Getting Around: Chicago, IL

Most recently traveled April 2025

Chicago transit is pretty straightforward. Transit has “tap to pay” like NYC and Portland, where you can just tap your credit card or phone to pay the fare.

Unlike NYC and Portland, however, you still have to confirm the payment on your phone.

It might mean a double-click, a FaceID check, or a fingerprint. So it works more like paying for a coffee. This can be a nuisance when you’re running to catch a train, or laden with bags. I had to crane my neck to activate FaceID, while keeping the phone close to the reader.

Many of the trains in Chicago are elevated (they’re called “The L”), including “The Loop,” a full loop of tracks downtown. Most of the trains pass through the loop, and each may go in a different direction. Also, some enter and exit at the same point, heading back on their same route, while others enter at one place and exit in another.

I love just riding through the loop. It’s super picturesque to be about 30 feet up with skyscrapers all around you. However, given the different routing of all the trains, it’s very tricky to just ride through the loop without being whisked out toward some far reach of Chicago.

Downtown Chicago also has an entire lower level beneath it. You can walk for blocks without coming up to ground level, which is really helpful during the winter.

There are shops, corridors, parking lots, and of course, a couple rail lines.

The buses… are buses. They run fine, no complaints.

Chicago also has pretty decent bike infrastructure… lots of protected lanes.

As a pedestrian, it was pretty friendly walking around. The streets are fairly narrow, traffic isn’t too heavy, and the lights change frequently.