Twilight on the Chicago River… | Chicago’s Architechtural Boat Cruise

“Take the boat tour. You have to take a boat tour in Chicago.”

Any time I mentioned to anyone that I had my ticket ready for Chicago, Illinois the next words out of a mouth? Boat Tour. The main excursion nearly 99% of all former visitors, prior residents, and current travelers told me to take. Needless to say, I grabbed my ticket for Chicago’s First Lady River Cruises immediately.

If you’ve ever spent time in Chicago, you know the city holds so many adventures that you can’t possibly enjoy them all in a weekend. (and if you don’t, read more about those here!) But taking an architectural boat tour topped my weekend in the Windy City. Without debate. I loved every sweet, albeit chilly, moment along the river.

docking for chicago boat tourChicago River hosts different cruises to meet your every desire–including one at Navy Pier!–but I recommend Chicago’s First Lady. And no, they didn’t sponsor this post. I found First Lady’s on a Google for top boat tours in Chicago. Their name popped up several times. Why I enjoyed them? Aside from the spectacular views, our tour guide knew everything about that skyline. Not just the beautiful high rises, but even the smaller, older buildings that hid inside the metal jungle of skyscrapers. Plus, she was enthusiastic to boot–nothing beats an excited tour guide when you’re freezing.

Main branch of Chicago River on the boat tour


Related Post: D.C. Brunch Cruises

Twilight on the River…

skyline on the boat tour in chicago
The Wrigley Building: built in 1925 at the end of Warehouse style

Again, each company offers more than one cruise to suit your tastes. Sunrise rise cruises, midday cruises, Chicago’s First Lady even offers a cruise exclusively for photography. You know that one tempted me… in end (mostly for scheduling sake), I went with the Twilight Cruise. I flew into Chicago midmorning and coupled with everything else I had planned, touring the skyline as the sunset seemed the best fit.

Chicago’s First Lady docked not three minutes from my hotel right on the Chicago’s River Walk. No matter who you ride with, I recommend arriving at the dock 30 minutes before departure to ensure you get the seat you want. The boat tour had fingers foods and wine, as well as inside seating. Depending on the time of the year you tour (I went in September; good mix of temperatures) and your tolerance for cold air, that inside seating is gold. But I wanted the views to slap me in the face…and they did, along with that brisk Chicago wind!

down on the river during chicago boat tour

downtown Chicago on the boat tour
Style: close to mid 20th Century
Here’s a tip:
If you take a boat tour anytime after August, bring a jacket. If you take a tour after September, LAYER UP. lol. Why? Well, you’re already in Chicago, the Windy City. Plus you’re on the water, so temperature drops anyway. That’s just science. I didn’t layer up as much as I should have so my nose felt frozen by the end of the 90-minute tour. But other than lack of wool clothing, I have no complaints about my tour of downtown.

Our guide broke down all the architectural styles by period as we rode down the Main, North, and South branches of the Chicago River. Early Warehouse styles lined the back of the North Branch, some of the first buildings ever built in downtown.

skyline on the boat tour
mix of art deco styles blending in with mid-20th Century

My favorite: Art Deco. Felt like a bulk of the buildings along the branches had this style in mind. By the middle of the Twentieth Century, styles shifted again to reflect a more minimal approach–a contrast to the more decorative style preceding it. This period gave us Sears Tower (now Willis Tower) and the John Hancock Building.

Okay, I take it back…I have one other complaint: I wish I had down this tour twice. Once in the morning, and once at night. Because some of the designs really pop in sunlight rather than moonlight. Mostly the older buildings hidden back along the North branch. And especially the Aqua a Lakeshore East–a truly beautiful example of Contemporary style in downtown Chicago.

twilight skyline on boat tour
turning from the Main branch down the South branch. Pictured: (left) Merchandise Mart (Art Deco style) and (right) 333 West Wacker (move into Post Modern)

So…you know I had to get a shot of Sears Tower (really called Willis Tower, but no one calls it that. Honestly, I tried about 50 different times I get a grand shot of this building. I wanted perfection. lol.

I encourage photos while on your boat tour, but honestly, the sights take your breath away. You almost forget to tap the shutter. After a while, I forgot about the cold and the numbness in my cheeks and just sat in silent awe of the rising lights around me.

architecture on chicago boat tour
Sears Tower down the South branch of Chicago River. Former the tallest building in the US

Unlike the daylight hours, Chicago quieted down into the early hours of night… Not peaceful, exactly. More like formidable. Not suspicious, but mysterious. You found yourself wondering what secrets lay just around the forest of architectural history. Our guide left moments of quiet so all you heard was the distant sound of cars, wind clipping around buildings. You saw the rise of smog from the city streets, the flashing colors from blue spires to bright orange, yellow to white light. Light that danced on along the river’s mirror, beckoned off the reflections of each building. Downtown Chicago at night is a photograph I’ll never truly capture.

Honestly, when I see Chicago, I think of Gotham City. I see the Dark Knight riding through the Loop, I see batlines arching between buildings as he zip lines down to his target. Criminals run scared down dark alleys, fearful of the silence… Sounds silly? I can’t help it. Metropolis always felt like New York, but Gotham? That’s Chicago. Maybe the city holds such a special place in my heart because I get to see my favorite comic storyline from DC come alive.

Best. Skyline. Ever.

Chicago skyline has graced many a list of best skylines in the country. And the world, for that matter. It’s easy to see why when you get even a glimpse at its expanse from Lake Michigan. Thankfully, my boat tour took us right into the open waters–the coldest portion yet–and we got a vivid shot of the full skyline…

full skyline on boat tour skyline on boat tourLet me just say, I had no idea how cold that wind could get until I no longer had the protection of the high rises… Then the wind didn’t just slap, it clawed and scratched. It damn near screamed for attention. And would have won except…that skyline… From far out in the Lake, the dark mysterious quality fell away and became just magnificence. The city invites you in; you can’t help but crave to exist inside that sparkling light. You want to climb atop each colored spire and yell. You want the noise, the clamor. Hear the clank of rickety train tracks and annoyed honking horns. Smell the barbecue and the melted cheese, see the swirls of innocence as Navy Pier lingers behind… You want downtown Chicago.

No photo does the experience justice.



Related Post: 10 Attractions in Chicago!


Ever taken an architectural tour of Chicago? Or another major city? How does it compare? Tell me below…


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  1. Mia

    Chicago is one of my favorite cities! I would totally do this boat cruise at night to see the beautiful city come alive. I think I’ll wait for the summer because I don’t like cold weather and being on a boat at night sounds cold!!

  2. Kelly

    This cruise looks amazing and I love the skyline and how it glows in the dark. And good advice about the jacket because I have heard it’s really windy in Chicago. I have actually never been to Chicago but will take your advice when I visit!!

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