Fun on the Windy City's Waterways: A Guide to Chicago Architectural River Cruises

Enjoying Chicago’s Architectural Art Aboard a Boat

When you want to see art, where do you go? I imagine most of you would answer, “Why, I would go to an art museum, of course!” And normally, you would be absolutely right.

But I would argue that you would have to answer differently when it comes to the city of Chicago. Oh, don’t get me wrong, the Windy City has plenty to offer aficionados of paintings, sculpture and the like. The Art Institute of Chicago boasts world-famous selections from Georgia O’Keeffe, Edward Hopper, Georges Seurat and Dante Gabriel Rossetti.

Yet you don’t have to go there to see some of the city’s best art. You can enjoy that from the streets.

Or should I say from the Chicago River? Because the architectural masterpieces that line the waterways of America’s third-largest city are works of art in and of themselves. And nowhere can you see them better than from the deck of a riverfront cruise. Following you will find our guide to the best Chicago architecture boat tours.

What You’ll See: The Towering Treasures of the Chicago River

What can you expect to see on a Chicago River cruise? If you answered “buildings,” know that you are technically right, but you won’t get any points for it. Calling the architectural juggernauts that line the shores buildings is like calling a diamond a rock. It is both correct and not entirely helpful.

Fortunately, most architectural river tours follow a T-shaped section of the Chicago River, starting around the New East Side neighborhood and diverging north or south just past North Orleans Street. So most cruise goers can have an idea about what they will see prior to actually seeing it. As you travel west on the river’s main branch, you will behold…


Aqua (225 N. Columbus Drive ), a soaring edifice that looks like a race of man-sized wasps decided to colonize it as their home. From ground level, gleaming windows seem enfolded in papery swathes of organic material. They are just concrete balconies, but it makes for a strikingly soft look.

The brainchild of Jeanne Gang’s Studio Gang, it is the largest project to date ever awarded to a female-fronted architectural firm.

Tribune Tower

Though still called Tribune Tower (435 N. Michigan Ave.), this nearly century-old landmark no longer houses the offices of the Chicago Tribune. But the Windy City’s signature newspaper has its proverbial fingerprints all over this gorgeous neo-Gothic structure. Originally designed in 1922 as part of an architectural competition, Tribune Tower looks like a medieval church.

But instead of the design praising a deity, its lobby is adorned with quotes about the freedom of the press.

Marina City

Like Aqua, the two towers of Marina City (300 N. State St.) play with perspective, only it’s a decidedly more geometrical effect. From ground level, clusters of hemispheres overlap one another, making the building seem as though it is aping an edifice from the Golden Age of Science Fiction.

Actually, that’s not too far from the truth. Architect Bertrand Goldberg designed it as a futuristic residential structure to draw people back from the suburbs. Today, one of the towers serves as home to the House of Blues.

The Merchandise Mart

At one time, The Merchandise Mart (222 Merchandise Mart Plaza) was the world’s biggest building. Though since surpassed in size by other structures, this giant slab of art-deco goodness is glorious to behold. Recent environmentally-friendly renovations have earned the structure a LEED certification. Not bad for a big old building that once had its own zip code.

333 W. Wacker

333 W. Wacker is similarly stupendously sized, but it has an entirely different impact than the Merchandise Mart. While the Mart harkens to the past, 333 W. Wacker is entirely postmodern. A giant curved slab of mirror, the structure catches the skyline and throws it back at you. That’s intentional.

Architect Kohn Pedersen Fox designed its curve to mimic the particular bend of the river where it sits. Fun fact: Chicagoans have repeatedly voted the structure as their favorite building in the city.

At 333 W. Wacker, the Chicago River branches north and south. If your cruise takes you to the right, you’ll see…

Erie on the Park

Erie on the Park (510 W. Erie St.). This decidedly angular residential tower echoes parallelogram-shaped boundaries of its plot. A quirk of history, multiple railroad tracks crisscrossed the original location where this structure was built.

Montgomery Ward Complex

Four buildings compose the Montgomery Ward Complex, but you can’t see them all from the water. The river will bring you by a trio of structures built in 1899, 1907 and 1930. The 1974 building is downtown. An impressive slab of clustered units, the complex’s buildings no longer have anything to do with the now-closed mail-order retailer. They’ve since been converted into condominiums and office space.

Let’s go back to where the river splits and head south. As your boat slides through the water, you can glimpse…

The Boeing Corporate Offices

The Boeing Corporate Offices (100 N. Riverside Place), which no longer actually serve as the headquarters for the plane manufacturer. Boeing moved to Seattle in 2003, but still owns the property. A 36-floor-high building, it now hosts a number of corporate clients. Its clock tower rises high above the building’s top floor.

CME Centre

Once a hubbub of screaming traders making (and losing) fortunes in the blink of an eye, the CME Center (20 S. Wacker Drive) was once known as the Chicago Mercantile Exchange, a place to trade futures and options. Today, though, much of that action occurs in utter silence online.

A no-nonsense edifice every bit as serious as the financial business transacted within, it has at least one unique architectural feature. In order to accommodate the giant, unsupported trading area the Exchange needed, the building’s towers curved outward to support the weight of the ceiling.

Sears Tower

With our next building, understand one thing: Chicagoans don’t call it the Willis Tower (233 S. Wacker Drive.). Yes, that’s technically its name. However, the 110-story-tall skyscraper with the twin white spires will forever be known as the Sears Tower despite Willis Group Holdings opening an office in the building in 2009 and changing the name.

Once the largest tower in the world, other structures in Dubai, New York and Taiwan have outstretched it.

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How You’ll See It: Finding the Best Boats to See the Stupendous Structures

When it comes to seeing The Second City’s structures, there are almost as many companies offering architectural river cruises as there are buildings scoring the Chicago skyline. Is that an exaggeration? Maybe, but it is not that far off. The boom in cruises has not only improved tourism, it has also caused a raft of somewhat sketchy operators to appear.

How can you make sure you get to enjoy the best Chicago architecture boat tour? Well, one way is to limit yourself to the operators connected with, the city’s official tourism arm. These include…

Wendella Tours & Cruises

Wendella Tours & Cruises ((312) 337-1446), the oldest company that cruises the Chicago River. Having existed since 1935, it bills itself as Chicago’s Original Architecture Tour. Most of the vessels contain a climate-controlled lounge, so you won’t have to worry about sweating your way through a 75-minute cruise during the sweltering summer months.

Bartenders also serve up drinks and snacks, and you’ll even find bathrooms on board. The Chicago River Experience cruise offers an abbreviated version of the architectural tour that families with young children might find more enjoyable.

Additional cruises include a lake and river tour (which focuses on The Windy City’s history), a sunset cruise (which seems geared for couples), and a fireworks cruise (which lets you enjoy pyrotechnics on Wednesdays and Sundays from late May to early September).

Shoreline Sightseeing

Though Wendella may be the oldest architectural cruise, it’s not currently the most popular. That honor goes to Shoreline Sightseeing ((312) 222-9328), which TripAdvisor declared to be America’s most-booked tour. Participants have praised the guides’ enthusiasm, wit and humor in addition to their architectural knowledge.

Shoreline boasts 11 touring vessels, several of which were custom built for the best touring experience. Try to see if you can book a cruise on the open-decked Skyview, Cityview or Riverview vessels for a striking perspective on the buildings.

In addition to providing lake and firework tours, Shoreline operates a water taxi service. If you don’t want to fight traffic, search for a cab or Uber, or wear your legs out walking the streets, the water taxi can ferry you to many of Chicago’s favorite destinations.

First Lady Cruises

Some river cruise operations have earned reputations as being little more than spirit-soaked party barges. But that’s the furthest thing from the experience you will have on Chicago’s First Lady Cruises ((847) 358-1330). Partnered with the Chicago Architecture Center (which maintains an excellent database), it staffs its vessels with preeminently knowledgeable docents.

Indeed, knowledgeable is the appropriate word, because all of the tour guides have undergone 90 hours of training. “You can actually pay attention and learn something,” Janet Moon of Naperville told the Chicago Tribune. “It’s not just drunk people messing around.” Perhaps the additional commentary explains why First Lady’s architectural cruises run for a hour and a half rather than the usual 75 minutes.

Mercury Skyline Cruiseline

Mercury Skyline Cruiseline ((312) 332-1353) bills itself as the family-friendly river cruise option. Having operated for 83 years, it also provides architectural cruises. However, it spices things up with themed offerings. The Urban Adventure Cruise will provide the closest counterpart to most of the architectural cruises in this article.

It also has night cruises where participants get glow-in-the-dark wands, and the company hands out 3D glasses for its fireworks cruises. Do you have pooches rather than kids? No worries. Mercury offers a canine cruise, too.

Chicago Line Cruises

A smaller company, Chicago Line Cruises ((312) 527-1977) still has all of the excellence and expertise you would want for an architectural Chicago river cruise. Just glance at the biography page to see its certified docents, who have served as guides for an average of 17 years. They know their way around the place.

What’s more, Chicago Line also serves complimentary cookies, lemonade, tea and Starbucks coffee on its cruises and spices things up a bit by running an early evening architectural cocktail cruise. Then there are its Eco Boat Cruises, a partnership with The School of the Art Institute of Chicago to provide a unique limited series of outings examining the ecological issues facing the area.

Kayak Chicago

For an entirely different experience, consider trying a kayaking architectural cruise. Kayak Chicago ((312) 852-9258) hosts a three-hour-long architectural paddle that you can enjoy solo or in a tandem kayak. There’s also a nighttime tour where you can see the city lights spill across the water. The best part? You don’t need to have ever kayaked before.


Besides an architectural tour, Wateriders ((312) 953-9287) adds a Ghosts and Gangsters Tour. Learn about the rough-and-tumble history of the area during the 19th century as the sun sets over the river.

No matter which of the Chicago river tours you book, make sure you’ve landed with a reputable operator. No company should pick you up at strange locations or near businesses around the Riverwalk. They should also show their credentials whenever asked. If your guide won’t, you’ve likely booked with an unlicensed outfit. Consider walking away and finding someone else.

Why You’ll Walk It Out: There Are So Many Other Ways to See the City

Chicago boat tours are hot right know, and it’s easy to see why. They afford an opportunity to sit back, relax and watch The Second City’s sights unfold before you. There’s only one problem with it, though: You’ll hardly get to experience Chicago at its fullest that way.

An architectural cruise won’t give you more than the merest glimpse of notable buildings such as, say, The Rookery Building, the Chicago Board of Trade, the Sullivan Center, the Chicago Federal Center, and a whole host more.

How can you see them, then? A great place to start is the Chicago Architectural Center itself. In addition to river cruises, it offers themed tours by foot, bus, bike or “L” (Chicago’s elevated train system) — more than 80 of them. Chicago is one of America’s greatest cities, and an architectural cruise should only be the start of your fun.

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