Explore the Chicago L: Private History & Architecture Train Tour

One of the oldest public transportation networks in the US, the Chicago “L” is a bona fide character in the Windy City’s story, inextricably linked with its history and urban development. Stretching across 8 lines and over 100 miles of track, the L is not only a great way to get around but also a chance to immerse yourself in the spirit of the city. Our private 2-hour tour around the most iconic parts of the L system is a unique experience full of quirky history, local legends, and interesting trivia, ensuring a truly memorable journey through the heart of Chicago.

On this 2-hour private tour, you will:

• Explore Chicago in style via its most iconic transport network;
• Enjoy the undivided attention of your local guide, well-versed in Chicago’s history and culture;
• Learn to navigate Chicago’s rapid transit system like a local with a full day CTA pass included;
• Hear the history of the L and how it has shaped the city;
• Admire the majestic architecture of the Chicago Theatre;
• Step back in time at the meticulously restored Quincy Station;
• Pass by major Chicago landmarks like Willis Tower and the Harold Washington Library;
• Pause for a local treat along the way;
• Discover the Loop, a vibrant downtown area and the beating heart of the L network;
• Take in stunning views of the Chicago skyline;
• Stroll along the Chicago Riverwalk;
• Get insider recommendations for shopping, dining and more.

Capture the essence of Chicago on an urban adventure that blends history, architecture, and local legend, all while riding the city’s most iconic transit system: the "L." Beginning beneath the glowing marquee of the historic Chicago Theatre, your expert local guide will lead you on a fascinating 2-hour exploration of the city’s past and present, where every station and skyline view tells a story.

From the very first elevated trains that stitched together a growing metropolis to the steel and glass towers that define Chicago today, this immersive tour reveals how the "L" has shaped the character and growth of the Windy City. With your own full-day CTA pass in hand, you’ll learn how to navigate the system like a seasoned local, hopping between stations and neighbourhoods as your guide shares tales of innovation, resilience, and some of Chicago’s most renowned citizens.

Along the way, you'll pass legendary landmarks like the soaring Willis Tower and the grand Harold Washington Library. You’ll have plenty of time to admire beautiful buildings from street level and elevated tracks alike as your guide offers insights into Chicago’s distinctive architecture. A visit to Quincy Station — one of the oldest and best-preserved in the system — offers a glimpse back in time to the golden age of transit, while a stroll through the bustling Loop reveals the beating heart of Chicago’s cultural and financial life. Weather permitting, you’ll have an option to take a short stroll along the Chicago Riverwalk and soak in spectacular city views.

The tour includes a stop to enjoy a tasty local treat, and your guide can also provide plenty of insider recommendations for the best places to eat, shop, and explore after the tour ends. Whether you’re a first-time visitor or returning to Chi-town, this is your chance to experience Chicago the way locals do, with a view from the tracks and a story at every stop.