* ComplacentGamingSyndrome: The vast majority of players tend to play the MS version over the Lynx version, mainly because its various glitches and design flaws make it the better version to SpeedRun.
* EarWorm: Turn the music on. [[SchmuckBait Go ahead]].
** Teeth monsters, due to their habit of permanently going after Chip.
** Walkers and Blobs, due to their erratic movements which makes them unpredictable.
* EvenBetterSequel: ''Chip's Challenge 2'', which basically takes the first game and adds Melinda as a playable character with her own set of rules and a metric ton of new puzzle elements.
* FauxSymbolism: Levels 54 (''Grail'') and 142 (''Pentagram''). They're shaped after a cross and a pentagram, respectively, but they're otherwise normal levels.
* FirstInstallmentWins: Between ''Chip's Challenge'' and ''Chuck's Challenge''. Knowledge of ''Chip's Challenge'' and its mechanics (both in the original Lynx version and the MS port) has risen dramatically over the years, and fans are still creating custom level packs to this day, most of which tend to be very well-designed. In contrast, ''Chuck's Challenge'' is mostly unknown, suffers from sketchy controls (at least in the iOS version), the built-in levels are fewer in number and are generally of lower quality than the ones in ''Chip's'', and the user-generated levels are [[SturgeonsLaw mostly terrible]].
* IAmNotShazam: While ''Chip's Challenge'' does star Chip, ''Chuck's Challenge'' doesn't star Chuck; you play as Woop, playing through puzzles ''created by'' Chuck.
** The "Bummer!" sound heard when Chip dies. [[NintendoHard Get used to it.]]
** If you're in a level where an enemy is controlling the buttons, expect the constant BOP-BOP-BOP to drive you mad until you turn the sound off. It's even worse in the Lynx version (and, by extension, the Steam release, which takes its sound effects from the Lynx version), where the sound for pressing a button is a louder, more high pitched beep.
* NightmareFuel: Teeth are damn creepy when you're playing this as a kid. It doesn't help that they're the only enemy that actively pursues you.
* PortingDisaster: The original Windows version lacks the smooth, fluid movement and animation of the original game and its numerous other ports; most noticeably, Chip and monsters "jump" from tile to tile instead of moving between them. In addition, it has several bugs that totally [[GameplayDerailment break the way that some levels were intended to be played]] (in some cases [[GoodBadBug for the better]], in other cases [[FakeDifficulty not so much]]). Yet, in an interesting case of TropesAreNotBad, this version is by far the most well-known due to its wide distribution and has still long been adored by thousands of players; in fact, most people introduced to the game on Windows didn't even know about the original game's mechanics until they were resurrected in ''[[GameMod Tile World]]'' and later the [[VideoGameRemake remake]]/sequel. The latter even has an option that [[AscendedGlitch emulates]] the "tile jumping" for those who are more comfortable with it. It's also the version of choice for speedrunners, since several glitches allow levels to be completed much more quickly than normal.
* ThatOneLevel: For most players, any level that takes longer than 5 minutes. For others, a level with a time limit of under a minute is even worse. Notable examples include:
** Level 23, ''Blobnet''. For the first appearance of blobs in the entire game, having to deal with '''80''' of them while trying to collect 88 chips, where ''any misstep means you have to start from the beginning'', makes this a huge DifficultySpike, and the most difficult level in the first half of the game.
** Level 33, ''On The Rocks''. It's your first real MarathonLevel, having you use a block generator to build bridges to get to tiny islands with the chips on them. It's exceedingly time-consuming because there's only a handful of generators throughout the level, and if you make ''one'' slip, you'll have to restart the level.
** Level 61, ''Rink''. Did you want a SlippySlideyIceWorld where you can't tell whether a direction is open or will bounce you back until after you've slid? No? Too bad, because this level is exactly that for the entire map. "Thrash-a-thon", indeed.
** Level 73, ''Morton''. You're '''not''' going to beat it if you can't trap the teeth within a spot from which it can't bother you any more.
** Level 87, ''Cityblock''. You thought you hated block puzzles before? Get ready to despise them as you have to contend with ''four'' of them in one level (one of which doubles as a KaizoTrap, since it's located after the chip socket and can block you from reaching the exit if you do it wrong). With a long completion time, even for a perfect run, and the game's trademark airtight window for error when it comes to block puzzles, you'll likely have had more than your fill of block puzzles by the time you finally finish this beast.
** And what's your reward for completing that block-pushing nightmare? ''Spirals'', the ''very next level'', is one of the most notoriously difficult. In case a maze filled with ever-increasing numbers of random walkers wasn't bad enough, some Microsoft versions of Chip's Challenge have a [[http://chipschallenge.wikia.com/wiki/Spirals_corruption corrupt level file]], making the level nearly UnwinnableByMistake.
** Level 89, ''Block Buster''. The blocks that are replicated by the clone buttons are ''very'' difficult to dodge in the Windows version due to a [[GameBreakingBug glitch]] that causes them to move erratically instead of remaining at a constant speed. And since Chip is a OneHitPointWonder, he must ''never'' fail at dodging any of them.
** Level 91, ''Jumping Swarm''. Like ''Spirals'', another level notorious for its large numbers of randomly moving walkers.
** Level 105, ''Short Circuit''. A nasty maze of chip sockets and recessed walls, which forces you to memorize the layout of the maze.
** Level 131, the aptly titled ''Totally Unfair'', which requires you to memorize the layout of a previous level, titled ''Totally Fair'', and do the puzzle part of it while effectively blind.
** Level 134, ''Pain''. Takes over 13 minutes even in the best attempt where you know what you're doing and make no mistakes. Beyond that, it's ExactlyWhatItSaysOnTheTin.
** Level 136, ''Doublemaze''. It's [[ExactlyWhatItSaysOnTheTin two mazes]] shuffled together. There's a huge amount of chips to collect, you need every single one of them, and thanks to the level design (ice and thin walls) it's hard to tell which maze a given chip is in.
** Level 140, ''Icedeath''. Solving this level without a map is nearly impossible, as sliding even once in the wrong direction results in death, and [[FakeDifficulty you can't see whether a given direction is safe until it's too late]]. It takes over 60 slides to reach the skates. Have fun.
** Level 147, ''Force Field''. Mazes alone can be difficult to tackle, but this one consists of force floors that hugely increase the difficulty level. The player has to frequently overcome their motion directions to make his/her way to the chips needed to obtain the suction boots and walk directly to the exit.
** This is '''without''' getting into the [[FanSequel Fan Sequels]].
*** [=CCLP3's=] second half is often regarded as '''nothing''' but That One Level back to back to back to back [[OverlyLongGag to back to back]]. Special mention goes to ''You Can't Teach an Old Frog New Tricks'' ([=CCLP3=] 144) for being harder than the already ridiculously difficult levels surrounding it. Solving it requires setting up no less than 5 rooms ''flawlessly'' so that one tooth monster can navigate through them in sequence to release Chip from a trap, so said tooth monster can control a toggle switch and then be trapped on ice so Chip can walk to the exit. Interestingly, in playing back the solution in Tile World, the focus switches to that of the tooth monster when Chip enters the trap. Ande like all fan-made level packs with more than 144 levels, [=CCLP3=] treats this one as a DiscOneFinalDungeon only, so you'll still have to tackle five more levels, including the formidable duo ''Suspended Animation'' (146) and ''Avalanche'' (147).
*** [=CCLP2=] has levels that rely on unintuitive tile placements and a bigger focus on booby traps and random-working hazards and enemies, resulting in levels like ''Block Away!'', ''Exit Chip'' and ''Blocked Trap'' where it's almost impossible to foresee a deadly trap on the first attempt. This reaches its zenith (nadir for the less experienced players) with the 93th level, ''Exit Chip'', which does a ''deliberate'' attempt to troll players in every possible opportunity. Even then, there are more traditional levels that are still infamous for their difficulty, such as ''Mazed In'' ([[SchizophrenicDifficulty which for some reason is put as the 12th level]]), ''Warehouse II'', the two ''Oracle'' levels and ''Cloner's Maze''.
** Chuck is certainly aware of the infamous nature of some of these levels and provided achievements in the Steam release just for beating them. These include the previously mentioned Blobnet, On The Rocks, The Last Laugh, Rink, Cityblock, Jumping Swarm, Totally Unfair, Blobdance, Icedeath and Force Field.
** "Crazy" in the sequel, with lots and lots and lots and lots of sliding block puzzles in ''very'' tight quarters. The only saving graces you get are that there's no official time limit and if you just want to beat the level you only have to complete four of the puzzles to proceed (and you can pretty much pick and choose which ones you want to complete). If you're looking for a high score, though, you have to complete ''all'' 26 of them with no mistakes, while racing against a logic gate timer that locks you out of some multiplier flags after 10 minutes.