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With the Council for Tall Buildings and Urban Habitat (CTBUH), now renamed the Council on Vertical Urbanism (CVU) in Toronto this week for their annual international conference — the world headquarters for this arbiter of everything tall is located in Chicago — we thought it would be fun to run a short series of articles looking at the similarities and differences of 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 explores 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 share similarities in their histories, cultural influence, and skylines. Both have been famously known as the Second City in the past; Chicago trailed only New York in population int he United States after surpassing Philadelphia in 1888, (then lost second city status to Los Angleles in 1980), while Toronto surpassed Quebec City to become Canada's second city in 1871, but then took the crown from Montreal in 1976, having kept it since.
Chicago, whose growth spurt really began in the 1880s, became the birthplace of the skyscraper in 1885 with the construction of the 10-storey, 42 metre-tall Home Insurance Building, the first building to have a structural steel-frame in place of load-bearing masonry walls. Over time, the definition of what a skyscraper is has changed as buildings have gotten progressively taller: the more tall buildings there are in any given place, the more people have fretted over what's merely tall and what's really tall, and therefore what deserves special attention amongst the pretenders.
While there is no one definition of what constitutes a skyscraper, the most widely recognized benchmark is 150 metres, which we are using. In recent years, other terms have been added to the tall building lexicon to describe particularly tall buildings; supertall was coined to describe buildings over 300 metres, and most recently, megatall, was coined for buildings over 600 metres in height. While neither Chicago nor Toronto boast a megatall — there are only a handful of these in the world now — Chicago boasts 7 supertalls with 1 under construction and 1 proposed, while Toronto has 3 under construction, and 6 proposed.
Chicago boasts the second largest list of skyscrapers on the continent with 140 completed. (The title is held of course by New York with 308 completed skyscrapers.) Toronto’s recent and ongoing construction boom has propelled it to third place in North America for the number of skyscrapers, with 108 complete. For those chiming in that height isn't everything, and that architecture counts too, we admit that when quality comes into the picture, Chicago is recognized as having a much larger roster of outstanding examples of skyscraper architecture than this city.
Toronto has some winners too, but it's in the sheer numbers where Toronto's rapidly expanding skyline should soon climb over Chicago's count. While Chicago has 1 skyscraper under construction and 10 proposed, Toronto has 23 skyscrapers under construction, and 355 proposed (plus another 20 or so where the proposals are getting stale). There are no more skyscrapers under construction or porposed in the surrounding Chicagoland area, while there are 9 more under construction in the municipalities surrounding Toronto, and another couple dozen proposed.
Toronto's recent boom is the result of its rapid increase in population, combined with controls on sprawl. With the City of Toronto having surpassed Chicago in population in the last dozen years — now considered North America’s fourth most populous municipality — combined with the surrounding municipalities, the Greater Toronto Area continues to grow in total numbers at the fastest rate on the continent. While the CN Tower — completed in 1976, it held the world record for the tallest free-standing structure for 32 years — despite not being considered a skyscraper, still defines Toronto’s skyline as distinctly as the Willis Tower — completed in 1973 as the Sears Tower — does Chicago’s, yet the composition around each landmark has been shifting around both since either were built. So, how did we get here?
The Windy City’s first building to surpass 150m was the Chicago Temple Building (above), built in 1924. The 23-storey edifice stands at 173.1m, including its church-like spire. Over the following decades, Chicago solidified its dominance as the hub of the American Midwest with bold designs and towering structures, particularly during the 1970s and 1980s, an era that saw the completion of icons like the 100-storey John Hancock Centre at 343.7m (or 456.9m with its antennas) and the aforementioned 110-storey Willis Tower (below), standing 442.1m tall (or 527m including its antennas).
Today, Chicago’s skyline is defined by its 140 buildings over 150m, including 7 supertalls over 300m, the most recently completed of which is the 101-storey, 362.9 metre-tall St Regis, which opened in 2020. Most recently though, Chicago’s vertical growth has slowed. The city counted 26 cranes in 2019, a figure that has only dropped since. As of mid-2025, reports from Chicago YIMBY indicate approximately ten active cranes over its skyline, which itself is an uptick from six to seven cranes earlier this year. Current projects are the North Tower at 400 Lake Shore Drive, the Bally’s Casino Hotel, 370 North Morgan, and the Thompson Center renovation. Despite a few additional permits pending for developments like 410 North Elizabeth and 626 South Wabash, the overall picture shows a steady cooling of large-scale construction. With activity concentrated in the downtown core and in the Near North Side, Chicago’s cranes remain few, and a far cry from Toronto’s current 145 cranes.
Toronto's first building to reach 10 storeys was the Temple Building (completed in 1896 and demolished in 1970). A 1920s building boom brought several 20-storey-plus buildings, most of which have since been replaced, but the 21-storey, 99.8 metre Sterling Building in 1928 still stands at 372 Bay. A year later, the Royal York Hotel was the first to blow past the 100 metre mark to crest at 124m, while the Canadian Bank of Commerce Building, now known as Commerce Court North, took the lead at 145m in 1931. Those two wouldn't be surpassed until 1967 when Toronto's first 150m building, the Toronto-Dominion Bank Tower at the TD Centre, was completed until 1967 at 223m. A trio of taller bank towers were soon added to the financial core over the subsequent decades at the close of the 20th century, along with several others not quite as tall.
While there has been a spate of new office buildings over the last several years following 20 years of commercial office tower drought, Toronto’s recent height boom has mostly been propelled by the need to house people, with the residential sector generally realizing less architectural spectacle in it buildings than its commercial siblings. Across all current projects, the total gross floor area amounts to 5.13 million m² under construction, including nearly 3.85 million m² of residential space, indicating that Toronto’s skyline growth is now driven primarily by high-rise housing rather than office or institutional construction. In fact, Toronto’s three supertalls now under construction are all primarily residential: One Bloor West at 85 storeys / 308.6m, Pinnacle One Yonge’s SkyTower at 106 storeys / 351.85m, and Concord Sky at 85 storeys / 300.2m.
On January 1, 2024, the Greater Toronto and Hamilton Area boasted 359 cranes on its skylines, easily the highest on the continent. This year, Toronto’s construction momentum remains formidable by global standards, even as the pace of activity moderates with the impact of very recent slow real estate sales and high financing costs, still with 250 cranes on the skylines as of October 1, 2025.
The City of Toronto continues to dominate the GTHA's skylines 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 range up to 351.85m, with the Pinnacle One Yonge SkyTower the region’s tallest building under construction. The cranes cluster in many of same areas identified in High-Rise vs Low-Rise: North York Centre, Yonge–Eglinton, Etobicoke Centre, Scarborough Centre, Humber Bay Shores, Mississauga City Centre, and Vaughan Metropolitan Centre, each continuing to absorb new density around transit investments and mixed-use precincts.
With the city adding about 143,000 residents in 2024 alone, and the GTA adding 269,000 that year, the Greater Toronto Area is the fastest-growing urban centre in North America. This growth has placed massive pressure on the housing market, prompting a boom in high-rise residential construction to accommodate the influx. Urban planning policies have concentrated this development in the downtown core and key areas like North York, Scarborough, Etobicoke, and surround suburban city cores, creating dense clusters of skyscrapers.
Of late, Chicago’s population has remained relatively stable, with fewer drivers for large-scale housing expansions. Instead, the focus of development has been on maintaining the city's architectural heritage while investments continue mainly in shorter projects. Emerging mid-rise residential projects in neighbourhoods such as Fulton Market highlight this focus over competing in a numbers race.
These two cities, bound by a shared Great Lakes heritage, reflect two distinct paths of urban growth. As Toronto races toward new heights and Chicago holds firm in its architectural history, the question remains: is the true measure of a skyline its number of peaks, the quality of its works, or an impossible to pin down combination of both?
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UrbanToronto has a research service, UTPro, that provides comprehensive data on development projects in the Greater Golden Horseshoe — from proposal through to completion. We also offer Instant Reports, downloadable snapshots based on location, and a daily subscription newsletter, New Development Insider, that tracks projects from initial application.
