Why I Can’t Get Enough of This Chicago Tour

Some things never get old—like the stunning views of Chicago from the water. That’s why I’ve taken the Chicago River Tour by Shoreline not once, not twice, but three times. Each time offered something unique, but my most recent trip had a new twist: winter.

Chicago in the winter isn’t for the faint of heart. I’ll admit, I was hesitant to hop on a boat with temps hovering around 30 degrees. But the draw of seeing Chicago’s skyline—this time dusted with a touch of winter chill—was too strong to pass up. And spoiler alert: It was absolutely worth it.

Chicago River Tour – Getting There

The cruise departs from downtown, right near the iconic Wrigley and Chicago Tribune buildings. The address is 401 N Michigan Avenue.

Even if you’re not familiar with the area, there are plenty of signs guiding you down to the riverwalk and dock.

I booked my tickets online (super easy), but there’s also a ticket booth if you’re more of a spur-of-the-moment traveler.

Bundled up in hats, gloves, down jackets, and even some trusty long underwear, we made our way to the dock. Despite my layering efforts, I questioned my sanity for a moment—was I really about to sit outside on a boat in 30-degree weather? But here’s the thing: if you want the best views, you have to be on the upper deck. There’s just no other way to truly appreciate the towering beauty of Chicago’s skyline.

The Winter Experience

Unlike the longer summer tours I’d done before, this winter version clocked in at about an hour—a perfect balance of soaking in the city without freezing solid. Fortunately, it wasn’t that crowded (perks of a winter weekday), and the winds weren’t nearly as brutal as I feared. We even found ourselves enjoying the fresh, crisp air as we floated past some of Chicago’s most iconic buildings.

One thing I love about this cruise is that it’s never exactly the same. Each tour guide highlights different stories, focusing on various architects, design styles, and city history. Plus, the city itself is always evolving—new buildings rise, old ones gain fresh relevance, and each trip down the river brings something new.

Buildings That Caught My Eye This Time

Here are some of the standout buildings from this winter tour, with some fun facts that made them even more memorable:

150 North Riverside – This sleek, glassy skyscraper seems to defy gravity. Its narrow base fans out into a broader top, a design made possible by a unique structural system. It’s often called the “Yoda Tower” because of its inverted, balancing shape.

300 South Wacker Drive (River Mural) – You can’t miss this one thanks to its giant map of the Chicago River painted on the side of the building. What’s extra cool? A red dot marks exactly where you’re located when viewing it from the water.

Chicago Tribune Tower – A Gothic Revival gem, this building is a love letter to journalism and history. Embedded in its lower walls are fragments from famous landmarks around the world—including the Great Wall of China and the Parthenon.

Carbide and Carbon Building – If a skyscraper could channel the spirit of a champagne bottle, it would be this one. Its dark green terra cotta exterior with gold leaf accents is pure 1920s Art Deco glamour. Today, it houses the Pendry Chicago Hotel.

London Guaranty Building – This neoclassical beauty stands where Fort Dearborn once sat and is crowned with an ornate, four-story cupola. It’s now home to the London House Hotel, known for its rooftop views.

Marina City (Marina Towers) – Affectionately nicknamed the “corncob towers,” these round high-rises are iconic symbols of Chicago’s modernist era. Fun fact: The lower levels are open-air parking garages—cars literally spiral up and down the towers (which actually creeps me out a little).

Merchandise Mart – At one time, this was the largest building in the world. Covering two city blocks, it was originally built as a wholesale warehouse for Marshall Field & Co. Now, it’s a bustling hub of showrooms and creative workspaces.

Michigan Avenue Bridge – This double-deck bascule bridge is more than just functional—it’s historical. Completed in 1920, it played a key role in Chicago’s growth by connecting the north and south sides of the city.

St. Regis Chicago – Chicago’s third-tallest building, this twisting glass tower was designed by famed architect Jeanne Gang. Its shimmering, stacked design creates a wave-like illusion that beautifully reflects the sky and river. Very cool!

Trump International Hotel & Tower – Love it or hate it, this 98-story glass giant makes its mark on the skyline. It’s one of the tallest buildings in the U.S. and was designed to reflect the nearby river in its curved façade.

Wacker Drive Levels – A uniquely Chicago feature, Wacker Drive is a multi-level street system that runs along the river. The upper levels handle city traffic, while the lower levels keep delivery trucks and service vehicles (and sometimes lost tourists) out of sight.

Willis Tower – Formerly known as the Sears Tower, this black steel giant held the title of the world’s tallest building for nearly 25 years. Even now, its Skydeck offers some of the best city views—if you’re brave enough to step onto The Ledge’s glass boxes (no thanks!).

Civic Opera House – A true architectural statement, this Art Deco masterpiece was built in 1929. Its design was said to resemble a giant throne—fitting for a building dedicated to grand performances.

Wrigley Building – One of my all-time favorites, this gleaming white terra cotta tower is pure Chicago charm. Its clock tower is an unmistakable part of the skyline, and at night, it lights up beautifully against the dark river.

A Warm Ending

By the end of the hour, though, we were definitely feeling the chill. Luckily, there’s a Starbucks just steps away from the dock, and we made a beeline straight for it. That cup of hot chocolate? I’m convinced it was the best hot chocolate ever.

Would I Do It Again? You Bet.

So, would I take this tour a fourth time? Absolutely. And probably a fifth. There’s just something about seeing Chicago from the river that never gets old. The way the buildings rise up around you, each with its own story, makes for a perfect blend of history, architecture, and unbeatable views.

If you’re heading to Chicago and thinking about this river cruise, don’t let the weather stop you. Bundle up in the winter, grab that post-tour hot chocolate, and get ready to fall in love with Chicago from a whole new angle.

Find out more about our Chicago adventure: 36 Hours in Chicago: A Whirlwind Adventure