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Taking a boat tour along the Chicago River to learn about the amazing skyscrapers that dominate Chicago's impressive skyline

I have grown to love the skyline of Chicago. It is probably one of my favourites in the world – and almost certainly in the United States – including New York. There are many ways to admire the skyline – I am not big on helicopters – but you can also go atop one of the bigger buildings. Anyway, we decided what we’d like to do was take a boat tour along the Chicago River and see these impressive buildings from there.

The architectural boat tours take place every hour during the summer months and last for about ninety minutes. They start in the dock area close to the famous Navy Pier. The boat we were taking had an open deck and a downstairs deck, which is covered. We, of course, decided to sit on top, but it was a hot summer day in Chicago and there is no shade. You need to wear a hat, put on lashings of sunscreen, and of course take plenty of water. They do sell refreshments on the boat if you do forget to bring liquids with you.

As the birthplace of the skyscraper and home to one of the world’s greatest skylines, Chicago is in the midst of reinventing itself thanks to a new batch of tall, high-profile towers.

When the 836-foot-tall One Bennett Park opened in Streeterville this spring, it was Chicago’s first 800-footer to be completed in nearly a decade. It was followed this summer by the 896-foot NEMA Chicago project at the southern edge of Grant Park. Currently, there are three 800-foot-plus towers under construction in Chicago, including the 1,198-foot-tall Vista Tower in Lakeshore East. I was excited to see my old favourites as well as the new constructions.

The Chciago River

One of the first buildings we come across is the Trump Tower. It is fair to say I am not a big fan of the man – the building is impressive – but it still is a painful reminder of the state of American and the sad divisions that have appeared across the country under the reign of the 45th President.

The Trump Building

Not all the skyscrapers are modern – some like the New York Life Building and the Tribune Tower date back to the 1920s. They were some of the largest in the world in their time.

New York Life Building and the Tribune Tower date back to the 1920s

In the 1960s the role of skyscraper changed to be mixed-use, with business and residential units in the same building. They became like mini-communities in their own right. A classic example of this is Marina City, a pair of towers, with an outside appearance of a corncob. The Marina City apartments are unusual in containing almost no interior right angles. The bottom floors serve as a parking lot for around 1000 cars.

Marina City Apartments
The Willis (formerly Seat Tower)

Eventually, the river splits and we take one fork past an old bridge – which is only use once a year. Here we turned around and carried on down for a brief way along the second spur of the river, past some older and newer buildings.

Drawbridge on the Chicago River

As we turned to return back to port we finally got to see probably, along with the John Hancock Tower, the Willis Tower. Originally, the Willis Tower – still known by many by its original name the Sears Tower – was, at  1,450-foot, the tallest building in the world when it was completed in 1973. It remained so for 25 years and continued to be the tallest in the Western Hemisphere until the completion of the One World Trade Center in 2014.

The impressive black façade and twin white horns (actually television masts) give the Willis Tour an unworldly, evil persona against the rest of the bright shiny towers that dominated the Chicago skyline. I love its distinctness and dominance over its neighbouring towers.

The Willis Tower

Sadly, it was time to return home, but we got a chance to see a few more buildings on the way back, including some that had been hidden behind others on our way out.

 Our architectural boat tour along the Chicago River was amazing. We both love architecture ancient and contemporary and it was fascinating to learn about Chicago’s long history of skyscrapers and world-leading architecture. We also got to learn a lot about other aspects of the city’s interesting colourful history and culture. Well worth taking the time out to do this!

In Summary …

  • Chicago is a fabulous city with so much to do to suit all tastes
  • The river tour is the best way to see the impressive skyscrapers. Another way is to go up one of the sky decks and see the city from above. This is especially cool at night.
  • Speaking of cool – I am sure you know Chicago is freezing cold in the winter. It is not known as the windy city for nothing!

Planning your trip

Best time to visit Chicago

The best times to visit Chicago are April through May and between September and October, when the temperatures are warm, a variety of festivals take place and crowds are manageable. Summer marks Chicago’s peak tourist and festival season, with travelers from around the country hoping to take advantage of the warm weather and abundant activities. You’ll find higher lodging rates during these seasons, but you’ll also escape Chicago’s notoriously bitter winters. Chicago experiences frigid temperatures from November to March, but if you can hack it, hotel and airfare deals are easy to find.

Where to stay?

LUXURY

Just 2 blocks away from the famed shopping, dining and entertainment on Michigan Avenue’s Magnificent Mile, this luxury hotel towers above the city in a skyscraper designed by renowned architect Mies van der Rohe, offering upscale amenities and stylish comfort in the heart of downtown Chicago.

 Views of the city skyline, Chicago River or Lake Michigan can be enjoyed from floor-to-ceiling windows.

The award-winning wellness retreat, Chuan Spa, features healing holistic treatments to relax, renew and pamper, including a range of treatments inspired by Traditional Chinese Medicine, body rejuvenation and massage therapy.

MID-RANGE

Steps away from the Lake Michigan and the luxury shops, dining and entertainment on the Magnificent Mile, this all-glass triangular hotel is located in downtown Chicago and features upscale on-site restaurants and scenic views of the city. 

Guests can choose from an array of classic American fare from the breakfast buffet at The Palm. The Palm features premium prime beef and traditional Italian fare for lunch and dinner. For a more casual experience, the lobby lounge, Amuse, serves small plates and cocktails in a vibrant setting.

Millennium Park and the Art Institute of Chicago are both less than a mile away from the hotel. Navy Pier is a 7-minute drive away.

ECONOMY

Experience the excitement of Chicago at this beautiful historic hostel, offering comfortable and contemporary accommodations in the heart of downtown’s thriving university district. 

Hostelling International (HI) Chicago is one of America’s best hostels offering safe, clean, quality accommodations. Spacious gender-separated dorm rooms with either 4, 8 or 10 beds, many with ensuite bathrooms.

All dormitory rooms have individual lockers for personal belongings. The hostel also offers private rooms with shared ensuite bathrooms that also share a kitchenette and lounge/seating areas

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