Chicago, Illinois has many different names. The “Windy City” is probably the most famous moniker, but it’s also known as the “City of Big Shoulders” and the “City that Works”. Those aren’t quirky aliases, they’re references to Chicago's history.

When you're exploring history in Chicago, remember to treat these historic sites with the kindness and respect they deserve. Store your bags with Bounce luggage storage service in Chicago, then check out the attractions.

This city was at the forefront of America’s automobile boom during the late 1800s/early 1900s. The very name Chicago comes from the Native American word for wild leeks, Checagou. And we’d be remiss not to mention the slew of mobsters that called Chicago home in the 20s and 30s.

We can’t possibly fit all of Chicago’s history in one guide. Instead, we can highlight some of the city’s most prominent locales. Our history buff's guide to Chicago will show you several historic sites and tell you why they’re so important. 

Chicago through a bridge via Andrew Seaman on Unsplash

Auditorium Building

The Windy City’s architecture is a major draw. Skyscrapers and sculptures are very prominent in Chicago, especially in the Downtown district. However, the Auditorium Building is a real stand-out.

This 19th Century multi-story complex is a staple of the city. Architects Dankmar Adler and Louis Sullivan built it in 1889. The building was originally constructed with operas in mind, but you can find everything from a library to a hotel these days.

Biograph Theater

The Biograph Theater is another notable performance art center. However, this venue is famous for a different reason. Back in the day, this place used to screen movies. Notorious bank robber John Dillinger was a frequent patron in the 1930s.

It’s here, at the Biograph Theater, where Dillinger was gunned down by the FBI. As fate would have it, Dillinger perished after watching Manhattan Melodrama (1934) – a film about crime, deception, and death.

Chicago History Museum

All things considered, Chicago is a relatively young city. It was founded in 1833. Compare that to a place like New York, which has been around since the 1600s. Nevertheless, the City of Big Shoulders has a lot of history.

The Chicago History Museum educates guests about the city’s past with immersive exhibits. This venue is really big on interactivity, which is why kids adore it. There’s also a dedicated research center that preserves some of the city’s oldest documents.

Chicago Water Tower

Some readers might have imagined a “Warner Bros - esque” water tower with this entry. Instead, we’re talking about one of the oldest and most revered structures in the city. The Chicago Water Tower was built in 1869, a mere 36 years after the city was founded.

William W. Boyington is the architect behind this marvel. Back then, Chicago used the water tower to help fight fires. This structure is one of several buildings to survive the Great Chicago Fire. The tower’s importance to the city genuinely can’t be overstated.

Cloud Gate

You’d think that a structure like the Cloud Gate had been around forever. After all, this iconic sculpture seems to appear in almost every picture of Chicago. In reality, Cloud Gate was built in 2006 by Sir Anish Kapoor. 

The Bean, as most people affectionately call it, incorporates many complex themes. Its smooth, reflective surface gives it an otherworldly theme. Kapoor said that he wanted to create something that exists in its “own reality” yet coincides with ours. Cloud Gate is very abstract yet very iconic. 

The Green Mill

Bars, music, and organized crime tend to go hand in hand in American history. Take The Green Mill for example. This cocktail lounge was a major hotspot for Chicago’s Jazz artists. However, it also attracted a lot of guys who were… connected. 

In fact, Jack “Machine Gun” McGurn became a co-owner of this club during Prohibition. As you can imagine, things got very dangerous here. Comedian and singer Joe E. Lewis stood up to McGurn and nearly lost his life for it.

Holy Name Cathedral

Many American cities have Roman Catholic cathedrals, which sometimes comes as a shock to visitors. Truth is, America wouldn’t be the nation it is today without its religious roots. 

The Holy Name Cathedral played a big part in shaping Chicago. That’s in large part because this church is the home of the Archdiocese of Chicago. Thousands of people attend mass here every week. Guests from all walks of life are welcome to join them.

Little Bohemia Lodge

So, we’ve already talked about John Dillinger’s demise at the Biograph Theater. However, that wasn’t the FBI’s first attempt to book this notorious crook. Dillinger loved movies, but he also loved the Little Bohemia Lodge.

This venue was one of John Dillinger’s favorite vacation spots. It’s also the place where a fierce gunfight took place between the FBI and Dillinger’s gang on April 20th, 1934. Two casualties were reported – an FBI agent and a civilian – while Dillinger’s gang escaped.

U-505

We’ve talked about art, we’ve talked about architecture, and we’ve talked about Prohibition-era gangsters. Might as well add German submarines to the list. U-505 is an ancient sea vessel that was built during World War II.

The Germans completed 12 patrols with this sub before it was captured in 1944. The U.S. Navy proceeded to study this sub inside and out. When the war ended, U-505 was gifted to the Museum of Science and Industry. Now, anyone can explore this piece of the past at the awesome Museum of Science and Industry.

Willis Tower

Chicago’s skyline is bristling with a wide array of gorgeous buildings. However, there’s one that stands out among the crowd – Willis Tower. This 108 story structure is one of the tallest buildings in the world.

Architect and engineer Fazlur Rahman Khan designed this building in the 1970s. For decades, Willis Tower was known as Sears Tower. Regardless of the name change, this building is considered the crown jewel of Chicago’s architecture. The view from the Skydeck is well worth a visit.

And there is so much more in this Midwest gem. Head to Chitown and poke around. You'll never know what history is right around the corner.

Chicago Jewelers Building via Drew Gilliam on Unsplash