How to do Chicago in 2 Days with Kids!

Hey y’all! This is Jasha here. I am so excited to share our quick trip to Chicago. I am not going to lie, I was NERVOUS to head to the windy city with the kids… without Jereme. But it ended up being SOOOO much fun! So let me start from the beginning…

I am famous for planning our next road trip while on a road trip haha! So, as I was driving us through Missouri, we decided that we had to go visit our dear friends that were staying in Chicago for the summer. We really didn’t have any idea how long of a trip Chicago would be from Dallas, but it turns out that it’s only 13 hours away! I mean, we drive that far to Colorado for our ski trips and we’ve definitely gone farther before. Once we ran the idea by our hubbies, we booked our hotel on Expedia (book now/pay later of course). Which was brilliant, because we originally planned to go in early July but we ended up stranded up in Wyoming and Colorado with our Yukon issues. I am so happy that we were able to go, we had a great time on this road trip!

We left on a Sunday afternoon and stopped in Joplin, Missouri for the night. Then we woke up early and ventured to Springfield, IL. Click here to see our All Things Abe Lincoln Blog! We finally arrived to our hotel late Monday night. We stayed at the Congress Plaza Hotel in Chicago. It was lovely. I was nervous about driving through Chicago & unloading our things in the city, you know these are the things Moms worry about when traveling alone. Fortunately, there was a little driveway to pull into and we valeted the car for the 2 days we were there. It did cost $50 per day, but I was okay with that price, mainly because we didn’t really have a choice! We pretty much went straight to bed so that we could wake up early and get together with Roz and the girls! Their apartment in Chicago is amazing! Check out these views of the lake!!

The Wright’s Lake House

Day 1: Our hotel was only 2 blocks away from Roz’s “lake house.” We walked straight to their place and then headed to breakfast. After we ate, we started our adventures with the kiddos. We had the best tour guides, too! Emma and Hayley (my former kinder and 1st grade students) were the best at guiding us through the city! We walked from breakfast to Shedd Aquarium, which is another place I’ve added to my list of “places to work when I grow up” haha! There was so much to see and do. I don’t think we even touched the surface of all the things there, but we did see some neat exhibits and watched a dolphin show! The kids also found some great souvenirs! You can actually see the aquarium from the Wright’s apartment, so I am sure you can imagine how gorgeous the walk was back to their place. We took in the sights from the city and went back to swim in their pool and hot tub! After swimming, we went back to the hotel for a quick rest/do some work (I was still styling for Stitch Fix at the time). We met back up with Roz and the girls and had some deep dish pizza at Gino’s East. Then we called it a night. We walked a grand total of 8.1 miles this day and the kids did awesome!

Walk along the lake to Shedd Aquarium

Shedd Aquarium

The fountain from Married with Children LOL!

The most beautiful pool I’ve been to!

These kids have it so bad ha!

Had to pose with some deep dish pizza! My secret… I hate pizza LOL!

Day 2: I think this day was my favorite! We met up with Roz and the girls at The Bean. It was so sunny and bright, but we were able to snap a few pics to mark our time here. From The Bean, we actually loaded up on a bus and took public transportation to the famous Portillo’s for lunch. My anxiety was through the roof in this place. So many people, so many choices, so many workers yelling. But let me tell you, THE FOOD IS WORTH IT! I had the best chopped salad I have ever had with a side of Italian beef LOL. It was to die for! After lunch, we walked through downtown Chicago down by the river. This city is so beautiful. Then, we went to Jojo’s Milk Bar for a fun treat! Check out these milkshakes!!! They were an instant tummy ache, but oh so yummy! From here, we took the kids to Adler Planetarium. It was super cool and kept the kids entertained for hours! It was another fabulous walk back to the hotel and we had fun spending some time out by the lake on our way back . We finished the day with dinner at Roz’s and watched a firework show over the lake from their living room! Apparently, there’s a firework show over the lake every Sunday and Wednesday in the summer. Then, we hugged the girls goodbye and went to the hotel for our last night in Chi-town. As you can tell, we packed in a lot for our two full days in the city. And, we walked a grand total of 10.3 miles this day!

The Bean

Braving the bus!

Inside Portillo’s

jojo’s Milk Bar

Adler Planetarium

Fireworks over the lake!

Day 3: We had to head back this day, but we were SOOOO close to the infamous Home Alone House. I mean, when you’re only 20 miles from the filming location of the BEST Christmas movie of all time, you have to go visit. OMG, I was so nervous the closer we got. I didn’t know what we would encounter. But I was also super excited. I honestly think I may like this movie more than my kids. When the house came into view, I was pumped! This has been a dream of mine for years! We parked the car, jumped out and took the quickest pic in history haha! Looking back, I wish I would’ve knocked on the door and asked for a tour. Click here for the address.

My childhood dream come true!