Iraq's national airline resumed international flights on Saturday, 14 years after war and sanctions forced it to halt operations.
The 737's delighted pilot waves to the press at Damascus airport
An Iraqi Airways Boeing 737 jet flew from Amman in Jordan to Baghdad before flying on to Damascus in neighbouring Syria.
It is not clear if the 737 - the only aircraft available to Iraqi Airways - was carrying any passengers.
The company plans to expand operations and begin daily flights to Damascus.
Iraqi Airways flight IA164 left the Jordanian capital, Amman, at 0845 (0545 GMT) for Baghdad.
The plane then left Baghdad for Syria, arriving at Damascus airport at 1430 (1130 GMT).
The carrier has not flown to Damascus since 1980, when the two countries cut off ties over the Iran-Iraq war.
Iraqi Airways also has plans to fly to Dubai in the United Arab Emirates, but will need to find more aircraft first.
The BBC's Jon Leyne, reporting from Amman, says the rest of its ageing fleet is rotting away on the tarmacs of airports across the Middle East.
An airline official called Saturday's flight a "first step".
Our correspondent says information on the flight was not widely available.
It did not feature on the departures board at Amman airport, the check-in desk denied all knowledge of it, and even the control tower did not know about it until shortly before take-off, he says.
It is unclear how strong demand for tickets will be, especially as security concerns persist across Iraq.
Most airlines are staying away from Baghdad because of the dangers, but passengers who do fly on this route work on the basis that it is probably safer than attempting the journey on Iraq's notorious roads.
There are continuing attacks on coalition troops and Iraqi police, as well as suicide bombings and kidnappings.
Isaac Esho, deputy director of Iraqi Airways, played down the threat to passengers.
"We're not scared," Mr Esho told the Reuters news agency. "Our aircraft will take the same security risk as all the others, probably much less."
A return ticket to Damascus is expected to cost about $600 (493 euros; £335), to Amman about $750.