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The Windy City is having another season to make other theatre cities envious.

By the time the Tony Awards roll around in June, a record number of Chicago productions and plays will have gusted over to New York.

Local playwrights Keith Huff and Tracy Letts both had dramas on Broadway this fall, while new Chicago-originated musicals Million Dollar Quartet and The Addams Family are headed there soon. (The Goodman Theatre wants to take its Stratford-born double bill of Hughie and Krapp’s Last Tape, starring Brian Dennehy, to the Great White Way too, if it can find a space.)

Chicago's buzz extends to off-Broadway, with the work of director David Cromer, and beyond with the ongoing success of Letts's 2008 hit, August:

Osage County, which recently visited Toronto and crossed the pond to London.

Given all that recognition, isn't it a little embarrassing that the City of Toronto website is still claiming that Hogtown is "the third-largest English-language theatre centre in the world”?

While Toronto may have indeed vied for that unscientific title in the 1990s, it's decidedly been in the dust in the past 10 years. Even a Canadian company like Cirque du Soleil would rather test drive its new vaudeville show Banana Shpeel in Chicago rather than Toronto.

Toronto's theatre artists have talent to burn, of course - so what's Chicago theatre got that TO has not? Here are the four Cs that Canada's biggest metropolis could learn from the so-called Second City.

Civic leadership

This year, Chicago celebrates the 10th anniversary of the theatre district. A decade ago, long-time mayor Richard M. Daley poured over $100-million into transforming the city's downtown Loop from a place you'd not want to venture after dark into a hopping area anchored by the arts. A block that contained an empty lot and the shells of two porn cinemas became the new home of the Goodman Theatre, while several bigger theatres were renovated to host touring shows and pre-Broadway tryouts like The Addams Family starring Nathan Lane.

"We're starting to do economic-impact surveys, but even the most simple statistics would indicate that the theatre district has pumped far more revenue into the city than the city put into it," says Roche Schulfer, executive director of the Goodman.

The mayor's largesse has extended beyond the Loop, too, with companies such as Chicago Shakespeare Theater and Lookingglass getting fancy new and heavily subsidized digs.

Over all, Chicago spends about three times as much per capita on arts and culture than Toronto does, though its efforts to brand the city as a theatre town are simple and inexpensive – like giving theatres street-lamp space to fly banners promoting their shows.

Meanwhile back in Toronto. … The street lamps fly banners asking citizens "TO Live With Culture," generically (and confusingly) promoting the idea of the arts rather than the actual living cultural institutions in town.

While Mayor David Miller came into office talking a big game about the arts, as he leaves many arts professionals quietly say that he's been a disappointment. "Of the major cities in North America, we are still funded municipally the lowest by a long shot," says Toronto Arts Council executive director Claire Hopkinson.

The problems are myriad and well-known: Commercial producer Dancap – which has investments in Broadway-bound shows like The Addams Family - has struggled to find space to produce and present downtown, while lifeblood not-for-profits like Factory Theatre and Tarragon Theatre are still struggling with substandard spaces.

Almost as old as Chicago's Theatre District is a Theatre Ontario report called "Spaced... Out?" detailing some of these issues. "It may as well have been written last month," says Jacoba Knaapen, head of Toronto Alliance of the Performing Arts. "So little has changed, it's appalling."

Collegiality

This is an oddly formal term you hear from everyone in Chicago theatre, but it's more than just a buzzword. In the front lobby of the Steppenwolf Theatre, there’s a display case celebrating not just the regional Tony they won in 1985, but the other three Chicago theatres that have won it since, a record for an American city: the Goodman Theatre (1992), Victory Gardens (2001) and Chicago Shakespeare Theater (2008).

Martha Lavey, artistic director of Steppenwolf, suspects the sense of co-operation between theatres dates back to birth of the city's "storefront" theatre movement in the 1970s. "It tended to involve ensemble-based theatres like Steppenwolf," she notes, "and that sense of fellowship maybe engendered itself across the actual ecosystem of the community."

Through the League of Chicago Theatres alliance, over 190 theatres, from small non-union companies to the giant Broadway in Chicago organization, promote and advocate together. "We've been able to achieve things here because we've been willing to work together, because we haven't stayed in our own separate backyards," says Schulfer.

Meanwhile, back in Toronto. … The Toronto Alliance for the Performing Arts tries to perform the role of the LCT, but to a certain extent it is still rebuilding after a major financial crisis in 2004.

As for Toronto theatres' ability to play together nicely, perhaps the simplest example of the lack of communication between the various theatres is how often two of the bigger not-for-profits – Soulpepper and Canadian Stage Company, say – will schedule their openings on the exact same night.

"That's terrible," says Deb Clapp, executive of the LCT, when I tell her how often this happens in Toronto. "I'm not going to say it doesn't happen here, but certainly never among the major theatres."

Comprehensive criticism

Perhaps the most astonishing thing about talking to Chicago theatre practitioners is how enthusiastic they are about their local critics.

Composer Jean Sibelius once quipped that no one had ever raised a statue to a critic, but in Chicago they are about to name a theatre after one. Playwrights David Mamet and Letts are among those who donated money so that Victory Gardens would name its new studio space after Richard Christiansen, retired critic for the Chicago Tribune.

While he wasn't always kind, Christiansen is revered for reviewing shows big or small, union and non-union, no matter where they took place in the city. "He would seek out new work wherever it was and new companies and give them visibility akin to a Broadway touring show," says Schulfer, long-time executive director of Goodman. It's a tradition his successors have kept up.

Why does this matter? Well, it means Chicago has developed as a city where graduates from the city's many universities stick around and start companies, instead of immediately going to try their luck on the coasts in New York or Los Angeles. They know that they'll be taken seriously even before they get their Equity card.

"My first play was done here with a budget of something like $1,000," says Letts, who relocated from Dallas in the 1980s. "But not only can you get a play on for $1,000 here, you can actually get the critics out to see it, and then you will find audiences who will support it."

Meanwhile back in Toronto. ... While the alternative weeklies cover the independent scene, the city's local daily newspapers are less than fully supportive and almost never cover non-union shows. Local playwright Brad Fraser recently complained on his Facebook page that the city's biggest daily gives more space to reviews of Broadway productions than some local shows by established playwrights. (The Globe and Mail's policy is only to review Equity shows, as well.)

Confidence

Ask Chicagoans about the state of their theatre scene right now and few will brag about the number of shows headed to New York.

“I don’t think there’s a sense this is a particularly strong moment,”

says Bob Mason, artistic associate at Chicago Shakespeare Theater.

“It’s just being noticed elsewhere.”

Chicago theatre gets "discovered" about once a decade, says Robert Falls, artistic director of the Goodman, since Mamet emerged in the 1970s.

Chicago Tribune critic Chris Jones’s blog boasts that Chicago is "America’s hottest theatre city,” which may not be climatologically correct, but is at least more easily defended than Toronto's "the third largest English-language theatre centre in the world” claim.

Says Letts: “I can't imagine, frankly, why an English-language playwright would want to live in any city other than Chicago or London."

Meanwhile back in Toronto....