Way back in March when Joey told me he was taking a work trip to Chicago, I floated the idea of Lori, the kids and I joining him for the weekend but then the work part of the trip seemed to be falling through so we turned the whole thing into a full out 8-person family vacation and wow, traveling with three children is not for the faint of heart but we had so much fun!

Joey, Lori, Demps, Lyds and I flew out Thursday afternoon and why’s it take your whole day to travel, even when you’re not going that far? By the time we got into O’Hare, walked a million miles to baggage claim, picked up our rental car and drove to our Airbnb, it was dinnertime! The kids did good on the flight though. Demps watched a movie and our party girl didn’t want to sleep and stayed up the whole time. I scheduled pizza pick up for us knowing we’d be tired from traveling all day and the kids not napping like usual. Went with Pequad’s and it was alright. We stayed in the Lakeview neighborhood and liked the location a lot, though we had a three story unit and no bathroom on the first floor so lots of stair climbing.

We wanted to save all the good quintessential Chicago stuff for after Lauren, Adam and Landon came in so we had a low-key Friday exploring the Wicker Park neighborhood. Unfortunately it was raining all morning, but fortunately we were armed with umbrellas and found some fun things to do. Had breakfast at Sun Rey Café and man was it good! Just a little place, that we had all to ourselves, with EXCEPTIONAL service and really delicious food. We walked over to a big record store — Dempsey spent most of the vacation swinging between two people 😂 — stopped at Ipsento Coffee where I had the most delicious honey lavender latte and fed Lyds into a little coma then walked the Bloomingdale Trail aka The 606, an old rail line that’s been converted into a nice path. After the kids got some rest and everyone got cleaned up, we met Emily (who lives in Chicago) and my aunt (who was visiting Emily) at Crosby’s Kitchen. Got a table for our big group right away and the meal was super good! Dempsey ate two chicken legs and every time I looked across the table, Joey was feeding Lydia a bite of mashed potatoes or roasted chicken 😂 It was so nice seeing Em and my aunt and the kids loved it too 😍 Joey dropped Lori, the kids and I off at the Airbnb and headed to the airport to pick up Lauren, Adam and Landon and I waited up for them and chatted for a minute before we all headed up to bed.

We had planned to have Dempsey sleep in his own room but all those stairs made me nervous and it turned out the rooms were not situated so that we could be on the same floor as him, so Grandma offered to share a bed. I think he only kept her up late every night, asked to go to the bathroom multiple times and woke up at 3:30 AM once, so it went good overall 😂😂😂 She sent Joey that sleepy head photo on Saturday morning 😍 Lori, Lauren, Adam and Landon had tickets for the Chicago Architecture Center River Cruise at 10 that morning so we tried to grab breakfast at Egg Harbor Café but by the time we got ourselves ready and over there, there was a 20 minute wait so the river cruisers had to bail and find something quicker. The rest of us were definitely in need of food and coffee by the time we got a table but then we had a nice time just the four of us. I had a really good iced Pumpkin Spice Latte! After, we walked through the city, along the river for a bit then over to Millennium Park. Dempsey was having a BLAST running around in the water at Crown Fountain and actually so was I 😋 I told Joey to never forget I AM a water sign! Once the rest of the group had joined us we got a quick peek of The Bean (it’s fenced off for paver replacement right now!), grabbed some very glamourous concession stand Chicago Dogs and hit up City Mini Golf. Someone was tired and kind of lost interest in actually putt putting half way through but we had fun. For dinner, we drove out to Oakbrook to meet Chris, Amanda, Carmen and Zach for dinner and OY, THE CHICAGO TRAFFIC! Took over an hour to get there but otherwise, we had a very lovely time. Ate at Alter Brewing + Kitchen and very nearly finished a 1.5 pound pretzel. By the time we go home and got everyone into bed it was 11 PM!

Sunday at Wrigley! We had such a fun day. Long, but fun. Started with breakfast at Frances’ Deli and Brunchery and I felt so overstimulated afterward from Lyds trying to climb from the highchair she was fully buckled into and Dempsey being Dempsey. But that’s just dining with children 😂 Walked to the game and met up with Emily and my aunt and it was just a really good time at the ballpark (and in the shade). I ate a surprisingly good hot beef sandwich. It was already dinnertime by the time we walked back so we headed back out to Summer House Santa Monica and I loved it there! Both Lauren and I had to leave the table to feed our children, which is never super ideal but what can you do? Demps was pretty wrecked from not napping and definitely knocked over his Shirley Temple but everything else — drinks, apps, entrees, dessert, service and vibe — was great!

Another rainy day in Chicago! We had breakfast at Southport Grocery and Café, which came highly recommended by Emily. She said the bread pudding pancakes would change our lives and I think they did! I’ve never had pancakes that luscious inside. I brought home some of the mix for my mom. The guys needed to hit up a convention for a few hours, so the rest of us spent the morning at Shedd Aquarium and it was the perfect rainy day activity. They have beluga whales there! One of them splashed Dempsey and he seemed really excited about it 😂 Afterward, we all grabbed lunch at Cupitol and then Joey, the kids and I headed back to our place so the kids could nap and the rest of the group continued on to Navy Pier. Not the best weather for walking around but it sounded like they made the most of it. We picked them up later on and all headed to dinner. Rainy weather always means ramen for us and luckily everyone else was on board. Service was SOOOO SLOW but Ramen San Deluxe downtown was otherwise very good!

One last breakfast in Chicago and then another long travel day. May all those pictures of Dempsey sleeping serve as evidence of how wiped the kids were after this vacation but they were all troopers! We got all packed up and were deciding between a quick coffee shop breakfast or a good diner and Lauren voted good diner, so that was that! I need her to come on all my vacations because I’m so bad at making decisions 😂 I thought Irene’s was so so good and I wish it was in Denver now. Joey is usually the biscuits and gravy orderer but it sounded really good to me and it was! Hauled all our gear to the airport and why is Lydia so cute eating her Cheerios?? Dempsey fell asleep about twenty minutes before we landed and slept through landing, being transferred to the stroller, the train ride to baggage claim, being moved to his car seat and the entire drive home!!!! We woke him up for dinner and he was a total nightmare until bedtime. Just on a warpath 😱 Joey left for ten minutes to pick up dinner and I texted him to “GET HOME NOW.” Woof. But once he was in bed, he slept good and we’re so proud of how well he did on this trip considering he’d been potty trained all of a week. Vacationing with children could not be more different than how we vacationed in the past but I still love it so much and we really did have the best time 🤍