Choosing Boat Tours in Chicago

As summer winds to a close this Labor Day weekend, we can still take advantage of the many boat tours of Chicago. Chicago is bursting with boat tour options, all that can be a fun way to experience Chicago architecture. To help you out as you plan a boat tour with family and friends, I decided to sort through the many boat tours in Chicago.

boat tours in chicago water taxi
The water taxi is one of the cheapest and quickest boat tours in Chicago. (Photo Credit: Wikipedia)

Water Taxi

Chicago’s water taxi is a quietly brilliant idea. The Chicago River is underutilized today, but it was once the city’s main artery for transportation. The water taxi has been putting it to that use again for over 50 years. Routes run on the North, South, and Main branches of the river and tie together spots as disparate as Chinatown and the Mag Mile.

The water taxi does not have a tour guide. It is simply transportation. While it’s not designed as a sightseeing experience, the water taxi is probably the cheapest and quickest of the boat tours in Chicago.

Kayak Tours

The original way of getting around Chicago’s waterways were canoes and kayaks paddled by Native Americans and French-Canadian voyageurs. Reconnect with that heritage by heading to the riverwalk for a kayak tour of the Chicago River. It’s an ideal outing during Chicago’s balmy summer weekends. In fact, the whole Chicago Detours team went on a kayaking tour with Urban Kayaks in May and had a blast.

River Boat Tours

Tour boats on the river are a very common sight during the summer. The most popular tour boat operators are Wendella Boats and Chicago’s First Lady. Both offer architecture and sightseeing tours from their docks near the Michigan Avenue bridge. The Wendella tours are a bit cheaper, though it’s worth noting that the prestigious Chicago Architecture Foundations organizes the tours on Chicago’s First Lady. These companies are the mainstays of the boat tours in Chicago, so I’d think either choice should work out.

Lake Michigan Cruises

The wide blue expanse of Lake Michigan offers up a variety of different cruise experiences. If you have a need for speed, Seadog Cruises does a speedboat cruise that looks thrilling or terrifying, depending on your disposition. Shoreline Sightseeing has a lakefront sightseeing tour that runs at day or at night beneath the bi-weekly Navy Pier fireworks. Anyone looking for a unique date idea can look into the dining cruises offered by Entertainment Cruises on its small fleet of yachts. That fireworks outing sounds terrific to me.

 boat tours in Chicago sailing cruise lake michigan
Sailing charters and cruise on Lake Michigan are among the most spectacular boat tours in Chicago. (Photo Credit: Pixabay)

Charter Sailing

As I mentioned in the list of the Top Ten Things to Do in Chicago this Summer, charter sailing tours are an amazing experience. Outfits like Chicago Sailboat Charters set your small party up with an experienced sailor. Most tours allow you to bring drinks and snacks, too. Sailing charters offer stunning sights and a beautifully slow-paced experience. Maybe you’ll even get close to the lighthouses?

Private Yacht

Not a casual affair, if you really want to do it up for your boat tour, then rent a private yacht! Likely more appropriate for a special occasion, companies like Windy City Cruises and Anita Dee have beautiful private boats for a luxury experience. And then of course, you could consider bringing on our Executive Director Amanda Scotese as your boat tour docent.

Our city is uniquely situated for aquatic sightseeing and has a surprising variety of boat tour options that allow you to see Chicago architecture from a unique perspective. And locals and visitors alike should have a good time with the boat tours in Chicago. Most boat tours run around March through November, so hurry up as your time is running out this season!

-Alex Bean, Chicago Detours Tour Guide


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Private Tour Coordinator and Tour Guide

There is no shortage of things to discover in Chicago—I love being an urban explorer and uncovering its hidden places. I have an MA in Public History from Loyola University Chicago, and I have worked as a museum educator and kindergarten teacher. My desire to learn new things fuels my passion for educating others, which I get to experience every day as a Chicago tour guide. I live in the northern neighborhood of Rogers Park.

“Our guide Ellen was exceptional and gifted with a great personal touch.”


Tour Guide

Whether you are a first-time visitor or a lifelong resident, the vibrant history and modern majesty of Chicago never ceases to amaze. I’m a graduate of Columbia College with an M.A. in Interdisciplinary Art. I’ve worked for many years as an educator at City Colleges of Chicago. As tour guide at Chicago Detours, I integrate my enthusiasm for culture and architecture with my passion as an educator. West Town/Noble Square area is home for me.

“Jen was a perfect storyteller and kept us spellbound for hours.”


Tour Guide

With our Chicago neighborhoods, vibrant cultural institutions and nearly two centuries of larger-than-life stories, there’s never a dull moment here! I’m a fifth generation Chicagoan and a graduate of Washington University in St. Louis. In addition to guiding tours, I’m a creative writer and amateur genealogist. I also enjoy the city’s dynamic theater scene. You can also read overlooked stories from 19th-century newspapers on my “Second Glance History” blog. I live in River North.


Tour Guide

Chicago is unique as it always evolves into the future while holding on to the past. I’m fascinated by how people latch on to old architecture but happily pave over others. My background is in theater and performance and I’ve been a tour guide here for more than 10 years. Currently I’m finishing my Master’s in Public History at Loyola University because I love to teach the history of this scrappy city. I’m in the Edgewater neighborhood.


Operations Coordinator and Tour Guide

Chicago’s history is so fascinating, you could spend a lifetime uncovering its secrets…I’m willing to give it a try! I have an M.A. in US History from the University of Nevada-Las Vegas and then pursued doctoral studies in Urban History at the University of Illinois at Chicago. I love to learn new aspects of Chicago’s rich history and then share my knowledge as a tour guide with Chicago Detours. I live in Ravenswood.

“Marie was a bubbling fountain of information and contagious enthusiasm.”


Operations Coordinator and Tour Guide

As a fourth generation Chicagoan, I have been living and loving Chicago by bike, on foot, public transit or automobile. I am a graduate of UIC where through the College of Urban Planning and Public Affairs, began my eagerness to understand the nature, history and impacts of urban planning and development. It is incredibly rewarding to give back to this wonderful city by helping out in the office of Chicago Detours. I live in the incredibly diverse neighborhood of Albany Park.
“Sonny was extremely knowledgeable about all things Chi-town.”
Wade K


Content Manager and Tour Guide

Chicago has so many neighborhoods, buildings, and by-ways that it’s hard to go long without seeing something new, or something familiar from a new angle. I studied Cinema History for my M.A. from the University of Chicago. I’ve worked as a culture writer for various publications and as an educator of the humanities at the City Colleges of Chicago. I’m thrilled to share my love of this city’s busy past and unique architectural spaces with Chicago Detours. I live in the Chicago neighborhood of Lincoln Park.

“Alex was fascinating to listen to. He clearly knows his history and it shows.”
Katie K

Amanda Scotese

Executive Director and Tour Guide

I’m an interpreter of personal stories from the past and the city’s landscape. I love to imagine what originally happened inside old unmarked buildings, and what forces have shaped their design. I studied Chicago history, architectural history, and anything Chicago-related through my M.A. in the Humanities at the University of Chicago. My love for stories was enriched by my B.A. in Literature from the University of Michigan. I’ve written travel articles for publications like Rick Steves’ Italy best-selling travel guides, the San Francisco Bay Guardian, and The Chicago Food Encyclopedia. I live in the Chicago neighborhood of West Avondale.
“You can TELL Amanda is hyper-passionate about doing the research and getting the story that nobody’s heard before.”
Shelby F

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