Ah, that's because I lived in the DC area for five years and consider it home far more than Toronto! 

The crime rate in DC is indeed high, and while we lived there it was considered the "murder capital of the United States". But crimes were mostly all occuring in a few well-known (and avoided) neighbourhoods, and I never, ever felt threatened during those five years... despite commuting by bicycle.

I miss those days! Going to the Smithsonian with the kids was always a treat (especially when we got to see an original star destroyer from Star Wars... )

Did you drive in Chicago or use mass transit/taxis? I'm interested in how accessible places in a big city are to mass transit vs. how difficult the driving and parking situation is.

For instance, I rented a car in Los Angeles because it's just easier that way. In spite of the supposed awful freeway traffic, I didn't find it that bad depending on the time of day and the other roads weren't bad. The drivers actually seemed way more mellow than New Jersey drivers. But even though I rented a car in San Francisco, I actually most got around via mass transit because it was pretty good. Also, some of the hills had bad sightlines, so it seemed like it would be stressful driving.

I used a shuttle from airport to the C2E2 hotel. .then used a taxi to get to Field Museum (and then walked to most other things).

the next day I used a Taxi again, to get me to the Bean, then walked to where else I wanted to go and then taxi'd it back to the hotel.

Didn't get to use the trains, but they seemed very convenient. . just so happened that the day I was going to use trains, my friend/and Toyboy creator/C2E2 exhibitor, Tom Stillwell, drove me to the Science Museum, the only one that was set apart from the other things I wanted to do.

so I didn't drive in Chicago, but had no issues getting around.

on our trip to Virginia/Washington DC, we drove from Williamsburg (Busch Gardens/Kings Dominion/Colonial Williamsburg visit) to our hotel near National Mall in DC, but then we never moved the car.  The whole 4 days we were in DC, we used the train system to get where we needed to go, and had no issues.

but SOME cities?  (LA, Houston, Dallas, Austin).. you really do need a car to get around in.

In Chicago, I was thinking about the jazz and blues clubs. Chicago was where the New Orleans pioneers like Louis Armstrong first made their mark outside the South, and was the last wellspring of urban electric blues for many years.

I'm sort of the opposite - I love to travel and can't wait to get to my next trip.

I will echo some of the others in suggesting you start semi-local. One thing I've noticed in my travels is that people often will go great distances to see "exotic" sites, but may never visit the places right under their noses. I purposely have spent time in recent years visiting some of the many, many historical sites in my area that I previously had just never bothered to visit. Places like Walden Pond, Louisa May Alcott's house (where Little Women is set), Ralph Waldo Emerson's home, the battlefield where the Revolutionary War started.... and those are all just in one town! I'd suggest seeing what overlooked sites may be near you.

Another thing is to look at events - festivals are a big thing around these parts, and you can find all sorts of interesting experiences you may not do otherwise. Last weekend, for example, a town near me had a Steampunk festival. I missed that, but my girlfriend and I are going up to Vermont next month for a Hot Air Balloon Festival, where we might take a balloon ride over the Green Mountains.

You could also think about travels nationally an internationally in terms of events, rather than places. For instance, if you ever wanted to go to Comic Con, taking a trip would also give you a great excuse to visit San Diego and see the sites there, like the Zoo, Coronado, and nearby places such as Tijuana, L.A., and Disneyland. Plus Comic Con itself. Or you could visit New York for New York Comic Con (or any one of a thousand other events - I was there once and almost randomly wandered into the NFL Draft), or Las Vegas during the Star Trek convention. Or something like Mardi Gras in New Orleans, or the cherry blossoms in Kyoto, or Carnivale in Venice.

For me and my girlfriend, who luckily also has the wanderlust, narrowing down the hundreds of choices is the hard part. This year we're still trying to figureo ut where to go overseas for a big trip - China, Iceland, and Cuba are the places we've been looking at the most.

There's so much cool stuff to see everywhere!