* 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.
* 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.
** 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.
* 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 Windows version introduced several glitches, most notably certain buttons not working consistently. Ironically, this version is the most well-known (and was pretty much the ''only'' known version until the fan program ''Tile World'' brought the Lynx version back into the limelight).
* 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 anymore.
** 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 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 105, ''Short Circuit''. A nasty maze of chip sockets and recessed walls, which forces you to memorize the layout of the maze.
** Level 131, ''Totally Unfair'', which requires you to memorize the layout of a previous level, titled ''Totally Fair''.
** 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 [[ThatOneLevel 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, resulting in a CrowningMomentOfAwesome.
*** [=CCLP2=] has levels that rely on unintuitive tile placements, 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. Even then, there are more traditional levels that are still infamous for their difficulty, such as ''Warehouse II'' and ''Cloner's Maze''.