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
| Route | Side | When |
|---|---|---|
| Atlanta to Chicago | Left | on the way down |
| Boston to Los Angeles | Left the other side is usually better on this route | 106 min after takeoff |
| Boston to Chicago | Left the other side is usually better on this route | on the way down |
| Charlotte to Chicago | Left | on the way down |
| Chicago to Dallas-Fort Worth | Left | on the climb, 2 min after takeoff |
| Chicago to Boston | Right | on the climb, 3 min after takeoff |
| Chicago to Houston | Left | on the climb, 4 min after takeoff |
| Chicago to New York | Right the other side is usually better on this route | on the climb, 4 min after takeoff |
| Dallas to Chicago | Right | on the way down |
| Dallas-Fort Worth to Chicago | Right | on the way down |
| Denver to Chicago | Left | on the way down |
| Detroit to Phoenix | Right | 31 min after takeoff |
| Detroit to Denver | Left the other side is usually better on this route | 33 min after takeoff |
| Fort Lauderdale to Chicago | Left | on the way down |
| Houston to Chicago | Right | on the way down |
| Houston to Chicago | Right | on the way down |
| Indianapolis to Chicago | Left | on the way down |
| Kansas City to Chicago | Right | on the way down |
| Kansas City to Chicago | Right | on the way down |
| Las Vegas to Chicago | Right the other side is usually better on this route | on the way down |
| Los Angeles to New York | Right | 183 min after takeoff |
| Los Angeles to Chicago | Right the other side is usually better on this route | on the way down |
| Miami to Chicago | Left the other side is usually better on this route | on the way down |
| Minneapolis to Chicago | Left | on the way down |
| Nashville to Chicago | Left | on the way down |
| New York to Denver | Right | 89 min after takeoff |
| New York to Chicago | Left | on the way down |
| Newark to San Francisco | Right | 90 min after takeoff |
| Newark to Chicago | Left the other side is usually better on this route | on the way down |
| Newark to Denver | Right | 101 min after takeoff |
| Orlando to Chicago | Left | on the way down |
| Philadelphia to Denver | Right | 81 min after takeoff |
| Philadelphia to Chicago | Left | on the way down |
| Phoenix to Chicago | Right | on the way down |
| Portland to Chicago | Left | on the way down |
| Raleigh/Durham to Chicago | Left | on the way down |
| Salt Lake City to Chicago | Left | on the way down |
| San Diego to Chicago | Right the other side is usually better on this route | on the way down |
| San Francisco to Newark | Right the other side is usually better on this route | 199 min after takeoff |
| San Francisco to Chicago | Left | on the way down |
| Seattle to Chicago | Left | on the way down |
| St. Louis to Chicago | Right | on the way down |
| Tampa to Chicago | Left | on the way down |
| Washington to Chicago | Left | on the way down |
| Washington to Seattle | Right | 78 min after takeoff |
| Washington to Chicago | Left | on 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.
More
Rate Field Willis Tower United Center Navy Pier University of Chicago Atlanta (ATL) Chicago (ORD) Boston (BOS) Los Angeles (LAX) All routes