The best simulation games like Crimson Skies are Crimson Skies: High Road to Revenge, Ace Combat 7 and Blazing Angels. Below are 5, each with the reason it is here — and, at the end, what filtering to simulation costs you.
Filtering to simulation means you want a system to run or a routine to inhabit. It is the right filter when what you liked was being somewhere rather than beating something.
What you get: A game that does not need you to be good at it, and that rewards paying attention over reacting quickly.
What made Crimson Skies worth playing in the first place is covered on the full list. This page is the simulation part of that answer, and only the simulation part.
The Xbox sequel, and the definitive version of the idea.
The best arcade flight game still being made, and just as pulpy.
Straightforward wartime arcade flight with co-op.
For the dieselpunk-era charm, from the other side of the plane.
Modern arcade-leaning combat flight that does not demand a HOTAS.
Urgency. Simulations are deliberately slow, and the ones with no fail state give you nothing to push against.
Specifically, these are strong answers for Crimson Skies that are not simulation games, so they are not on this page:
The full list is on games like Crimson Skies — 9 picks, no genre filter.
Crimson Skies: High Road to Revenge. The Xbox sequel, and the definitive version of the idea.
No. Crimson Skies released on the Microsoft Xbox, but a recommendation is only useful if you can play it, so the picks above span platforms and eras. What they share is the genre and the reason.
A simulation with no fail state and no time pressure. The label describes how it feels to play rather than what genre it is in.
No — one is about running a system well, the other about inhabiting a routine. Recommending across that line is where most simulation recommendations go wrong.
By hand. Each pick was written for the full Crimson Skies list first, on what the game actually does, and this page is the part of that list that is simulation — never a genre tag lookup, which is how "best racing games like Super Mario 64" used to be a page on this site.
Or read the simulation guide for where to start in the genre generally.