Both the Chicago departure and Dallas arrival offer brief but genuine skyline views on the right side, while the cruise portion over Illinois, Missouri, and Arkansas is flat and largely featureless on either side, making the right side the modest overall winner.
Flown MDW to DAL? Did we get it right?
Flight Path
Chicago to Dallas is 794 miles (1,277 km), a flight of about 1 hour 55 minutes.
The route crosses the Mississippi River near St. Louis, passes over the flat farmland of southern Illinois and the Missouri Bootheel, then continues over the plains of Arkansas and northeast Texas before descending into the Dallas area.
Great circle distance and headings ›Phase by phase

Takeoff from MDW
RIGHTDepartures out of Midway toward the southwest typically climb out with a turn that keeps downtown Chicago's skyline and the Lake Michigan shoreline visible off the right side for a minute or two before the route settles onto its southwest heading over flat Illinois farmland.

Landing at DAL
RIGHTOn approach into Love Field from the north, the flight path passes just west of downtown Dallas, putting the Reunion Tower and Bank of America Plaza skyline in view off the right side during the final turn, along with the Trinity River's green floodway below.
Will your flight be in sunlight?
Pick a date and time in the Sun Map to watch the sun move across your whole flight.
About This Route
Which side of the plane should I sit on flying from Chicago Midway International (MDW) to Dallas Love Fld (DAL)?
Sit on the Right side of the plane for the best views on flights from Chicago to Dallas. Both the Chicago departure and Dallas arrival offer brief but genuine skyline views on the right side, while the cruise portion over Illinois, Missouri, and Arkansas is flat and largely featureless on either side, making the right side the modest overall winner.
What can I see during takeoff from Chicago Midway International in Chicago?
During takeoff from Chicago Midway International (MDW), sit on the Right side for the best views. Departures out of Midway toward the southwest typically climb out with a turn that keeps downtown Chicago's skyline and the Lake Michigan shoreline visible off the right side for a minute or two before the route settles onto its southwest heading over flat Illinois farmland. Notable sights include: Chicago skyline (Willis Tower, Loop), Lake Michigan shoreline, Midway's dense residential grid.
What can I see when landing at Dallas Love Fld in Dallas?
When landing at Dallas Love Fld (DAL), sit on the Right side for the best views. On approach into Love Field from the north, the flight path passes just west of downtown Dallas, putting the Reunion Tower and Bank of America Plaza skyline in view off the right side during the final turn, along with the Trinity River's green floodway below. Notable sights include: Downtown Dallas skyline (Reunion Tower, Bank of America Plaza), Trinity River floodway, North Dallas suburban sprawl.
How long is the flight from Chicago to Dallas?
The flight from Chicago Midway International (MDW) to Dallas Love Fld (DAL) takes about 1 hour 55 minutes. The shortest flight path between them is 794 miles (1,277 km); winds and air traffic control usually add a few percent.
What does the Chicago to Dallas flight path pass over?
The route crosses the Mississippi River near St. Louis, passes over the flat farmland of southern Illinois and the Missouri Bootheel, then continues over the plains of Arkansas and northeast Texas before descending into the Dallas area.