Chicago River Architecture Tour

The first skyscraper was built in Chicago and completed in 1885 after William Jenny won an 1883 building design contest by the Home Insurance Company.  The first skyscraper at 138 feet had a 10-story design using a metal cage covered in stone for fireproofing. Preventing fire in downtown Chicago was a major concern after the great fire of 1871 destroyed much of the city’s business core. In 1890 two more stories were added to the Home Insurance Company building raising its height to 180 feet.  The Home Insurance Company building was demolished in 1931.

Leroy Buffington of Minneapolis designed the first metal cage skyscraper in 1880, but failed to secure financing for the project. He was eventually given the patent for the skyscraper in 1888 after several skyscrapers had already been built. The first skyscraper in New York, The Tacoma Building, was completed in 1889.

Chicago’s First Lady

In November 2011 I attended a press media tour of Radisson Blu Aqua Chicago. The Chicago Tourism Board provided some sightseeing excursions for the press. The Chicago Architecture River Cruise on the boat First Lady was a relaxing activity to rest for 90 minutes as the boat motors along the Chicago River and a docent sped through the history of so many skyscrapers along the waterfront that my head was spinning trying to figure out at times which building was being discussed. The tour was quite informative.

Now nearly six months have passed and I look at the photos taken from the First Lady and wonder what I see. The beauty of the internet is I can  spend a few hours doing some internet research and document the details from my photos. I love living with an internet library at my fingertips.

The Chicago River architecture tour covers an area known as the Michigan-Wacker Historic District. The area is known for eleven skyscrapers built in the 1920s.

The architecture attracts me to downtown Chicago. I don’t know much about the culture of Chicago as a tourist who has been twice in the past 18 months for a total of about one week in downtown Chicago.

The river boat architecture tour is one of the top activities for a Chicago visit. You get to see how the city kissed the sky.

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The Tribune Tower at 435 North Michigan on the right, home to the Chicago Tribune newspaper, was another skyscraper design winner completed in 1925.

The Wrigley Building, two white buildings on left in above photo was built in 1920-24 and was the first skyscraper in Chicago to have air conditioning.

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The Tribune Building features neo-Gothic design with flying buttresses at the top. There are apparently rocks from famous sites around the world, and even a moon rock, in this building.

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The clock tower of the Wrigley Building is 425 feet.  The building is illuminated at night, as it has been since 1921, and offers viewers one of the landmark sights of Chicago.

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There is a 14th floor walkway between the Wrigley towers. A courtyard passage takes you to McDonald’s, a small store, grassy space and Trump Tower. Thiese close-up photos of Wrigley are from my 2010 trip and these features are not seen from the boat.

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Terra cotta detail of Wrigley Building. The white terra cotta cladding gives the building vibrant exterior walls in daylight.

Trump Tower Chicago

This building has 98 stories and its rooftop at 1,170 feet is the second tallest building in Chicago and the United States. The spire rises to 1,389 feet.

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The lower floors of the building are the Trump Hotel. I toured the hotel rooms in October 2010 and published a Loyalty Traveler review of Trump International Hotel Chicago.

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London Guarantee Building built in in 1923, now known as Crain Communications, is the curved building on the left.

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London Guarantee Building at 360 North Michigan on the riverfront.

Mather Tower at 75 East Wacker in the background at 521 feet high has an octagonal tower on top of a traditional building. It was Chicago’s tallest building when completed in 1928. Apparently the Mather Tower building was in disrepair with terra cotta falling off to the street below in the 1990s and there was discussion of dismantling the top section. It is a skinny skyscraper. The octagonal top was rebuilt only a decade ago. The building now functions as the River Hotel Chicago and the octagonal top floors as Club Quarters corporate hotel rooms.

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Hotels are a major aspect of the Chicago skyline along with corporate office buildings. One of the largest hotels in the city, and I read somewhere one of the hotels most used by U.S. Presidents for Chicago visits due to its secure accessibility, is the Sheraton Chicago Hotel and Towers .

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Sheraton Chicago Hotels & Towers.

35 East Wacker, also known as the Jewelers Building, was built from 1925-27 and originally designed as commercial offices for diamond jewelers with 22 floors of parking and car elevators as a security measure. At 522 feet the dome at top was originally the Stratosphere Restaurant. Chicago lore says Al Capone had a speakeasy in the dome during Prohibition.

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35 East Wacker Drive, Jewelers Building (1927)

Hotel 71, independent luxury boutique in Chicago with rates under $150. Obviously Hotel 71 is not a discussion part of the architecture tour, but I spy a hotel beside the Mather Tower in my photo from the boat.

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Hotel 71, Chicago and the Mather Building.

While not historically significant from the 1920s, all eyes marvel at the cylindrical towers of Marina City. House of Blues Chicago, Sax Chicago Hotel (a Thompson Hotel) and Westin Chicago River North hotel are located right around the towers.

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Marina City towers, Chicago (1964)

The lower floors are parking levels. I recall hearing comments from other passengers on the First Lady boat referencing the car through the window scene of Ferris Bueller’s Day Off and imagining this as a good movie scene location. It has probably already been done.

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Another view of Trump International Tower and Wrigley Building.

Victim of the Recession

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Could have been Shangri-La Chicago Hotel?

This building shell at 111 West Wacker was supposed to be a 90 story skyscraper and the first hotel in the US for the Hong Kong-based luxury hotel brand. The builder ran out of money in 2009, work ceased and Shangri-La Hotels contractually exited the project. Plans are now to build a 65-story apartment building.

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View east from Chicago River.

For some reason this next building at 333 West Wacker is a favorite of Chicagoans. It is at the confluence of the river where it changes from east-west to north and south in the city.

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333 West Wacker Drive (1983)

This is where Ferris Bueller’s dad worked in the movie. The building reflection in late afternoon is cool.

The massive building on the other side of the river is the one that held my attention.

The Merchandise Mart (1930)

Marshall Field & Co. opened the largest building in the world with 4 million square feet of floor space as The Merchandise Mart in 1930 to bring wholesale goods vendors and buyers together. The Pentagon captured the biggest building in the world title when it opened in 1943. Today The Merchandise Mart  Chicago offers trade shows, design rooms and fairs.

The boat heads north to Goose Island, then south past the Willis Tower (formerly Sears Tower) and then back out to the lake and Navy Pier.

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Willis Tower (Sears Tower) is tallest building in the Americas at 110 stories and still the third eighth tallest building in the world at 1,450 feet, but losing height ranking fast. There is a 103rd floor Skydeck with a glass ledge extending four feet out from the building at 1,353 feet over the ground that is a major tourist attraction.

The building is more interesting to see from a distance than close up. The architecture tour boat passes by the Willis Tower twice.

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Willis Tower Chicago.

The Chicago River Architecture boat tour was 90 minutes long and the time passed quickly. The boat had a bar, but nobody among 100 or so passengers was drinking on a chillish November afternoon and the bar was beneath the deck. The wind in the shade was a bit chilly and the tour ended near Lake Michigan with the fading rays of sun on our faces and the skyscraper buildings of downtown mostly in backlit shadow.

This Chicago Architecture Tour on the Cruise Chicago First Lady river boat was a freebie sponsored by the Chicago Convention and Tourism Bureau and Radisson Blu Aqua Chicago as part of a media tour I attended in November 2011 for the grand opening of the hotel.

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Radisson Blu Aqua Tower Chicago, in center, has a wavy appearance due to the alignment of balconies and glass. The hotel was honored with an award from PETA for its bird-friendly design. Apparently many birds die every year flying into skyscraper glass and the Aqua Tower design is more visible to birds.

Related posts:

Radisson Blu Aqua Chicago (Nov 18) – this post has links to a few other articles I wrote about the Radisson Blu hotel stay in Chicago. I never finished the series to tell about the restaurants. Perhaps one of these days I’ll post the food photos.

About Ric Garrido

Ric Garrido of Monterey, California started Loyalty Traveler in 2006 for traveler education on hotel and air travel, primarily using frequent flyer and frequent guest loyalty programs for bargain travel. Loyalty Traveler joined in 2008.

More articles by Ric Garrido »



  1. Great post and terrific pictures. I actually live in one of the building on the river (not pictured here). Whenever a guest/visitor asks for a suggestion on a must do activity in Chicago, I always recommend the architecture boat tour.

    Thanks for making my city look so good.

  2. Ric, wonderful post! My wife and I visited Chicago together last September on a Delta run to MKE. Took the same boat tour! Can’t believe that you took all the pictures and remembered all the details of the buildings! Impressive!

  3. I’ve lived in Chicagoland all my life and just took this tour about a year ago. Something else really cool in Chicago if you’re into architecture is all of the Frank Lloyd Wright stuff that we have here.

    This same company offers a FLW bus tour or you can go directly to his home and studio in Oak Park and do an interior tour. That is cool because it was his actual home and tells about his personal life. There is another house, the Robie house, that you can tour over in Hyde Park, but I believe it’s just a house he designed, not someplace he actually lived.

    This same company also does a Devil in White City tour to go along with that book. I haven’t done that tour, but I’d like to do it sometime. They actually have a bunch of tours besides just the boat tour.

  4. In the Tribune building, the rare/interesting stones and bricks are actually embedded in the front facade, so you can see them (and touch some of them, IIRC) when you walk by on the sidewalk.

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