Last week, O and I loaded up the car (as we often do) for a road trip to Chicago. I was born and raised in Chicago, I started fashion school in Chicago, O and I had our first date in Chicago-something about pulling up in that city will always feel like home. We were in town for my beautiful cousin’s wedding but we wanted to make the absolute most of our visit despite it being shorter than usual.

We left super early on Wednesday morning with a plan to drive 9 hours, spend the night in St. Louis and then arrive in Chicago after four hours of drive time the next day. For anyone wondering why in the world we’d drive for 14 hours with four kids rather than fly for 3.5, read about our scary hospital stay with the baby in my newsletter here. I’ll be sharing a full road-trip guide since it’s been a minute, but I’m thrilled to report that it was somehow genuinely enjoyable. I asked O this morning now that the dust has settled what his final thoughts are and his exact words were, ” Honestly, I enjoyed it! I’d do it again.” So there you have it, folks. Here’s our photo diary.

What I Packed:

Oak Park
Last week, O and I loaded up the car (as we often do) for a road trip to Chicago. I was born and raised in Chicago, I started fashion school in Chicago, O and I had our first date in Chicago-something about pulling up in that city will always feel like home. We were in town for my beautiful cousin’s wedding but we wanted to make the absolute most of our visit despite it being shorter than usual.

We left super early on Wednesday morning with a plan to drive 9 hours, spend the night in St. Louis and then arrive in Chicago after four hours of drive time the next day. For anyone wondering why in the world we’d drive for 14 hours with four kids rather than fly for 3.5, read about our scary hospital stay with the baby in my newsletter here. I’ll be sharing a full road-trip guide since it’s been a minute, but I’m thrilled to report that it was somehow genuinely enjoyable. I asked O this morning now that the dust has settled what his final thoughts are and his exact words were, ” Honestly, I enjoyed it! I’d do it again.” So there you have it, folks. Here’s our photo diary.

What I Packed:

Oak Park

I knew we wanted to stay in Oak Park before heading to the group hotel for the remainder of the trip so we booked this Airbnb and it was perfection. After two long travel days, we always like to do something fun for the kids. I looked up some toy shops and restaurants before our trip and found that we were only a four minute drive from downtown which meant the evening’s plans were sorted.

I made sure some treats from Wheat’s End Cafe were waiting for us when we arrived and it was so, so delicious. My gluten and dairy free babes loved sharing some doughnuts and cinnamon buns and I devoured the biscuits and popovers with honey butter. It’s always such a dream when we get to eat like normal humans while traveling.

After some homeschool work and naps for the littles, we headed into town and my goodness y’all, I fell in love. We had so much fun in Gepetto’s Toy Box and Sugarcup Trading and something about wandering around tucked under awnings and umbrellas in this sweet town just felt a big magical. We had a little bit of time before we needed to do baths and bedtime for the youngest two so the local library was the perfect stop. We’re library obsessed and I always try to explore the children’s section of the library whenever we travel.

Everyone slept like a dream (although Keogena did have an allergy-induced bloody nose all over the bedding in the Airbnb which used to happen to me all the time as a kid. Not ideal.) and the next morning we just ate the cereal I had packed to save some pennies for exploring later in the weekend.

We headed back to the downtown area for some wandering as well as lunch at Q’s barbeque. My kids are barbecue obsessed (they get it from their mother) and we were thrilled to find that all their meats were gluten free. You’d be surprised how rare that is. O enjoyed the brussel sprouts and hush puppies as a vegan man and we went to town on everything else.

That night was the rehearsal dinner which was in my hometown, Barrington, at my aunts house. I grew up having sleepovers in that house. When O wanted to meet me for the first time, my dad-who was hundreds of miles away-said the only way he’d allow it was if we met in that house. It’s one of my favorite places on earth. The rehearsal was Cowboy themed since they’re moving to Texas for work and this is the only photo I have:

Wedding Day

All the humans I get to call mine. Zeameh breaks my heart in this photo, y’all. I got this dress on super sale and while it’s almost sold out, I felt so comfortable in it despite being less than 3 months postpartum and that’s worth it’s weight in gold.

brothers-in-law working their magic with the five days apart babies

the Singletary Seven and our beautiful parents. I treasure this photo so, so much.

My grandparents with all the great-grands. Is this not the sweetest thing you’ve ever seen?

Congratulations to the groom and the beautiful sweet bride. My baby cousin. Our angel. We’re so happy for you two.