Three Kids and a Dog

Wednesday, August 05, 2026

Summertime in Chicago is the Best

Hailey has fallen in love with the city of Chicago. She wants to go every chance she gets. I think it's because she's secretly hoping she'll run into Connor Bedard - her longtime Chicago Blackhawks crush. But, I'm not kidding when I say that every weekend she's asking us to go to Chicago. 

Sox game with city views
I loved Chicago...and I lived there for 17 years. Until I did not. I can't say I miss it with three kids. Definitely not the life I wanted my kids to have - growing up in the city. So I was glad we moved when we did. Maybe at one point we talked about going back and living there as empty nesters but I think that was very short-lived. I never want to go back and live there. 

Don't get me wrong, it's nice to visit for a bit and reminisce. All the bars and restaurants we used to go to. The parks we used to play all of our coed sports at. The places by my work I used to frequent. My doctor. My dentist. The places we used to live. The church we got married in and the place we had our reception. Our apartments and then condos. Our neighborhood. Our kids' school. Where their friends lived. The sidewalks where we walked a thousand times with our kids and Adler. The benches Adler would jump over. So many memories in Chicago for us but I don't want to go back. 

Hailey does though so we indulge her every once in a while. We went to a restaurant a few weeks ago in our old neighborhood and took just Hailey (the other two were working). We saw an old neighbor whose family lived and owned all the houses on the opposite side of the block from us. They've been there for 50 plus years. We got to catch up. It was nice. But I still don't wish we stayed. 

There's another restaurant right on the river that's a hot spot for teens so I stalked Open Table to get a reservation one Monday night for dinner so we all could go to Pizzeria Portofino. It was every bit as good as everyone said and the views were amazing (although we didn't get to sit outside). 

We also have gotten to attend a few Sox games this summer. There's nothing like a baseball game in the city in the summer. In fact, recently a friend said to me, I thought you were a Cubs fan, you always went to Cubs games. We did both in our 20s. My friends and I would frequent both parks. Oh to be young and in your 20s in the city again. There's nothing quite like it - especially when it's summertime in the city. 


Peyton was working


River view






Pizzeria Portofino




Brassero in West Town w/ just Hailey