Chicago, the vibrant city on the shores of Lake Michigan, effortlessly blends a rich history with modern charm, making it a must-see destination for travelers of all types. Known for its towering skyline, world-class museums, and iconic deep-dish pizza, the Windy City offers endless experiences for families, foodies, and culture enthusiasts alike. From wandering through the bustling streets of downtown to exploring scenic lakefront parks and unique neighborhoods, there’s something captivating about Chicago’s mix of urban energy and Midwest warmth.

Here are some fun facts about Chicago that kids will enjoy, many of which we learned on our architecture tour:

Chicago is known as the "Windy City," but it got this nickname because of its politicians' "windy" speeches, not just the weather!
The first Ferris wheel was built in Chicago for the 1893 World’s Fair. It was over 260 feet tall and could hold more than 2,000 people!
Chicago River is one of the only rivers in the world that flows backward! Engineers reversed it in 1900 to keep pollution out of Lake Michigan.
Willis Tower (formerly known as the Sears Tower) was once the tallest building in the world. Its Skydeck lets you stand on glass floors 1,353 feet above the ground!
Deep-dish pizza, famous in Chicago, is known for its thick crust and gooey layers of cheese and sauce. Chicagoans love it!
Every year on St. Patrick’s Day, Chicago dyes the Chicago River bright green, a tradition that’s over 60 years old.
The Field Museum in Chicago is home to “Sue,” the largest and most complete T. rex fossil ever discovered.
Lincoln Park Zoo in Chicago is one of the oldest zoos in the U.S. and is free to the public!
The “Bean,” officially called Cloud Gate, is a giant reflective sculpture in Millennium Park where you can see cool reflections of the city.
Chicago O’Hare International Airport is one of the busiest airports in the world, named after a WWII hero named Edward "Butch" O'Hare.

Flexibility of homeschooling

One of the best parts about homeschooling on the road is the flexibility it gives us to adjust our schedule around unique experiences, like exploring Chicago’s museums during the day. Instead of being tied to a strict classroom routine, we can shift our lessons to the evening or spread them out over the week. This freedom allowed us to visit places like the Field Museum and the Art Institute while they were open and vibrant, taking advantage of daylight to wander the city streets and enjoy sights we’d otherwise miss. Homeschooling lets us turn every trip into a hands-on learning opportunity, where our kids get to absorb real-world knowledge and gain firsthand experiences that bring their studies to life.

Before we got to the Windy City..

Shipshewana

Visiting Shipshewana and experiencing the Amish way of life was like stepping into a different world. One of the highlights was riding in a traditional Amish carriage, taking in the quiet, scenic countryside at a slower pace that felt both relaxing and eye-opening. Afterward, we enjoyed a hearty meal at the Blue Gate buffet, where the homemade dishes were just incredible—everything from fried chicken to fresh-baked pies, all with that authentic, home-cooked flavor. It was such a unique experience, and I left with a new appreciation for the Amish community’s simple and intentional way of life.

Indiana Dunes National Park

Indiana Dunes National Park is a favorite escapes along Lake Michigan’s southern shore. The highlight of our visit was definitely the dune climb—a real workout but so worth it for the incredible views from the top! The visitor center was our next stop, and it gave us a great overview of the park’s unique ecosystem with some cool, interactive exhibits that got everyone excited about what we’d see. My personal favorite was the Dune Succession Trail. Walking this loop, we got to experience the different stages of dune development, from shifting sands to lush, mature forests—a fascinating glimpse into how nature slowly transforms over time. For anyone looking to combine adventure, learning, and stunning lakeside scenery, Indiana Dunes is a perfect Midwest destination.

Chicago CityPASS

Getting the Chicago CityPASS was one of the best decisions we made for exploring the city! It gave us access to several top attractions at a discounted rate, which made planning our days easier and saved us money. With the CityPASS, we skipped some of the long lines and got to focus on enjoying spots like the Shedd Aquarium, the Field Museum, and the Architecture Tour. Each place offered something unique, and the pass allowed us to make the most of our time without feeling rushed. Every activity that we did in Chicago was included in the CityPass. For anyone looking to explore Chicago’s highlights without breaking the bank, the CityPASS is definitely worth it!

Field Museum

Visiting the Field Museum in Chicago was an unforgettable experience that brought out the explorer in all of us. Walking through the exhibits, we marveled at Sue, the world’s largest and most complete T. rex, and couldn’t believe the incredible detail in the dinosaur hall. The Ancient Egypt exhibit was a real highlight, too, with its mummy cases and reconstructed tomb—like stepping into another world. I loved how the museum combines science and storytelling, making it fascinating for everyone in our group. There’s so much to see, from ancient artifacts to gemstones and nature displays, that we could easily spend an entire day exploring!

Shedd Aquarium

Our visit to the Shedd Aquarium was an absolute highlight, and we were all captivated by the incredible sea life on display. My favorite part, hands down, was seeing the beluga whales up close. They’re such gentle giants, gracefully gliding through the water with their ghostly white color and expressive faces—it was mesmerizing to watch. The sea lion show was another unforgettable experience, especially for the kids. The sea lions were so full of personality, performing tricks and showing off their playful skills, making the whole audience laugh and cheer. It was amazing to be able to see these beautiful animals in action and learn more about their behaviors and habitats.

Museum of Science and Industry

The Museum of Science and Industry in Chicago quickly became my favorite museum in the city! Every corner offered something fascinating, but a few exhibits truly stood out. Seeing the U-505 submarine up close was incredible—it’s not every day you get to walk through a captured WWII German submarine and feel the history surrounding you. The dome theater was another highlight, immersing us in stunning visuals that felt so real; it was like being part of the film itself. And the hands-on experience of stepping inside airplanes and historic trains brought out the kid in all of us. Each exhibit was more exciting than the last, making this museum an absolute must-see for anyone visiting Chicago.

Lincoln Zoo

*Meerkat, the only picture from the zoo haha*

Our visit to Lincoln Park Zoo didn’t quite live up to our expectations. While I’d heard great things about the zoo, we found that there weren’t as many animals out and visible as we’d hoped. We strolled through several exhibits only to find empty enclosures or animals resting out of sight, which left the kids a bit disappointed. It’s a beautiful space, and I can see its appeal, but it just didn’t have the same variety or energy that we’ve experienced at other zoos. Still, we enjoyed walking around and appreciated the free admission, but I’d probably choose a different spot if we’re looking for an up-close animal experience next time.

The Bean & Playground

Visiting the Chicago Bean, or “Cloud Gate,” and Maggie Daley Playground was a fantastic mix of art and play! The Bean is even more impressive in person; its mirror-like surface reflects the city’s skyline and creates funhouse-like images that the kids (and we adults) loved capturing in photos. We spent a good amount of time admiring its unique design, and it’s amazing how something so simple can be so mesmerizing.

Afterward, we headed to Maggie Daley Playground, where the kids had a blast climbing, sliding, and exploring all the different play areas. It’s an expansive playground with something for every age, and it let them burn off some energy while we relaxed nearby, taking in views of the city. Both spots are must-visits and perfect for a family day out in Chicago!

Architecture Tour & Navy Pier

Taking the Shoreline Architecture Tour at night was a magical way to see Chicago’s iconic skyline! The city lights reflected off the water, making the buildings look even more stunning against the dark sky. Hearing the history behind each skyscraper as we glided along the river added a new appreciation for the city’s architecture. Before the tour, we had just a bit of time to explore Navy Pier, so we grabbed a quick snack and enjoyed the bustling atmosphere. The Ferris wheel lit up the pier, adding to the evening’s charm. Even with our brief visit, we felt the energy of Navy Pier and loved ending the night with such a unique view of Chicago.

*He was pretty proud of his “Can of Corn”! (candy corn)*

FOOD- we certainly splurged more this week than in previous weeks

Lou Malnati's Pizzeria

Lou Malnati’s Pizzeria is my go-to spot for classic Chicago deep-dish pizza. The buttery crust, gooey mozzarella, and rich tomato sauce make every slice unforgettable, especially with their signature sausage topping. Even when I’m not in Chicago, I love that I can have Lou Malnati’s shipped straight to my door to get that authentic taste at home. It’s truly a slice of Chicago!

Portillo's

A trip to Portillo’s is essential for their classic Chicago hot dog and Italian beef sandwich. The Chicago hot dog is perfect, loaded with all the traditional toppings—yellow mustard, neon green relish, onions, a pickle spear, tomato slices, sport peppers, and a dash of celery salt—all on a poppy seed bun. And their Italian beef sandwich? It's a messy, delicious masterpiece, with tender beef and spicy giardiniera, especially when dipped. Nothing beats that authentic Chicago flavor!

Colectivo Coffee

While Drew worked from Colectivo Coffee, the kids and I spent the morning at Lincoln Park Zoo, enjoying some time with the animals (trying to write positivily, but well, lack there of, see my Lincoln Zoo paragraph). Afterward, we turned our day into a little “cafe-school” session at the coffee shop with Drew. It was the perfect spot to settle in with some hot chocolate and a latte while we tackled a bit of reading and math. The cozy vibe and big windows made it a great setting for our lessons. Once we wrapped up, we headed downtown to see the Bean, making it a memorable mix of learning and sightseeing in the heart of Chicago!

JoJo’s ShakeBAR

During our Chicago trip, I visited JoJo's ShakeBAR at 23 W Hubbard St. The nostalgic 80s/90s-inspired decor, complete with arcade game tables, created a fun atmosphere. I indulged in their signature Biggie Shake, which was as delicious as it was Instagram-worthy. The combination of creative desserts and classic diner fare made it a memorable experience.

The Pasta Bowl

On a recent visit to The Pasta Bowl in Chicago, I tried a couple of their standout dishes, and they did not disappoint! The Gnocchi Aurora was deliciously rich, with pillowy gnocchi in a creamy tomato sauce that felt like the perfect comfort food. I also loved the Farfalle Pollo; the bowtie pasta with tender chicken, sun-dried tomatoes, and a hint of garlic was so flavorful and satisfying. It’s now one of my favorite spots in the city for hearty, classic pasta dishes!

Where we stayed

Camping at Camp Sullivan in Oak Forest was a fantastic experience for our RV family. The site is well-maintained, and it’s got everything we needed, from RV spots to clean facilities and convenient access to trails. The campground connects to the Tinley Creek Trail System, so we took advantage of the trails for some hiking and biking. It’s such an accessible spot for anyone wanting to camp near Chicago with a good mix of nature and amenities.

Tips for Visiting Chicago with Kids:

Public Transportation: The L train and buses are convenient for getting around the city. Kids usually find the elevated train rides exciting.
Weather: Chicago’s weather can be unpredictable, especially in spring and fall. Be sure to dress in layers and bring comfortable shoes for walking. We were in shorts and tee during the day and winter coats at night!
Chicago CityPass: If you plan to visit multiple attractions, consider purchasing a Chicago CityPass, which gives you discounted admission to several top sites.
Dining: Chicago is known for its deep-dish pizza. Kid-friendly restaurants like Lou Malnati’s or Giordano’s are a great way to try this local favorite.

Our Chicago visit was an unforgettable adventure, filled with incredible sights, delicious food, and plenty of family memories. Exploring the city in our RV allowed us to experience the best of both worlds—urban excitement and the comfort of having our home on wheels nearby. From iconic landmarks like the Bean and the Field Museum to cozy cafe-school days and indulgent meals at local favorites, every day brought something new and exciting. As we packed up and hit the road, we left with a deeper appreciation for this vibrant city and plenty of stories to share from our time in the Windy City!

The Windy City!