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12 results | All Chicago Tours

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Train & Walking Tour: Chicago's Prairie District - Street of the Elite

Train & Walking Tour: Chicago's Prairie District - Street of the Elite

star-5
9
Step off the typical tourist trail, and discover one of Chicago’s oldest and most scenic neighborhoods, on this walking tour of the Prairie District. Meet your guide in the morning at the Chicago Athletic Association, and set off with just a small group for company. The Prairie District is just a short L ride away; you can look forward to seeing the Second Presbyterian Church, Glessner House, Motor Row, and otherwise discovering how Chicagoans lived at the turn of the 20th century.
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  • 4 hours
  • Free Cancellation
From
USD90.00
From
USD90.00

Train & Walking Tour of Chicago Loop - Home of the Modern Skyscraper

Train & Walking Tour of Chicago Loop - Home of the Modern Skyscraper

star-5
6
Discover the architectural splendor of downtown Chicago—and learn all about the city’s early skyscrapers, urban planning, and modern history—on this small-group tour. Meet your guide in the morning on Michigan Avenue and set off by foot and by L train. You’ll see world-renowned landmarks like the Rookery Building, will visit the Chicago Cultural Center to admire the world’s largest Tiffany dome, will explore the Fine Arts Building, and much more.
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  • 3 hours
  • Free Cancellation
From
USD60.00
From
USD60.00

Chicago City Tour: Elevated Architecture Tour with Train Ticket Included
Likely to Sell OutLikely to Sell Out

Chicago City Tour: Elevated Architecture Tour with Train Ticket Included

star-5
5
Explore Chicago’s amazing architecture from the unique perspective of elevated trains and station platforms. Learn the history behind the famous "L" system and hear how it has shaped the development of buildings within the Loop. The city's first elevated train started making trips in 1892. Now considered one of Chicago’s most defining features, the "L" offers incredible views of downtown. By being more than 20 feet off the ground, you'll see architectural details that are missed by most pedestrians at street level. This is our most comprehensive tour in the Loop, passing hundreds of buildings and highlighting ones of architectural significance.
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  • 2 hours
  • Free Cancellation
From
USD34.00
From
USD34.00

Train & Walking Tour: Chicago's River North - Historic Pubs
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Train & Walking Tour: Chicago's River North - Historic Pubs

star-5
3
Eat, drink and discover Chicago's Loop and River North neighborhoods on our Chicago historic pub tour via the Brown Line!  Join us for a combination of great Chicago stories and adult beverages as we tour historic sites and legendary pubs in the city’s Near North Side. We'll kick off our Chicago tour at Revival Food Hall in the Loop for a bite to eat then stop for a drink at Adams Street Brewery, part of The Berghoff, Chicago's oldest, continuously-operating restaurant. Next stop, we board the Brown Line to River North. In River North, we'll visit Brehon Pub with a fascinating story involving bribery and the Chicago media. The Green Door Tavern is next on our list. It's the oldest pub in Chicago and sits above a well-hidden, authentic Prohibition-era speakeasy.  We'll then board the train again and make our way back to the Loop where we'll have "last call" at historic, antique-filled Monk's Pub.
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  • 3 hours
  • Free Cancellation
From
USD60.00
From
USD60.00

Pilsen Neighborhood Train & Walking Tour in Chicago with Local Guide

Pilsen Neighborhood Train & Walking Tour in Chicago with Local Guide

Go for a scenic stroll through Chicago’s urban neighborhoods on this private tour accompanied by a friendly guide. Admire the oldest skyscraper and learn everything about the American dollar at the Money Museum at the Federal Reserve Bank. Tune into stirring vibes of Pilsen neighborhood, absorb the beauty of Mexican culture and then relax with a pint of special beer in the family-run brewery. · Discover one of the most diverse and artsy neighborhoods of Chicago · Enjoy dedicated attention from a personal guide · Learn more about the history of the American dollar at the Money Museum · Sample the best Mexican dishes in Chicago
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  • 3 hours 30 minutes
  • Free Cancellation
From
USD138.00
From
USD138.00

Chicago Architecture River Cruise

Chicago Architecture River Cruise

star-5
7509
Cruise down the Chicago River to see the city's famous architecture on this boat tour. With commentary from your onboard guide, watch the spectacular skyline glide by, including more than 40 notable buildings like Navy Pier, the Wrigley Building, and the John Hancock Building. Cover all three branches of the Chicago River, passing the East Bank Club, the old Post Office Building and the Willis Tower (formerly known as the Sears Tower).
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  • 1 hour 15 minutes
  • Free Cancellation
From
USD46.87
From
USD46.87

Chicago Premier Dinner Cruise on Lake Michigan

Chicago Premier Dinner Cruise on Lake Michigan

star-3.5
168
Take a gourmet dinner cruise on a high-end luxury yacht with the stunning skyline of Chicago serving as your backdrop. Climb aboard your recently renovated vessel, featuring a sumptuously-appointed rooftop lounge and stylish interior design, for your cruise along Lake Michigan. Then sit down for a 3-course dinner, informed by some of the world’s top celebrity chefs and composed of fresh ingredients cooked right on-board. After dinner, enjoy coffee and tea, captivating views of Chicago landmarks like the Willis (formerly Sears) Tower and Navy Pier, plus musical entertainment provided by the onboard DJ.
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  • 2 hours 30 minutes
From
USD180.18
From
USD180.18

Chicago Sunset Cruise

Chicago Sunset Cruise

star-4.5
215
Drink in a one-of-a-kind perspective on the Windy City when you go for an evening cruise, perfectly timed to coincide with the sunset. Hop aboard your open-top vessel in the heart of the Magnificent Mile, and cruise along the Chicago River, where your guide will point out architectural highlights. Then, see the skyline from a distance, and watch the skyscrapers light up, when you continue to Lake Michigan for a sunset viewing.
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  • 1 hour 30 minutes
  • Free Cancellation
From
USD42.00
From
USD42.00

Underground Donut Tour: Chicago's First Donut Tour
Likely to Sell OutLikely to Sell Out

Underground Donut Tour: Chicago's First Donut Tour

star-5
386
Sample some of the Windy City’s tastiest donuts on this Underground Donut Tour, celebrating the magic of Chicago’s tastiest sugar-filled concoctions. Donut-lovers are sure to enjoy this visit to some of Chicago’s tastiest donut purveyors, offering a chance to savor all of your favorite varieties, on the city's only donut-themed excursion. All tastings are included, and vegan, gluten-, and nut-free options are also available.
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  • 2 hours
  • Free Cancellation
From
USD40.00
From
USD40.00

Big Bus Chicago Hop-On Hop-Off Tour

Big Bus Chicago Hop-On Hop-Off Tour

star-4
998
Don’t spend time figuring out what to see in Chicago and how to get there—this hop-on hop-off tour provides a mapped-out itinerary of the city's top sights. With several strategically located stops, the tour allows you to explore the Windy City at your own pace. See the world-class Art Institute and landmark skyscrapers, while audio commentary onboard gives you insight into the city's colorful history.
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  • 2 hours
  • Free Cancellation
From
USD44.99
From
USD44.99

BYOB Spray Paint 'n' Sip at Studio W.I.P. Chicago

BYOB Spray Paint 'n' Sip at Studio W.I.P. Chicago

star-4.5
118
Enjoy a unique creative outlet—and learn the ins and outs of graffiti and street art—during this hands-on urban art workshop. Pick from multiple class times, and make your own way to the Chicago studio. You’ll learn different styles and techniques from your instructors (including guest artists), can try out stenciling and spray-painting, and can even create your own work of art on canvas to bring home at the end of class.
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  • 1 hour 30 minutes
  • Free Cancellation
From
USD40.00
From
USD40.00

Chicago Favorites Ultimate Food & Walking Tour

Chicago Favorites Ultimate Food & Walking Tour

star-5
384
Stroll through downtown Chicago on this walking food tour. Visit Millennium Park, the Palmer House Hotel and other city landmarks. Taste quintessential Chicago foods such as deep-dish pizza, hot dogs, plus chocolates and pastry. All food tastings are included, and the tour covers an easy 1.5 miles (2.4 km) suitable for most fitness levels. Upgrade your tour to include three pours of local craft beer.
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  • 3 hours
  • Free Cancellation
From
USD74.99
From
USD74.99

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What people are saying about Rail Tours in Chicago

star-5
Train & Walking Tour: Chicago's Prairie District - Street of the Elite
"We like to know the history of cities we visit, and this tour gave us a glimpse of Chicago of the 1800s visiting homes, grand hotels and also simply strolling around places with a story. The tour guide was excellent."..."
star-5
Train & Walking Tour of Chicago Loop - Home of the Modern Skyscraper
"Our guide was very personable, knowledgeable, and accommodating. He paced the tour in such a way that we could appreciate and enjoy the history and architectural details of the many sites we visited. He went above and beyond most guides in ensuring we had an enjoyable learning experience. I highly recommend L Stop Tours when visiting Chicago."..."
star-5
Chicago City Tour: Elevated Architecture Tour with Train Ticket Included
"Doug, our guide, had great knowledge and good presentation. Gives a different perspective of the great architecture downtown."..."
star-5
Train & Walking Tour: Chicago's River North - Historic Pubs
"Had a great time! Took my relatives from out of town who are very picky about activities and they loved this tour a lot. Tom is a great local guide who knows his city very well and brought lots of neat materials and photos to bring the sometimes sordid histories of each pub to life. Chicago is a city steeped in the tradition of libations so it would be a mistake to miss exploring the city from within her pubs!"..."
star-5
Chicago Architecture River Cruise
"Great cruise. Spiro was a fantastic guide!! Seeing Chicago from the river was educational and exciting!!"..."
star-5
Chicago Premier Dinner Cruise on Lake Michigan
"Great time with my wife and friends. Wonderful views of Chicago. If your not expecting the Ritz you will enjoy it."..."
star-5
Chicago Sunset Cruise
"The experience was perfect, from the sunset to the views just an immaculate experience. I totally recommend to everyone to experience this opportunity."..."
star-5
Underground Donut Tour: Chicago's First Donut Tour
"Nick was a great tour guide. We really enjoyed our tour! The donuts were delicious, it was fun to try each of the 4 donut shops and to hear the background stories behind each"..."
star-5
Big Bus Chicago Hop-On Hop-Off Tour
"Great way to see the city then decide where you would like to spend more time. It was great to have the headphones so you could hear all the highlights."..."
star-5
BYOB Spray Paint 'n' Sip at Studio W.I.P. Chicago
"It was something new and different and also inspiring, 10/10 would definitely come back and do it again!"..."
star-5
Chicago Favorites Ultimate Food & Walking Tour
"Awesome food. Friendly and extremely knowledgeable guide! Visited great restaurants and lovely sights all over that we wouldn’t have known about otherwise!"..."

Frequently Asked Questions

The answers provided below are based on answers previously given by the tour provider to customers’ questions.
Q:
What are the best Rail Tours in Chicago?
Q:
What Rail Tours in Chicago are taking additional safety precautions?
Q:
What Rail Tours in Chicago are good for avoiding crowds?