Skip to content
WanderNerd
Check a flight

Window Seat

Oakland → Chicago

OAK–MDW · Oakland International Airport to Chicago Midway International Airport

Best bet

Left side

Good betA real difference, not a rounding error.

Wasatch Range leads it, with 2 more on the same side.

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.

OAK to MDW: 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.OAKMDWLEFT SIDERIGHT SIDE12345
Distance from the route is to scale (up to 53 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. Lake Tahoe

    LeftEarly50 mi off the route

    Lake Tahoe is about 50 miles off the left, early in the flight.

    Distant possibility

  2. Mono Lake

    RightEarly37 mi off the route

    Early in the flight, Mono Lake sits roughly 37 miles to the right.

    Distant possibility

  3. Wasatch Range

    LeftQuarter in24 mi off the route

    Look left about a quarter of the way in for Wasatch Range, about 24 miles out.

    Good possibility

  4. Uinta Mountains

    LeftHalfway28 mi off the route

    Uinta Mountains is about 28 miles off the left, around the halfway mark.

    Distant possibility

  5. Longs Peak

    RightHalfway53 mi off the route

    Around the halfway mark, Longs Peak sits roughly 53 miles to the right.

    Distant 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

1,840 mi
Great-circle distance
70°
Course out of OAK
93°
Course into MDW
5
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?

Chicago → OaklandRight 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.

Keep nerding