Chicago Travel Tips! The perfect four day itinerary to make sure you see all the trademark/touristy things that matter yet live and eat like a local. Planning a vacation is very similar to planning an event. You get recommendations from friends, do research on the Internet, make a budget, etc. I was extremely lucky because I had a great tour guide who was able to orchestrate seeing all of the sites without feeling rushed. Here's a look at my whirlwind itinerary.