'The City That Made Chicago Famous' Is A Historic Gem With An Electric Downtown, Galleries, And Canal Walks

Chicago just won "Best Big City in the U.S." for the 8th consecutive year in Condé Nast Traveler's 2024 Readers' Choice Awards, and honestly, it's not hard to see why. The city delivers on every front that few cities can match, from its world-class architecture to neighborhoods that feel like cities in themselves. According to a recent U.S. News survey, Chicago ranks as one of the most racially diverse places in America, which explains the incredible variety you'll find block by block. Diaspora communities form distinct pockets throughout the city, from Bridgeview's thriving Middle Eastern community to Ukrainian Village's European flair. Even the historic neighborhoods surprise you — with Victorian-era architecture along the cobblestone streets of the Old Town Triangle's artsy enclave.

Getting to Chicago is simple enough, with both O'Hare and Midway airports serving as major entry points. But what most visitors don't realize is that an hour's drive southwest of the city is the place that arguably made Chicago's dominance possible in the first place. Lockport might not appear on many tourist itineraries, but this small Illinois city of around 20,000 residents holds the key to understanding how Chicago became the powerhouse it is today.

This historic community played a pivotal role in establishing Chicago as the Midwest's trading powerhouse, thanks to its position as headquarters for the Illinois and Michigan Canal construction in the 1830s. Today, Lockport boldly calls itself "the city that made Chicago famous" — and while that might sound like small-town bragging, the history backs it up. The difference is that now, instead of just being a transportation hub, Lockport has evolved into a modern hub teeming with art galleries, live music venues, and canal walks that let you trace the very waterway that changed American commerce forever.

The Illinois and Michigan Canal (also known as the I&M Canal) cuts right through downtown Lockport, and walking along it almost feels like getting an insider peek into the story of how America was built. This waterway was the missing piece that connected the Great Lakes to the Gulf of Mexico and the Atlantic Ocean — basically creating a highway for commerce that nobody had ever seen before. Abraham Lincoln pushed hard for this project when he was a congressman, and when it finally opened in 1848, he announced that sugar had been shipped from New Orleans straight up to Buffalo, New York. That was what ended up putting Chicago on the map as the Midwest's trading center.

These days, you can walk or bike the same path that mules used to haul barges over around 170 years ago. The original townpath is now a trail that stretches over 60 miles in both directions, part of a network that includes more than 109 different routes covering nearly 5,000 miles around the area. History markers dot the route like breadcrumbs leading you through the story of how this little canal town helped reshape American commerce.

Starting at Division Street where you can still see the remains of Lock Number 1, you can then make your way through Lincoln Landing in the city center — a trail that takes you past stone warehouses that have been standing since the canal's boom days and some of the best-preserved canal walls in the entire system. You can go west and walk all the way to LaSalle, or head north to Isle a la Cache, winding through riverbanks and historic sites.

What catches you off-guard about Lockport is how its music scene operates on a completely different frequency than what you'd expect from a small town. The Studio, located right in the center of town, books local and regional bands every single night. The space feels intimate in the best way, with small audiences and homemade cocktails that you can nurse while discovering your new favorite band. Don't eat dinner beforehand; their appetizers are meant for sharing and pair perfectly with whatever's happening on stage. For more mystique, take the elevator up to the third floor above Embers to find 933 Speakeasy, where the Prohibition-era atmosphere feels authentic rather than forced. The hand-crafted cocktails honor prominent women from the 1920s, each with its own backstory. The vintage-inspired setting works amazingly well in transporting you back to an era when places like this were the most exciting secret in town. Every Friday and Saturday night brings live music that ranges from acoustic sets to performances.

Art gets equal treatment here, with the Illinois State Museum's Lockport Gallery staging rotating exhibits in a gorgeous 1850s grain processing facility right on the canal. The Norton Building itself is absolutely stunning, with its original hardwood floors and massive arched windows that once loaded and unloaded cargo. Now they frame paintings, sculptures, and quilts from Illinois artists, and the $5 admission (free if you're under 19, over 64, or a teacher) makes it one of the best cultural deals around.

But if you can time your visit in June, do it. Lockport Canal Days transforms the entire downtown into a festival that draws thousands of people across Illinois. This weekend-long festival is what amounts to the city's biggest celebration of the waterway that started it all. The festival brings together live bands, food vendors, carnival atmosphere, and local artisans, all centered around the historic canal district. The whole thing wraps up Sunday night with fireworks over the canal — a fitting end to a festival honoring the waterway that made Chicago famous and gave this small city its lasting claim to greatness.