This guide will introduce you to the software chess world, with advice for players who just want to play casually online or offline, as well as those who want to seriously study opening moves and analyze historical matches.
The best free online chess games
Lichess is my preferred online chess game. It's free and supports plenty of match styles, including multi-day correspondence. The best thing about it is that you can play anonymously without creating any kind of account, though I find that means I'm more likely to encounter players who resign or request a draw immediately—you never know who you might be paired with. For practice, you can also play against the Stockfish engine (more on what that is in the sections below).
Chess is a good commercial free alternative. You have to put up with a few ads, and it'll bug you to pay for an optional premium subscription, but as a way to quickly start playing chess online at any skill level, it's one of your best bets. It runs in your browser with a simple, clean board design, and has a ton of players so I've never had a hard time finding a match with someone of a similar skill level (which is to say, not very much skill).
The best chess videogame
Chess Ultra is a gorgeous chess game for those who just want to play chess without dealing with the complicated software in the sections below. It includes VR support, an AI opponent with several difficulty levels, as well as local and online multiplayer, Twitch integration, and the option to export matches. It also includes basic tutorials for newcomers. For anyone who simply wants to play chess, this is your game—simple and beautiful, like chess itself. It's a good deal, too: just $13 on Steam, and $9.09 right now during the Halloween sale.
For a free-to-play alternative, try Simply Chess. It's not nearly as slick as Chess Ultra, and it crashed on me pretty quickly, but hey, it's free. It supports online play with a separate account, and comes with a good computer opponent via the Stockfish engine (see the section below for an explanation on that).
The best chess engines and GUIs
If you want to play against a powerful, customizable computer opponent for the purpose of studying chess, you'll want a chess engine, such as the free and open source Stockfish engine or its derivatives. Komodo is also highly ranked, though you'll have to pay a subscription for the latest version (Komodo 9 is free), and Houdini costs €40 for the standard edition.
These engines are primarily for training—you can play against them, analyze chess positions, and pit them against each other—so they're for people who seriously want to study the game. If you're not sure a chess engine is something you want to tinker with, don't buy anything—free engines are extremely powerful.
An engine alone won't do much for you, though, as they don't include any kind of graphical user interface, just a console. To play against a chess engine or use it to analyze boards, it must be paired with a chess GUI, but there are lots of free ones. Most come with many engines installed already, so you can get started with one download.
Lucas Chess: Simple and easy to understand for beginners, Lucas Chess is a good place to start. It includes a bunch of engines and training tools, and the UI isn't too confusing, even if you're unfamiliar with the more complicated functions of chess engines.
Arena Chess GUI: Arena Chess is more daunting for newcomers than Lucas Chess, but it includes a great deal of features, as well as support for 19 languages and a Linux verison.
WinBoard: It isn't the prettiest GUI, but WinBoard and Xboard are feature rich and include support for chess variants, too.
SCID: Like the other GUIs on this list, SCID can be used to play against an engine, but it's most useful as a fast way to organize and analyze databases of chess games. You'll want to pair it with MillionBase, a massive database of chess games in PGN format (scroll to 'Data Downlods' here) or other chess game databases. If you like the SCID interface, you can also try SCID vs PC as a GUI for playing chess.
Commercial chess software
You can play and learn a lot about chess without spending a dime, and that's where I recommend starting, but pro packages come with lots of bells and whistles if you have the cash. Much of what you're paying for is their completeness, and the quality of their training tools.
Fun chess-related games
For something a little different, below are some entertaining chess and chess-adjacent games.
