I discovered a few cities that have very convenient transportation that is cheap or even better, free.
In downtown Denver, there is a free shuttle that travels up and down 16th street. Hop on and off whenever you feel like it. Shuttles come every few minutes, making it very convenient to spend all day exploring.
A day pass for $5 in San Diego gets you from the airport to downtown on any bus or trolley. It doesn’t hurt that the trolleys make you feel transported back in time to the 20th century.
The best city I visited was Chicago with its transportation system. I still cannot comprehend the complex systems of subways under and above ground, with buses zigzagging in between, all for a day pass costing $5.75. Although the train ride from O’hare feels long, it is definitely worth the value.
In New York, the AirTrain and subway connection was conveinent, but felt like more of a challenge understanding how it worked. The subway lines twisted all over the map which is great to get places quickly, but often overlapped a lot and was a bit intimidating to a newbie. A day pass is apparently available for $8.25 but isn’t compatible with the AirTrain.
For the price of a sandwich or less, you can have an awesome ticket to ride the town as much as you want. I found it gave me more confidence to venture farther and discover places I would otherwise have missed. I feel I got my money’s worth out of the day pass.
Although someone has to pay, I believe it can be beneficial for cities to offer free transportation from nearby airports to a central destination (like a transportation hub) in their city. Some airports are hubs for airlines and have travellers sitting bored out of their minds waiting during layovers. If they were enticed to hop on a shuttle and head downtown, they will be just as willing to shop or eat at local shops as the overpriced options in the terminal.