Chicago Spire, Elon Musk’s ‘X’ and more: Chicago projects that won mayor support but were later sidelined

Chicago mayors have known over the years that re-election can be one major legacy project away.

That may have been on Mayor Lori Lightfoot’s mind when she selected Bally’s $1.74 billion casino, hotel and entertainment development for the city last week. But the plan still faces a long approval process and is still far from a sure thing.

In other words, we’ve seen this before. The casino may in fact be built, but many fantastical ideas have gotten mayoral support yet still failed — some of them famously.

Here are our top 10 near misses, with three historians — Ann Durkin Keating, North Central College professor and co-editor of the Encyclopedia of Chicago; Tim Samuelson, the first city of Chicago cultural historian; and Paul Durica, director of exhibitions at the Chicago History Museum — explaining what happened.

Chicago Spire

Proposed for a 2.2-acre parcel near Lake Michigan and the Chicago River

Proposal: Originally dubbed the Fordham Spire, after Chicago developer The Fordham Co., it was to have been the tallest skyscraper in the U.S. — and the Western Hemisphere. Announced in July 2005, the project aimed to turn an unruly 2.2-acre patch of land into “a tower utterly different from the boxy forms found elsewhere on the Chicago skyline: A skyscraper with gently curving, concave outer walls attached to a massive reinforced concrete core,” the Tribune reported.

Others also tried to build a skyscraper to top the 110-story Willis (then known as Sears) Tower, which was completed in 1974, including the 125-story Miglin-Beitler Tower in 1989 and the 112-story 7 S. Dearborn project in 1999.

Yet only Donald Trump — before he became president — actually got such a project under way. His namesake hotel and condo tower was then under construction along the Chicago River. And, he didn’t care for Fordham’s project.

“Any bank that would put up money to build a building like that would be insane,” Trump said, citing the Sept. 11 terrorist attacks on skyscrapers less than four years earlier. Though his own tower would top out just 89 feet shorter than Willis Tower.

Mayor’s reaction: “Chicago is known [for] great skyscrapers,” Mayor Richard M. Daley told reporters in 2005. “I am excited about it.”

“It is quality construction, architectural design,” he added at an unrelated City Hall briefing. “It would be a great skyscraper and it is something you should think about.”

Daley shrugged off other concerns about whether the Spire might become a target of terrorism or opposition from some neighbors.

“Why don’t we just close up everything and just say, ‘OK, let’s stop everything. Terrorists have won. Let’s change our whole life.’ We have to move on with life. ... We should do what we did in the past.”

As for neighbors’ opposition, Daley said, “If someone builds in front of you, no one likes that.” But everyone “should be able to have an open mind on this.”

What happened: Irish developer Garrett Kelleher — once an aspiring tennis pro — took over the project in 2006. Foundation work was begun on the planned 2,000-foot-tall tower, designed by Spanish-born, Zurich-based architect Santiago Calatrava, without a construction loan. A 76-foot-deep hole still occupies the site. Calatrava finally added a piece of his own work near the Chicago River in 2020 — a flaming red sculpture.

Status: Two apartment towers — 875 and 765 feet — are now planned for the site. Related Midwest, which gained control of the property in 2014, calls the project 400 Lake Shore Drive and expects it to be completed in 2024.

What historians say: “Big building projects often founder on real estate cycles, none more spectacularly than this big hole in the ground!” — Keating

“Here was a cool speculative dream that would have been an instant architectural landmark in Chicago’s cityscape had it been built. To prove that the project was serious and thereby attract enough pre-construction tenants to jump-start construction, the alluring circular foundation was constructed. But the proposed building was so large and costly, it was a challenge to line-up enough pre-construction tenants to make things happen. Too bad! Many people were genuinely sad when the circle finally vanished for other purposes. As long as that strange circular hole existed, people clung to hope. Chicago’s past is filled with similar fizzled dreams.” — Samuelson

”The definition of ‘make no little plans,’ which seemed like a natural extension of Chicago’s rich array of architectural masterpieces, but was it necessary?” — Durica

Block 37 “super station” for the Chicago Transit Authority

Proposed express rail service from downtown to O’Hare International and Chicago Midway International airports

Proposal: The CTA and Mills Corp. announced in March 2004 plans to build a station below the long-dormant Block 37 that would sit between CTA’s Red and Blue Lines and include a link between them. Those lines would also link south of Roosevelt Road to the Orange Line, which runs to Midway. The estimated cost for the station — which would offer premium express rail service outfitted with airline-type seats to both airports and station-based airline baggage checking — was $213.3 million.

The 2.7-acre Block 37 site — bounded by State, Randolph, Dearborn and Washington streets — was first proposed for redevelopment in 1983 under then-Mayor Harold Washington. Mayor Richard M. Daley’s administration cleared the block of structures in 1989, to make way for new development but the project was scuttled in 2001. Construction of the development finally began in late 2005, after the city sold the land to Mills for $12.3 million after having bought it back from the previous development group for $35.2 million.

What happened: A privatization plan was proposed for the project in 2006 — after myriad false starts and delays in trying to develop Block 37. The move was also an acknowledgment by the Daley administration that the city could not entrust such a major transportation improvement to the CTA alone.

While the CTA plowed ahead with excavation and preconstruction on the downtown station, it had no timetable or funding to do the track work needed to route the express trains around the slower all-stop trains on the Blue Line to O’Hare and the Orange Line to Midway, the Tribune later reported.

Another hitch — initially, service times weren’t planned to be any faster because trains would run on existing CTA infrastructure. But, passengers would pay more for the amenities. At the time, CTA President Frank Kruesi likened it to travelers who are willing to pay extra to fly first class instead of coach, or who hire a limousine instead of hailing a taxi, even though both vehicles arrive at the destination at the same time.

Status: Work was stopped at the station site in 2008, due to massive cost overruns.

Mayor’s reaction: Asked when the project would get back on track, Daley said at the time: “We’ll see what we can do. You have to come up with new technology. You just can’t put it in there. That would be a disaster, I thought.”

What historians say: “Underground Chicago is a complex place fraught with existing obstacles — both natural and human-created. What literally stands in the path would present a formidable challenge in time, cost and the risk of major disruptions topside. But as you know, there’s a ghostly uncompleted station below Block 37 as a haunting reminder.” — Samuelson

”Like the Boring Co. project, this one addressed a real desire held by a lot of Chicagoans: a faster connection between the Loop and O’Hare. Given how far this project progressed, its ultimate failure I find depressing.” — Durica

‘X:’ High-speed, autonomous passenger vehicles by elon Musk’s The Boring Company

Proposed for travel from downtown to O’Hare International Airport

Proposal: On June 14, 2018 — almost 10 years to the day after the CTA board suspended work on the Block 37 station — then-Mayor Rahm Emanuel and billionaire serial entrepreneur and high-tech investor Elon Musk announced a high-speed transit proposal in which driverless 16-passenger vehicles would zip back and forth at speeds exceeding 100 mph in tunnels between the Loop and O’Hare International Airport.

For $20 to $25 per ride, passengers would complete the route in just 12 minutes, according to the proposal.

Boring’s plan — which offered no timeline for the project’s completion nor estimated cost but agreed to pay for the entire project — was picked from four competing bids as an alternative to the city’s traffic gridlock and slower “L” trains.

“In choosing Boring, Emanuel and senior City Hall officials are counting on Musk’s highly touted but still unproven tunneling technology over the more traditional high-speed rail option that until recently had been envisioned as the answer to speeding up the commute between the city’s central business district and one of the world’s busiest airports,” the Tribune reported.

Emanuel had preliminary discussions with Musk about the possibility of direct express travel to O’Hare International Airport, but emails show it was Valor Equity Partners founder Antonio Gracias who connected them. Emanuel and Gracias, a former director of Tesla where Musk is CEO, discussed the idea over lunch in 2017.

Later the same year, Emanuel put out a call for respondents interested in forming a public-private partnership to design, build, finance, operate and maintain an express train from downtown to O’Hare.

Musk confirmed days later, via Twitter, that Boring would bid on the project.

Mayor’s reaction: “Chicago is always on the cutting edge, Chicago is always looking over the horizon to see what’s next,” Emanuel said during the announcement on June 14, 2018. He placed Musk’s plan to whisk riders from downtown to O’Hare in 12 minutes among other great civic projects in Chicago history.

“Were there doubters when Chicago reversed the flow of the river? Yes. Where are they today?” Emanuel asked as Musk looked on. “Were there doubters when Chicago said we’re going to build the first skyscraper in America? Yeah. Where are they today? Were there doubters when we said we’re going to have the tallest building in the world known before as the Sears Tower? Yes, there were doubters. Where are they today? My view is it’s easy to be a critic or a cynic. What jobs do they produce, what economic growth do they produce?”

What happened: The project took a hit after Emanuel announced he would not seek re-election.

“The next mayor won’t have enough skin in the game to feel a need to push through the engineering roadblocks facing O’Hare express” service, DePaul University transportation expert Joseph Schwieterman told the Tribune in 2018. “Unless Elon Musk surprises us with answers to all the lingering questions — and does it soon — I expect this project to fall out of the spotlight and eventually be dropped.”

Status: Prior to her election, Mayor Lori Lightfoot Lightfoot called the idea that the project — which was estimated to cost $1 billion — could be built without public funds “a fiction,” and did not include it in her extensive transportation plan for the city.

What historians say: “The presence of today’s ultimate dreamer of them all — Elon Musk — made his underground tunnels to O’Hare even more stirring to the imagination.” — Samuelson

”I don’t want to be snarky, but this project was like the monorail episode of “The Simpsons” set in Chicago, but without Leonard Nimoy or the jokes.” — Durica

Crosstown Expressway

Proposed as a single highway to help drivers bypass the city

Proposal: In 1960, the Chicago Motor Club proposed the city build a highway that would connect to other expressways while skirting downtown to “account for large savings in travel time, but also will save many lives each year by reducing the heavy traffic loads and resultant number of accidents on parallel streets.”

In one early version, the Crosstown, which was supposed to link the other four expressways the way the rim of a wheel links the spokes, was to run on Cicero Avenue from the Kennedy-Edens junction south to the Eisenhower Expressway, then to roughly 75th Street, where it would have turned east and run to the Dan Ryan Expressway.

A later version had the south leg angling farther south, to Interstate Highway 57 near 99th Street.

Yet another version had the north leg-raised on stilts to minimize neighborhood displacement-running along the Belt Line Railroad tracks just east of Cicero Avenue.

Besides routing traffic around downtown, the Crosstown would have given trucks from the industrial belt on the West and Southwest Sides direct access to the regional expressway network without having to use arterial streets or the downtown route.

Mayor’s reaction: Calling it the last major highway to be built in Chicago, Mayor Richard J. Daley made the project his priority. Yet, funding became difficult to secure.

What happened: The project was mothballed after Daley’s death on Dec. 20, 1976. A month later, Republican Gov. Jim Thompson denounced the Crosstown as “an idea whose time has gone.”

Yet the funds put aside for the project continued to grow — to more than $2.5 billion.

Status: Eventually, Mayor Michael Bilandic and then Mayor Jane Byrne were persuaded by Thompson, to “redesignate” the Crosstown funds, giving half to the state and using the remainder to do routine road improvement work in Chicago.

What historians say: “Initially part of the broad circumferences routes envisioned in the 1909 Plan, the Crosstown was proposed as part of the Interstate Highway System in 1967 — Richard J. Daley pushed but strong local opposition along the route (Cicero Avenue between the Kennedy and Stevenson Expressways), as well as changing national environmental standards and attitudes toward highway expansion ended finally in 1979 (Daley pushed until his death in 1976).” — Keating

“The much-touted Crosstown Expressway never happened, but its discussions launched many subsequent roadway and public transit improvements that give it a ghostly and largely positive presence today.” — Samuelson

”Traffic congestion remains a problem but considering the communities that still exist because this project failed and the need to think seriously about our fossil fuel use now and in the decades ahead, it’s probably for the best. Like a lot of these projects, years of planning and lots and lots of funding went into this project before the plug was ultimately pulled.” — Durica

Lucas Museum of Narrative Art

Proposed for Chicago’s lakefront near Soldier Field

Proposal: “Star Wars” creator George Lucas was looking for a site to build a major museum to house his significant art and movie memorabilia collection in 2014. Chicago was not only his part-time residence, but also the hometown of his wife. A task force considered several sites and other cities, but settled on a 17-acre stretch of lakefront occupied by Solder Field parking lots.

Under Mayor Rahm Emanuel’s plan, the two Chicago Park District-owned parking lots would have been be leased to the museum for $1, which was similar to arrangements other large cultural institutions have with the Chicago Park District.

But unlike other museums, the Lucas museum would not receive taxpayer subsidies to cover a portion of its operations, a top mayoral aide said.

The parking lots would be moved underground at Lucas’ expense, the city said.

Mayor’s reaction: “Just imagine, you’ll leave the Field Museum, studying a dinosaur from 30 million years ago, three million years ago, you’ll walk across, go into another another museum and through computer and digital work you’ll be designing a dinosaur,” Mayor Rahm Emanuel said in 2014. “It’s an incredible opportunity for us.”

What happened: Though Emanuel led an aggressive lobbying effort on behalf of the museum, the Lucas plan faced strong opposition. Where would tailgaters spend their pre-Chicago Bears game celebrations if the museum were built atop their lots? Friends of the Parks, a local watchdog group that advocates for open spaces, argued against giving the prime location to the privately funded museum and filed a federal lawsuit blocking its construction. Then, there was the pesky ordinance.

Among the 14 “basic policies” of the Lakefront Plan of Chicago, adopted by the city council in 1973, is that “in no instance will further private development be permitted east of Lake Shore Drive.” And the Lakefront Protection Ordinance says that the plan commission’s decisions “shall be made in conformity with” those policies.

Status: Facing an uphill legal battle, Lucas announced in June 2016 that he was abandoning plans to build the museum in Chicago.

“Unfortunately, time has run out, and the moment we’ve consistently warned about has arrived,” Emanuel stated after Lucas backed out of Chicago. “Chicago’s loss will be another city’s gain. ... We tried to find common ground to resolve the lawsuit — the sole barrier preventing the start of the museum’s construction. But despite our best efforts to negotiate a common solution that would keep this tremendous cultural and economic asset in Chicago, Friends of the Parks chose to instead negotiate with themselves while Lucas negotiated with cities on the West Coast.”

Lucas now plans to open his namesake museum in Los Angeles.

What historians say: “Stopped primarily by Friends of the Parks, ongoing siting issues. Activists managed to portray this as an outsider project — even though his wife, Mellody Hobson, is a Chicagoan.” — Keating

“In my personal assessment, this one breaks my heart. When initially proposed, people were trampling all over this project — claiming it would be a tawdry personal ode by George Lucas to “Star Wars” and Norman Rockwell. What an insulting and totally inaccurate rebuff to something that was to be a thoughtfully-curated and highly diverse museum that would break down the walls separating notions of what constitutes art and culture. Subjectively, I wasn’t crazy about the building design, but improving a tawdry parking lot site with a thoughtful cultural asset amidst an area that (Daniel) Burnham’s 1909 plan set aside for a museum purposes seemed like an appropriate addition. In the course of this dispute, I sometimes wondered if some people who wielded Burnham’s name as a sword against the Lucas Museum had even read the 1909 Plan of Chicago. Or for that matter, the prospectus for the Lucas Museum itself.” — Samuelson

”Chicago has many amazing cultural institutions, and there’s no reason not to add to them. But Chicago also has an amazing lakefront and many other areas that would benefit from having a museum sited there.” — Durica

South Loop Stadium

Proposed for a 60-acre railroad yard south of Roosevelt Road on the South Branch of the Chicago River

Proposal: Why not build one complex that could house all of the city’s baseball, basketball, football, soccer and hockey teams? The idea was floated in the 1960s and 1970s, but revived during Mayor Harold Washington’s tenure. The plan originally called for a domed stadium compound built, in part, by the city.

Though both played in aging ballparks, the Cubs and White Sox hated the notion.

“We’d like a new facility,” acknowledged White Sox board chairman Jerry Reinsdorf in June 1985. “But we wouldn’t want to play in the same stadium with the Cubs.”

“I’m totally against the idea of two major-league baseball teams sharing a ballpark,” said Dallas Green, president and general manager of the Cubs. “Historically, it’s never worked. My recommendation to my superiors at Tribune Co. would be not to share a stadium.” (The Tribune bought the Cubs from the Wrigley family for $20.5 million in 1981.)

Mayor’s reaction: “All the elements needed to create a superb sports center are right here in Chicago — the site; the funds, both public and private; the financial creativity of our business leaders; and most important, the civic spirit,” Washington said in June 1985.

What happened: As Washington announced his preferred site for the project — a 60-acre railroad yard south of Roosevelt Road on the South Branch of the Chicago River — the White Sox owners were considering building a stadium with a retractable roof in suburban Addison.

Worried the team would leave the South Side, Washington modified his plan in December 1985. Now, he proposed a $125 million baseball-only, open-air ballpark built by private developers that would only house the White Sox.

Though pressured by the American League to find a new ballpark, the team had its own list of demands for the project, including keeping almost all income from ticket sales, concessions, parking and in-stadium advertising and not paying rent.

Washington presented his final offer to the White Sox — a combined baseball/football stadium at a cost of $255 million — in April 1986. “Here’s the package,” he said. “You want to negotiate? Fine. If not, no stadium.”

Status: The White Sox tentatively accepted the city’s offer, but Bears President Michael McCaskey didn’t. In November 1986, talks of moving to DuPage County ended when results of a referendum showed residents had mixed feelings about the stadium ending up in Addison.

The city and White Sox executives regrouped and presented a plan to Gov. James Thompson in early December 1986, that called for a new stadium near the site of Comiskey Park at 35th Street and Shields Avenue. A few days later, the Illinois General Assembly approved — on its second try — a new 45,00-seat South Side stadium for the White Sox that would be ready by the 1990 season.

Washington, who won re-election in April 1987, died suddenly of a heart attack on Nov. 25, 1987, leaving Gov. Thompson to line up votes for a new, tax-subsidized $167 million Sox stadium. The team was threatening to move to St. Petersburg, Fla., but was awarded the project in its 11th hour before the Illinois General Assembly on the last day of its legislative session in 1988. The White Sox were shut out by the Detroit Tigers in the first game inside “Comiskey II” on April 18, 1991.

What historians say: “Lois Wille discussed this nicely in her book ‘At Home in the Loop.’ When acquiring land becomes complicated, projects seem to die or move to a location where it is easier to acquire land.” — Keating

“Discussions of where to land quarters for sports teams is a perennial question. Some cities have successfully landed their sports teams in close adjacency to their central business districts and the expanses of rapidly-diminishing rail yards south of the loop offered some tempting possibilities. But there were many investment and city-planning eyes focused on the same available land, so nothing ever materialized.” — Samuelson

”The Bears resented the White Sox being brought into the deal first at a time when both teams were looking to relocate to the suburbs. Given that mixed-sports stadiums have fallen out of use, it’s probably for the best that this project faltered. The Sox did get a new ballpark, and the Bears got a renovation to Soldier Field, but, as we all know, the latter is looking to move again.” — Durica

Lake Calumet airport

Proposed for Chicago’s Southeast Side

Proposal: Three different mayoral administrations considered the landfill area for a potential third Chicago airport. In 1985, Mayor Jane Byrne suggested it as a revitalization project — an airport for cargo planes. The following year, Mayor Harold Washington’s public works commissioner Paul Karas revealed his department was conducting a study to determine the feasibility of a Lake Calumet airport — slightly larger than Midway — serving 10 million passengers yearly.

But it was Mayor Richard M. Daley who proposed the largest footprint and price tag — $5 billion — for the property. Unveiled in February 1990, Daley’s plan required multiple phases and the razing of about 8,500 homes in the Hegewisch and South Deering neighborhoods as well as in suburban Burnham and Calumet City to complete the project on 9,400 acres. He said the construction of the international airport would create thousands of jobs and, eventually, generate billions of dollars in economic benefits annually in an area hit hard by industrial decline. And, how to pay for the project? Through passenger facility charges added to tickets purchased for flights out of O’Hare and Midway.

Mayor’s reaction: “This is real,” Daley declared on Feb. 15, 1990. “This [represents] a major commitment by everybody in my administration.”

What happened: Daley called the project — which had ballooned to an estimated $10.8 billion — “dead” after the state Senate narrowly rejected legislation necessary to advance it.

Status: The estimated $90 million in airplane ticket taxes collected to help fund construction of the Lake Calumet airport will be used instead for improvements at O’Hare and Midway airports, Daley announced in September 1992.

What historians say: “Richard J. Daley’s 1960s ‘airport in the lake’ plan, opposed by Businessmen for the Public Interest (BPI), funded by businessman Gordon Sherman (Midas Mufflers). A 1970 campaign slogan ‘don’t do it in the lake,’ helped turn the tide against the proposal. Unlikely to get support today with environmental standards.” — Keating

“During a time when Chicago critically felt the need for a third major airport, expanses of what remained of Lake Calumet offered an appealing option for a site accessible within the city limits potentially accessible by existing highways and extended public transit. But, looking back, it would have presented some serious issues for nearby communities — including ones to the immediate East that could have been potentially removed altogether. And when looking at the site with today’s lens, the environmental impact would be a serious issue to consider.” — Samuelson

”The dream of a third airport continues to be revived from time to time. This project failed due to political infighting, but it would have taken business from Midway and created a lot of additional environmental issues for the Lake Calumet area. Strengthening existing airports, like Midway and O’Hare, seemed like the better plan in the 1990s and remains so today.” — Durica

Central Area Circulator

Proposed trolley-style light rail system for downtown Chicago

Proposal: With buses reduced to a crawl in the busy downtown area in 1989, the Metropolitan Planning Council proposed a $320 million electric-powered light rail system that could whisk tourists and commuters alike throughout the Loop with connections to the lakefront, River North and South Loop.

The trolley-style rail cars would connect to thin overhead wires mounted on light poles and hidden through trees and operate about 30 percent faster than buses, the group claimed.

Mayor’s reaction: Newly elected Mayor Richard M. Daley went to Washington to stump for federal funding for the system, which was expected to cost $600 million. He returned to Chicago empty handed.

What happened: By 1994, the trolley system had won backing from Gov. Jim Edgar, but its estimated cost had grown to $800 million and still lacked financial support from the federal level. And, other local transportation entities — the CTA, Metra and Pace — were also seeking funding for repairs and expansion.

Status: Returning from an all-expenses-paid trip to England in late May 1995, Daley declared the project dead.

Only limited funds had been pledged to the project — which was set to connect McCormick Place, Michigan Avenue, Navy Pier and other commuter train stations near the Loop — by the Republican-controlled state legislature and Congress.

What historians say: “Many cities have experimented with central area circulators using a trolley-based system. Many studies were made on the usefulness of such a system in the downtown area, and generated projections on how many people would find it useful in relation to such a system’s cost. The Loop’s revamped bus circulation system has some ancestry in this proposal.” — Samuelson

”I am of two minds about this project. I’ve lived in cities with similar trolley systems to what was proposed in Chicago, and from my completely subjective experience, they seemed to work well. But I also understand the challenges a project like this faced in Chicago. The Loop Link attempts to address a similar need, and like any other civic project has its fans and detractors.” — Durica

1992 World’s Fair bid

Proposed for Chicago’s Near South lakefront

Proposal: Within its three-volume, 700-page application submitted to the U.S. Department of Congress in August 1981, the not-for-profit Chicago World’s Fair Corp. detailed the reasons the city should host the event, named “The Age of Discovery,” and predicted to be the largest of its kind. Primarily, the city was looking to boost its reputation.

“I’m tired of people saying that Chicago and the Midwest are going downhill,” Thomas G. Ayers, the Fair Corp.’s president, told the Tribune at the time. “The whole point is to show off Chicago to the world in a very favorable light.”

In celebration of the 500th anniversary of Christopher Columbus’ landing in America, Chicago planned to welcome an estimated millions of visitors to attractions built on its lakefront.

Mayor’s reaction: “It gives me great pleasure to officially extend an invitation to the people of all nations to come to the Chicago World’s Fair in 1992,” Byrne said in June 1982. “This can do nothing but improve Chicago.”

Mayor Harold Washington, however, was skeptical of continuing planning for the fair after his election in 1983: “The jury is still out on the question of the World’s Fair. The over-riding question is, can we afford it? I don’t know that we can or not.

What happened: Though the Bureau of International Expositions awarded Chicago official world fair status in June 1983, many questions remained. Cost ($365-$743 million) and attendance (52-75 million) estimates varied widely. No public debate had been sought by the private Fair Corp.

The civic and corporate titans who launched planning for the ‘92 fair back in 1978 never did volunteer to front the money to build it. But in 1983 they got the Illinois legislature to appropriate $8.8 million to continue planning and establish a state authority and governing board, to which several titans were appointed.

The fair’s plan, masterminded by architect Bruce Graham of Willis (then Sears) Tower fame, called for nearly 200 acres of new landfill off Northerly Island (then Meigs Field). This environmentally questionable “improvement” helped drive the estimated cost of construction past $675 million.

Status: Plans for the 1992 fair died on June 20, 1985 — though the exposition was not officially canceled until 1987.

Then Illinois House Speaker Michael Madigan delivered the death knell, saying the now estimated $1.1 billion exposition was “a bad risk” for taxpayers. John Kramer, general manager of the Chicago World’s Fair 1992 Authority, moved to dissolve the 20-month-old fair agency.

What historians say: “The 1992 World’s Fair bid allowed planners and others interested in Chicago development an opportunity to think about redeveloping the South Side (especially around the hospitals) in interesting ways. The 2016 Summer Olympics bid built to some degree on the ideas from the 1992 fair discussion. In some ways, I’m surprised that the casino discussion never came back here?” — Keating

“Chicago has a rich heritage of World’s Fairs, and many felt the time was right for a new one. But in the years approaching 1992, many were already questioning the viability and crowd-attracting potential of this kind of costly event.” — Samuelson

”The two previous World’s Fairs continue to excite the imaginations of many Chicagoans, so a third fair remains a real ‘what if.’ It could have been a failure, like the one in New Orleans in 1984, or could have become the fifth star on the Chicago flag. In any case, it would have directed time and resources from the city’s many other needs.” — Durica

2016 Summer Olympics bid

Proposed for Chicago’s lakefront and parks

Proposal: Mayor Richard M. Daley once called bidding for the Olympics a con game. But after meeting with an official involved in staging the 2004 Olympics in Athens, he began considered a bid for Chicago in July 2005. The move seemed surprising — considering the high price tag and the city’s lack of experience. The last major international sports event held in Chicago was the 1959 Pan American Games.

Daley assembled a a Chicago 2016 Committee of big names to assist in the effort — including Aon chairman Patrick Ryan, TransUnion LLC (and later Secretary of Commerce) chairman Penny Pritzker and Skidmore Owings & Merrill partner Tom Kerwin.

The team submitted its 458-page, 10-pound bid book to the United States Olympic Committee in January 2007 — reserving a seat for it on a flight bound for Colorado Springs. Chicago came up with $1.15 billion in guarantees against shortfalls in a projected $2.9 billion operating budget. When compared with bids from other prospective host cities, Chicago’s numbers for running the games were the largest — by far.

On April 14, 2007, Chicago was selected over two-time Olympic host Los Angeles as the U.S. candidate for the 2016 Summer Games.

What happened: Despite an appearance by President Barack Obama at the final presentations on Oct. 2, 2009, in Copenhagen, Chicago’s candidacy landed with a thud.

Chicago was ousted in the first round of voting for the 2016 Games, rejected before the mayor’s car could even arrive back at the convention center to witness the drama of the International Olympic Committee vote. He had the car turned around and headed straight to a suddenly deflated Chicago backers’ party.

IOC politics appeared to play a major role in explaining how Chicago, which many saw as the favorite, was eliminated so quickly.

The city’s main pitch was to put on games along the spectacular backdrop of Lake Michigan. That turned out to be no match for Rio, not because the beach at Ipanema outshines Oak Street, but because of a more powerful geographic symbolism. Time and time again in this intense contest, Rio de Janeiro hammered away at the fact that an organization devoted to international understanding through sport had never deigned to give the games to South America.

Back in Chicago, the celebration also ended practically as quickly as it began. Would-be revelers arrived at Daley Center and other locations expecting a tense morning culminating in a victory announcement just before noon locally. Instead, Chicago was out of the running by about 10:15 a.m.

Mayor’s reaction: About three hours after Chicago was eliminated, Daley made his first public statement, saying he was disappointed, “but you go on with your life.”

Asked if he’d shed tears, Daley at first said no.

But then added, “Sure, you have tears, you get disappointed — you’re human like anyone else.”

Status: Daley ruled out a bid for 2020, saying it was highly unlikely the IOC would return to the Americas so quickly.

The failed 2016 bid left a pricey legacy for taxpayers. The city was on the hook for about $140 million in principal and interest on the purchase of property for an Olympic Village to house athletes, and it was saddled with costly, 10-year union contracts that were hammered out to ensure labor peace during the Games.

What historians say: “A lot of people had their hopes riding on holding the 2016 Olympics in Chicago and put a lot of prideful time money and effort into it. It seems too close in time to comment negatively on this campaign, but the experiences of other cities that have actually hosted the Olympics would suggest that Chicago dodged a real financial and city-planning bullet with this one.” — Samuelson

”The Olympic bid had its supporters and opponents, but this was a project whose fate was ultimately outside the control of the then mayor or the city. Had it happened and failed financially, Chicago would be in a worse place today.” — Durica

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