Last year when we were trying to figure out our fall break plans, we knew that wanted to go 1) somewhere pretty and 2) somewhere new to us. After a little bit of brainstorming, we landed on Chicago, IL! Sadly, that trip did not happen because of a big storm that blew through on the same weekend we were supposed to be there. Thankfully, we were able to cancel our hotel and flights with no negative repercussions and rebook for later on. Summer break was the soonest we could reschedule, and we thought it would be epic to experience Independence Day in the Windy City. We were right -- it was definitely epic!
We flew out of GSP mid-morning on a Tuesday, picked up our rental car, and headed to the Hyatt Regency Chicago for the next 3 nights. This hotel was right on the Chicago River, and we were graciously upgraded to a room with the most fabulous view of the river and Lake Michigan. So picturesque! The location, in general, was practically unbeatable, too: just steps to the riverwalk & a short walk to Millennium Park, Maggie Daley Park, Grant Park, Navy Pier, Magnificent Mile, and more. We did a whole lot of walking around the city, which is our favorite way to explore!
One of our biggest motivations for renting a car for this quick 3-day trip was to explore the neighboring states. Last year (in 2023), we officially penned a family goal that we had been toying with: visit all 50 states together before our oldest child graduates high school. We had a good head start when we put it in writing, but we still have a long ways to go. One thing about me, though, is that I don't haphazardly set goals; if I set a goal, I will do everything in my power to see it through to completion (hehe). So, naturally, with 3 additional states just being a couple hours away from Chicago, I put together an itinerary that would only take us one full day to visit FOUR states in one day. And it was SO much fun!
We did the following in the neighbor states...
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I N D I A N A
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We drove 1.5 hours from Chicago to Michigan City, IN for begin our big roadtrip day! Zoos are a family favorite for us even when traveling, so when I saw that Washington Park Zoo was on the route towards Michigan I knew that would be the perfect first stop for us. We saw so many animals during our 2-hour stroll through the exhibits, and we even climbed an observation tower in the zoo that offered a stunning view of Lake Michigan. The kids were so happy to visit a new-to-us zoo in a new-to-us state!
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M I C H I G A N
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After passing through Indiana, we stopped in New Buffalo, MI to check an amazing thing off of our bucket lists: touch Lake Michigan. So exciting! The water was a crisp 57 degrees, and it was absolutely gorgeous. I didn't know that Lake Michigan was so blue, but it took my breath away in a good way. This particular beach was packed, which added to the fun culture that we were hoping to find, and we stayed with our feet in the water & searching for rocks and shells for over an hour. Before heading back out on the road, we enjoyed a Kona Ice treat and the kids played on the playground right off the beach.
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W I S C O N S I N
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From Michigan, we hopped back in the car and headed out on our longest haul of the trip so far: a 3.5 hour drive into Wisconsin! The drive wasn't originally supposed to be as long as it was, but we got caught in some heavy traffic a few times that slowed us down a lot. We were all happy to finally arrive in Kenosha, WI for dinner and another view of Lake Michigan. We ate at Tavern on 6th, and we ordered a big ol' basket of fried cheese cubes...because you can't go to Wisconsin without eating some cheese, right? The town of Kenosha was small with lots of character, and we were grateful for the 1.5 hours we spent there.
Even though there were lots of great moments and memories from our trip, we all agreed that the highlight of our trip was WRIGLEY FIELD! We bought tickets to the Cubs vs. Phillies game for the evening we arrived in Chicago, and it was the best welcome to this incredible city. We ate a Wrigley hot dog and belted Take Me Out To The Ballgame in the 7th inning, and those two things alone made for a core memory. Bethany and I were practically running after Braxton who was running after TJ to get to the Marquee, and I will probably always hear myself giggling over the sheer excitement of it all. It's hard to describe, but it was easy to feel. I don't consider myself a Cubs fan generally, but there was something so special about getting to experience a night like this with my family and with myself. Long live this memory.
Our second favorite things were exploring Navy Pier and Maggie Daley Park. Both offered endless activity and opportunity, and we easily could have spent half a day at each. We really loved that both of these areas was so close to our hotel, too!
I, personally, loved the Architecture Boat Cruise that we went on a sunset on our final evening in the city; everyone did, honestly, but I loved it most. The guide was so knowledgable (and funny), and it was so humbling and awe-inspiring to ride beneath the towering buildings lining the Chicago River. I will recommend this activity to anyone who is planning a trip to the Windy City!
All in all, if I had to pick just one word to describe Chicago as a whole, I would say C O O L. Chicago is just so cool! The atmosphere, the people, the sights, the sounds, the colors -- all of it. I really wished we'd had one more day in the city so we could have taken spent a little more taking our time, and that means that we'll just have to plan another trip in the future (wink, wink). Big cities are so out of the norm for us, and I think that's why we love them so much. Also, because they remind us that dreams ought to be big.
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