Yellow-Billed Cuckoos migrate to South America for the winter. East coast birds travel via Central America and the West Indies; western birds likely move down the western slope of Mexico and through Central America. 

The Prothonotary Warbler migrates across the Gulf of Mexico to Mexico where it follows the Atlantic slope south. Winters in the tropics in lowland woods and mangrove swamps. In southeastern swamps in summer, this bright golden warbler sings from high in the trees.

Baltimore Orioles spend summer and winter in entirely different ranges. From early April to late May, flocks arrive in eastern and central North America to breed from Louisiana through central Canada. They start to leave as early as July for wintering grounds in Florida, the Caribbean, Central America, and the northern tip of South America. 

Most Purple Martins that breed in eastern North American probably migrate across the Gulf of Mexico. They form huge roosts (of several hundred thousand birds) in late summer along the Gulf Coast from Texas to Florida. Others may fly over Mexico and through Central America. 

The Kentucky Warbler spends summer in the central and eastern United States, often ranging as far north as Wisconsin to Pennsylvania. Come fall and winter this bird will migrate back to the Yucatán Peninsula and the many islands of the Caribbean, flying non-stop across the Gulf of Mexico.

Redstarts breeding in eastern North America travel to Florida, the Greater Antilles, and northern South America, while those breeding in central and western North America migrate to Mexico and Central America. 

Orchard Orioles fly from eastern North America to wintering grounds in Mexico through northern South America. They spend less time on breeding grounds than other orioles, arriving by late May and departing as early as mid-July. Orchard Orioles migrate north late in the spring and head southward early, with some returning to their wintering grounds as early as mid-July. 

When migrating to and from Central American wintering grounds, Ruby-throated Hummingbirds may either fly directly across the Gulf of Mexico or follow a coastal route around the Gulf; the preferred strategy may be different between spring and fall migration. 

The Cerulean Warbler migrates at night across the Gulf of Mexico to South America. On the wintering grounds in South America the Cerulean Warbler is usually found in mixed-species canopy flocks, associating with tropical tanagers and other resident species.

The Bobolink is one of the world’s most impressive songbird migrants, traveling some 12,500 miles to and from southern South America every year. Throughout its lifetime, it may travel the equivalent of 4 or 5 times around the circumference of the earth. A migrating Bobolink can orient itself with the earth’s magnetic field, thanks to iron oxide in bristles of its nasal cavity and in tissues around the olfactory bulb and nerve. 

Swallow-tailed Kites from the U.S. migrate to South America. Migration is early in both spring and fall, with Florida birds arriving February-March, departing August-September. Some migrate around Gulf of Mexico but most Florida birds apparently cross Caribbean; their migration is poorly known.

Twice a year, Wood Thrushes cross the Gulf of Mexico in a single night’s flight. They spend the fall and winter in Central America. They return north in spring 2 to 6 times faster on a route that's generally somewhat farther west. Males arrive on breeding grounds several days before females.

Indigo Buntings fly about 1,200 miles each way between breeding grounds in eastern North America and wintering areas from southern Florida to northern South America. Indigo Buntings migrate at night, using the stars for guidance. The birds possess an internal clock that enables them to continually adjust their angle of orientation to a star—even as that star moves through the night sky.

Rose-breasted Grosbeaks fly from North American breeding grounds to Central and northern South America. Most of them fly across the Gulf of Mexico in a single night, although some migrate over land around the Gulf. Grosbeaks that winter in Panama and northern South America tend to be from eastern parts of the breeding range, while those wintering in Mexico and Central America tend to be from western parts.

Blackpoll Warblers are long-distance athletes and they hold the record for the longest overwater flight for a songbird. During the fall, these half-ounce warblers fly nonstop for up to 3 days, covering on average over 1,800 miles over the Atlantic Ocean to reach their wintering grounds in Puerto Rico, the Lesser Antilles, and northern South America. 

Common Nighthawks migrate at all hours of the day in large flocks, on one of the longest migration routes of any North American bird. Most travel over land through Mexico and Central America, although many do pass through Florida and Cuba, flying over the Gulf to reach their wintering grounds in southern South America. Common Nighthawks are among the last migrants to return to their breeding grounds in spring. 

Red-eyed Vireos leave the U.S. and Canada each fall to spend winters in the Amazon basin of South America. Western populations typically swing east before joining common flight paths south. The Red-eyed Vireo's magnetic compass guides migration between continents. Fatter birds head across the Gulf, while leaner birds hug the coastline or travel inland around the Gulf of Mexico.

The Black Throated Blue Warbler is a medium to long-distance migrant. Migrates at night to the Greater Antilles, the Bahamas, and occasionally the Caribbean coast of Mexico and Central America.

Chimney Swifts migrate to South America each winter flying across the Gulf of Mexico or skirting it along the Texas coast (a route they’re more likely to take in spring than fall). Many swifts use one of three distinct flyways: the Atlantic coast, the east side of the Appalachians, and the Mississippi River. They fly high in the sky during the day and roost in chimneys at night. 

Due to their long migration, Olive-sided Flycatchers arrive on breeding grounds late in spring and may depart again as early as August. Of all the flycatcher species that breed in the United States, Olive-sided Flycatcher has the longest migration, with some migrating between central Alaska and Bolivia, a distance of 7,000 miles.

Great Blue Herons generally move away from the northern edge of their breeding range in winter, with some flying as far south as the Caribbean. Populations in the Pacific Northwest and south Florida are present year-round. 

A captured female Whimbrel in 2009 was fitted with a satellite transmitter. Over the next three years, researchers monitored it for more than 50,000 miles traveling back and forth between its breeding area in Canada and her wintering site in British Virgin Islands. Some migrating Whimbrels make a nonstop overwater flight of 2,500 miles from southern Canada or New England to South America.

After breeding, the Hudsonian Godwit undertakes a migration from the subarctic to southern South America, in which it apparently makes nonstop flights of several thousand miles. Because of their far-northern breeding grounds and swift migratory passage through North America, Hudsonian Godwits were thought to be extremely rare until the 1940s.

The Buff-breasted Sandpiper is a champion long-distance migrant, leaving high-Arctic dry tundra nesting grounds and migrating thousands of miles to winter on the grasslands of Brazil, Argentina, Uruguay, and Paraguay.

Beginning in about February, they move northward through the middle of the continent, mostly west of the Mississippi River. They arrive on breeding territories in May. Adults begin moving south again in July with many individuals moving down the Atlantic Coast.

Golden-plovers fly fast—studies using geolocators found the birds averaged 30+ mph and sometimes achieved ground speeds of over 80 mph during their long over-ocean flights. Like many shorebirds, adult American Golden-Plovers leave the Arctic in early summer, leaving their young behind. The juveniles (only a few months old) set off on migration in late summer or fall—finding their way to South America on their own.

Twice a year, Scarlet Tanagers fly across the Gulf of Mexico between their breeding grounds in eastern North America and their wintering grounds in South America. They usually migrate at night. Individuals that spend the winter farther south migrate to breeding grounds later, and in more synchronized bursts, than individuals wintering further north.

Some Semipalmated Sandpipers from eastern populations probably fly nonstop across the ocean from New England to South America (some 2,500 miles), powered by extensive fat reserves. Semipalmated Sandpipers migrating through the Bay of Fundy, Canada, used to spend much of their time fighting over feeding space—and as a result it often took 2 weeks to fatten up before continuing their migration. 

Golden-winged Warblers migrate south mainly through a corridor of states east of the Mississippi River and west of the Appalachians, with peak movement in September. They begin to return on spring migration in April, during which month they are still regularly recorded in Costa Rica as well as in Texas and Kentucky.

The Bullocks Oriole is a medium-distance migrant. Most winter in western Mexico; a few individuals may be resident in coastal southern California.