You won't have to look hard to find any of those options for food in Chicago/ of course Lou Malnati's is always good and if you want huge portions check out Ritzy's on Algonquin rd in Arlington Heights. All of Chi town has great food! I miss it I was raised htere and been in AZ for the last 22 years. Have a gyro for me!
For Puerto Vallarta - Check out the CasaMagna Marriott resort, it is beautiful.. I have rooms reserved there in June for $99 a night! I recommend Los Milagros Restaurant in the city, it is fabulous... The margaritas are incredible. Have fun.