Chicago- Getting there and Getting Around

Driving
I don't recommend it.

It took us two and a half hours just to clear the suburbs. That's mostly idling in traffic, and also because the suburbs of Chicago stretch so far its possible to get authentic Boston clam chowder on one end and visit the first Starbucks store in the other.

The last time I was in Chicago, I took the megabus there. It picked me up in downtown St.Louis and dropped me in downtown Chicago, with a pit stop, good views, and free wifi and power outlets all the way there. If you're traveling alone, you'll end up spending more on gas for your car than the price of a round trip ticket.

Parking
Here's my advice on parking in Chicago: don't do it.

Parking is so expensive, its cheaper to simply hire people to carry you from place to place on their backs. Depending on your parking garage and duration, it's cheaper to simply buy people's cars on the street and abandon them at your destination. In all seriousness, parking for one of our cars for a total of 48 hours was more expensive than a round trip bus ticket to St.Louis. That's not even factoring in gas. I think once we factor in gas, and the other car we took to Chicago, it would have been cheaper for three of all to shelled out the $50 for megabus tickets. We didn't even drive around in the city.

Oh well, we learn. Slowly.

Walking
The loop and areas nearby are exceptionally walkable, and are really best experienced by the pedestrian. It's a great city to walk through, with the canyons formed by the towers of brick, glass, and metal, to pass through the clanking shade of the elevated train tracks, to be tempted by the wafting scent of deep dish pizza being baked, and to be part of the pedestrian city. Someone once commented that there's ten times as many people walking around Chicago as there are in St.Louis, and that New York has ten times as many people walking around as in Chicago.

But Chicago is also pretty big and walking can really wipe you out. Which is why I recommend

the 'L' trains
I don't know why they're called the L trains, because the red line is definitely not 'L'-ivated inside the loop. However, the elevated trains are convenient, frequent, and relatively cheap. We got a 24 hour pass which was about five bucks, and we used the train about five trips or so. It's quite enjoyable to stomp around the ancient steel and wood board structures, and to slowly shriek through the city above the streets, peeking in windows and taking in architectural details.