A Weekend Journey Through Stunning Architecture
Chicago is very versatile. Skyscrapers and villas. Old buildings but also many new projects. It can be a reason to plan a Chicago Architectural Weekend. I always like to have a specific point of interest during a city trip. If you have been introduced to the city’s highlights for the first time (see Chicago Razzle-Dazzle blog), architecture is certainly an interesting topic.
This itinerary helps you plan your own weekend trip. Depending on your hotel’s location, you can combine different sections, using my Chicago experiences. I prefer walking whenever possible, but biking/segway is also a good option (just not if it is below -13 degrees Fahrenheit! In that case try to avoid the waterfront and walk on the right street side for wind protection from the buildings).
Be aware that I did not do exactly everything described in this blog, I visited the city about ten times during the years my daughter lived there as well in spring, summer, autumn and winter. So this is an indication, plan your own tour depending on the time of year and weather conditions.
What to visit, Day 1: A Skyscraper Symphony
Morning Day 1
- Start at the Magnificent Mile, begin your day in this street with beautiful shops and iconic Towers, like the Willis Tower, once known as the Sears tower with a glass balcony on the 103rd floor, that allows views of Navy Pier and Wrigley Field. Or visit the Tribune Tower, this Gothic Revival building is mentioned as a masterpiece of architectural design.
- Architecture River Cruise: Embark on an architectural river cruise to admire the city’s stunning skyline from the Chicago River. Learn about the city’s rich architectural history from knowledgeable guides. You can start on the corner of Michigan Avenue and Wacker Drive.
Afternoon Day 1
- Visit the Chicago Architecture Center: Learn more about the city’s architectural history. Not only the history of the city with its great fire in 1871 but also new projects like the transformation of the Thompson Center into Google offices
The Great Chicago Fire in 1871 destroyed much of Central Chicago. The fire’s spread was aided by the city’s use of wood as the predominant building material in a style called balloon frame. More than two-thirds of the structures in Chicago at the time of the fire were made entirely of wood, with most of the houses and buildings being topped with highly combustible tar or shingle roofs. After the fire The city government improved building codes to stop the rapid spread of future fires and rebuilt rapidly to those higher standards. (Information based on visit and Wikipedia)
animation Chicago Architecture Foundation
- Explore the Loop: Wander through the Loop, the central business district, and marvel at the towering skyscrapers. Just walk around and see it as a first introduction. Enjoy the buildings like the Chicago Cultural Center and Art Deco building Pendry (Carbide and Carbon Building). Tomorrow we will take more time to visit Millennium Park.
Evening Day 1
- Cocktail at a Skyscraper, we have a tradition to order cocktails when visiting a city. In Chicago it was in 2009 for the first time in a skyscraper, the Hancock Tower. Although its name changed, and the atmosphere is quite different than in 2009, you can still enjoy a cocktail in 875 North Michigan Avenue
- Dinner at a Skyscraper Restaurant: Enjoy a delicious meal with panoramic city views at a restaurant located in one of the city’s skyscrapers or if you had enough skyscrapers today in any of the other restaurants.
What to visit, Day 2: A Neighborhood Tour
Morning Day 2:
- Millennium Park: Visit this world-class park and admire Cloud Gate, the iconic “Bean” sculpture by the British Indian sculptor Anish Kapoor, the Jay Pritzker Pavilion by Frank Gehry, Lurie Garden by Piet Oudolf, etc. It is a bucket list visit I also mentioned in my previous blog about Chicago.
- Enjoy Downtown: Take the River Walk, you are downtown and can enjoy buildings like
- Merchandise Mart, an Art-Deco building. Built in 1930, it was the world’s largest building.
- Reid, Murdoch & Company Building, the building has a monumental status because of the beautiful proportions of the bricks and the beautiful details of the terracotta finish.
- Trump International Hotel and Tower, a 100 100-story structure, which reaches a height of 1,388 feet (423.2 m)
- Salesforce Tower Chicago, if you look from the river walk in the direction of the neighborhood River North, you can see a new development from the Kennedy Family. This tower is completed in 2023.
Afternoon Day 2
- Explore the Gold Coast: Walk along Lake Michigan, you are now close to the Gold Coast. Stroll through this historic neighborhood, known for its elegant mansions and beautiful architecture in the form of brownstone homes. You can head north into Old Town and Lincoln Park. And if the weather is good, just relax on Oak beach.
Visit the Rookery Building: If you still want to visit a building, after all these strolls think of a historic landmark. The Rookery building is a prime example of Chicago School architecture.
Evening Day 2:
- Dinner in a Historic Building: Dine in a restaurant housed in a historic building, such as the Chicago Athletic Association.
- Art on the mart: between April and December is one of the world’s largest digital art platforms that transforms an architectural landmark (the Merchandise Mart) into a permanent, larger-than-life canvas. More information here.
- Catch a Show: Enjoy a Broadway-caliber show at one of Chicago’s many theaters. What about Chicago the Musical
Bonus Tips
- Addresses of the locations mentioned you can find in this google maps list I made.
- You need tickets for a lot of experiences; order, if possible, in advance. Skydeck from 30$, walking tours from about 15$, boat tours around 50$.
- If you have more time, think about visiting other Frank Gehry architecture sites like the Frederick C. Robie House
- Another tip for the evening: a nighttime river cruise to see the city illuminated.
- Consider joining a walking tour or bus tour offered by the Chicago Architecture Center for a deeper dive into the city’s architectural history. (and access to the center is included in the price for the tour)
- CityPASS: Consider purchasing a CityPASS to save money on admission to popular attractions. But check, because there are 2 attractions included, and if you do not want to go to the aquarium, you will be better off with a C3 pass.
- Wear comfortable shoes, as you will be doing a lot of walking.
- Camera: Bring a good camera to capture the city’s stunning architecture.
By following this itinerary, you will experience the best of Chicago’s architectural wonders and create unforgettable memories. Enjoy your Chicago Architectural Weekend!
