Crossword (Chicago Sun-Times)

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The Chicago Sun-Times' full-size daily crossword, free to play online.

Every day: One dated full-size crossword a day (Mon, Oct 5, 2026 on that date), the same for every reader; the Sun-Times posts its new puzzles daily at midnight Central time. New puzzle: Midnight US Central Time.

Play Crossword (Chicago Sun-Times) on chicago.suntimes.com

Crossword on the Sun-Times

The Chicago Sun-Times Crossword for Mon, Oct 5, 2026: a 15x15 grid and its across and down clues, with the info panel crediting Penny Press and a Start button

The Sun-Times Crossword is the paper's full-size daily grid, about fifteen squares across, with puzzle content from Penny Press. It runs on the Chicago Sun-Times games page, free and without a subscription, with a new dated puzzle each day.

About Crossword (Chicago Sun-Times)

The Chicago Sun-Times runs a small games page next to its news: a Chicago Mini Crossword, this full crossword, sudoku, Word Flower, a word search and a Chicago jigsaw. The full crossword is the classic newspaper grid, credited in its info panel to Penny Press, the puzzle publisher.

The grid is about fifteen by fifteen with a symmetric pattern of black squares, and the clues are the familiar daily mix: short definitions, fill-in-the-blanks such as a film title with a word missing, and a few names from music and pop culture. Each puzzle opens on an info panel with its date and a Start button, a timer runs while you solve, and the Assist menu checks or reveals letters, words or the grid. There is also a Print button for solving on paper.

It is free on chicago.suntimes.com, which is funded by reader donations rather than a paywall. New puzzles go up at midnight Central time. It suits solvers who want a regular weekday-style grid that takes a coffee break or two, rather than a quick mini.

How to play Crossword (Chicago Sun-Times)

  1. Open the Crossword on the Sun-Times games page and press Start on the dated info panel.
  2. Click a square or a clue; the matching across or down answer is highlighted.
  3. Type answers into the grid, using crossing letters to pin down the harder clues.
  4. Open Assist to check or reveal a letter, a word or the whole puzzle if you are stuck.
  5. Fill every square correctly to stop the timer.

Tips

  • Begin with the fill-in-the-blank clues; they are usually the quickest way into a corner.
  • Short three- and four-letter answers repeat often in newspaper grids, so learn the regulars.
  • Use Print if you prefer solving on paper with a pen.

Questions

When does a new Sun-Times Crossword come out?

The Sun-Times posts its new puzzles daily at midnight Central time.

Who makes the puzzle?

The info panel credits the crossword content to Penny Press, Inc.

Is it free?

Yes. The Sun-Times site is free to read and play, funded by reader donations.

How is it different from the Chicago Mini?

The Chicago Mini is a five-by-five grid with Chicago clues; this is the full-size daily crossword.

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