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Chicago → Portland

MDW–PDX · Chicago Midway International Airport to Portland International Airport

Best bet

Either side

Both sides workThe two sides come out close to level.

Both sides have something going for them, and the totals come out close enough that picking one would be a coin flip with extra steps.

Flight paths move around. Treat this as the better bet, not a promise.

What you might see

In flight order, with distance measured from the representative route.

MDW to PDX: where each landmark sits relative to the routeA diagram of the representative route running left to right, with the departure airport at the left and the arrival airport at the right. Landmarks on the left side of the aircraft are plotted above the route line and landmarks on the right side below it, each at its distance from the route. The numbered list below this diagram carries the same information as text.MDWPDXLEFT SIDERIGHT SIDE1234567
Distance from the route is to scale (up to 85 miles); the shaded ends are the 40-mile zones around each airport where the runway in use decides the view. Numbers match the list below. Hollow markers didn't count toward the recommendation.

  1. Hells Canyon

    LeftThree quarters24 mi off the route

    Hells Canyon is about 24 miles off the left, about three quarters of the way.

    Distant possibility

  2. Wallowa Mountains

    LeftNear the end36 mi off the route

    Late in the flight, Wallowa Mountains sits roughly 36 miles to the left.

    Distant possibility

  3. Mount Adams

    RightNear the end39 mi off the route

    Look right late in the flight for Mount Adams, about 39 miles out.

    Distant possibility

  4. Mount Rainier

    RightNear the end85 mi off the route

    Mount Rainier is about 85 miles off the right, late in the flight.

    Distant possibility

  5. Mount Hood

    LeftNear the end18 mi off the route

    Late in the flight, Mount Hood sits roughly 18 miles to the left.

    Strong candidate

  6. Columbia River Gorge

    Either sideNear the end6 mi off the route

    Whether Columbia River Gorge appears comes down to how you come into PDX, which is not something we can know in advance.

    Runway dependent

  7. Mount St. Helens

    RightNear the end41 mi off the route

    Mount St. Helens is about 41 miles off the right, late in the flight.

    Good possibility

The sun

Flying soon? Add your date and departure time and we'll work out where the sun should be, and which side gets less of it.

Airport codes or city names. SEA, Seattle, and Seattle-Tacoma all work.

Skip the date and you still get the landmark answer. Add it and we work out where the sun will be, using the departure airport's local time.

The route we used

1,747 mi
Great-circle distance
291°
Course out of MDW
266°
Course into PDX
6
Landmarks that counted

That is the shortest path between the two airports, used as a representative corridor rather than a flight plan. The first and last 40 miles are treated as uncertain, because that part of the flight is shaped by the runway in use and the published departure or arrival procedure. Anything in those zones is listed and marked, never counted toward the recommendation.

Left and right, from where?

Left and right are from your perspective sitting in the cabin, facing the front of the aircraft. Seat letters are not a reliable guide to which side you are on, because aircraft are configured differently.

Why this isn't guaranteed

Flights don't follow the same path every day. Runway configuration, weather deviations, traffic, and air traffic control all move the track around, and none of it is knowable in advance. We also have nothing to say about cloud cover, which is the other thing standing between you and Mount Rainier. The full method.

Flying the other way?

Portland → ChicagoEither side

Calculated from scratch, not by flipping this one. The landmarks arrive in the opposite order, the sun is somewhere else entirely, and the answer changes with them.

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