The Wrigley Building is an iconic terra cotta building boasting a huge clock tower and tons of character. It's named for William Wrigley, Jr., who made his fortune off of chewing gum! Beyond it is the lavish Hotel Intercontinental, which hides an incredible observatory within. New, Lifetime access, no expiry. Use it anytime, on any trip, as many times as you want.

The Michigan Avenue Bridge, also known as the DuSable Bridge, is architecturally beautiful, but that's not the only reason it's a stop on this tour. The bridge also sports some flags with a fascinating history, which you'll hear all about.

It's impossible to miss this enormous glass tower. At 1,399 feet tall and totaling 98 stories, it's one of the tallest skyscrapers in the entire country. The tower employs the same building technique as the Burj Khalifa in Dubai, currently the tallest building in the world.

Consisting of a sunken, rectangular pool and fountain, this memorial honors the Illinois residents who died in the Vietnam War. It's a somber yet strangely beautiful tribute to those who gave all.

These twin towers may look a bit like giant corn cobs, but they're nevertheless an iconic part of the Second City's skyline. The towers function as a “city in a city,” boasting an in-house theatre, gym, pool, ice-rink, bowling alley, 360 degree roof deck, and of course a marina.

The Dearborn Street Bridge, built in 1962, is one of Chicago's newer bridges. It was constructed to replace a badly-planned bridge that residents hated with a passion. You'll hear why and what they did about it as you admire this landmark.

Constructed in 1914, the building today is home to the Encyclopedia Britannica headquarters. It may appear short and unimpressive beside its much newer peers, but it's also a fascinating glimpse into Chicago's past.

This building is so big it has its own zip code! Designed in the art-deco style, the Mart encompasses a staggering four million square feet.

This museum doesn't just feature exhibits on the city's river and its significance to the city. It also offers birds-eye views of the river from the top floor!

This breathtaking neo-Gothic skyscraper is actually the result of a competition held by the Chicago Tribune for their 75th anniversary! They wanted to make sure their new HQ was “the most beautiful and distinctive office building in the world,” and it absolutely shows in the final product.

As Chicago's newest river-spanning bridge, the Columbus Drive Bridge offers not a glimpse into the past but a look at how the city's construction technology and philosophy changed over the decades.

This famous tower was modelled after 30 Rockefeller Center in New York City, and serves as another picture-perfect example of the art deco style. It was also the former recording spot of the Jerry Springer Show and the Steve Harvey Show.