Chicago, Illinois

A river runs through it.  The Chicago river runs through the downtown core of this city of 2.75 million. Once an industrial dumping ground, the river has been cleaned up and is a terrific asset to be proud of. The city takes full advantage of the Y-shaped river winding in and around the skyscrapers that line the city blocks. Architecture buffs from all over the world travel to Chicago to see its unique collection of both old and new architectural feats. The river is lined with a riverfront walk – a pedestrian path that follows the edge of the water and is lined with restaurants, small shops, and vantage points- perfect for an evening stroll. It is here that you can hop on a small river sightseeing boat. The architectural cruise is one option that is perfect for first timers to the city.

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If you can, I highly recommend the sunset cruise time. Reserve your spot by purchasing tickets online, then climb aboard and take a seat shortly before sundown. I enjoyed the architecture cruise aboard the Leading Lady at Cruise Chicago. Moving at a leisurely pace, you sit atop an open air top deck giving you a 360 degree view as you course your way past the giant behemoth buildings on either side.

For it is at night when the city comes alive. The architecture cruise is led by a Chicago Architecture Foundation volunteer docent who knows the history of each and every building you’ll pass by. The ship slowly glides past, underneath the many ornate bridges, and you look at the buildings in a whole new light. You don’t have to be an architecture student or engineering or construction geek to enjoy this sunset cruise.

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When you visit a big city, all the tall buildings look pretty much the same from ground level. As a pedestrian, all you see are the shop windows on the ground floor. When you are guided on a cruise to really see the buildings and to hear their stories, you begin to see each one for the uniqueness it brings to a skyline. Actually, no two are alike. Many of the buildings in Chicago downtown have been there since the 1920s, and have their own unique style with ornate stonework and flourishes. Other later arriving buildings are austere and simplistic, following the “less is more” mindset.  But for every action, there is a reaction, and the minimalist block-shaped buildings are giving way to more interesting designs once again. Who will be the first to build an eco-friendly skyscraper with green plants decorating the exterior of the building next?

The variety of architectural styles surprised me as I was expecting a lot of just plain, boring, industrial buildings. Even the immense building that housed the old Montgomery Wards catalog fulfillment center is an interesting building. A favorite of mine was the tall skyscraper with a map of the Chicago River on the exterior of the building and a “You Are Here” red dot on the side.

The highlight has to be at the end of one leg of the trip, when you are at a distance far enough away from the downtown core that you are treated to an outstanding view of the downtown skyline at night, with the lights of the city shining in picture postcard perfection.

In all fairness, I did experience this trip on a lovely, clear, warm, late summer evening which no doubt makes this open air experience all the more pleasurable. We could hear the “party boat” with music blaring and people enjoying their time on the river as it passed by. We also could hear music from a live band playing at one of the many restaurants along the RiverWalk. There was a feeling of a city alive, people out enjoying themselves, and a joy of living that gave the city such a good vibe. Kayaking tours also filled the river for an even more up-close experience. The architecture cruises run for a good part of the year, even as early as March. Weather has yet to be controlled, so you might have a slightly different experience in March than you might in May or August. You can always head below deck and order a hot coffee if you choose. You will get the most memorable views from up top though.  But as they say, there is no such thing as bad weather, only inappropriate clothing. In other words, bring a coat and gloves if needed, sun hat and sunglasses if called for, and just enjoy the tour!  You will never look at a skyscraper in quite the same way again.

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Reflections. Photo by Dawn Woolcott
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"You Are Here" building
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Chicago skyline at night. Photo: Dawn Woolcott
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Skyscrapers of all ages

Visit Chicago as the starting or ending point on a Great Lakes Cruise or rail vacation:

Journey Along the Upper Mississippi | Rail & Sail

Chicago to St. Paul, MN

  • 9 Nights
  • Please call for information on future dates.
  • From $3,051
Book Now More Info

Lakeside Treasure: Chicago River and Lake Michigan Cruise

Roundtrip Chicago

  • 15 Nights
  • June 4, 2022,June 18, 2022
  • From $6,699
  • Victory I
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Splendor of the Great Lakes-Victory II

Chicago to Toronto

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Great Lakes Grand Discovery

Chicago to Montreal

  • 12 Nights
  • August 25, 2022,September 23, 2022
  • From $5,999
  • Victory II
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