The comments section at Capitol Fax, one of my favorite places for taking the pulse of reasonably well-informed followers of politics, are divided over who came out ahead and behind during the the teachers strike. One point, above all, is important—which I don't know that people are factoring in, necessarily. Alexander Russo writes:

It was fun to watch, disturbing at times since strikes have become so rare, but always seemed to me to be more of a function of having two firebrand rookies in charge rather than the issues being debated.

It's worth remembering not only that Karen Lewis and Rahm Emanuel are big personalities, they're also new at this, in their first terms at their respective positions. Emanuel comes in with a financial mess and years of teacher complaints that built up during the last years of Daley's long term. Lewis heads a CTU that, for the first time in years, is unified and active. Ben Joravsky gives a must-read recent history that explains why the CTU was so willing to strike now, and why Lewis insisted on kicking the contract back to the membership:

As the union president through most of the 1990s, Reece had a cozy relationship with Mayor Daley and former schools CEO Paul Vallas. In 1998 Reece cut a deal with Vallas in which the teachers got a pay hike of roughly 7 percent over three years. But the rank and file thought the raise was too cheap. Reece rammed the deal through the House of Delegates.

[snip]

In 2003, it was Lynch's turn to negotiate a contract, this time with Vallas's successor, Arne Duncan. When she emerged from negotiations she claimed she'd won the "total package." In words that came back to haunt her, Lynch said she not only delivered "the bacon" but the "whole hog."

[snip]

Lynch's career was pretty much over. In 2004 she was defeated by Marilyn Stewart. And in 2010 Lewis defeated Stewart largely on an insurrection of teachers who felt, among other things, the union leadership was way too soft on issues like job security and school closings.

Ramsin Canon has much, much more on the balance of power between the city, teachers, and parents over the last two decades. 

The strike was positioned as Emanuel vs. Lewis, but Lewis was contending with a union that installed her in order to take a more active, aggressive stance—and Emanuel's stance, at least publicly, was similarly aggressive. That they would butt heads was inevitable; that the two would meet in the middle after a relatively short strike was something of a surprise. The narrow consensus at Capitol Fax is that the CTU won, and I tend to agree, even if Lewis admits that the actual contractual gains are unsatisfying to her and the union. CTU came through two decades of insufficiently strong (for the membership's desires) leadership, and Lewis took over after a major power shift. Expecting that, in the course of a couple years, CTU would change its internal stance, and elect a competent head, and achieve all its goals in an anti-union environment during a period of austerity, all while contending with a figure like Rahm Emanuel… it's a lot to expect. CTU positioned itself for future battles, such as school closings, without 

Emanuel catches a lot of grief in the CapFax comments: "tyrant and a bully"; "Karen Lewis ended Rahm Emanuel’s ability to become a long term Chicago Mayor"; "arrogant"; "going forward he’s lost the expert technocrat/master strategist reputation"; and so forth. 

Eh. Emanuel had a more difficult job with the CTU than a lot of people seem to appreciate. The years of conciliation between the union and the city left a lot of people unhappy on both sides; the massive expansion of TIF districts, which Canon covers in his post, undermined CPS finances. That uneasy balance fell apart, and Emanuel was left with a newly aggressive union—one that cleared the SB7 hurdle with ease—and no money to ameliorate everyone.

The mayor might have really looked like a bully if the injunction had made it to court, but it didn't; both sides wrapped it up before the courts got involved.

Lauren FizPatrick of the Sun-Times has a good summary of the contract. The gist, I think, is that neither side got all of what they wanted on any count, meaning that everyone got some of what they wanted. Russo has the rundown from the reform-backed National Council on Teacher Quality, which counted more wins for reform than misses. Catalyst scores some wins for the union, including ones you may have missed:

Heenan said a “Christmas present” in the contract was the right for teachers to format their lesson plans in the way they want. 

“When that was announced, cheers erupted,” he said, explaining that it takes a lot of extra time to format lesson plans according to the district’s model, and can be antithetical to the way a teacher naturally puts them together.

They also got a $250 reimbursement for teachers that have to buy classroom supplies.

Who won? No one really did, but no one really lost, either—in part because the game has completely changed. The strike was really the first big fight in what will likely be an ongoing relationship, so it doesn't make sense to call winners and losers just yet.