My Go at the Chicago Players Crossword Today
Okay, so today I decided to sit down and actually wrestle with one of those crosswords they call “Chicago players crossword”. Found it in the Sunday paper section I’d saved. You know how those big Sunday ones look kinda scary but also tempting? Yeah, that was the mood.

First thing I always do is just scan the whole grid. Look for the easy stuff, right? Those little three-letter words, the fill-in-the-blanks that jump right out. Got a few of those knocked out pretty quick. Stuff like ‘ERA’ or ‘USA’. Felt good, like getting a running start.
Then I started looking at the longer clues. Some were straightforward, just definitions. Others… well, they make you think. I saw some clues that seemed kinda related, maybe a theme? Wasn’t totally sure if “Chicago players” meant people from Chicago or sports guys or what. The clues didn’t immediately scream one thing. It felt more like a standard, tricky crossword from a Chicago paper, honestly. Those Sunday ones, they really make you work for it.
Got stuck pretty early on in the top-right corner. Just a block of white squares staring back at me. Had a couple of letters crossing, but nothing clicked. So, I did what I usually do: jumped somewhere else. Started working the bottom section. Sometimes getting answers in a different spot helps shake loose the answers in the stuck section. You know, you get a crossing letter you didn’t have before.
Here’s what I noticed, and it’s kinda typical for these tougher puzzles:
- Some clues were tricky wordplay. Took me a minute to realize one wasn’t a straight definition but a pun. Annoying, but satisfying when you finally get it.
- Had to guess a bit based on the letters I did have. Like, if it looks like it should be ‘SOMETHING’, you pencil it in lightly and see if the crossing words make sense later.
- There wasn’t an obvious “revealer” clue like some puzzles have, you know, the ones that explain a trick or a theme. This one just felt like a solid, challenging puzzle testing general knowledge and vocabulary.
Spent a good chunk of time just staring, sipping my coffee, trying different words in my head. Erased quite a bit. That’s part of the fun, I guess? Making a mess and slowly cleaning it up. Finally broke through that tough top-right corner when I figured out a longer answer that stretched across it. That opened up like three or four other words right away. Boom.
Didn’t quite finish the whole thing. There were maybe two or three words in the middle west section that just wouldn’t come to me. Probably some obscure name or place I just don’t know. But hey, got like 95% of it done. Felt pretty good about that. It definitely killed an hour or so and made my brain feel like it got some exercise.
Overall, a good challenge. These Chicago paper crosswords, they don’t mess around. Entertaining? Yeah, in that frustrating-but-rewarding way. Educational? Maybe, I probably learned a word or two I’ll forget by tomorrow. Worth doing again? Sure, why not. It beats staring at the wall.