Chicago Walking Tours

Due to the combination of its flat landscape, mild summers, and great architecture, Chicago makes an ideal city for tourists who enjoy sightseeing on foot.

Although a flat landscape can be boring for the eye, it is Manna from heaven for walkers, and Chicago, about as flat as American cities get coupled with its mild summers (thanks to the cooling effects of Lake Michigan), makes for a refreshingly walkable tourist destination. Contrasting the downtown with some of the city’s rich and varied, close-in neighborhoods allow travelers to both trace the city’s evolution from an architectural perspective and gain a more intimate view of this Midwest economic powerhouse; moreover, a Chicago walkabout is a healthy and relatively inexpensive diversion which is important to consider in these days of physical and budgetary belt-tightening.

Downtown Chicago

Chicago’s downtown is so chock-full of architectural wonders that it can be a bit overwhelming to decide what to see, but fortunately, the Chicago Architecture Foundation has done the hard part in grouping its walking tours around various architectural themes. For example, one walking tour focuses on early skyscrapers while another highlights Art-Deco buildings and yet another centers its attention on the city’s mammoth modern skyscrapers. If tours hold little appeal, head to the Chicago Cultural Center and, while admiring the ornate interior including the world’s largest Tiffany stained-glass dome, grab a map marked with the main architectural high-points and then set sail.

If gazing at buildings becomes monotonous, then intersperse the itinerary with some moments of repose in the shadow of world-class artists such as Chagall’s The Four Seasons mural at Chase Tower Plaza or Picasso’s untitled, monumental sculpture at nearby Daley Plaza.

The Gold Coast

Had enough tall buildings for one day? Then go north of downtown across the Chicago River to see how the other half lived at the turn of the last century. Lying slightly north and west of The Drake Hotel is the Astor Street District which forms the core of the aptly named Gold Coast neighborhood. Following Astor Street north toward Lincoln Park, a gambol here provides plenty of gilded age, residential architecture eye-candy including the Charnley House, designed by Louis Sullivan and Frank Lloyd Wright, which offers tours to the public on certain days, unlike the surrounding residences which remain in private hands.

Old Town

When Astor Street dead-ends into Lincoln Park, head west along North Avenue until it intersects with Wells Street, the commercial heart of the Old Town neighborhood replete with restaurants, watering holes, and specialty retail shops. While today an affluent, historic area of well-preserved Victorian homes, this urban pocket has hosted a variety of occupants over the years -from Bavarian and Puertorican immigrants to artists and gays to today’s yuppies- but its most famous resident is The Second City, a comedy club that has produced a massive progeny of comedic legends including Bill Murray and Mike Myers.

Lincoln Park to the Lake Shore Path

Migrating north into the tony Lincoln Park neighborhood, amble along Howe Street and admire the mix of residential architecture, which includes styles from Victorian to today’s neoclassical colossi which hark back to the gilded age extremes of the Gold Coast, making one wonder if the Credit Crunch ever hit here. Howe Street eventually empties into Oz Park, a whimsically themed green space anchored by detailed statues of the main characters of The Wizard of Oz: Scarecrow, Cowardly Lion, Tin Man, and, of course, Dorothy and Toto.

Head east on Webster Avenue, duck through the Lincoln Park Zoo, and connect to Chicago’s Lake Shore Path, a pedestrian and bike trail that leads back to the Magnificent Mile and downtown Chicago. Strolling south along this trail allows a splendid vista of The Drake Hotel set against the backdrop of the iconic John Hancock Center in the foreground and the rest of Chicago’s skyline in the background, a great image to end a memorable day of architectural sightseeing.

More Chicago Walking Tours

Listed below are some of the most popular Chicago walking tours offered. There are a wide variety of tours, some are not available year-round. Check with the tour operator.

Underground Loop Pedway

phone: 773.593.4873

EChicago’s Pedway, a series of heated walkways, passages and tunnels, serve as the backdrop for an amusing and enlightening tour of some of the hot-spots (or a least warm-spots) of downtown Chicago. Focusing on interesting anecdotes and tales about some of the great buildings downtown, the Chicago Pedway Tour is given by improviser and tour guide, Margaret Hicks. These are great tours for Chicagoans who want to learn more about the city and for tourists who want a full Chicago experience without ever going outside. “The Pedway is such a weird and wonderful place, it’s like a whole other world down there. Parts of it are scary, parts of it are beautiful but all it is pretty warm – and that’s a big plus,” says Hicks.

Monday/Thursday at 10:30AM. Meet at 40 W. Lake by Chase ATMs. Tour is 90 minutes and costs $15.00. Cash only and reservations are required.

Auditorium Theatre of Roosevelt University Tours

Auditorium Theatre, 50 E Congress Parkway, Chicago, IL, 60657

Theater tours allow an up-close look at the art and architecture of Dankmar Adler and Louis Sullivan, with fascinating stories of the Auditorium and its unique place in Chicago’s history. Tours are available Mondays at 10:30 a.m. and 12 noon, and Thursdays at 10:30 a.m.

Broadway In Chicago Theater Tours

Ford Center for the Performing Arts, Oriental Theatre & Cadillac Palace Theatre
(312) 977-1701

Chicagoans and visitors have the opportunity to get an unforgettable and in depth look at two of the most beautiful and historic venues of Chicago’s famed theatre District. Broadway in Chicago offers a weekly, guided tour of the Ford Center for the Performing Arts, Oriental Theatre, 24 W. Randolph St. and the Cadillac Palace Theatre, 151 W. Randolph St. The tour showcases the glittering decor inspired by the lushness of the Orient and the refinement of Versailles, as well as the cutting edge technology that makes each theatre the home to today’s most complex theatrical productions.

Chicago Architecture River, Bus, Walking Tours of Downtown, Suburbs

The Chicago Architecture Foundation (CAF) is a nonprofit organization dedicated to advancing public interest and education in architecture and design. CAF presents a comprehensive program of tours, exhibitions, lectures, special events, and adult and youth education activities, all designed to enhance the public’s awareness and appreciation of Chicago’s outstanding architectural legacy.

Chicago Chocolate Tours

230 S. Clark Street, Suite 119
Chicago, IL 60604
phone: 312-929-2939

Join us for a Chicago Chocolate Tour! We tour all year round, and our tours are exciting and inviting. Open tours take place every Friday, Saturday, and Sunday and private tours happen throughout the week and weekends. Join us in discovering wonderful chocolate in the Loop, Gold Coast and Wicker Park!

Chicago Cubs Wrigley Field Tours


Offering weekday tours (+ select weekend dates), tour stops include the terrace reserved seating, mezzanine suites, press box, home and visitors clubhouses, bleachers, security headquarters, dugouts and on-deck circles lasting a total of 90 minutes.  Personal cameras and video cameras are welcome. Tickets, @ $25 each, are available to purchase at the Cubs box office, online at or 1-800-THE-CUBS.

Chicago Food Planet – Food Tours

830 N. Michigan Ave. Chicago, IL 60611 (800) 979-3370

Chicago Food Planet specializes in Chicago food tasting and cultural walking tours through Chicago’s most famous, mouthwatering neighborhoods. All walking is suitable for every age group and fitness level and their 3-hour experiences are enjoyed by Chicago locals and tourists alike. All food tastings, enough for a hearty lunch, are included in the ticket price.

Explore the Old Town, Gold Coast and Lincoln Park neighborhoods with their award-winning Near North Food Tour ($45, all food included). Just west of Downtown, peruse the current artist colony that has become Chicago’s hidden foodie paradise on the Bucktown/Wicker Park Food Tour ($45, all food included). Enjoy China’s most famous, authentic cuisine from regions including Mandarin, Canton and Szechuan on their Chinatown Food Tour ($60, all food included). Get off-the-beaten-path and into the areas where Chicagoans call home.
Check out our video!

All food tours include mouth-watering food tastings from historic “mom-and-pop” specialty food stores and one-of-a-kind ethnic delis while offering a insiders view into Chicago’s rich history, treasured architecture and dazzling restaurant recommendations. Acclaimed by participants and media including CNN, USA Today and Bon Appétit, join us as we bring to life the local foodie artisans that are honored throughout Chicago.

Order tickets from Chicago Food Planet Food Tours or call 800.979.3370 or 212.209.3370.

Tastebud Food Tour… Super Saver Special !

550 N. Kingsbury 218. Chicago, IL 60654

For every Tastebud Food Tour ticket purchased by 5/31/2011 Tastebud Food Tours will donate $2.00 to Feeding America and provide each Tastebud guest a $2.00 discount. The Real Taste of Chicago. The Best Deep dish Pizza, Chicago style hotdog and more!

Chicago Ghost Investigations

446 North Wells Street, Suite 272, Chicago, 60610

Chicago Ghost Investigations seeks the unknown and invites you to do the same. Twice daily, guests conduct investigations at some popular and little known haunted locations. Armed with several types of sensors, detectors, imagers and cameras, you will be able to explore the unseen. You will be taught how to use ghost hunting equipment which will enable you to locate the spirit activity, as well as a psychic technique which will allow communication between you and the spirits. Veteran paranormal investigators will be with you for guidance. Reservations are preferred. Reservations required. The “investigation venue ” changes everyday and is disclosed while reservations are being confirmed. Private parties are available.

Chicago Greeter-Free Tours

Enjoy the local points of interest on these two to four hour visits as well as some of the Greeters’ favorite spots. Navigate the City with your Greeter on complimentary public transportation for the ultimate Chicago experience.

Chicago “L” Tours

Cell: 312-636-8968

Take a personalized tour of the world-famous Chicago “L” by the AUTHOR of the popular new book, The Chicago “L”. See where the “L” got started; ride the Loop “L” and key lines; hear how the “L” developed; learn about competitors of the “L”; discuss movies that feature the “L”; see beautiful architecture; take pictures; etc. Celebrate a working antique, Chicago’s greatest, most colorful icon!

Large or small groups can email or call to set up a time and place to meet.

Chicago Photo Safaris

Various Chicago locations, Rockford, IL & Madison, WI
phone: 1-815-222-2824

A professional photographer will give you an easy-to-understand orientation on good photography technique and take you to places to get the best shots. The 40 minute overview will truly help you understand and put you in control of your camera. We will explain what all those features on your camera do, especially the ones controlling F-stops, shutter speeds, white balance, and ISO.

At each point along the way we will review your photos as you are taking them, helping you to correct exposure, composition and white balance right on the spot, so that you can immediately see the effect of your own corrective measures. This hands-on training will give you invaluable photo techniques for your future travels. So, before you go on that big trip come see us first! Got a new camera and don’t know how to use it? Help is on the way through our Chicago Photo Safari!

Chicago Red Cap Walking Tours

Intersection of Dearborn St. and Adams St. Chicago, 60604
phone: 312-927-0689

Chicago Red Cap Walking Tours explore Chicago’s history through its architecture. On the tours you will see Beaux Artes, Chicago School, Art Deco, Modern, and Post-Modern architecture and learn how and why the skyscraper evolved and the part Chicago played in its evolution. The buildings are more than static monuments to the past and more than exhibits in an open air museum. They were also chess pieces in a larger game.
The city is dynamic; learn how the past still exerts its influence today especially for those who are aware of it.

Chicago Savvy Tours

401 N Michigan Ave, Chicago, IL, 60611
phone: 773.242.0084

The Chicago Savvy Architectural & Historical Tour is a 90 minute architectural and historical walking tour of downtown Chicago. Guests will explore the Chicago riverfront, the theatre district, the federal district, the Michigan Avenue cliff of buildings, Millennium Park, the Art Institute of Chicago, and more. The tour is composed of both historical and modern architecture as well as fascinating facts and stories about Chicago history. Reservations can be made on the website or by calling 773.242.0084. Tickets are $20.

Chicago Theatre Tour

The Chicago Theatre
175 N. State St., Chicago, IL 60601

The tour encompasses historical and architectural highlights of the building, including the grand lobby areas, majestic auditorium and backstage space (when possible) where performers through the years, have left their autographs on the walls of dressing rooms and corridors.

Guides will share with you the stories of the visionaries who opened The Chicago Theatre, whose influence on popular entertainment in Chicago is still recognized today. Tours also include the photo exhibit in The Chicago Theatre’s lower lobby, “Chicago: Three Centuries of Theatres.”

Chicago Theater Stories Walking Tour

Southwest Corner Randolph St & Michigan Ave Chicago

Stroll around the downtown theater district and hear stories from the Golden Age of Chicago theater, a century defined by a pioneering spirit and cataclysmic events. Against this backdrop, colorful personalities forge rivalries, emote passion and vie for audience adulation. Group tours available. Reservation required. 11am, 1pm & 3pm daily.

Chicago Underground Loop Pedway

phone: 773.593.4873

Chicago’s Pedway, a series of heated walkways, passages and tunnels, serve as the backdrop for an amusing and enlightening tour of some of the hot-spots (or a least warm-spots) of downtown Chicago. Focusing on interesting anecdotes and tales about some of the great buildings downtown, the Chicago Pedway Tour is given by improviser and tour guide, Margaret Hicks. These are great tours for Chicagoans who want to learn more about the city and for tourists who want a full Chicago experience without ever going outside. “The Pedway is such a weird and wonderful place, it’s like a whole other world down there. Parts of it are scary, parts of it are beautiful but all it is pretty warm – and that’s a big plus,” says Hicks.

Monday/Thursday at 10:30AM. Meet at 40 W. Lake by Chase ATMs. Tour is 90 minutes and costs $15.00. Cash only and reservations are required.

Foreign Language Tours of Chicgo

(773) 276-6683

Chicago Tour Guides Institute is an office of many foreign language speaking guides for walking tours, motorcoaches, limousines, museums, tradeshows. Rates vary on language. Our office has been providing tour guides in English and many other foreign languages for 18 years in the Chicago area. Whether it is one person or groups of two hunded. Call and ask for Michael Reis.

Guided Tours of Chicago


Tour Chicago with Beverly Livingston, a CTPA certified guide whose repertoire includes highlights, art & architecture, ethnic neighborhoods, the River, etc. French also available.

Haunted Historic Tours

11500 S. Beloit, Worth, IL 60482

You can experience the Historical Locations and their history along with the spirits that have become another historic part of the locations. These are not just bus tours, but the ability to explore many of the haunted historical locations and possibly experience the spirits that are within or surrounding the historical sites you will be visiting.

IIT/Mies Society Architectural Tour

3201 State Street, Chicago, IL 60616

Ludwig Mies van der Rohe’s influence reaches every skyline in the world, and is seen in every open-plan interior space. He inspired the most prominent architects of our time, and continues that influence today. Nothing better expresses Mies’ philosophy than the campus of the Illinois Institute of Technology (IIT), which contains his masterpiece, S. R. Crown Hall. A modern icon and National Historic Landmark, Time magazine called Crown Hall “one of the world’s most influential, inspiring and astonishing structures.”

Campus buildings by architectural stars Rem Koolhaas and Helmut Jahn, as well as a renewed interest in modernism, have led thousands of visitors to campus each year to experience this living museum of modern architecture, a recent addition to the National Register of Historic Places.

IIT’s Mies van der Rohe Society offers architectural tours that tell the story of Mies and IIT. Join us for a docent-led or self-guided audio tour – available Monday through Sunday, except major holidays. $5 per person. Call 312.567.5014 for details.

Millennium Park Tours

Learn more about Millennium Park, through one of its many free tour options that begin in May, including guided walks by Chicago Greeters and tours of the Lurie Garden led by volunteer University of Illinois Extension Master Gardeners.

Off the Map Chicago Architectural Excursions

South Michigan Ave., Chicago, 60605

Off the Map Chicago takes you on Chicago architectural tours in the most personal way possible—on private excursions that give you the chance to explore great architecture inside and out. The brilliance of Mies van der Rohe comes alive on our private visit to the Farnsworth House. We also focus on Frank Lloyd Wright with a private tour of the Robie House. And we’ll take you to see stunning examples of Prairie houses all over the Chicago area.

Visit our website:  for information, reservations and rates. Or call Larry Simon at 847.951.5521.

Route 66 Walking Tours in Chicago’s Loop

Jackson Blvd. & LaSalle St,, Chicago, IL 60602

Walking Tours are scheduled daily to help visitors find the path of Route 66 through Chicago’s Loop and to understand the rich history of the city’s highways of the past. Tours last about 2 hours, advance reservation required.

SculpTours: an inside look at outdoor sculpture

downtown Chicago
phone: 312-805-2625

In-depth walking tours of Chicago’s world class public sculpture. Join professional sculptors & educators, Christine Rojek & Carol Hammerman as they guide you through Chicago’s “museum without walls”. Discover both the iconic and the hidden treasures of the city’s diverse sculpture collection. The Rojek/Hammerman team will draw from their backgrounds in art education, as well as their intimate knowledge of the Chicago sculpture community to engage you in this unique open-air classroom.The tours are informative and accessible to art enthusiasts as well as beginners, providing tips and tales that you won’t find in any history book.Tours include Millennium Park, Millennium Park plus Grant Park, Loop and Chicago Sculptor’s Studio Tour. Private and custom tours always available.

The Second City Neighborhood Tour

1616 N. Wells St, Chicago, 60614
phone: 312-337-3992

The walking tour begins outside The Second City theatre on North Wells Street and winds its way through the historic Old Town neighborhood. The tour ends inside The Second City theatre and gives guests a chance to view the lobby photo display documenting over 50 years of comedy at The Second City.

SeeMore Shopping Tours

“See More” of Chicago’s Local Stores, Boutiques and Designers.
Chicago is an amazing shopping destination and navigating the local shopping scene can be a bit daunting. SeeMore Shopping Tours can guide you through Chicago’s favorite shopping destinations, while helping you discover a few hidden gems along the way.

Choose from our unique destination and themed tours. A different tour every weekend. SeeMore Shopping’s Tour Schedule:

Reserve tickets on-line, by phone: 312.902.2135 or email: .
Availability is limited. Advance ticket purchase is required

ShopWalk Neighborhood Tours

Bucktown Tour departs at Café de Luca: 1721 N Damen
Lincoln Park Tour departs at Vosges Chocolate: 951 W. Armitage
773 255 7866

Explore Chicago’s hippest and prettiest neighborhoods for shopping. Your ShopWalk guide will escort you on a walking tour to the neighborhoods’ most unique boutiques that you won’t find back home or on the Magnificent Mile, as well as neighborhood trivia, exclusive discounts, and local treats.
Open tours generally run on Monday through Friday 11am-1pm and Saturday and Sunday from 12 noon to 2pm. Advance ticket purchase is required.

Theatre Hikes

Various, including Morton Arboretum & The North Park Village Nature Center
At a theatre-hike audiences are taken on a two mile hike and a full play is presented bringing the audience to different outdoor locations for each of the play’s scenes.

Tours R Us Chicago

2600 N. Lakeview
phone: 773 575 3176

Specialize in personalized tours that meets the special requirements and desires of the client. Those tours may include architecture, sculpture, neighborhoods, history and special attractions.

Urban Shop Guide

(312) 533-1256

Break away from the traditional shopping alternatives to a truly unique Chicago experience. Urban Shop Guide is a full-service shopping tour of Chicago’s fashion treasures buried in its most vibrant neighborhoods.

Your party will be chauffeured in a luxury vehicle, be provided shopping itineraries for local boutiques, offered drinks and food of Chicago heritage and a personal guide for their shopping experience. Walking tours also available

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