I'm sorta of new to the hotel industry and I would like to know the best way or if someone can show me where to read some info.

I do a lot of flying and use aa citi cards and I collect the millage, I also collect a lot of points via Amex but I never have the option of using points in a hotel or getting a night free and I want to start doing it.

I travel a lot around the US on business and I just usually go to kayak.com to book the cheapest hotel rates. Is it better to use a certain type of credit card to book hotels stays to get better benefits? Also is there a certain chain I should look for that can give me more benefits as well so if I ever make a trip over seas then I can have like 4 nights free?

Any help would be mostly appreciated.