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October 7, 2025 589
Toronto vs. Chicago: The (friendly) skyscraper rivalry reaches new heights
Along with the Council for Tall Buildings and Urban Habitat (CTBUH), now renamed the Council on Vertical Urbanism (CVU), holding its annual international conference in Toronto this week – the global headquarters of this arbiter of all things tall is in Chicago – we thought it would be fun to publish a short series of articles dealing with deals with the similarities and differences between the two cities. The first part of our Toronto vs. Chicago series examined how each city balances its mix of high-rise and low-rise growth. This part examines in more detail how the two skylines have evolved and where they now stand in the race for height.
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Toronto and Chicago are the two largest cities on the shores of the Great Lakes. They have similarities in their history, cultural influence and skyline. Both were known in the past as the Second City; In the United States, Chicago was second only to New York in population, having overtaken Philadelphia in 1888 (and losing second city status to Los Angeles in 1980), while Toronto overtook Quebec City to become Canada's second largest city in 1871, but took the crown from Montreal in 1976 and has retained it ever since.
Chicago, whose growth spurt actually began in the 1880s, became the birthplace of the skyscraper in 1885 with the construction of the 10-story, 140-foot-tall Home Insurance Building, the first building to feature a structural steel frame rather than structural masonry walls. Over time, the definition of what a skyscraper is has changed as buildings have become taller: the more tall buildings there are in a given location, the more people have become concerned about what is merely tall and what is truly tall, and therefore what deserves special attention among pretenders.
Although there is no single definition of what constitutes a skyscraper, the generally accepted scale we use is 150 meters. In recent years, additional terms have been added to the building construction lexicon to describe particularly tall buildings; Supertall was coined to describe buildings over 300 meters tall, and megatall was most recently coined to describe buildings over 600 meters tall. While neither Chicago nor Toronto has a megatall – there are currently only a handful of them in the world – Chicago has seven supertalls, one under construction and one planned, while Toronto has three under construction and six planned.
With 140 skyscrapers completed, Chicago has the second largest list of skyscrapers on the continent. (The title, of course, goes to New York, with 308 completed skyscrapers.) The recent and ongoing construction boom has catapulted Toronto to third place in North America in the number of skyscrapers, with 108 completed skyscrapers. For those who are happy that this height is not everything and that architecture counts too, we admit that when it comes to quality, Chicago is recognized as having a much larger list of outstanding examples of skyscraper architecture than this city.
One Bloor East and One Bloor West rise higher and higher on Yonge Street, image by UrbanToronto Forum contributor Kris
Toronto has some winners, too, but the numbers are likely to see Toronto's rapidly growing skyline soon surpass Chicago's. While Chicago has 1 skyscraper under construction and 10 planned, Toronto has 23 skyscrapers under construction and 355 planned (plus another 20 or so where the proposals are starting to show their age). There are no more skyscrapers under construction or planned in the Chicagoland area, while there are nine more under construction and a few dozen more planned in communities surrounding Toronto.
Toronto's recent boom is the result of rapid population growth combined with control of urban sprawl. As the city of Toronto has overtaken Chicago in population over the last twelve years – now considered the fourth most populous municipality in North America – the Greater Toronto Area, along with surrounding communities, continues to grow in total numbers at the fastest rate on the continent. While the CN Tower—completed in 1976 and holding the world record for tallest free-standing structure for 32 years—despite not being considered a skyscraper, still dominates Toronto's skyline as prominently as the Willis Tower—completed in 1973 as the Sears Tower—does Chicago's, the composition around each landmark has changed since the two were built. How did we get here?
Chicago Temple Building, image from Google Maps
The Windy City's first building to reach a height of more than 500 feet (150 m) was the Chicago Temple Building (above), built in 1924. The 23-story building has a height of 173.1 m, including its church-like tower. In the decades that followed, Chicago cemented its dominance as the center of the US Midwest with bold designs and towering structures, particularly in the 1970s and 1980s, an era that saw icons such as the 100-story John Hancock Center, standing at 1,100 feet (343.7 m) tall (or 1,500 feet (456.9 m) with its antennas) and the aforementioned 110-story Willis Tower (below). with a height of 442.1 m (or 527 m including antennas).
Willis Tower (right), image by joestoltz from Pixabay.com
Today, Chicago's skyline is dominated by 140 buildings over 500 feet (150 m) tall, including 7 supertalls over 1,000 feet (300 m) tall. The most recently completed building is the 101-story, 1,200-foot-tall St. Regis, which opened in 2020. Recently, however, Chicago's vertical growth has slowed. In 2019, the city counted 26 cranes, a number that has only declined since then. By mid-2025, reports from Chicago YIMBY indicate about ten active cranes across its skyline, again an increase from six to seven cranes earlier this year. Current projects include the North Tower at 400 Lake Shore Drive, Bally's Casino Hotel, 370 North Morgan and the renovation of the Thompson Center. Despite a few additional pending approvals for construction projects such as 410 North Elizabeth and 626 South Wabash, the overall picture shows a steady slowdown in major construction activity. With activity concentrated in the downtown core and Near North Side, there are still few cranes in Chicago and a far cry from Toronto's current 145 cranes.
An aerial view of the Chicago skyline, image from Pexels from Pixabay.com
Toronto's first ten-story building was the Temple Building (completed in 1896 and demolished in 1970). A building boom in the 1920s brought several 20-story-plus buildings, most of which have since been replaced, but the 21-story, 300-foot-tall 1928 Sterling Building still stands at 372 Bay. A year later, the Royal York Hotel became the first to exceed the 100 meter mark, reaching a height of 124 m, while the Canadian Bank of Commerce building, now known as Commerce Court North, took the lead in 1931 at 145 m. These two were not surpassed until 1967, when Toronto's first 150m building, the Toronto-Dominion Bank Tower at the TD Centre, was completed in 1967 at 223m. At the end of the 20th century, three taller banking towers were soon added to the financial core in the following decades, along with several others that were not quite as tall.
Toronto skyline, image by UrbanToronto Forum contributor ImmenselyMental
While recent years have seen a flood of new office buildings following a 20-year drought in commercial office towers, Toronto's recent height boom has largely been driven by the need to house people, with the residential sector generally realizing fewer architectural spectacles in its buildings than its commercial siblings. Across all current projects, the total gross floor area under construction is 5.13 million m², including nearly 3.85 million m² of residential space, suggesting that Toronto's skyline growth is now driven primarily by high-rise construction rather than office or institutional construction. In fact, the three Toronto supertalls currently under construction are all primarily residential buildings: 85-story/308.6m One Bloor West, 106-story/351.85m Pinnacle One Yonges SkyTower, and 85-story/300.2m Concord Sky.
Looking north at One Bloor West, image by UrbanToronto Forum contributor jer1961
On January 1, 2024, 359 cranes were seen in the Greater Toronto and Hamilton area, by far the highest on the continent. This year, construction momentum in Toronto remains impressive by global standards, although the pace of construction activity is slowing due to recent slow real estate sales and high financing costs, with 250 cranes still on the horizon as of October 1, 2025.
Historical map of cranes in the GTA in dark blue, Hamilton in light blue, July 2022 to October 2025. Data from UTPro.
The City of Toronto continues to dominate the GTHA skyline with 145 cranes (more than half the regional total), followed by Peel Region with 32, York with 30, Halton with 27, Hamilton with 14 and Durham with 6. Among the 172 active projects, tower heights are up to 351.85 m, with the Pinnacle One Yonge SkyTower the tallest under construction located buildings in the region. The cranes are clustered in many of the same areas identified in High-Rise vs. Low-Rise: North York Centre, Yonge–Eglinton, Etobicoke Centre, Scarborough Centre, Humber Bay Shores, Mississauga City Center and Vaughan Metropolitan Centre, each continuing to add density around Transit investment and mixed-use districts absorb.
Looking south toward the SkyTower at Pinnacle One Yonge, image by UrbanToronto Forum contributor mburrrrr
With the city adding approximately 143,000 residents in 2024 alone and the GTA adding 269,000 residents that year, the Greater Toronto Area is the fastest-growing urban center in North America. This growth has put massive pressure on the housing market and led to a boom in high-rise apartment construction to cope with the influx. Urban planning policies have concentrated this development in the downtown core and key areas such as North York, Scarborough, Etobicoke and surrounding suburban cores, creating dense clusters of skyscrapers.
Toronto skyline, image by UrbanToronto Forum contributor hawc
Recently, Chicago's population has remained relatively stable and there is less incentive for large-scale housing expansion. Instead, the development's focus has been on preserving the city's architectural heritage while continuing to invest primarily in shorter-term projects. Emerging mid-rise residential projects in neighborhoods like Fulton Market underscore this focus over competition in a numbers race.
These two cities, linked by a shared Great Lakes heritage, reflect two different paths of urban growth. As Toronto soars to new heights and Chicago clings to its architectural history, the question remains: Is the true measure of a skyline the number of peaks, the quality of its structures, or some impossible-to-determine combination of the two?
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UrbanToronto has a research service, UTPro, that provides comprehensive data on development projects in the Greater Golden Horseshoe, from proposal to completion. We also offer instant reports, downloadable snapshots based on location, and a daily subscription newsletter, New Development Insider, that tracks projects from the first application.​​​