Adventure Collective
Discover Chicago’s Iconic Architecture Aboard a Private Train Tour - Chicago

Discover Chicago’s Iconic Architecture Aboard a Private Train Tour

Chicagoeasy

Difficulty

easy

Duration

2–3 hours

Fitness Level

No special fitness required, accessible for all ages and mobility levels

Overview

Experience Chicago’s legendary architecture from a fresh vantage point on a private, customizable train tour. Explore the city’s skyscrapers and historic buildings with expert guides and panoramic views.

City Tour
Guided Tour
Private
Train
Chicago, Illinois

Private Chicago Architecture by Train Experience

From $262|Private| 2 Hours | Join us for a ride and discover the ins-and-outs of Chicago's L Train!

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Adventure Photos

Private Chicago Architecture by Train Experience photo 1

About This Adventure

Experience Chicago like a local on this unique tour of the iconic ‘L’ train system. With an all-day pass, explore historic stations, enjoy skyline views, and savor a local snack. Your knowledgeable guide will share fascinating stories and tips, ensuring you uncover the city's hidden gems and vibrant culture.

Highlights

  • See the city aboard the Chicago ‘L’, with an all-day train pass included!
  • Hear the history of the L and how it has helped shaped the city
  • Enjoy an included local beverage and snack along the way
  • Visit landmarks like the hub of Chicago Public Library & historic Quincy Station
  • Learn how to navigate Chicago’s rapid transit system like a true local!

InclusionsLocal English-speaking guide, All-Day CTA pass, and small treat

Exclusions Additional food and drink, souvenirs, tips and gratuities for the guide.

Summary

The ‘L’ in Chicago is one of the most widely-recognized landmarks in the American Midwest. Join us for a ride and discover the ins-and-outs of this groundbreaking and beloved elevated train system as well as the subterranean subway lines beneath the central part of the city and the Chicago River! From historic stations to beautiful skyline views across the city, you’ll be sure to discover a few surprises along the way.

You’ll meet your tour guide at the historic Chicago Theater, where you’ll be introduced to the scale of Chicago’s system (the CTA) and the intricacies of the L. With your pass and map in hand, we’ll start our ride with a background on the L’s historic beginnings, its environmentally friendly impact, and cameos in blockbuster films.

Our first tour stop will be a historic station, beautifully preserved and restored to reflect the style and decor of the early 1900s. Here, you’ll see more than just intricate light fixtures and period tilework. This station also features decades-old advertisements, signs, and maps of the original system, from when the train lines were privately owned.

Among the neighborhoods we’ll visit, the Chicago Loop is a lively downtown area where locals shop and dine day and night. Your tour guide will point out the best places to grab a bite of a Chicago staple – deep dish pizza or a loaded hot dog – following your tour. While we’re enjoying the city’s architecture or stretching our legs in the park space along the Chicago River, your tour guide will treat you to a small snack and beverage before hopping back on the L.

Among other tour stops we’ll have time to experience are the majestic Union Station and other classic Chicago architecture like the equally impressive Chicago Public Library.

As your tour comes to an end, your guide will be happy to give you some final tips and recommendations for other Chicago tourist attractions, happy hour bars, shopping, or a great place to grab dinner later that evening.

Adventure Tips

Book Early for Peak Availability

Reserve your private train tour well in advance to secure your preferred date and group size.

Dress for the Season

Layer clothing to stay comfortable in climate-controlled train cars while accounting for Chicago’s variable weather.

Bring a Camera with a Wide-Angle Lens

Capture the expansive skyline and architectural details visible through panoramic train windows.

Consider Off-Peak Hours

Tours during early morning or late afternoon offer softer lighting and fewer crowds around key stops.

Local Insights

Wildlife

  • Urban peregrine falcon
  • Squirrels frequenting Millennium Park

History

Chicago’s elevated train system, known as the 'L,' dates back to 1892 and revolutionized urban transit, deeply influencing the city’s development.

Conservation

Tours emphasize sustainable transit use and support preservation efforts of Chicago’s historic architectural landmarks.

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Adventure Hotspots in Chicago

Frequently Asked Questions

Recommended Gear

Comfortable walking shoes

Essential

Ideal for short walks during select train stops and platform access.

Camera or smartphone

Essential

Essential to capture Chicago’s dynamic cityscape through train windows.

Weather-appropriate layers

Essential

Spring can be chilly; layers help maintain comfort inside and outside the train.

spring specific

Sunglasses

Protect your eyes from glare during bright daytime tours.

summer specific