Flying from Boston to Chicago?
Add a departure date and see which side gets the sun.
Flying from Boston to Chicago?
Add a departure date and see which side gets the sun.
Flying from Boston to Chicago?
Add a departure date and see which side gets the sun.
Boston → Chicago
A short flight within United States. The clock rolls back 1 hour when you land.
The Cradle of Liberty
Boston is a compact, old city built on a tangle of colonial-era streets that famously refuse to run in a grid, wrapped by the Charles River and the harbor. The T, the country's oldest subway system, covers the core well, and much of the city is genuinely walkable. Winters are cold and snowy, summers humid, and a car in the center is more liability than asset given the narrow streets and scarce parking. The city's many universities give it a younger, more transient population than its old buildings suggest.
Surrounding hubs
| 300 km / 186 mi | |
| 322 km / 200 mi | |
| 409 km / 254 mi |
The Windy City
Chicago lines the southwest shore of Lake Michigan, a flat, gridded city with one of the great American downtowns at its heart. Elevated trains and a deep commuter-rail network make the core genuinely transit-friendly, and the lakefront ties the city together. Beyond downtown and the north-side neighborhoods, Chicago spreads into a huge belt of suburbs. Winters are hard, and the wind off the lake lives up to the nickname.
Surrounding hubs
| 537 km / 334 mi | |
| 700 km / 435 mi | |
| 965 km / 600 mi |
Find out which side of the plane to sit on.
Pick your airports, set your departure time, and you're done.
We calculate the sun's position based on your flight path and departure time, then tell you which side of the plane gets direct sun and which stays shaded. No guessing, just math.
Enter your flight
Pick your departure and arrival airports and set your departure time at the departure airport. FlightSide estimates the duration and you can adjust it if you know the exact schedule.
We track the sun along your route
Your flight path is broken into hundreds of points. At each one we check where the sun is and which side of the plane it faces.
You get a recommendation
Which side of the plane to sit on, left or right, depending on whether you'd rather avoid the sun or enjoy it. The percentages and the map are there if you want to see why.
Want to go deeper? Accuracy, edge cases, polar routes — see the FAQ →
Notes from the product.
Small updates, route observations, and clearer explanations for how the app keeps evolving.
Type less, wait less, wonder more
Airport search now understands metro codes and old city names, FlightSide loads noticeably faster, and a new Feeling lucky button chooses a flight for anyone without one in mind.
A closer look at the route, not just the seat
FlightSide now shows the two cities and key details about the flight alongside the seat recommendation: confirm you picked the right airports, read the time change off two clocks, and check the return leg.
It's all about the sun (after all)
Not all sunlight reaches the side windows. FlightSide now weighs the sun’s angle to the cabin and shows twilight along the route.