrust.

I had the Deep Dish The Lou with basil, garlic and onion seasoned spinach, mushrooms and Roma tomatoes on garlic buttercrust.

The verdict? Definitely better than I remember Giordano’s being! I liked DJ’s more though. Mine felt it was missing something, adding sausage would have made it perfect I think! Now on a whole, nothing has yet topped Via 313’s Detroit style pizza in Austin, TX.

Hopefully I’ll get to Part 2 soon!! Thanks for visiting the Windy City ‘with us’. If you know Chicago, I’m open to more recs too because we would love to go back when time allows! It’s a fairly easy weekend trip!

Oh oh oh ! And I forgot to mention we are officially moved into our new place! Been a whirlwind of a couple weeks but so worth it!

Questions for you:

– What style of pizza is your favorite?

– Any summer travel plans?

<3,

Mackenzie