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THE EXPLORER'S ITINERARY

With so many sights to see, it's nice to have a guide. See all of Chicago's unique sights with specialty tours great for private groups.

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If you're someone who likes to take the road less traveled, consider some of Chicago's many off-the-beaten-path options. These Chicago companies are the go-to for groups looking to do private tours for corporate outings, convention attendees, student/youth groups or other small groups.

 

UNIQUE HISTORY

Chicago Architecture Foundation
224 S. Michigan Ave., Chicago
Looking for a unique journey through Chicago history? Sign up for the Devil in the White City Tour, where volunteer docents from the Chicago Architecture Foundation will bring Erik Larson's bestselling, true story of Chicago's 1893 World's Fair to life.

Chicago Hauntings
For an eerie walk through Chicago's supernatural past, hop aboard a bus with Chicago Hauntings for The Original Chicago Hauntings Tour, which takes groups through the city's most haunted historical sites.

 

UNIQUE VIEWS

Chicago Detours
Go underground with the Pedway Tour, which guides groups through a web of concealed tunnels underneath approximately 40 blocks of Chicago streets. 

Inside Chicago Walking Tours
It's one thing to see a building on a bus or boat, but the exterior is only half the fun! Go inside for the complete story, and hear tales from a unique perspective — the settlers, immigrants, architects and revolutionaries who explored, created and lived their lives in Chicago.

Chicago Helicopter Experience 
2420 S. Halsted, Chicago
Give your group an unforgettable experience from the air with a daytime, twilight or nighttime helicopter ride. They'll marvel at the spectacular views of the skyline and Lake Michigan.

Wateriders
950 N. Kingsbury St., Chicago
Once your group has seen the city by land and air, it's time to grab a kayak and see it from the water. A professional guide with navigate alongside your adventurous travelers through downtown Chicago by way of the Chicago River.

 

EXPLORE BY BOAT

With Lake Michigan providing some of the best skyline views and the Chicago River cutting right through the downtown area, a boat tour is one of the best ways to acquaint your group with our city.  

Chicago's First Lady
Michigan Avenue and Wacker Drive
This cruise company is partnered with the Chicago Architecture Foundation to provide one of the most authoritative, architecturally focused tours in the industry.

Shoreline Sightseeing 
Navy Pier
Shoreline Sightseeing has shown off Chicago for over seventy years with a variety of river and lake tours. For a fast and fun way to see the sights, take your group on a Shoreline water taxi.

Spirit of Chicago
Navy Pier
And for a cruise ship experience, don't miss a trip on a newly-renovated vessel that offers dinner, entertainment and, of course, an amazing view.

Wendella Sightseeing Tours
Various Locations
For a trip that includes a journey out to Lake Michigan and some food and drink tastings, book a Wine & Cheese or Beer & BBQ cruise with Wendella.

 

EXPLORE BY BUS

After your group has cruised the water ways, it's time for them to hit the pavement with some of our city's amazing bus tours.

Big Bus Tours
This hop-on hop-off bus takes groups on an extensive route and offers the flexibility to get off the bus to explore areas of interest. Choose from 24-, 48- and 72-hour tickets.  

Chicago Gray Line
For a comprehensive tour of all things Chicago, consider Gray Line's Inside Chicago - Grand Tour. The four-hour tour covers most of Chicago's expansive outer drive, parks, and includes stops at the Lincoln Park Conservatory and Museum Campus.

Chicago Trolley & Double Decker Co.
The Hop-On Hop-Off sightseeing tour with covers 13 miles of our city's amazing retail, cultural, and family attractions. Guests can stay on board for a full orientation of Chicago, or hop off at any one of their many stops and start exploring the city first hand. 

 

EXPLORE BY BIKE

With more than 170 miles worth of bike path, including a 26 mile-long stretch along the city's lakefront, we encourage your group to pedal its way through Chicago.

Bike and Roll
Various Locations
Choose from several guided tours, ranging from an exploration of Lincoln Park to a nighttime ride to the fireworks on Lake Michigan. 

Bobby's Bike Hike
Various Locations
This is a convenient option for groups who are looking for a fun, guided tour through some of Chicago's off-the-beaten path spots. Bike through neighborhoods, sample iconic Chicago foods or even take a night tour.

 

EXPLORE BY SEGWAY

For a unique perspective on Chicago, your group will have a blast with our city's Segway tour options.

Absolutely Chicago Segway Tours
228 E. Monroe St., Chicago
This fun Segway company offers an eight mile glide that starts in either Millennium Park or Navy Pier. See landmarks, architectural masterpieces and public art pieces. 

Segway Experience of Chicago
224 S. Michigan Ave., Chicago
Glide your way down the Riverwalk and through parks in style with this Segway company, offering a variety of architecture and themed tours.

Steve's Segway Tours
155 N. Harbor Dr., Chicago
Choose from an array of tours, from Lakefront/Museum Campus tours to themed trips like a Hot Chocolate and Cool Segways Tour.  

 


Segway Experience of Chicago
224 S. Michigan Ave., Ste. 113
Chicago, IL 60604
(312) 663-0600
Absolutely Chicago Segway Tours
238 E. Monroe
Chicago, IL 60603
(312) 552-5100
Shoreline Sightseeing Company
Navy Pier
Chicago, IL 60611
(312) 222-9328
Chicago Detours
Various Locations
Chicago, IL 60603
(312) 350-1131
Bobby's Bike Hike - Quality Tours, Rentals, & Urban Adventures
540 N. Lake Shore Dr.
Chicago, IL 60611
(312) 245-9300
Spirit of Chicago
Navy Pier
Chicago, IL 60611
(888) 957-2634
Chicago Trolley and Double Decker Co.
Water Tower Pumping Station
Chicago, IL 60611
(773) 648-5000
Shoreline Sightseeing Company
Navy Pier
Chicago, IL 60611
(312) 222-9328
Wendella Sightseeing Boats
400 N. Michigan Ave.
Chicago, IL 60611
(312) 337-1446
Chicago's First Lady Cruises
112 E. Wacker Dr. on Chicago's Riverwalk
Chicago, IL 60601
(847) 358-1330
Chicago Architecture Foundation
224 S. Michigan Ave.
Chicago, IL 60604
(312) 922-3432
Chicago Helicopter Experience
2420 S. Halsted St.
Chicago, IL 60608
(855) 414-8687
Inside Chicago Walking Tours
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Chicago, IL 60625
(312) 799-0164
Bike and Roll Chicago
239 E. Randolph St.
Chicago, IL 60601
(312) 729-1000
Big Bus Tours Chicago
630 W. 41st St.
Chicago, IL 60609
(877) 285-4796
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