Exploring Chicago: Family-Friendly River Cruise Experience

Intro

This is my last entry of my Los Angeles – Las Vegas – Chicago trip. You can see the other posts here:

A Day at Universal Studios Hollywood: Attractions and Experiences

Halloween Horror Nights 2025 in Hollywood: A Memorable Night

Your Guide to The Wizard of Oz Show at The Sphere in Las Vegas

Universal Horror Unleashed: An Honest Review

Exploring Chicago: Sunset Views and Unique Experiences

As you can see in the last post, I had already explored a lot of the Northern part of the city, closer to the Magnificent Mile. So, in this post I wanna share my experience on a boat tour I did on the Chicago River, and many spots on The Loop and south of said river.

45-Minute Family-Friendly Architecture River Cruise

I purchased this tour on Get Your Guide, and I glad I did. There was a 90 minutes option, but I did not think I had it in me lol. 45 minutes was enough to see everything I wanted to see, and understand a little bit more about the history of this city. The tour guide was amazing, very funny, and gave us a lot of tips for our visit, besides all the amazing facts about the buildings and the city.

After scanning the ticket, we were instructed to come on the boat, and there were options to sit at the top (outside) or inside. Most of the people were on top, but it eventually started raining, and a lot just went inside.

Since I am in the construction field, I was fascinated by all the engineering, architectural and city development facts that the tour guide was give. It definitely takes a lot of energy to build a city as huge as Chicago.

The tour was packed. I really was not expecting this many people showing up, especially in a rainy day.

The tour guide kept mentioning the story of the stars in the Chicago flag, so I feel like I should mention it:

Each of the four red six-pointed stars represents a major event in the city’s history, and each point has its own symbolic meaning too.

• The first star stands for Fort Dearborn, the original military post that marked the city’s early beginnings.
• The second star honors the Great Chicago Fire of 1871, which destroyed much of the city but also led to its incredible rebirth.
• The third star represents the World’s Columbian Exposition of 1893, a celebration that put Chicago on the global map.
• The fourth star was added later for the Century of Progress Exposition of 1933–34, showcasing the city’s innovation and resilience during tough times.

Built in 1914, the Reid Murdoch Building red brick facade and clock tower make it instantly recognizable, a little slice of old Chicago surrounded by sleek glass towers. What I love most about it is how it’s been reinvented over the years — from a busy food warehouse to a government office and now home to modern businesses. It’s a perfect example of how Chicago blends history and progress in one beautiful view.

The new buildings added to the skyline started to show up, the more West we would go.

150 North Riverside Plaza is one of those buildings that instantly makes you stop and stare. It looks almost impossible — a 54-story glass tower that seems to balance on a narrow base right at the edge of the Chicago River. Opened in 2017, it’s a stunning piece of modern architecture and a real statement of what’s possible with smart engineering. The way its mirrored surface reflects the skyline and the water makes it feel like part of both at once. It’s one of those spots that reminds you just how bold and futuristic Chicago’s architecture can be.

And of course, The Willis Tower is one of those landmarks that never loses its wow factor, no matter how many times you see it. Rising 1,450 feet above the city, it’s still Chicago’s tallest building and one of the most iconic skyscrapers in the world. What I love about it is how it captures both the city’s ambition and its grit — a true symbol of Chicago’s “go big or go home” spirit. And if you step onto The Ledge at Skydeck Chicago, standing on glass more than a hundred floors up, you get that perfect mix of thrill and awe that makes you appreciate just how massive and alive this city really is. It is incredible that I did this 12 years ago in 2013. Time flies.

If the Willis Tower represents Chicago’s bold, classic power, then The St. Regis Chicago is its sleek, modern counterpart. Designed by Jeanne Gang and completed in 2020, this shimmering glass tower twists gracefully above the river, blending art, architecture, and luxury in one stunning statement. Where the Willis Tower feels like old-school ambition — strong, grounded, and iconic — The St. Regis feels fluid and forward-looking, almost sculptural in how it reflects the sky. Together, they tell the story of a city that never stops evolving: one built on strength, but always reaching for something new and beautiful.

One of the coolest facts the tour guide told us, and I did not know was that Chicago actually reversed the flow of its river. Originally, the Chicago River flowed into Lake Michigan — which was also the city’s main source of drinking water — causing major pollution problems in the late 1800s. To fix this, engineers did something incredible: they literally changed the direction of the river’s flow. Through an enormous engineering project completed in 1900, they dug canals and installed locks that made the river flow away from the lake and toward the Mississippi River basin. It was a groundbreaking feat for its time and is still considered one of the greatest engineering achievements in U.S. history.

Chicago was sued three times by other states and cities over reversing the river.

After the Chicago Sanitary and Ship Canal opened in 1900, Missouri, Wisconsin, and other downstream communities were outraged because Chicago’s wastewater was now flowing toward the Mississippi River instead of Lake Michigan — meaning it eventually reached their water supplies.

• The first major lawsuit came in 1900, when Missouri sued Illinois and the Sanitary District of Chicago, claiming the reversed flow was contaminating the Mississippi River.
• Another major case reached the U.S. Supreme Court in 1922, when Wisconsin, Minnesota, Ohio, and New York joined forces, arguing that Chicago was taking too much water from the Great Lakes.
• A third dispute arose in the 1960s–1980s, leading to another Supreme Court ruling in 1980, which strictly limited how much water Chicago could divert from Lake Michigan — a regulation that still applies today.

So overall, Chicago’s ambitious river reversal sparked three major legal battles, each shaping the way the city and the Great Lakes states manage water to this day.

It started raining hard, and most guests went inside. I had my umbrella so I stayed on top, but it was also super breezy. By the time we came back to the wharf, the sun was out again.

Millennium Park

After having coffee and then deep dish pizza from Lou Malnati’s Pizzeria, I went to Millennium Park, one of Chicago’s most popular and vibrant spots — a mix of art, architecture, and green space right in the heart of downtown. It’s home to the famous Cloud Gate (better known as “The Bean”), the Crown Fountain, and the Jay Pritzker Pavilion, where free concerts and events happen all summer long. Whether you’re taking photos, relaxing on the lawn, or skating in winter, it’s the kind of place that perfectly captures the energy and creativity of Chicago.

Of course, The Bean is most visited spot in this area.

The Jay Pritzker Pavilion was kinda enclosed and closed, but I was able to peeked and see it. It reminded me a lot of my visit 12 years ago.

The Loop

The Loop is Chicago’s bustling downtown core — the city’s business, theater, and architectural heart. Surrounded by the elevated “L” train tracks, it’s packed with skyscrapers, historic landmarks, and energy from morning to night. I literally just walked here from Millennium Park, getting in all the daily routines Chicagoans had that day.

From the iconic Chicago Theatre, I walked then to London House. Since a friend recommended me going up there. You just go into the building and they guide you to the elevators and into the lookout at the terrace. It’s free and has a nice view.

Just a few hours ago I was going down into this river on a tour lol.

Portillo’s & Barnelli’s Chicago

I had already tried the deep dish pizza and the Chicago thin crust pizza, but tonight I was feeling something different. I was recommended to do the Chicago Style Hot Dogs, and that I did. I took an Uber this late, and went to the closest Portillo’s & Barnelli’s Chicago.

Wow, it was really big inside. The menu was very expansive, but everything seemed so good.

I got a Chicken sandwich and a Chicago Style Hot Dog. I liked them both, no wonder why this spot is so famous.

Navy Pier

Navy Pier is Chicago’s iconic lakeside playground, full of fun, food, and stunning views of Lake Michigan. From its Ferris wheel and boat tours to theaters, restaurants, and seasonal events, it’s a lively spot where both tourists and locals come to soak up the city’s waterfront energy.

I decided to get a Citibike after lunch, and bike to this place, far from any subway, in this very beautiful day.

When I came in 2013 I was not able to explore inside (I think it was in construction), but now it looked amazing. I was full of so many things to do. Like on a cold day you could just spend the entire day here.

After walking the entirety of the Pier inside, and seeing what was in there, I started walking outside and checking the skyline.

From the very tippy toe of the Pier you could see easily the Chicago Harbor Lighthouse.

And the entrance at the very end of it.

Time to go back to get a bike on the dock, but the views of the skyline, including the iconic John Hancock Center.

Got my Citibike, and went really quick to Milton Lee Olive Park, next to the Navy Pier, where more beautiful views of the skyline were waiting for me. The lake was incredibly blue today.

United Lounge at ORD

My trip was finally over, so after a quick check out, I went to the airport using the Blue Line. I had another of those free passes to the United Lounge, so I decided to use to wait for my flight, and get some snacks on my way to New York City.

The United Club Lounge at O’Hare (ORD) is a sleek, comfortable retreat from the airport hustle. With cozy seating, quiet workspaces, complimentary snacks and drinks, and fast Wi-Fi, it’s perfect for relaxing or catching up on work before a flight. Large windows often offer great runway views, making it a surprisingly peaceful spot to watch planes take off and land.

There is supposedly one that is bigger than the one I used, but I was equally impressed by this one.

The food, service and drinks were really good. For something complementary I thought it was quite good.

But this concluded this quick post about Chicago, and my entire trip. Now back in NYC I am waiting for more adventures, still in the US. Stay tuned!