The Trippy distance calculator measures both the driving distance and the straight line flight distance ("as the crow flies") between any two locations. This lets you compare the total distance in miles or kilometers, and also figure out how long it would take to drive or fly. You can compare driving time to flight time directly, or plan a longer road trip or check the best airports to fly between.
Once you have an idea of the distance between two cities, you can either use the road trip planner if you're driving, or the flight planner if you're flying. Use the recommendations from Trippy members to plan out your full itinerary.