The course continues to Sheridan Road before turning back south along Broadway, passing through Boystown, Old Town, and River North.

The course continues down Jackson Boulevard then turns south through Little Italy and Pilsen before crossing the river again via Cermak Road.

[10] Other competitors in the field included three-time Olympian Fionnuala McCormack and Amy Cragg, however, she later pulled out of the race in August due to a hamstring injury.

[7] Not long before the day of the race, Gelete Burka, who had won the 2019 Paris Marathon and had run a personal best of 2:20:45, joined the field.

[11] In the men's race, defending champion Mo Farah returned, having run 2:05:11 in 2018 and 2:05:29 at the 2019 London Marathon in April.

[12] Rupp had been recovering from a surgery on his left foot to treat Haglund's deformity, a congenital bump on the heel which causes problems for the Achilles tendon.

[22] The weather forecast for the race was expected to be 46 °F (8 °C), with no chance of rain and 15–25-mile-per-hour (24–40 km/h) winds, described as "near ideal conditions" by the medical director.

[23] The race was held a day after Eliud Kipchoge ran the first sub-2 hour marathon during the Ineos 1:59 Challenge in Vienna, Austria.

[25][26] In the elite women's race, Kosgei set out very fast, passing 2 miles (3.2 km) in 9:54 and 5 kilometres (3.1 mi) in 15:28 with Ababel Yeshaneh and Burka 8 and 35 seconds behind, respectively.

[27] Saina, who had been running in fourth place, dropped out halfway through the race, having struggled with food poisoning on the journey to the United States from Kenya.

[34] Six men, Debela, Cherono, Karoki, Mengstu, Chumba, and Tura, led for most of the race with a chasing pack close behind, however after 5 miles (8.0 km), the leading group had grown to nine runners with the addition of Abdi, Farah, and Rupp.

[37] At 38 kilometres (24 mi), Cherono made an attempt to break from the lead group, but was caught by Debela, Mengstu, and Karoki.

[34] The other three runners left Karoki behind before the final turn of the race[22] before Cherono made a surge with 400 metres (1,300 ft) to go to and, following a sprint finish, won in a time of 2:05:45.

[38] Nicholas Thompson, the editor in chief of WIRED, wrote about the race in an article titled "To Run My Best Marathon at Age 44, I Had to Outrun My Past.