Guide to Chicago Boat, Bus, Bike, Walking, Theatre & Segway Tours

Intro

Chicago is a large urban landscape with much to offer. Multiple, diverse neighborhoods, unique architecture, well-known attractions and lesser-known treasures can be found throughout the city. Yet with this endless list of choices, a visitor to Chicago can easily feel overwhelmed. If you only have a limited amount of time in the Windy City, how can you see it all?

An excellent way to see more of the city is by tour. Tours allow visitors to glimpse parts of Chicago that they might not otherwise discover, as well as learn information about the city from a knowledgeable tour guide. Yet even the sheer number of tours available to visitors can be daunting. Chicago Traveler has organized tours of the city in this article, ranging from boat tours to walking tours and everything in between. This way, you can choose precisely what you want to see and how you want to see it!

Prices for tours are quite affordable. While the range is of course quite broad, you can expect to find a tour that fits your budget and your interests. For more information about all tours available in Chicago, check out our helpful Chicago General Tour Information Directory.

Boat Tours

Boat Tours typically depart from Navy Pier and can vary widely in price and level of luxury. You can choose from different routes, including Lake Michigan, the Chicago River, or a combo of both. These tours usually include narration by a guide, but also allow time to eat, mingle and simply gaze at the view. For the visitor who wants a leisurely tour on a comfortable carrier, boat tours are the way to go. See the skyline in style and create memories that will last a lifetime.

One of the most popular boat tour choices is Odyssey. Odyssey is a luxury boat located at Navy Pier that offers Saturday and Sunday Brunch cruises, weekday Lunch cruises, Dinner cruises, Dinner and Fireworks cruises (in the summer), a Sunday Sunset cruise and a Moonlight Lounge cruise. The Odyssey promises a picturesque, ambience-filled afternoon or evening and is perfect for that special anniversary or date. Even if you don’t have a special occasion in mind, this cruise will put you in a celebratory mood! Prices vary widely and there are discounts for children on some of the cruises. Cruises are 1.5 hours to 3 hours, depending on the type.

Shoreline Sightseeing is another cruise company that offers a variety of tours. Laid-back and sure to offer breathtaking sights and a breezy good time, Shoreline is very popular amongst tourists and locals alike. Most of its tours depart from Navy Pier, with the exception of the Skyline Tour which departs from both the Shedd Aquarium and Buckingham Fountain. Popular tours offered by Shoreline include the Architectural Cruise on the Chicago River, offered from April through November. There are also Fireworks cruises, Water Taxis and a Two-Day City Sampler. Most tours offer snacks and are ½ hour to 1 hour on average. Prices are affordable, with tours under $30 and special pricing for children. Read a review of this tour.

Other popular choices include Mystic Blue, Seadog, Spirit of Chicago and Wendella. For more information about all boat tours offered in Chicago, see our Chicago Sightseeing Cruise Directory. Also check out the Boat Tour Comparison Chart, which puts all pricing, location and dining info in one easy to read chart.

Bike Tours

Bike tours are a fun way to see Chicago. These tours are not limited to professional riders; visitors of all ages, including children, will be able to keep the pace and have a good time. Bike tours allow you to cover more ground than a walking tour, and thus are a good choice if you want to see a lot of the city in just one day. Also there is certainly something festive about spending the day bicycling in a group! Bike rental is always included in the cost of the tour.

Bobby’s Bike Hike provides you with a comfortable cruiser-style bicycle and a helmet; with these, you’re ready for one of the most unique and relaxing tours of the city. There are three tours from which to choose: the Lakefront Neighborhoods Tour, the Quintessential Chicago Tour and the Sunglasses at Night Tour. Prices vary depending on the tour, with discounted prices for children. Each tour lasts 2 to 3 hours and departs from the Bobby’s Bike Hike office at River East Docks, 465 N. McClurg Court.

Bike Chicago is another excellent company that offers bike tours. Strap on your helmet, hop on your high-performance cruiser and get ready to hit the pavement! Choose from several tours, including a Lakefront Tour, Neighborhoods Tours, the Spectacular Sculpture Tour and Sites at Nite, which includes a boat tour in the price. Prices vary, with special discounts for students, seniors and military personnel. Tours depart from Millennium Park and from Navy Pier.

Bike and Roll is another company that offers bike tours, and is affiliated with Bike Chicago. For more information about bike tours and to book a tour, see our Chicago Bike Tours Directory.

Neighborhood Guided Walking Tours

Taking a walk through Chicago’s various neighborhoods can be a great way to get off the beaten path and really get a taste for the diverse flavors the city has to offer. Each of the city’s neighborhoods is distinct and the more you experience, the better you appreciate how multifaceted the city really is. You will find as much that will excite and engage you as you will at the mandatory tourist attractions. Come take a walk and see!

The Chicago Cultural Center offers several Neighborhood Tours, including Devon Avenue, Historic Bronzeville, Greek Town, Little Italy, Ukrainian Village, Uptown and several others. Many of these tours take you to ethnic neighborhoods where the friendly residents, imported goods and aromatic food will draw you in and make it very difficult to leave! There are also special interest tours including The Great Chicago Fire, Chicago’s Magnificent Churches and Great Cemeteries of Chicago. All tours depart from the Cultural Center. There are special discounts for children, students and seniors. Tours are four to five and a half hours long and the price includes light refreshments or lunch, depending on the tour.

The Chicago Architecture Foundation is also an excellent resource for walking tours. The CAF offers dozens of tours that focus on specific neighborhoods or themes; some of these include Devil in the White City, Frank Lloyd Wright, Lincoln Park Zoo Architecture, Loop Retail Historic District, Historic Skyscrapers, Old Town, Printers Row and Wicker Park. Many of these tours are seasonal; more information can be found by contacting the CAF at 312.922.3432. Tours depart from different locations, depending on the type of tour. One of the best features of a CAF tour is that each one is led by a docent, or trained guide. Each guide is given hours of special training about Chicago history and architecture to ensure an excellent tour experience. Prices vary; there are discounts for children and seniors, and CAF members are free.

Walking tours offered by other companies include ShopWalk, Chicago Food Planet and Chicago Chocolate Tours. Delve into Chicago’s haunted history with a Ghost tour! Check out Chicago Ghost Investigations or Chicago Hauntings Ghost Tours. For more information on all walking tours, please check out our Chicago Walking Tours Directory.

Bus Tours

Bus Tours are a popular way to see Chicago in comfort. If you have small children, or do not wish to be on your feet for the day, walking or bike tours may not be the best option for you. Instead, get on board a comfortable bus! Buses are also a great choice when the weather is less than ideal.

The Chicago Architecture Foundation offers several bus tours with specific themes, such as Churches by Bus, Highlights by Bus and Parks & Boulevards by Bus. As with the CAF’s walking tours, bus tours are seasonal and depart from different locations, depending on the tour. Each tour is led by a specially trained guide with a passion for Chicago architecture and history. Prices vary and discounts are available for children and seniors. Admission is free for CAF members. For more information, contact the CAF at 312.922.3432.

The Chicago Trolley and Double Decker Company is another company that offers bus tours. Specializing in Hop-On Hop-Off tours, these double decker buses will transport you around the city, hitting several Chicago attractions and giving you the chance to get off at each one and explore; when you’re done checking out a particular stop, just hop on the next bus! Buses come by every 10-15 minutes. The tour is fully narrated and includes the following stops: Sears Tower, Millennium Park, the Art Institute, Museum Campus, Navy Pier, Water Tower and several more! Tours run year-round, seven days a week, excluding certain holidays. Prices vary depending on the package you purchase. Read a review of this tour.

Another company that offers bus tours is See it ALL Chicago Tours; this tour whisks you around the city in a mini-bus. For more information on all bus tours of Chicago, check out our Chicago Bus Tours Directory .

Theatre Tours

Chicago’s theatre scene is highly developed and draws visitors from around the world. While catching a show is usually high on the priority list for any visitor, a true theatre enthusiast will be thrilled to know that you can get a glimpse of what really happens behind the scenes at Chicago’s most famous theatres! How can you do this? It’s simple. Just take a theatre tour.

Broadway in Chicago Theatre Tours give you a unique perspective of the Ford Center for the Performing Arts, Oriental Theatre and the Cadillac Palace Theatre. These two venues have a long history in Chicago and currently feature award-winning Broadway musicals. Thousands of theatre patrons flock to these venues on a weekly basis, yet few know how things really work behind the curtain. This tour, offered on a weekly basis, guides you through each theatre and gives you a firsthand account of daily operations. You will hear how each theatre got its start, discover the origins of the plush and detailed décor and learn little-known, often humorous tales of the early days of each venue. Tours are very affordable and depart from the Ford Center.

A tour of the Chicago Theatre is available as well. Learn about the history and architecture of the theatre and hear stories of the famous people who have performed there, including Frank Sinatra, Sammy Davis Jr., Liza Minnelli and The Pointer Sisters! Gain a new appreciation for how historic the stage of the Chicago Theatre really is. Tours take place once or twice a week depending on the season. Each tour is one hour and is very affordably priced.

Wicked is a Broadway musical that is making great waves in Chicago. In honor of this show, there is a special Wicked tour available at the Ford Center for the Performing Arts. Offered twice a week, this tour will give you a glimpse of the actual set, props, costumes and masks used in the musical. Be “Wicked” in a way you never have before! Best of all, you will even have a chance to meet cast members and ask them questions. The tour lasts one hour.

Theatre Club Chicago also offers a guided walking tour of the Theatre District. For more information about tours of Chicago theatres, visit our Chicago Walking Tours Directory.

Segway Tours

Segway tours are a newer addition to Chicago’s roster of tours. Take a walking tour without actually having to walk when you climb aboard one of these personal transportation devices! You can whiz around the city with minimal effort. Make sure you get pictures of your family aboard these devices; they’ll be instant conversation starters! Kid-friendly and uniquely fun, a Segway tour is sure to be a hit.

City Segway Tours offers a guided tour of Chicago, hitting several stops and providing stories and facts along the way. You will visit Museum Campus, Grant Park, Buckingham Fountain, Millennium Park, the Lakefront, several famous Chicago skyscrapers, the Art Institute and several other attractions. Tours are offered three times a day and last 2 to 3 hours. Tours run between April 1st and November 15th and depart from 400 E. Randolph. All tours begin with an orientation to ensure that all participants are comfortable on their Segways. Reservations are required; call 1.877.SEG.TOUR.

The Chicago Segway Experience Tours are authorized by the manufacturers of the Segway. There are two tours to choose from: the Park Glide Tour and the Chicago Architecture Foundation Tour. The Park Glide Tour lasts two hours and takes you through Millennium Park, Daley Plaza, the Lakefront, Museum Campus and Grant Park. This tour is offered three times a day, seven days a week. The CAF Tour is led by a CAF docent and takes you along the Lakefront parks, giving you a detailed understanding of the architecture you encounter along the way. This tour is 2.5 hours long and is offered at 10 am on Saturdays only. There is a discount for CAF members. Please reserve beforehand, either online or by calling 800.979.3370.

For more information on Segway tours of Chicago, please visit our Chicago Segway Tours Directory.

Other Tours

While most visitors tour Chicago via the methods mentioned above, there are also some other options available to you.

Fly high above the city and witness views few are lucky enough to see; take a helicopter tour. There are several helicopter tour companies, including Magic Carpet Helicopters and Len Jablon Helicopters. For more information, visit our Chicago Air Tours Directory.

You can savor simpler times with a romantic horse and carriage tour; try either Chicago Horse and Carriage or Magnificent Mile Carriages. For more information, check out our Chicago Carriage Tours Directory.

Conclusion

Whether you choose to explore Chicago by foot, by bus or by boat, you can expect a truly unique experience. There are tours available year-round and all are meant to welcome you to Chicago’s landscape. Indeed, they welcome you to become part of the landscape as you whirl throughout the city, learning more about Chicago than you could have thought possible!