It’s a weekend morning in the University of Illinois Chicago’s student center, and about 200 people are waiting anxiously for a proctor to hand out sheets of paper. A timer starts and everyone simultaneously flips their sheets, pencils in hand, and gets to work.
But it’s not an exam or essay, and these aren’t students; the sheet contains a crossword puzzle, and some of the Chicago area’s most engaged puzzlers have gathered for the challenge.
Welcome to the Midwest Crossword Tournament, the first of its kind dedicated to serving Midwestern puzzle solvers and crossword constructors. Tournaments like these have existed for decades on the East Coast, but this regional competition — held this past Saturday and already on the books to return in October 2026 — makes the case for the Midwest as a blossoming talent market for word games.
The beauty of a Midwest tournament is that it is hyperlocal, with clues like “Uses C.T.A.’s Blue Line, e.g.” (answer: TAKES THE L) or “Iconic menu option at Ole and Lena’s Minnesota State Fair food stand” (that’s HOT DISH ON A STICK). On Saturday, crossword enthusiasts self-sorted into three categories: Chicago Fire (the expert level), Minnesota Nice (everyone else in the solo division) and Pairs (exactly what it sounds like).
It only took a few minutes in the totally-silent room for hands to start appearing in the air — a signal that a solver was finished — and proctors quickly collected puzzles to account the finish time accurately. The conversation among friends old and new continued outside the solving room in the fluorescently-lit hallway until the timer on the puzzle ran out. This routine would repeat for five puzzles over the course of the day, with the goal of whittling down the fastest and most accurate to three finalists. (Attempt this year’s puzzles at home, and find details about the 2026 tournament, here.)
Among the hallway denizens were Chicago doctoral students Nathalie Korhonen and Frances Pool-Crane, who were among the approximately 65 first-time tournament attendees. They competed in the Pairs division, and stood out particularly because one is left-handed and the other right-handed. This seemed to make an efficient solving strategy since they could write on a page at the same time without bumping wrists or blocking sightlines.
“It was definitely a motivation in being a pair,” said Pool-Crane. “It does make it easier, I think!”
Korhonen said the pair had to adjust its strategy since the tournament puzzles are on paper. “Normally we type, and we each type on separate laptops,” she said. “We realized that probably starting from either corner and then working inwards would be best.”
The analog format of the competition forced other adjustments. Mathan Shanmugham of Des Plaines attended the tournament online last year, where he could solve the puzzles on a laptop. “This year I’m doing it in person, in pencil, and boy is it different,” he said. “I want my ego checked, that’s mission accomplished.”
Shanmugham attended the event solo, and spent the downtime between puzzles embracing the “nerdfest” of it all. “I’ve made quick friends here. I’ve met constructors, and the vibe is just awesome,” he said.
Shanmugham also said it’s a particular point of pride that the Midwest now has its own tournament.
“I think the fact that the Midwest now has a crossword puzzle tournament is a really important thing,” he said.
Co-organizers Sally Hoelscher and Shannon Rapp said they started the event because, prior to last year, Midwest puzzlers had little access to in-person events.
“I’m a big fan of crossword tournaments. Until just a couple of years ago, they were essentially restricted to the East Coast,” Rapp said. She noted that, last year, a West Coast tournament called Westwords launched, too, broadening the map for regional solvers.
On the East Coast, tournaments revolve around a limited field of puzzle constructors. Hoelscher said she wanted to give local crossword talent a chance to have their puzzles put front and center, and she did: All seven puzzle constructors for the tourney are either current or former Midwesterners.
There were some commonalities among the group: a love of puns, enthusiasm for pencils over pens and a passion for learning.
The room had a real collegiate feel: Experienced puzzlers met up again in a sort of homecoming, while the newbies, not unlike college freshman, were eager to meet and form new friendships.
But once the puzzles were out, silence. The 30 couples in the Pairs division spoke in such hushed tones that you could barely tell that they were talking at all.
A few crossword celebs appeared, including Tracy Bennett, the editor of the popular New York Times online game Wordle, and Christina Iverson, a crossword editor at the New York Times, who both edited the puzzles used in competition. Ben Bass, who writes the twice-weekly print-exclusive cryptic puzzle at the Times, competed in the Minnesota Nice division. Quiara Vasquez, who edits and constructs puzzles for the online magazine Slate, landed in the top three of the Chicago Fire.
After five puzzles, the event boiled down to three finalists, who solved the puzzles on comically large whiteboards in front of the audience.
Observers watched in silent bewilderment, some even filming on their phones, as the finalists frantically scribbled letters in dry-erase marker. It was like watching a sporting event on mute.
All three finished with zero errors, but the fastest was Iowa City resident Christopher Adams, who completed his in a tight six minutes and 35 seconds.
“Did not think this would be happening,” said Adams, a crossword constructor himself who had not participated in an in-person tournament in a few years. “I was, like, come here, have some fun, solve some great puzzles. You know, head home early, because it’s a couple hour drive back home. And I guess, if we’re gonna delay the drive back home, that was well worth it.”
With the competition wrapped, Bass and several puzzlers set off for dinner in Little Italy. “This is like a traveling circus or family reunion,” Bass said before running out of the student center. “Everybody here feels like a friend.”
Sofie Hernandez-Simeonidis is a digital producer on WBEZ’s Arts & Culture desk.
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