I drove into Canada from New York City with my friend Dylan, we drove a day trip to Trois Rivieres and Quebec City, and would drive out back to New York, never seeing the city from above.
The feeling of driving into a city vs. flying in is quite different.
When you fly in, you see the whole city from above. You get a sense of it in relation to the land around it- but only the land you were able to see from the time you descended low enough through the clouds.
When you drive in, you understand how the city connects to other cities, to the land; how the outskirts and suburbs bleed out, gently rising from farmland or tundra up to the city center.
When you fly in, you drop into the city quickly and suddenly, it's like...teleporting (but not quite as exciting). Then you get to move from the airport to the center, usually seeing a gritty suburb, usually on public transportation, letting yourself join the fray and noise of the people, melting into the crowd.
When you drive in, the atmosphere builds slowly. It wraps around you, slithers in through the air vents, slides over the windshield. Your license plates betray your foreignness, but you've worked a little harder to be there, so the city is yours more immediately than if you had flown.
Overall, the choice to dry or fly is often made for you- cost analysis, distance, availability, etc.
Driving keeps the string connected, from departure to destination, where flying severs that cord.
One method is not necessarily better than the other, but they're different, and the different psychological/emotional feelings should be considered when planning your next trip!