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.
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.
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.
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.
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 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
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
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
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
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.