Chicago Line Cruises

"Without question the best architectural tour available in Chicago; witty, informative, engaging."

Offering architectural boat tours on the Chicago River and Private charters.

Architectural Cruises

Explore the City that Defines Upward Mobility

If you’re looking for a great story, this one is incomparable. Not only does the river run through it - the river runs backwards. This is the city that put up the first skyscraper, and virtually redefined the 20th-century urban landscape. No matter how you look at it, this is an American saga writ large. Chicago’s growth took almost everyone by surprise, and it will take your breath away when you see it by water.

“One thing that makes Chicago so appealing is the fact that the river does run through it, so the buildings are spaced very nicely,” Kathleen Murphy Skolnik, docent.

“Here’s this narrow, sheltered river, with all of these magnificent buildings, almost so close to the boat that you could reach out and touch them,” Diane Gonzalez, docent.

“Having a tour from the river is a totally different perspective than from being on a bus or from being in a car or just walking by, “ B. Victor Adams, docent.

“You’re going to travel down through one of the greatest mixes of modern architectural styles, just sort of almost as though somebody deliberately said, ‘Let’s arrange these in a very effective manner,’” F. Patrick Kelly, docent.

“You’re looking at some of the most interesting architecture in the world, and you have the ultimate urban experience. You’re on a boat, in the river, and you see an elevated go overhead. You can’t have that experience anywhere else in the world,” Judith Randall, docent.

Chicago is a legendary city, with a legendary resume: The Great Fire, the “L” train, the birthplace of modern architecture. And there’s no better person to teach you that than a docent on the Chicago Line. Critics say that if you have only two hours in Chicago, this is how to spend it.

“Docent means ‘teacher’ or ‘tour guide.’ The whole point is to teach people something,” Judith Randall.

“I’ve had people tell me - they’ve been to Chicago three or four times - ‘I know what I’ve seen, now I understand what I was seeing,’” Al Walavich, docent.

“The credibility for Chicago Line Cruises comes down to the fact that we have great tour guides,” B. Victor Adams.

“Most of the tour guides have a background in history, or art, or architecture,” Kathleen Murphy Skolnik.

To book your exciting trip on the Chicago Line, you can call 312-527-2002, go online to, or ask your hotel concierge.

“Chicago Line tour is located on Ogden Slip, which is another part of Chicago history. We’re two blocks from Navy Pier,” Judith Randall.

“And with the Spire going up right across from us on Ogden Slip, I don’t think we can ask for a greater location,” B. Victor Adams.

“I would encourage anyone who’s interested in the city, in architecture, in water travel, to see the city this way, “ Diane Gonzalez.

“You’re gonna be getting some history, you’re gonna be getting some architecture, you’re gonna understand a bit of the characters of Chicago,” Al Walavich.

“You’re gonna see Chicago and you’re gonna enjoy it and you’re gonna get a nice ride through a beautiful city,” B. Patrick Kelly.

Sail with us and discover the city that redefined cities.

Read Video Transcript | Hide Transcript

In the world of iconic architecture, only a few images are so instantly recognized they need no subtitle. 

Think of St. Peter's Basilica, the Taj Mahal, and the Notre Dame Cathedral.

Or the unmistakable skyline of Chicago.

Each year thousands of architecture lovers make a pilgrimage to this birthplace of the skyscraper. Countless more book passage aboard our enthralling river tour, widely considered the best 90 minutes a visitor can spend anywhere in the city.

Critics say that no other city has influenced and embodied the state-of-the-art in high-rise design and modern architecture as prominently as Chicago; virtually every major architect has a signature building here.

It [modern architecture] all started here ... in the long grass of the prairie.
— Frank Lloyd Wright, famous Chicago Architect

Join us for a jaw-dropping excursion through the city that defied all expectations ... even the laws of gravity.

Chicago's ambitious business leaders in the late-1800s (after most of the commercial district had been erased by the Great Fire) faced a quandary. Hemmed in by water on three sides and a rail center to the south, they knew that if the city were to grow, it would have to grow up. "Limited as to ground, business sought the air," wrote an observer, as quoted in Donald L. Miller's City of the Century.

"Not since man began to pile one stone upon another," wrote an influential French critic, "has so difficult a problem (as tall buildings) been presented to the architect."

The Merchandise Mart

Chicago is where that problem was solved.

Sail with us and learn how the devastating Fire jumped a river and cleared the way for visionaries of plate glass and structural steel such as Jenney, Root, Burnham and Sullivan (Wright's mentor). Over less than a decade, the Chicago School of ingenious grillage foundations and steel-frame construction techniques lifted all architecture heavenward.

However, not all of Chicago's landmarks are vertical.

On board our expert-narrated cruise you'll learn how smoldering debris from that 1871 inferno hastily plowed into Lake Michigan, forming the basis of the 2,800-acre landscape masterpiece that today is Grant Park (now home to Frank Gehry's inimitable concert Pavilion).

And you will learn how a merchant by the name of Montgomery Ward, virtually alone, waged a fanatical 25-year legal crusade to keep our glorious lakefront "free and clear" from other Chicago barons who wanted Grant Park for an industrial factory zone.

Panoramic Buildings by Bob Segal Bob L. Segal is a Chicago photographer who currently resides in Lincoln Park Illinois. He has an economics degree from Georgetown University and an MBA from Northwestern University. Click here to find a larger collection of his work.   

Panoramic Buildings by Bob Segal

Bob L. Segal is a Chicago photographer who currently resides in Lincoln Park Illinois. He has an economics degree from Georgetown University and an MBA from Northwestern University. Click here to find a larger collection of his work. 


If you are thinking that they should build a monument to Ward – they did.

Ward's countenance is one of eight large busts that front the Merchandise Mart. Originally built as a warehouse for Marshall Field and once the crown jewel of the Kennedy family portfolio, the fabled "MM" holds more office space than any structure on earth, except for the Pentagon.

Chicago also has more moveable bridges than any city in the world, including the forebear of all bascule spans, the great Michigan Avenue Bridge. Opened in 1920 to fireworks and marching bands, this bridge was (and still is) an engineering marvel that befits a city which decades earlier managed to reverse the course of the river on which it stands.

Come aboard. Discover why Theodore Dreiser called Chicago the "Florence of the Midwest." There is no place like it, and no better way to see it than from the deck of our flagship Ft. Dearborn or the classic Innisfree.

Our expert-narrated Architecture Tour will take you up, up and away.

Click HERE to see the Architectural Cruise Route.

Private Architectural Cruises are available, Monday through Thursdays, up to 35 passengers, during the evening and day, and can travel on the lake or the river.  Starting at $2,240 for two hours, includes all that is listed below.


Passage is $42 per adult, $35 per senior (65+), and $20 per child (ages 7-18) and each includes complimentary Starbucks Coffee, Twinings Tea, soft drinks, and fresh-baked muffins or cookies.

State and local taxes are not included. Children 6 and under are allowed free passage, space permitting. Tickets are non-refundable; however tickets may be exchanged for other dates/times, space permitting. Routes and schedules are subject to change due to weather, Chicago lock operations and bridges. Please call to confirm schedule. 

Ticket Office

465 N. McClurg Ct.


Chicago Line Cruises

North Pier Docks

Ogden Slip at McClurg Ct.

Chicago, Illinois 60611