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Top Chicago Historical & Heritage Tours


Chicago Architecture Walking Tour: Dazzling Interiors™ of the Loop

clock 2 hours
  • Sign up for an architectural and walking tour in Chicago which allows a person to explore the mesmerizing beauty of the beautiful city.
  • Learn more about the architectural significance from an expert guide Read more

    What You'll Do:

  • Get a chance to visit some amazing places with exceptionally beautiful architecture
  • Tiffany stained glass dome at Chicago Cultural Center which is the largest in the world is put up for exploration for the people on this cost saving and highly entertaining trip.
  • Get intrigued by art-deco gem at the Chicago Board of Trade Building
  • Starting point for this tour is the 425 S Financial Pl, Chicago, IL 60605, USA
  • Build your stamina to explore every tit-bit of this glorious city and do not leave any corner unseen
  • What It Includes:

  • The tour lasts for approximately 2 hours
  • A efficient local guide is present to lead all who take part throughout the journey
  • The breathtaking beauty of Chicago is enough to make a person speechless in amazement.
  • People of most age groups can participate in the tour
  • Travellers Talk:

  • The people participating on this trip loved their guides and got a lot of information from them
  • One of them found the tour easy to understand and follow
  • Tourists were involved in the tour and the architecture and found it really amusing
  • Is It Right:

  • If one likes learning more about the architectural marvels of any place they visit then this trip is perfect for them
  • Architecture enthusiasts are always welcome to come join this trip
  • Couples and family members can take part in this journey together
  • Read lessRead more

Chicago in a Day: Food, History and Architecture Walking Tour

clock 5 hours
  • Come on as we help you discover some of the best sights and food Chicago has to offer with a local guide by your side.
  • Join an epic tour of some of the city's greatest hits: incredible architecture, both old and new, delicious local treats and iconic Chicago dishes, along with a unique Chicago transit ride, stunning river views, and much more Read more
  • Enjoy a couple of classics made-in-Chicago snacks like Chicago-style popcorn and homemade chocolates
  • Realise why locals have so much passion for their Chicago-style classics
  • What You'll Do:

  • Visitors on this trip have to meet at The Chicago Theatre, 175 N State St, Chicago, IL 60601, USA
  • Everyone needs to be there at 10:00 AM to meet their guide
  • Learn more about the history, cuisine, and culture of Chicago with some of the finest details this city has to offer with fun activities and food
  • What It Includes:

  • Visit places like The Chicago Theatre, Chicago Pedway, Chicago Riverwalk, Chicago River, Cloud Gate, and many more
  • Water Taxi or Subway Tickets are included
  • Entry/Admission for Chicago River is also included
  • Travellers will be provided with enough food to satisfy their hunger for the day
  • Trip is wheelchair friendly and all age groups are welcomed to participate
  • Travellers Talk:

  • Travellers liked the local guides and their presence and knowledge
  • They loved the city, its architecture, food and the tour itself
  • Is It Right:

  • Rediscover the city of Chicago by booking this journey
  • Other than weather conditions, nothing can stop you from taking part while you are enjoying yourself on this trip
  • Read lessRead more

Chicago Night Crimes Bus Tour

clock 120 to 150 minutes
  • Come join this fun bus hop on hop off tour where tourists can learn all about the crime history of Chicago
  • Learn about the mind-blowing histories of the leading gangster and mobster figures of Chicago. Read more
  • Visit the legendary gangster shootout sites like the St. Valentine's Day Massacre, the handshake murder, and The Enforcers safe, and tunnels, and much more as the tourists get to enjoy themselves to the fullest.
  • What You'll Do:

  • Explore historic crime scenes after dark.
  • Explore landmark buildings like Biograph Theatre and Harry Caray's Italian Steakhouse, and many more iconic places.
  • Drive to several historic crime scenes throughout Chicago and get to know about its history
  • Travellers can also drive by the park on the way to several historic crime scenes throughout Chicago.
  • What It Includes:

  • Find your way with the help of a local, informative, and courteous tour guide
  • The time taken for this tour is approximately 2 hours
  • This tour includes multiple stops on and off the bus.
  • Traveller pick up and drop off is available in this tour.
  • Live commentary provided by the tour guide is available on board in this unique bus tour.
  • Arrive at least 10 minutes early for check-in to hop on the bus.
  • Travellers Talk:

  • According to travellers the tour has been said to be indeed awesome by the travellers
  • The tour guide has been said to be great, personable, and knowledgeable.
  • The guide had lots of knowledge to share and was very professional as well according to the travellers
  • Travellers said the tour guide took the travellers to some interesting places and they were able to hop off the bus easily for conducting photoshoots.
  • Is It Right:

  • Come be a part of an experience that will leave you thoroughly entertained
  • All travellers, even people with certain walking disability, can take part in this tour
  • Read lessRead more

Eastside Chicago: "The Art Heist" Exploration Game

clock 1 hour 35 minutes
  • Play a city game where you will follow clues to discover amazing places and local stories in Chicago.

    You’ll tour Chicago’s famous Millenium Park and learn about the iconic works of art that populate the area on your way to riches beyond your imagination.

    Are you up for an adventure in Chicago?

    Explore...Read more

A Storied Neighborhood: A Self-Guided Audio Tour with Bill Ayers

clock 40 to 60 minutes
  • This self-guided audio tour begins at the Laboratory Schools founded by John Dewey, and winds through the University of Chicago. Along the way, walkers will encounter world-renowned architects and Nobel Laureates, robber barons and artists, the DuSable Museum of African American History and the birthplace of the Atomic Age.

    In storied...Read more

Vice, Crime and Gangsters in Chicago: A Self-Guided Audio Tour

clock 75 to 115 minutes
  • Are you looking for a way to see the wicked city without joining a tour group? Explore at your own pace with this affordable walking tour.

    • Find the city’s dark side with stories of opium trade, the city’s first vice, and a shanty town filled with criminals and prostitutes
    • Hear from producer Richard Junger, an urban historian...Read more

Chicago’s Ragtime & Jazz Eras: A Self-Guided Audio Tour

clock 45 to 60 minutes
  • See Chicago through the eyes of Al Capone and the Everleigh Sisters at your own pace with this affordable walking tour.

    • Walk in the footsteps of the gangsters, bootleggers, hoodlums, gunmen, and crooked cops and politicians who made up what was known as the “Chicago Outfit”
    • Hear from producer Richard Junger, an urban...Read more

The Loop, River North and Chicago’s Theater District: A Self-Guided Audio Tour

clock 120 to 150 minutes
  • Are you looking for a way to see Chicago without joining a tour group? Explore at your own pace with this affordable walking tour.

    • Take in Chicago’s concrete giants and hear fascinating stories about quirky artworks, local tragedy, and the city’s journey to revitalisation
    • Hear from producer Phil Biedron, an actor and tour...Read more

Pilsen Neighborhood Train & Walking Tour in Chicago with Local Guide

clock 3 hours 30 minutes
  • 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...Read more

Art Institute of Chicago Private Guided Tour with Skip-the-Line Ticket

clock 2 hours 30 minutes
  • The Art Institute of Chicago attracts nearly as many visitors as other leading galleries like the Met, Louvre & British Museum. On this 2.5 hour private guided museum tour, you’ll be able to skip the line and explore it’s most famous pieces with the help of an engaging guide who will lead the way.

    Highlights Generally Include: (if...Read more

Art Institute of Chicago Skip-the-Line Small-Group Guided Tour

clock 2 hours 30 minutes
  • The Art Institute of Chicago attracts nearly as many visitors as other leading galleries like the Met, Louvre & British Museum. On this 2.5 hour semi-private (8 Guest Maximum) guided museum tour, you’ll be able to skip the line and explore it’s most famous pieces with the help of an engaging guide who will lead the way.
    Highlights...Read more

Private 45-Minute Chicago Skyline Helicopter Tour

clock 45 minutes
  • This tour is unique as it offers the ability for you and two of your friends or family (a total of 3 passengers) to experience what it is like to fly over the city of Chicago on a 45 minute thrill seeking guided tour. The price is the total for all 3 passengers (saving you money compared to other operators who charge per...Read more

Prairie Avenue Haunted History Tour and Ghost Hunt

clock 2 hours 20 minutes
  • Chicago's original Millionaire's Row, meet the ghosts of the Gilded Age. Marshall Field, George Pullman, Philip Armour, and many more used to live in this amazing area, the most desirable address in the city before the fire.

    Many of the incredible homes are still standing and the spirits linger, waiting to divulge their secrets in a...Read more

The Devil in the White City: A Haunting History Tour

clock 3 hours
  • We are Chicago's first and best Devil in the White City tour, offering the history, legends and lore surrounding H.H.Holmes, the World's Fair and Victorian Chicago. We visit Prairie Avenue, Chicago's Victorian "Easy Street" and site of the Fort Dearborn Massacre, travel to the World's Fairgrounds and the Midway Plaisance at the University of...Read more

Train & Walking Tour: Pilsen Neighborhood - Creativity & Community

clock 3 hours
  • Get ready to experience beautiful and unique public art. Meet your guide in front of Chagall’s “Four Seasons” mosaic in the Loop. Next, we’ll board the Pink Line train at the historically-restored Quincy L Stop (1897) and make our way to Pilsen — a vibrant Chicago neighborhood just southwest of the Loop, originally settled by Czech...Read more

Walking Tour Chicago Passageways - Pedway & Riverwalk

clock 2 hours 30 minutes
  • Chicago’s Pedway is a system of underground tunnels and passageways that are laid out underneath the city so you can get from one end of the Loop to the other without ever going outside. We begin at the Cultural Center and after viewing the famous Tiffany dome, we descend into the Pedway which takes us past murals, stained glass windows and into...Read more

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

clock 3 hours
  • 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...Read more

Train, Boat & Walking Tour: Chinatown - The Far East in the Midwest

clock 3 hours 5 minutes
  • We begin this Chicago walking tour in front of the iconic Chicago Theater. After introductions, we’ll hop on the Red Line and head south to Chinatown.

    Upon arrival, we’ll start our Chicago Chinatown tour at the famous Dragon Wall then stroll down Wentworth Ave – the heart of Chinatown. We’ll stop at a bakery and enjoy authentic...Read more

Underground Donut Tour - West Loop & Restaurant Row

clock 2 hours
  • The West Loop (or Restaurant Row) Donut Tour is a sister tour to our Original Downtown Tour. Geared towards those who want to see Chicago’s authentic foodie focused food scene, this is the tour for you! We’ll start on the west side of the loop and wander our way along Randolph and various side streets, showing off some of the more unique spots...Read more

Chicago History and Food Tour

clock 3 hours
  • Consider this evening an Edible Education! Roll your sleeves up and get ready to taste the Chicago's quintessential foods in it's Downtown Loop neighborhood on this dinner food tour! Indulge in Chicago’s favorites while involving all the other senses and enjoying the historical sites and stories along your...Read more