Chicago's Best: Self-Guided (GPS) Audio Driving Tour, Illinois - Main Sites, Iconic Buildings & Famous Filming Locations
Places: 21 POIsDistance: 12.02 miDuration: 57m
Tour #2702
About this English self-guided 57m driving tour in Chicago
Welcome to Chicago’s Best,
your self-guided GPS audio driving tour through the heart of the Windy City, packed with popular spots and must-see places.
Over the next hour or two, you’ll explore downtown Chicago and beyond, from the grand halls of Chicago Union Station to the legendary ivy-covered walls of Wrigley Field.
We’ll cruise past architectural icons like Willis Tower,
once the tallest building in the world,
and the historic Chicago Board of Trade Building.
You’ll see masterpieces of design at The Rookery Building and public art at Daley Plaza, home to the famous Picasso sculpture.
We’ll pass cultural treasures like the Art Institute of Chicago, then roll by Buckingham Fountain and “The Bean” at Cloud Gate, no doubt a must-see selfie spot.
Drive along the famed Magnificent Mile, marvel at the architectural wonders of the Chicago Riverwalk, admire the resilience symbolized by the Chicago Water Tower, and soak in the vibrant atmosphere of the Chicago Theatre,
all this, while also spotting famous filming locations that have graced the silver screen,
offering a unique perspective on the city's cinematic history.
There's so much to see.
And, with UCPlaces, you’re in control.
Go at your own pace, start and stop whenever you like,
skip a stop, or, linger longer,
it’s "your" schedule,
your Chicago experience.
So,
Let’s hit the road and enjoy the city’s main sites iconic buildings and famous filming locations,
one story at a time.
We'll start the tour near the Chicago Union Station, on South Canal Street.
Meet you there.
Jackson & Canal, S Canal St, Chicago, IL 60606, USA
Chicago Union Station
Alright, welcome to your first stop: Chicago Union Station, coming up on our left,
one of the great railroad terminals of America and a true Chicago landmark.
This Beaux-Arts beauty opened in 1925, built on the vision of famed architect Daniel Burnham, the same mastermind behind Chicago’s 1909 Plan that shaped much of the city’s modern layout.
Interesting fact:
Daniel Burnham didn’t actually live to see his masterpiece come to life. The terminal was completed by Graham, Anderson, Probst & White, after his death.
But, his philosophy of - “Make no little plans”, clearly lives on in this impressive structure,
there’s nothing little about this place.
If you have a chance to step inside the Great Hall, please do.
The soaring 115-foot barrel-vaulted skylight, the marble columns, the sweeping staircases, it feels more like a Roman bathhouse or a European palace than a train station.
At its peak during World War II, Union Station handled hundreds of thousands of passengers a day, sending troops off to war and welcoming them home again.
Now, Chicago itself was built on transportation. This city grew fast in the 19th century thanks to railroads, shipping, and its strategic location between the Great Lakes and the Mississippi River system.
After the Great Chicago Fire of 1871, the city rebuilt bigger, stronger, and more ambitious, and Union Station reflects that spirit.
Movie fans might feel a sense of déjà vu here.
The dramatic staircase scene with the baby carriage in The Untouchables was filmed right inside this station.
You may also spot it in films like The Fugitive and Public Enemies. Directors love this space for its scale and timeless drama.
Just imagine,
this place was here, in the midst of Prohibition in the late 1920s and early 1930s,
while notorious figures, like Al Capone, might have brushed shoulders with everyday commuters.
Today, it’s one of Amtrak’s busiest stations and a major commuter hub.
Nearly a century later, it remains exactly what Chicago has always been:
a gateway city, where journeys begin,
end,
and sometimes change direction entirely.
Now look left and lift your eyes to one of the most recognizable silhouettes in the world, Willis Tower.
We'll be taking the next left, circling the tower, while I tell you some interesting stories.
Completed in 1973 as "Sears Tower",
it was built for retail giant Sears Roebuck and Company.
At the time, Sears was the largest retailer on the planet, and wanted a headquarters that reflected that dominance.
The result,
The tallest building in the world,
a title it held for nearly 25 years.
Designed by the legendary firm Skidmore Owings & Merrill, the tower introduced the revolutionary “bundled tube” system.
Instead of a single vertical shaft, it’s essentially nine square tubes bundled together,
allowing it to rise higher while staying stable against Chicago’s winds.
At 1,450 feet tall, 110 stories up, it redefined what a skyscraper could be. In a city that invented the skyscraper after the Great Fire of 1871, that’s saying something.
You might want to visit the Skydeck on the 103rd floor, with views of up to four states on a clear day.
And, if you’re feeling brave, step onto - “The Ledge",
those glass boxes extending out over the street more than 1,300 feet below. It’s a thrill.
Officially renamed as Willis Tower in 2009,
many locals still call it “Sears".
Around here, some names just stick.
Tour itinerary stops | Additional places you'll see on this self-guided tour
Place 1Chicago Union Station
Place 2Willis Tower
Place 3City Hall
Place 4Daley Plaza
Place 5The Rookery Building
Place 6Chicago Board of Trade Building
Place 7The Spearman & The Bowman
Place 8Grant Park's Buckingham Fountain
Place 9The Art Institute of Chicago
Place 10The Bean in Millennium Park
Place 11Chicago Cultural Center
Place 12The Chicago Theatre
Place 13Chicago Riverwalk
Place 14The Wrigley Building
Place 15Navy Pier
Place 16Magnificent Mile
Place 17Chicago Water Tower
Place 18875 North Michigan Avenue
Place 19Free Urban Zoo
Place 20Wrigley Field
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How to take a UCPlaces tour
Taking a UCPlaces tour is fun and easy.
Download the app (Android or iOS), purchase the tour (either here on the website, or from within the app).
That's it, you're ready to go!
When you want to start the tour, find the tour in the app (via a quick in-app search or by clicking the tour link received in your confirmation email) and click "Start Tour" (headphones recommended for best experience.)
* After purchasing a tour you will receive a purchase confirmation email including the tour link and instructions on how to take the tour, so you don't have to remember anything now.
How does the tour work?
UCPlaces acts as your personal tour guide, providing self-guided audio tours fully navigated within our app using GPS-based navigation. You won't need to switch between external navigation apps.
Whenever you approach a point of interest (POI) on the tour, our app will automatically play the relevant audio story at the right time and place.
If you start the tour before reaching the first POI, the app will navigate you to the starting point and then begin the tour.
How is this more convenient than a traditional tour?
UCPlaces offers an innovative and flexible way to explore exciting destinations on your terms.
Here are some key advantages over traditional tours:
No need to commit upfront or purchase in advance; buy a tour only when you're ready to go.
Walk at your own pace.
No waiting for groups; go on your schedule.
Take the tour in your preferred language.
Start, stop and continue the tour whenever you want.
Returning to the same destination? Take the tour again, and again, and again... And bring a friend!
Enjoy preferred prices.
What's included?
A self-guided audio tour taken via the UCPlaces app [Android / iOS (iPhone) / Apple CarPlay].
Tour route map and in-app GPS navigation (via the UCPlaces app).
Audio stories for places visited during the tour.
Apple CarPlay connection (for iOS users); for a seamless driving tour experience.
What's NOT included?
Earphones (highly recommended).
Smartphone.
Any kind of transportation (including tickets and passes).