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From skyscraper views to world-class museums and boat rides on the Chicago River, Chicago offers a perfect mix of fun and learning for families.
360 CHICAGO at the John Hancock Building
We kicked off our trip at 360 CHICAGO, located at the top of the John Hancock Building. The views of Lake Michigan and the skyline were incredible. If you’re feeling adventurous, try the Tilt experience. It tilts you outward from the building’s edge for a thrilling look straight down. I was the only one who got nervous, but Nami and the kids loved it!
Magnificent Mile and Garrett Popcorn
Afterward, we strolled down the Magnificent Mile. This stretch of Michigan Avenue is lined with shops, historic buildings, and restaurants. We stopped at the five-floor Starbucks Reserve Roastery and grabbed a bag of Garrett Popcorn. Their Garrett Mix, a combo of caramel and cheese, disappeared quickly in our hands.
Chicago River Architecture Boat Tour
One of the highlights was the architecture boat tour on the Chicago River. Our guide, an architecture student, shared stories behind the Gothic towers and modern glass buildings. The ride lasted about an hour and gave us a whole new perspective on the city.
If you visit in early spring like we did, dress warmly because we nearly froze in 35°F (1°C) weather!
Museum of Science and Industry
On Day 2 we rented a car to reach the Museum of Science and Industry. This was one of the best science museums we’ve ever visited. We explored the massive U-505 German submarine, the Apollo 8 space capsule, and Colleen Moore’s Fairy Castle. The transportation gallery and enormous model train exhibit were also family favorites.
The University of Chicago & Robie House
Since our son is starting to look at colleges, we stopped at The University of Chicago. Its Gothic-style campus felt like stepping into another era. Nearby, we toured Frank Lloyd Wright’s Robie House, a Prairie-style gem filled with stained glass and open spaces. The tour was excellent and we highly recommend it.
Frank Lloyd Wright Home & Studio
We also made the trip to Oak Park to tour Wright’s own home and studio. The tour explained his design philosophy and how Japanese architecture influenced his work. We were surprised to learn that his son invented Lincoln Logs!
Ernest Hemingway Birthplace Museum
Just down the street from Wright’s home is the Ernest Hemingway Birthplace Museum. The restored house gave us a glimpse into the author’s childhood in the 1890s. It was a treat for literature lovers.
The Art Institute of Chicago
We started Day 3 at the Art Institute, and it was by far our favorite museum of the trip. We visited twice during our trip, thanks to the museum membership that let us enter an hour early. Van Gogh’s The Bedroom, Monet’s water lilies, and Georgia O’Keeffe’s Sky Above Clouds IV were unforgettable. The Thorne Miniature Rooms, with tiny historic interiors, fascinated us and the kids alike.
Chicago History Museum
This museum tells the city’s story with exhibits on the Great Fire of 1871, sports, and fashion. Melted artifacts from the fire were especially striking. It’s a family-friendly spot that works well for school-age kids.
Skydeck Chicago at Willis Tower
One evening we headed up to Skydeck Chicago at Willis Tower. The nighttime views of the city lights were spectacular. The kids were braver than me and stepped onto the glass ledge, which juts out 1,300 feet above the street.
Shedd Aquarium
Day 4 started at Shedd Aquarium, home to an impressive range of marine life. The Oceanarium was huge, and our son, who loves marine biology, enjoyed every minute. While the aquarium felt dated compared to others we’ve visited, it was still worthwhile.
Field Museum
Next door is the Field Museum, which could easily fill a whole day. From Sue the T. rex to Ancient Egypt and Pacific Island artifacts, the exhibits were fascinating. If your kids are older, this is the one to prioritize.
Exploring Downtown and Parks
We loved walking around downtown Chicago despite the chilly weather. Cloud Gate, known as “The Bean,” was even more fun in person. We also enjoyed Millennium Park and the lakefront paths, which must be even better in warmer months.
Visiting Northwestern University
Lastly, we visited Northwestern University in Evanston, where our former intern Kylie gave us a campus tour. It was a heartwarming stop that added a personal touch to our trip.
How to Get to and around Chicago
By Car
Chicago is a central point for the nation’s interstate system. If you are driving, major highways like I-55, I-90, I-94, and I-80 lead directly into the city. Approximate drive times from major cities include:
- From Milwaukee, WI: 1.5 hours
- From Indianapolis, IN: 3 hours
- From Detroit, MI: 4.5 hours
Driving offers flexibility, but be prepared for heavy traffic, especially during peak hours. Parking in downtown Chicago can also be expensive. On our second visit to Chicago, we didn’t rent a car and Ubered around instead for ease of travel. The cost was similar to renting a car because hotel parking fees are so expensive these days.
Our Family’s Take on Visiting Chicago
Chicago offers stunning views, fascinating architecture, and some of the best museums in the country. Our spring break trip gave us both excitement and family bonding time.
It’s very clean compared to other major cities in the US, and we would highly recommend it for a family trip.
More to Explore Nearby
Once you’ve experienced Chicago’s highlights, consider adding these nearby destinations:
- Milwaukee, Wisconsin – Just 90 minutes north, known for its lakefront, breweries, and Harley-Davidson Museum.
- Indiana Dunes National Park – A beautiful stretch of Lake Michigan shoreline with beaches and trails.
- Oak Park – Home to Frank Lloyd Wright’s studio and the Ernest Hemingway Birthplace Museum.
- Evanston – A charming college town anchored by Northwestern University.
