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Chicago Chess Instructors

Browse these chess instructors with great ratings from Thumbtack customers in Chicago.

Caveman Chess
from 2 reviews
  • 41 years in business
Kevin H.
Verified review

Kevin provided chess instruction not only to me personally, but he went out of his way to provide feedback on the games of my high school players as well as instruction for them - both in a small group setting and individual setting. The quality of the instruction is excellent - he breaks chess down to simple to remember principles and his approach of learning through historical games (and then working your way up to modern ideas) is highly effective. He is always the first person I recommend when I am approached by my players to get individual chess coaching.

Ryan O'Donnell
from 2 reviews
  • 2 hires on Thumbtack
Aara'L Y.
Verified review

Ryan is extremely helpful! He knows his stuff and made sure I left each lesson with a clear understanding of core math and physics concepts. He is great at explaining the material, and he took his time answering my questions. He's also very detail oriented which is a major plus! I felt very comfortable asking him anything related to the material. I would highly recommend him to anyone who wants to learn.

Play Chess-Chicago
from 1 review
  • 2 hires on Thumbtack
Tom V.
Verified review

Thomas is great at chess, and a very insightful teacher. Other people bid lower but I felt like he was the best bet. No regrets at all, two lessons in and I'm already improving significantly.

Howex Unincorporated

New To Thumbtack


    I teach games and game strategy to kids and anybody who just wants to improve at or learn how to play chess, backgammon (I'm a former Top 50 players in the USA), or bridge. I'm an affable college-educated father.

    Chess Lessons

    New To Thumbtack


      Teaching chess from an earlier age allows children to develop skills such as problem solving, critical thinking, spatial awareness etc. I have specifically designed courses for each level and I teach high quality lessons and unique positional training with structured plans of improvement. This summer, give your child something which s/he will never regret in his/her lifetime.


      I teach math, chess, and SAT/ACT prep. My accomplishments are as follows: * I placed 3rd in the Illinois Math Competition in 2011 for juniors * I am a USCF Class A rank chess player * I have a 36 on the ACT and am a National Merit finalist

      Q & A

      Answers to commonly asked questions from the experts on Thumbtack.

      How do you learn to play chess?

      The earliest forms of the game we now know as chess originated in India during the fifth and sixth centuries A.D. Chess lessons can give you a strong foundation for a hobby that will keep your mind lively for your lifetime. Chess is a game of strategy; you can learn to play and understand the basic rules of chess in a short period of time — often you can cover all the basics in the first chess lesson — but understanding the strategies of chess will be a lifelong pursuit.  

      During beginning chess lessons you learn the basics of the board and how to set up the chess pieces. You will learn the use for each of the different chess pieces: the king, queen, pawns, knights, bishops and rooks. You can learn about movements such as check, fleeing, blocking, capturing and checkmate. As you advance, your chess teacher will coach you on strategies and the finer points of the game. Chess lessons are great for any age player, from those just starting out to grandmasters looking to refine their skills.

      What makes a good chess player?

      If you want to be a good chess player, practicing often and studying strategies and techniques of more masterful players can help you advance. Good chess players have the ability to remember patterns, openings, endgames, tactics, guidelines and can visualize moves ahead and combinations. They can also sit comfortably for many hours and concentrate on an active game.

      Research has shown that almost anyone can be a good chess player if they practice often and put in the time. Being a truly great player however involves more than just practice, and requires good general cognitive abilities and agile decision-making skills. It also helps if you first learned to play chess at a young age.

      The US Chess Federation offers these additional tips for becoming a good chess player:

      • Look at your opponent's move.
      • Make the best possible move.
      • Have a plan.
      • Know what the pieces are worth.
      • Develop quickly and well.
      • Control the center.
      • Keep your king safe.
      • Know when to trade pieces.
      • Think about the endgame.
      • Always be alert.

      Whether you are young or old, new to the game or advanced in your practice, chess lessons can be a good way to refine your game, sharpen your strengths, and keep your mind nimble. A chess coach can make you a good chess player by helping you develop opening moves, tactics, positions and endgames, and by helping you find and fix weaknesses in your game.


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