Chicago Essentials
- Tap a credit card or device.
- You’ll have to confirm payment (e.g. FaceID).
- Transit app works.
Pros
- Easy and efficient
- Operates late night
Cons
- Trips within loop are confusing
- Underground can be a challenge to navigate
April 2025, May 2024, April 2023
See Also: Chicago Metra
Getting Around: Chicago Metra
Riding Rail
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.
Lower Level
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.
Entrances to the lower level are often not labeled.
You’re just expected to know that all the mysterious staircases go to an expansive extra layer of city.
Airport to Downtown
The Blue Line from O’Hare to Downtown is super easy to find and ride. I’ve taken it once; it takes the better part of an hour. Sorry, no pictures; I rode it before I started this project.
The more chaotic option is Amtrak to Milwaukee, which leaves a few times a day. I have taken Amtrak to the Milwaukee airport (I was staying in Milwaukee), and it was pretty painless. There’s a shuttle bus waiting for the train.
Other Ways to Get Around
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.
