Family-Friendly Trip Ideas Before School Starts
Can you believe summer is almost over? Soon, it will be back to school — schedules, lunch packing, sports practices, and games will take over our calendars. My two college kids will be heading back soon: my daughter into her fourth year and my son into his second.
This summer was extra special because they were both home! However, between their busy work and social lives, we carved out time for a fun, end-of-summer trip together to Chicago.
Why Chicago?
I’ve visited Chicago several times and thought it would be the perfect big-city experience for the kids as they start imagining where they might want to live and work in the future. Chicago is fun, full of energy, and chock full of things to do — from iconic attractions to hidden gems. It’s also a fantastic destination for a quick family getaway, especially if your kids are teenagers or older.
If you’re looking for a family trip idea before school starts, here are 11 fun things to do in Chicago that we loved during our visit.
1. Ohio Street Beach
We happened upon Ohio Street Beach and it was beautiful! Amazing views of Lake Michigan and some of the best sunsets in the city. Perfect for a relaxing afternoon or evening stroll by the water.
2. Navy Pier
Navy Pier is a Chicago must-do! Shopping, great restaurants, boat tours, and gorgeous lake views — there’s something for everyone here. We spent hours just wandering and people-watching.
3. The Magnificent Mile
A shopper’s paradise with endless stores, stunning architecture, and delicious food options. Even if you’re not shopping, the atmosphere is fun and worth experiencing.
4. Chicago River Architecture Boat Tour
This was one of the highlights of our trip! It’s beautiful, informative, and surprisingly relaxing. A great way to learn about the city’s history and design.
5. Giordano’s Chicago-Style Pizza
When in Chicago, deep-dish pizza is non-negotiable. Giordano’s was cheesy, delicious, and worth the wait.
6. The Willis Tower Skydeck
If your family is up for an adventure, step out onto the glass ledge for a thrilling view 1,353 feet above the city. It’s an amazing experience!
7. Chicago Union Station
This historic landmark gave the kids a glimpse into Chicago’s bustling commuter life. It’s beautiful inside and worth a quick stop.
8. Lakefront Trail on Lake Michigan
A scenic walking and biking trail with stunning lake views. We loved getting in some steps while soaking in the fresh air. The Navy Pier ferris wheel was also in the background when we took our evening walk and was a gorgeous backdrop!
9. Museum of Science and Industry
From trains to space exploration, this museum has exhibits for every interest. You could spend an entire day here!
10. Stan’s Donuts
A sweet ending to our trip — literally! We went multiple times, and the glazed raised donuts were the family favorite.
11. The Bean (Cloud Gate) in Millennium Park
And last, but not least, Chicago’s iconic public art installation and a perfect photo op! Plus we were able to catch a group practicing for a concert in the Jay Pritzker Pavilion and the sounds was outstanding!
Final Thoughts
Our family trip to Chicago was a wonderful way to wrap up the summer. The city felt safe, clean, and easy to navigate. Plus, we stayed near Navy Pier, which meant we could walk almost everywhere and this made exploring stress-free.
If you’re looking for fun things to do with kids in Chicago, I can’t recommend it enough. Whether you’re planning a weekend getaway or a longer stay, Chicago is packed with activities, beautiful views, and delicious food that make it the perfect destination before the busy school year begins.
Looking for additional ideas for a family vacation? Check out my Five Unforgettable Family Vacation Ideas for Summer blog article!
Disclaimer: I’m not a licensed therapist, medical professional, nutritionist, or fitness expert. The thoughts and tips shared here are based on my own experiences and are meant for general inspiration. Always consult a qualified professional if you need personal or nutritional advice or support.
