Wingate took the news bitterly, voicing disappointment to all who would listen, including Allied commanders such as Colonel Philip Cochran of the 1st Air Commando Group, which proved to be a blessing in disguise. Cochran told Wingate that cancelling the long-range mission was unnecessary; only a limited amount of aerial transport would be needed since, in addition to the light planes and C-47 Dakotas Wingate had counted on, Cochran explained that 1st Air Commando had 150 gliders to haul supplies: "Wingate‚Äôs dark eyes widened as Phil explained that the gliders could also move a sizable force of troops. The general immediately spread a map on the floor and planned how his Chindits, airlifted deep into the jungle, could fan out from there and fight the Japanese". With his new glider landing option, Wingate decided to proceed into Burma anyway. The character of the 1944 operations differed from those of 1943 in that they aimed to establish fortified bases in Burma out of which the Chindits would conduct offensive patrol and blocking operations.

Operation Thursday. Wingate planned that part of 77 Brigade would land by glider in Burma and prepare airstrips into which 111 Brigade and the remainder of 77 Brigade would be flown by American C-47 transport aircraft. Three landing sites, codenamed "Piccadilly", "Broadway" and "Chowringhee" were selected. On the evening of 5 March as Wingate, Lieutenant General Slim (the British Commander of Fourteenth Army), Brigadier Michael Calvert (the commander of 77 Brigade) and Colonel Cochrane waited at an airfield in India for 77 Brigade to fly into "Piccadilly", an incident occurred which Wingate's critics later claimed to show his lack of firmness or balance.

Wingate had forbidden continuous reconnaissance of the landing sites to avoid compromising the security of the operation, but Cochrane ordered a last-minute reconnaissance flight which showed "Piccadilly" to be completely obstructed with logs. By Slim's account, Wingate became highly emotional and insisted that the operation had been betrayed, and that the Japanese would have set up ambushes on the other two landing sites. He passed the responsibility for ordering the operation to proceed or to be cancelled to Slim.

Slim ordered that the operation was to go ahead. Wingate then ordered that 77 Brigade would fly into "Chowringhee". Both Cochrane and Calvert objected, as "Chowringhee" was on the wrong side of the Irrawaddy and Cochrane's pilots were not familiar with the layout. Eventually, "Broadway" was selected instead. The landings were initially a failure, as many gliders crashed en route or on "Broadway", but Calvert's brigade soon made the landing ground fit to take aircraft and sent the success signal. It was later found that the logs on "Piccadilly" had been laid there to dry by Burmese teak loggers.

Once all the Chindit brigades (less one which remained in India) had marched or flown into Burma, they established base areas and drop zones behind Japanese lines. By fortunate timing, the Japanese launched an invasion of India around the same time. By forcing several pitched battles along their line of march, the Chindit columns were able to disrupt the Japanese offensive, diverting troops from the battles in India.

The value of Wingate's Chindits has been disputed. Field Marshal William Slim argued that special forces in general had an overall negative effect on the prosecution of war by separating the best-trained and most committed troops from the main army. However, Sir Robert Thompson, a Chindit who went on to become one of "world's leading expert on countering the Mao Tse-tung technique of rural guerrilla insurgency", wrote in his autobiography that, "Every time I look at the picture of General Slim and his Corps Commanders being knighted by Lord Wavell as Viceroy on the field of battle after Imphal, I see the ghost of Wingate present. He was unquestionably one of the great men of [the 20th] century."