The Windy City is known for its pristine streets, incredible attractions, raucous sports fans—and downtown traffic. Driving in Chicago isn't for the faint of heart, as streets are not only packed with vehicle traffic, but they teem with jaywalking pedestrians and cyclists.

Finding cheap parking downtown can be difficult. One way to get around expensive parking is to do your research ahead of time to find cheaper parking spots. Some parking garages offer special rates on event days or you can reserve garage parking in advance from one of many services.

The very features that make Boston so charming and beautiful—labrynthine, narrow brick streets and one-way roads that rarely follow a straight line—also make for parking and navigation migraines. Factor in stringent parking rules and the historic New England city is a downright tricky place to park (even for locals).

Finding cheap and easy parking is possible, however, with just a little bit of patience and planning.

Running late for your flight? If you've ever had the dismal experience of waiting in a long, snaking security line, it's time to make a mental note to sign up for an expedited-screening program. But which one?

Along with TSA PreCheck and Global Entry, there's another program to consider called CLEAR. And for re-entry into the U.S., consider the Mobile Passport app.

Do a fair amount of driving in Florida, and you'll run into a toll road. When that happens in a rental car, it can be a pricey gotcha.

Slicing a few cents off the price of a gallon of gas can lead to significant savings over the course of a road trip, but hunting for a bargain can be tricky. Wandering too far off the beaten path can cancel out the purpose of seeking more affordable fuel, but pulling into the first gas station off the highway might mean missing out on a better option right around the corner. Never fear— several tools can help you find the cheapest gas no matter where you are.