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The Big Bend
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Ahh, I built that in Minecraft! 
Unbuilt Chicago Megatalls
Frank Lloyd Wright’s The Illinois
FLW’s fanciful 1957 concept for a mile-high 528 story tower was never backed up by any developer and probably couldn’t even have been built back then, but it has proven influential. Chicago architect Adrian Smith’s perpetually under construction 1 kilometer tall Kingdom Tower in Jeddah, Saudi Arabia is clearly a ripoff of The Illinois.
Comparison with Smith + Gill’s Kingdom Tower.
The Chicago World Trade Center
It’s very hard to find information about this project. Apparently there were three separate designs during the 1980s, between 2,100-2,500 feet tall.
The first design was by architect Bruce Graham and structural engineer John Zils of Skidmore, Owings and Merrill. It stood 181 stories and 2,300 feet tall with a bundled tube structure similar to Sears Tower.
The design was revised by Graham and engineer Fazlur Rahman Khan, based around Khan’s concept of a telescoping frame. This new iteration kept the 2,300 foot height but was 168 stories. The Graham/Khan team was also responsible for Sears and John Hancock.
Both of these SOM iterations would have been located next to the Chicago Merchandise Mart at 300 North Lasalle.
After a nasty breakup with SOM that left the firm with thousands of dollars in unpaid fees, developer Stanley Raskow hired Harry Weese to design a 2,500 foot Chicago World Trade Center near Grant Park.
The images below are definitely of the Graham/Khan telescoping design.
Khan’s telescoping structural frame
I believe the images below are of the Graham/Zils bundled tube design, but it might be the Harry Weese design.
@rgarri4 Do you know anything more about the Chicago World Trade Center? I saw that you included it in your excellent unbuilt Chicago video.
Miglin-Beitler Skyneedle
This 1988 Cesar Pelli-designed 2,000-foot tower is probably familiar to most skyscraper nerds. It was put on hold after the early 90s recession and eventually shelved when developer Lee Miglin was murdered. It would have been located across from Pelli’s similar 181 West Madison, at the current site of a parking garage. Knowing Pelli, the facade details and corner solutions would have been very elegant. But I always thought this one looked like it belonged in New York more than Chicago, with its Art Deco-esque setback massing and spire.
A look at Pelli’s signature corners
7 South Dearborn
This sleek 1999 Adrian Smith/SOM-designed tower is technically not a megatall since those are antennas and not spires. The roof height was 1,567 feet. Smith clearly took cues from this design for his later Trump Tower Chicago and Burj Khalifa. This is my favorite unbuilt Chicago tower, I think it suited the city very well with its sleek modern design and bundle of antennas that echo the multiple masts atop Hancock and Sears. The 570-foot One South Dearborn was completed on this site in 2005.
Chicago Spire
Santiago Calatrava’s torqued tower, doomed by the 2008 crash, needs no introduction. The round pit still sits off Lake Shore Drive today.
Closer look at the base
Design evolution
Gateway Tower
Gensler designed this concept for the Chicago Spire site as a public in-house design exercise. It was not backed up by any developer. The goal was to integrate private and public space in a 2,000 foot mixed-use tower.
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If you want to build a skyscraper in the United States, don’t propose it in Chicago. 
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For the Chicago WTC, The boxy Bundeled tube design proposal came first in 1981 designed by Burice Grahm and John Zilis of SOM. It was also proposed at a different location near Grant park so who ever created that rendering has it in the wrong location. The site moved to the location by the river with Fazlur Khans proposal in 1982. This one had the telescoping design (image with the triangles and image with the plans and structural axo) Then the developer switched architects completely in 1986 to Harry Wesse. His proposal is an enhanced squared tube structure based on a study he had previously done. (First 2 images you show)
Speaking of proposals for that exact site along the river, here’s Project 2000
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Wow, thanks so much for the info rgarri! I had assumed the boxy design with square windows in the first 2 pics was the Graham/Khan telescoping design because, well, it sort of telescopes. Thanks for the correction. So are there any renders floating around out there of what the Graham/Khan telescope design would have looked like with cladding, or are those structural diagrams I posted the only known images of it? Most of the info I included in my post about Chicago WTC was from some old Skyscraperpage or Skyscrapercity thread from years ago that I stumbled upon. It appears they had uploaded images of all three designs, but the images were long since deleted.
Also, cool video as always, I hadn’t heard of that proposal. Looks like Ricardo Bofill’s other Chicago towers (77 West Wacker and Dearborn Center) blown up to insane proportions.
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If anyone wants to see the rest of the 1980 “Late Entries to the Chicago Tribune Tower Competition”, you can find them here: https://twitter.com/JoshLipnik/status/1175448793044721664
I like Charles Moore’s the best but Helmut’s is cool too.
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looking southwest
looking north and north east
The original design for the extension of the Tribune Tower.
Collection Mackensen
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Chicago’s un-built Place Du Sable
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The un-built Waldorf Astoria
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The list of the tallest Unbuilt Skyscrapers in NY:
https://www.emporis.com/city/101028/new-york-city-ny-usa/status/unbuilt/1
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What exactly is that?
pipe dreams
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LOL and on the pond in the foreground for some reason they inserted what looks to be about a 400 foot megayacht shrunk down to the size of a rowboat
Thanks bmosborne for this pic
In 1930, a new 150 floors skyscraper was proposed above City Hall (architect’s vision).
The Civic Center
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Well that certainly would make for a stand-out tower, especially for the time. But was that even physically feasible? With the tech of the time. Even ignoring there was no way this thing was getting financed during the Great Depression
This looks to be about 2.5 times the height of the municipal building which is 591, so i don’t think it would have been an issue to build since the ESB seems to be doing just fine.
Oh. Well that’s fine. I thought it was a lot bigger than that. So definitely possible.