Chocobo Challenge is a set of remixed versions of the standard tracks, where players must place higher than special NPC opponents in order to clear the challenge. The first clear of each challenge yields very large amounts of MGP, and unlocks more chocobo training manuals at the Tack & Feed Trader. This mode was added in patch 3.25.
Each challenge has a specific minimum rating in order to challenge it, starting at rating 41. Unlike standard racing classes, there is no maximum allowed rating.
Participating in challenge races counts toward the achievement Off to the Races IV (participate in 3,000 races).
However, placing first in a challenge race does not count towards Winningest Jockey (place first in 500 races).
Experience and MGP values with an asterisk (*) are approximated, based on applying the reward scaling weights to confirmed experience and MGP values. The approximations should be within 1 point of the true value.
Values without an asterisk have been confirmed in-game.
The "Roulette Bonus" replaces the experience earnings of one random racer in 2nd-7th place.
Maps:
Certain chests may not always appear in every race. The annotated maps include all known chest spawn locations.
Rewards
Chocobo Challenges reward MGP upon the first clear, but otherwise they don't give any MGP.
Experience payouts depend only on which of the 3 courses is used for the challenge. The exp amount does not scale higher in later challenges.
The amount of exp given is equivalent to the exp of a Maiden race.
Lightfoot Longstrider is immune to Heavy. Don't bother using Graviballs on them.
Avoiding Heavy is critical - every Heavy you eat gives the special opponent more of a lead.
The first gold chest is a trap - upon landing, you will probably hit the purple panel, unless you steer hard right.
Bringing Heavy Res IV is possible, however it isn't full immunity, so may fail with unlucky RNG. Learning the course and bringing other generally-useful abilities is probably better.
Heavy Res V's manual isn't unlocked until after beating race 10.
The special opponents will usually respond with Feather Field whenever any AoE is used near them, including Briar Caltrops. Try to make them spend their shields early, so they are vulnerable afterwards.
Red panels flanking the track make it difficult to avoid getting hit when an AoE is out. The red panel's -15% stamina is generally the worse effect - the only thing worse is taking the full damage of a Briar Caltops (-20%). If you have to choose, Just eat the field instead of the red panel. If it's a caltrops, still eat it instead of the red, but escape as soon as posssible.
Super Sprint is effective here - aim for the green panels as you go.
The Coblyn on the bridge has been moved further left, meaning holding left is no longer an effective way to avoid it. Holding left still works on the red panels there, but it's safer to jump over the panels due to the coblyn (you cannot jump over the coblyn).
Experience and 
MGP values with an asterisk (*) are approximated, based on applying the reward scaling weights to confirmed experience and MGP values. The approximations should be within 1 point of the true value.
Sagolii Road
Costa del Sol
Tranquil Paths
Choco Shock II
Choco Silence II
Choco Silence III
Heavy. Don't bother using Graviballs on them.
Heavy Resistance V
Choco Cure (level unconfirmed)
Choco Reflect III
Choco Dash (level unconfirmed)
Choco Reraise (level unconfirmed)
Feather Field III
Choco Shock III
Choco Drain (level unconfirmed)
Choco Esuna (level unconfirmed)
Head Start
Super Sprint
