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We saw the Windy City from a different point of view by taking an architecture river tour. The views at night were amazing, and we went with Shoreline Sightseeing.
I grew up around Chicago, but it was years later on a visit, that we decided to learn about the buildings. When I used to walk by them all the time, I never realized how majestic they were.
I’ll tell about our experience, what to know and expect, and share personal photos from our trip. You’ll want to see it all too!
Getting There
On this trip, we were staying in a historic hotel on the Magnificent Mile. It was only 2 miles away, and it’s walkable along Lake Michigan.
One of the main areas to access tours is on Navy Pier. We took the bus, as it was an easy and direct way to get there.
We’ve driven here before too, but then you’ll have to deal with traffic and parking. So, public transportation or ride share is a no-hassle way to get there.
Touring with Shoreline Sightseeing
We went with Shoreline Sightseeing because they had an evening tour and the price was reasonable. There are a few other touring companies you can choose from.
From checking the website, the company runs several tours a day. They depart from Michigan Street or Navy Pier.
During the open season, they’re open daily, except for holidays. You’ll want to check the online schedule before buying a ticket.
Don’t expect them to run in the winter. If you know about the Midwest, it can get terribly cold and icy in the winter.
By the way, Shoreline has been around since 1939, so they’ve got history. They’re Chicago’s largest fleet, and you’ll see many of their boats on the river.
Buying Tickets on Navy Pier
We decided to buy tickets at the last minute. Actually, we were just walking around Navy Pier, and weren’t planning on doing a tour.
We walked past a few boat tour companies during the day. As the evening approached, we thought about our plans.
But as we passed the Shoreline booth, they told us that we could catch the next tour, which would leave in about an hour.
So we bought tickets, which were around $50 per person. Then we had to walk to North Streeter Drive to catch the boat, and that took us about 15 minutes.
Our tour would leave at 7:30 p.m. and last for 75 minutes. But we got to the dock earlier to check in and listen to the little safety spiel.
Traveling the Chicago River
We started the tour right on the Chicago River in the midst of August. The days were still warm, and the night was cool and pleasant.
We boarded what looked like a giant flat ferry boat. There was plenty of seating, and not many people on our tour.
The boat was very wide, so you have a great view no matter where you sit.
There was a bar in the back, and you can get drinks on the ride. I saw many people hanging out back there and walking around, but we stayed in our seats.
Windy City Skyline Views
If you’ve seen the architecture in Chicago while walking the streets, you’ve got to see it going down the river. It was one of the most amazing things I’ve done in the city.
At night the buildings are lit up, and that’s a spectacular show of its own. I saw many of them in a whole different array of colors, and it was inspiring.
We had a great tour guide who took us back in time as he told us the stories behind the iconic buildings. There are over 40 landmarks to see, and I was enlightened by the history.
He took us to where the Great Chicago Fire happened in 1871. Was it really started by a cow, like people say?
No one really knows, but it wiped out over 17,000 buildings and killed many people. This took place in the business district on the west side.
Today, you wouldn’t even know there was such a disaster, as the area has been totally rebuilt. Many architects came from all over and designed buildings that you’ll see standing today.
Millions of dollars have been poured into these structures, and you can tell. You’ll see many unique and modern designs, and luxury high-rises, dotted amongst historic landmarks.
Some of the iconic buildings we saw were the Chicago Tribune, Merchandise Mart, Wrigley Building, and the Jewelry Building.
We saw the Willis Tower, which I knew as the Sears Tower growing up. Well, times have changed, but the city I knew back then still pretty much looks the same.
We also saw a film projected on buildings under one of the bridges. By the way, it was interesting to see the construction from underneath.
Chicago Riverwalk
Now, before or after taking the architecture tour, you might also want to take a stroll along the Chicago Riverwalk. This takes you along part of the tour’s route.
This was something I used to do a lot when I lived here. You’ll see many boats passing through and incredible views of the buildings.
You can access the Riverwalk from Upper Wacker Drive. Look for entry points and stairways taking you down.
You’ll find many stores and restaurants along the river. We also found people fishing, sitting around relaxing, and enjoying the weather.
You can also walk around Upper Wacker Drive to see the views. We crossed over some of the bridges, which are just as historic as the buildings.
The most popular ones are the Michigan Avenue Bridge, Wells Street Bridge, and Clark Street Bridge. You can find nice views here.
I love the industrial look of Chicago. It’s surreal how intricate some of the architecture looks. I didn’t really notice all of this when I used to pass by them on my commutes.
Travel Notes
A great way to spend a whole day or two would be to do Riverside Walk, a boat tour, and hang out at Navy Pier. By the way, you can check out Navy Pier’s calendar for more.
The absolute best time to go on a tour would be in the fall, as the weather is pleasant, especially at night. From growing up around here, the summers can be sweltering hot.
I brought my own snacks and water on the boat, and the guy said it was okay. You might want to bring a hat during the day, as the boat is exposed.
Final Thoughts
It wasn’t on our radar to take an architecture river tour while visiting Chicago. But I’m glad we did, as it was a great way to view its grandeur and beauty besides walking the streets.
Our time with Shoreline Sightseeing was a great experience. I’d love to return to the Windy City and explore more by taking other tours.
More Travel Adventures
I have many other related posts that might interest you on my blog. You might want to check them out.
- If you travel a little outside of Chicago, you can visit Indiana Dunes State Park.
- Another place they go in the summer is Silver Beach, which we love.
- Dowagiac is a small, historic town near Lake Michigan, where many people from Chicago hang out in summer.
- For another unique experience, why not visit Shipshewana, the Amish country in Indiana?
I’d love to hear about your travel adventures!
Originally published: October 29, 2025
