The last time I visited Chicago, the relatively new Sears Tower was the tallest building in the United States. Yeah, it’s been that long.

The Bean in downtown Chicago

Fast forward a few decades and Sears Tower is now branded Willis Tower and One World Trade Center has (somewhat dubiously) taken the title of tallest building in the western hemisphere (the spire is the tallest, but its rooftop is still lower than the Chicago landmark).

Regardless of who holds the height title, there’s no arguing that Chicago has a pretty spectacular skyline. In fact, the world’s first skyscraper was built here in 1885. And as you make your way along the shores of Lake Michigan or through Millennium Park, it’s hard not to be in awe of these amazing buildings.

Jay Pretzker Pavilion in Chicago's Millennium Park
Jay Pritzker Pavilion in Chicago’s Millennium Park

Speaking of Millennium Park, it has to be in the top ten of great urban parks. Filled with changing art exhibitions, stunning gardens and of course, the famed Cloud Gate “Bean”, the park is framed on three sides by the city skyline. The space-age looking Jay Pritzker Pavilion hosts a variety of concerts throughout the year, many of them free. Which is good since the parking garage charges $27 for 0-3 hours. Ouch!

Cross Columbus Drive and you’ll find yourself in Maggie Daley Park where there’s a playground, climbing walls, mini golf, tennis courts, ice skating, and paths leading down to Lake Michigan. Having lived in California for many years, I’ve spent a lot of time at quite a few beaches and harbors. So I was surprised to see how much this Great Lake resembled the ocean. The beaches have lifeguard towers, sand volleyball and waves lapping at the shore. The only thing missing was the smell of salty sea air.

Lakefront Trail in Chicago
Lakefront Trail at night

We didn’t have a lot of time to explore more of the city, so we’ll definitely need to come back to Chicago. Maybe for a college tour in the next year or two…

Accessibility: 5 out of 5. The parking garage was expensive, but conveniently located. We took an elevator up, the parks were ramped and easy to navigate, and the 18.5-mile Lakefront Trail makes it easy to stroll along the shoreline of Lake Michigan.