Seeing Chicago from a plane

The city built the first skyscrapers and reversed its own river in 1900. Look for the dead-straight lakefront, the grid running inland to the horizon, and the Willis Tower's stepped black profile.

46 of our routes pass it. Illinois · rated 9 of 10

The easy pick

Chicago to Dallas-Fort Worth: sit on the left, on the climb, 2 min after takeoff.

Which side, by route

RouteSideWhen
Atlanta to ChicagoLefton the way down
Boston to Los AngelesLeft
the other side is usually better on this route
106 min after takeoff
Boston to ChicagoLeft
the other side is usually better on this route
on the way down
Charlotte to ChicagoLefton the way down
Chicago to Dallas-Fort WorthLefton the climb, 2 min after takeoff
Chicago to BostonRighton the climb, 3 min after takeoff
Chicago to HoustonLefton the climb, 4 min after takeoff
Chicago to New YorkRight
the other side is usually better on this route
on the climb, 4 min after takeoff
Dallas to ChicagoRighton the way down
Dallas-Fort Worth to ChicagoRighton the way down
Denver to ChicagoLefton the way down
Detroit to PhoenixRight31 min after takeoff
Detroit to DenverLeft
the other side is usually better on this route
33 min after takeoff
Fort Lauderdale to ChicagoLefton the way down
Houston to ChicagoRighton the way down
Houston to ChicagoRighton the way down
Indianapolis to ChicagoLefton the way down
Kansas City to ChicagoRighton the way down
Kansas City to ChicagoRighton the way down
Las Vegas to ChicagoRight
the other side is usually better on this route
on the way down
Los Angeles to New YorkRight183 min after takeoff
Los Angeles to ChicagoRight
the other side is usually better on this route
on the way down
Miami to ChicagoLeft
the other side is usually better on this route
on the way down
Minneapolis to ChicagoLefton the way down
Nashville to ChicagoLefton the way down
New York to DenverRight89 min after takeoff
New York to ChicagoLefton the way down
Newark to San FranciscoRight90 min after takeoff
Newark to ChicagoLeft
the other side is usually better on this route
on the way down
Newark to DenverRight101 min after takeoff
Orlando to ChicagoLefton the way down
Philadelphia to DenverRight81 min after takeoff
Philadelphia to ChicagoLefton the way down
Phoenix to ChicagoRighton the way down
Portland to ChicagoLefton the way down
Raleigh/Durham to ChicagoLefton the way down
Salt Lake City to ChicagoLefton the way down
San Diego to ChicagoRight
the other side is usually better on this route
on the way down
San Francisco to NewarkRight
the other side is usually better on this route
199 min after takeoff
San Francisco to ChicagoLefton the way down
Seattle to ChicagoLefton the way down
St. Louis to ChicagoRighton the way down
Tampa to ChicagoLefton the way down
Washington to ChicagoLefton the way down
Washington to SeattleRight78 min after takeoff
Washington to ChicagoLefton the way down

From the real paths of every nonstop on these routes in the last 10 days, at the usual time of day.

Questions

Which side of the plane do you see Chicago from?

It depends on the direction: the left on most of our routes (25 of 46). The table lists each route's side.

When can you see Chicago from a plane?

Near the airport, on the climb or on the way down, and mid-flight on longer routes: see the table for each route.

Can you see Chicago at night?

Yes, by its lights. The app scores lit places at night by how bright they are.

Do clouds matter?

Yes. These answers assume a clear day. Within 3 days of your flight, pick your exact flight in the app for the cloud forecast.

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