Southwest® flights from San Antonio to Chicago (O'Hare) from $133

No matter when you choose to visit Chicago, you’re in for weather quite unlike anything back home in Texas. Thanks to being on the shore of Lake Michigan, the Windy City has humid summers and snowy winters—sometimes exceptionally so. Don’t fret: Chicago has plenty of indoor activities if you need to get out of the elements, and the City in the Garden is full of parks that are picture perfect examples of municipal parkland all year long.

Whether you’re packing snow boots or swimsuits, plan to partake in at least one slice of Chicago-style pizza while you’re in town. And, no: Chicago-style pizza is not the deep dish tomato sauce-topped pie you’ve seen comedians poke fun at. Thin crust, tavern cut pizza is what locals will lead you to. Rather take down a couple of hotdogs? Try one Chicago-style: covered in mustard, relish, onion, tomato, celery salt, sport peppers, and a pickle spear. If “dragged through the garden” doesn’t sound good, just make sure not to garnish your dog with ketchup.