Both shows have ghosts/supernatural beings that deal with their pasts. Both are also two of the best dramas of the past couple of years.
Recommended by disthymia
Bridal mask is probably the best" jeoson / japan" era dramas.. i just love it, i am not comparing these two drama for they are different in theme but overall here are the similarities i saw:
1- the jeoson / japan era.
2- the freedom seekers and under-covered agents plus the under-covered male / female lead.
3- the bromance <3 (esp Chicago typewriter).
4- the war romance.
5- the old story of the male saving the female (become their first love).
6 - the goal of freeing the country which comes before anything else.
basically the main points u will notice too if u have seen both dramas.
and they are both worth watching although to me bridal mask is on a different level <3 :).
Recommended by misha2pm
A patriotic woman disused as a male is part of a rebellious group out to remove Japanese corruption from her country out of Patriotism in both shows.
Both female leads are excellent at using a gun
Both female leads lost close family members are killed which is behind their motivation to be part of the rebel group.
Recommended by Bloom C
If you watched RiaBB because you love books you will enjoy CT. While one is a romantic comedy and the other is a drama they both share the love of books and reading as well as beautiful quotes.
Recommended by Cascadeis
If you loved the period flashbacks of Chicago Typewriter, then you'll love Youth of May! Youth of May is another period flashback of a time in Korea that was filled with protests and movements and politics. It starts off light and sweet, but soon explores the serious events that unfold, much like Chicago Typewriter does. The romance is sweet as well in this drama. There is also a heartbreaking aspect to this story like there was with Chicago Typewriter. On the surface, the dramas may sound very similar, but they are quite different once you start watching! But if you loved Chicago Typewriter and want another period/historical drama with talks of movements and romance, then Youth of May is the one for you.
Recommended by existingsouls
Modern day fantasy stories, with ghosts hanging around. Both sets of characters deal with a muddy past. There are similarities in the cinematic directing, tone and overall feel of the two pieces.
Recommended by Jleety
Both about past lives and how that affected the characters' current lives.

In both dramas, the leads remember their past.

Both have supernatural elements outside of the past life/future life trope.

Both have wonderful OSTs. CT is more artfully done while Legend is more quirky and fun.
Recommended by Irene
Both shows have similar premise - three people whose unfortunate fate is so entangled that it continues to their next life.
Recommended by Alvea
Both shows have reincarnation theme. In chicago typewriter ml and fl were reincarnated and in tale of the nine tailed fl was reincarnated
Recommended by thatkdramagirl
Both the kdramas have "reincarnation" concept

The female leads in both the kdramas have strong personality.

There's a love triangle in both kdramas.

"Chicago Typewriter" involves profession related to novel author, while "To All The Guys Who Love Me" involves webtoon artists.
Recommended by Kiirosan
It occured in the same era where Joseon is fighting for their liberation from the Japanese occupation. There you can see the iconic Carpe Diem where they frequent to. Both main characters have the nationalism in them, though in Chicago it is much strongly shown. Both male leads fights with their pens through writing literatures.
Recommended by Cimaco
Both have reincarnation of leads. They both loved each other greatly but because of bad circumstances died.
Recommended by Eleanor
Both are about the professional life and struggles of modern script-writters.

Both have a girl, which talks to a ghost, who was once in love with her and revolve around making peace with him.
Recommended by Loving_Roots
Both dramas are about japanesse ocupation and in both of them you can find beautiful love story.... but what i loved most about these dramas is that even if it had a love but did not get lost in it... i just loved watching their fight for independence... Also in both dramas characters just rocks. Of course Chicago typewriter is better drama, but Rookie agent rogue is great drama on it´s own way.
Recommended by ladytristeza
Both shows have reincarnation theme. In chicago typewriter ml and fl were reincarnated and in tale of the nine tailed fl was reincarnated. In ct as well as in totnt characters get to discover what happened during their past life.
Recommended by flwrjievn
Chicago Typewriter (2017) poster

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