Wednesday, February 18, 2026

Entering A City: Chicago and Comparisons

I wanted to think about how cities ask you to enter them when you arrive as a tourist (or anyone, I suppose, since tourists don't have a monopoly on entering cities, but I'm going to focus for the moment on the tourist experience). I want to suggest that what the entering space emphasizes deeply affects the sense the tourist may get of how to navigate the city and what it's like, and compare a few examples. 

Note thatI'm going to try to avoid comparing total apples to oranges here. The temptation to compare say Amsterdam Centraal to Chicago O'Hare would be unfair; a rail station and an airport come with different affordances, to use a technical term: different possibilities and options for what they could communicate. So train station to train station or airport to airport is a fairer approach, and the one we'll use here.

1. Amsterdam Centraal vs Chicago Union Station: what place does the car have?

So if not O'Hare, let's consider Union Station. I spent a whole school year commuting for my PhD between Chicago and Rochester, NY monthly (approximately) and mostly by train, so I have a lot of experience entering the city via train. The Megabus to Louisville also used to drop off across the street from Union Station, adding to my knowledge of this spot. I even took the train to Seattle from here, which was the only picture of from it I could actually find:



So even though we might think of the airports as the distinctive way of entering Chicago, there are plenty of us first experiencing the city via Union Station too (Amsterdam Centraal is an obvious entry point, given the greater prevalence of passenger rail there and the high speed lines to the UK and France).

At Union Station you'd be forgiven for not noticing that Chicago has mass transit besides buses and commuter rail. It has no L stop for some reason -- you can walk to the Blue Line or with a bit more effort the other lines in the Loop but it's neither obvious nor signed for visitors. There are bus stops and the Metra is present, but for travel within the city you're really not clearly given anything to do or anywhere to go except on foot or by car.


This Greyhound depot isn't quite next to there--but that's also kind of the point, isn't it? Union Station isn't well-integrated even with the long-distance buses, let alone the city transit.

Amsterdam Centraal has the Metro, the boats across the IJ, and multiple tram routes (as well as also pedestrians and buses, and well-indicated bike routes). It's a completely different experience of the city, one that emphasizes the ability to go about your day without a car and your interconnection with the rest of the city. It also physically presents those options to you more clearly.


I know I probably overuse the shots of this angle, but it's so notable: the tramlines are between this metro entrance and the main station, and the main station itself is clearly in a mostly pedestrian zone.


Here we can see the trams better, as well as yes, a motor vehicle as well--but that's not what the spot is emphasizing.

2. Chicago Midway vs. Toronto Billy Bishop 

Now let's look at airports, specifically smaller, secondary Great Lakes-region airports. The irony here is that Midway has much better connections to the city than Billy Bishop: more bus lines to the point of being a major bus hub, and an actual L stop! Billy Bishop has a tram line not tooooo far away, a bus line or two, and a shuttle to downtown. 

But Billy Bishop presents the connection to the city much more positively: you can just walk out of the airport into Toronto. Midway hides its bus and L depot as far from the active part of the airport as possible and does not want you exiting on foot if you can help it. It is all car-oriented, and the other options (which, again, are superior) are hidden like a separate secret level in a videogame.


How close to the airport do you think this is? Whatever you guessed, I'll bet it's too far.

And that's not even considering the ferry, which again just makes a visibly pleasant integration into the city.


Midway is so much more transit-integrated, but not showing it.


This is after ten minutes of walking within the terminal to get to the bus depot.


And actually getting to the train (here) takes another few minutes of walking. It's like they are ashamed to be connecting their airport to the city so well!

At least there's nice public art.



3. Boston Logan vs. Chicago O'Hare 

Lest this just look like dumping on Chicago, let's think about the big airport. O'Hare has a much easier and more clearly communicated link to the city than Logan, and a better system of transit within the airport too.


Cute lil' people mover.

O'Hare gives the vibe of being very connected to Chicago by transit even though it is much farther out than Logan is. And it wears its urban nature proudly.


Enjoy the trains to the City! They go straight from the airport!

For Logan, the line is still Blue, but there's an issue:


This train doesn't actually go to the airport.


This bus does. But since it's a bus, you have less tracking, less visible clarity on where it will be or where it goes, and (unlike O'Hare) no walking path.

Actually, there is a walking path.


But I don't recommend it.

Basically, while Logan is actually much closer in to Boston and much easier to get to from major parts of that city than O'Hare is from Chicago in terms of travel time or crow-flies distance, it's not actually presenting that part of itself except from the plane window.


What it's really showing you is just that it's a bunch of tarmac and buses--and eventually those will get you towards the city. O'Hare wins hands down.

What do you think? What other cities do a good job of clarifying how the city and its transit interact? Where else does Chicago do a good job? Let me know what you think!

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Entering A City: Chicago and Comparisons

I wanted to think about how cities ask you to enter them when you arrive as a tourist (or anyone, I suppose, since tourists don't have a...