Print PDF duller than JPG

Photoshop is not doing this. It all depends on how, where and if you are assigning profiles.

There are lots of balls to keep in the air here.

First thing, what are your Color Settings in Illustrator, in particular what do do with CMYK Embedded Profiles.

Second, did you embed a Color Profile when saving your TIF and JPG. e.g. If one has an embedded profile and the other doesn't, then they will be treated differently in Illustrator depending on how the above settings deal with them.

Is the CMYK profile assigned to your images the same or different than what is assigned to the Illustrator document?

Here's an example scenario:

Say one file (e.g the TIF) has a GRACOL profile assigned to it, and the other (say, your JPG) was saved from PS without embedding a profile at all (untagged). Place these in an Illustrator file with Color Settings of US Sheetfed Coated, with your Illustrator Color Settings set to honor CMYK Embedded profiles.

Your TIF will display as GRACOL (and indicate as such in your Links panel) 

Your JPG, since it is untagged (indicated merely as CMYK in your Links panel), will be assume the profile of the Illustrator document, hence US Sheetfed Coated.

This will cause each to appear differently: The JPG, as US Sheetfed Coated, will probably appear darker than the TIF on the same page.

All this being said, this day and age, it's better to keep your image as RGB to maintain its original vibrancy, and allow the CMYK converion to happen downstream.

Is the color management synchronized in the Creative Cloud?

Did you convert the color profile at any time in the workflow? Import/Place or Exporting to PDF?

Which app do you use to view the PDF? Acrobat?

Hello @Joyful_nature5C80,

We understand that encountering technical issues can be frustrating. Would you mind sharing more details, like the exact version of the OS/Illustrator and public links to a sample AI/JPEG/TIFF file after uploading it to Dropbox/Google Drive/etc., so we can investigate this further?