Okay, so the other day I found this crossword puzzle titled “Boston or Chicago”. Sounded kinda specific, right? Didn’t know what to expect, maybe clues about deep-dish pizza versus clam chowder? Anyway, I had some time to kill, so I thought, why not give it a shot.

Grabbed my trusty pencil – always use pencil for crosswords, gotta have that eraser handy – and settled into my favorite chair. Spread the newspaper out on the table. First glance, the grid looked pretty standard, not too many tiny boxes, which was a relief.
Getting Started
I always start with the ‘Across’ clues, just a habit. Scanned through looking for the low-hanging fruit, you know, the fill-in-the-blanks or super obvious ones. Got a few right off the bat. Felt pretty good, like maybe this wouldn’t be so tough after all.
Then I hit the theme clues. Stuff that seemed to want answers specific to one city or the other. Some were easy, like famous landmarks or sports teams. Put those in, and they helped unlock some of the ‘Down’ answers. That’s always satisfying, when the letters start fitting together across both directions.
Hitting a Wall
But man, some clues were real head-scratchers. Stuff about neighborhoods I’d never heard of, or maybe some local slang? I wasn’t sure. There was this one clue, something like “Windy City rail system, 3 letters”. Got the ‘L’, of course. Another asked about a “Boston garden resident”. Had me stumped for a bit until I realized it probably meant the Celtics, not actual plants.
I worked on it for maybe half an hour, filling in bits and pieces. Sometimes I’d get stuck on one section, jump to another part of the grid, and then come back later with fresh eyes. You know how it is. A few times I was sure I had the right word, wrote it in confidently, only to find it messed up all the connecting words. Out came the eraser.
- Found myself humming tunes associated with those cities.
- Almost looked up an answer online, but decided against it. Feels like cheating, doesn’t it?
- Took a break to make some coffee, hoping the caffeine would help.
The Final Push
Came back after coffee, and suddenly a few answers clicked into place. Funny how stepping away helps sometimes. Managed to finish most of the grid, maybe left two or three stubborn squares blank. The theme was interesting, definitely made me think about those two places. Didn’t know there were so many things to compare or contrast in a crossword format.
Overall? It was a decent way to spend an hour. Challenging enough to keep me engaged but not so hard I wanted to rip the paper up. It’s just a simple crossword, but it felt good to work through it, you know? Just using my brain for something other than the usual routine.