The birds require large areas, greater than 160 acres (65 hectares), of dense young jack pine for breeding habitat.

The population of the species spends the spring and summer in their breeding range in the Great Lakes region of Canada (Ontario) and the United States (Wisconsin and Michigan, especially in the northeastern Lower Peninsula), and winters in the West Indies.

[5] The first specimen was shot at sea somewhere between the Abaco Islands of The Bahamas and Cuba in mid-October 1841 by the ornithologist Samuel Cabot III.

[6][7] Ten years later the holotype, a juvenile male, was shot on Jared Potter Kirtland's farm near Cleveland, Ohio, in mid-May 1851.

[9] Baird decided to name the bird after Jared Potter Kirtland: "a gentleman to whom, more than any one living, we are indebted for a knowledge of the Natural History of the Mississippi Valley".

It has black lores (cheeks) and a distinctive, large and conspicuous broken white eye ring,[13][14] which it only shares with Setophaga coronata.

[16] Its mating song is a loud chip-chip-chip-too-too-weet-weet often sung from the top of a snag (dead tree) or northern pin oak (Quercus ellipsoidalis) clump.

[8] In the mid 20th century the breeding range of Kirtland's warbler was reduced to a very limited area in the north of the Lower Peninsula of Michigan.

In recent years, breeding pairs have been found in the Upper Peninsula of Michigan, Wisconsin, and southern Ontario due to the expanding population.

It has otherwise been found in all habitats on the islands, including, albeit uncommonly, suburban gardens and Bahamian pineyards, with the exception of high coppice which has never been clear cut -it has never been seen here.

[17] Other common plants in this habitat are blueberry (Vaccinium angustifolium), sweet fern (Comptonia peregrina), Canada mayflower (Maianthemum canadense) and various grasses.

[22] When the pine stands grow so tall so as to lose their lowest branches near the forest floor, the environment no longer provides sufficient cover.

[13] Such stands are ideally densely stocked with young pines, but also contain small occasional patches of open areas or with sparse tree cover.

Lee et al. (1997) also believed that the warbler inhabits shrubs, but they concluded that the species is entirely dependent on pineyards, stating that before the advent of deforestation of the high coppice after the colonisation of The Bahamas by pre-colonial Lucayan peoples, the bird must have been restricted to the northwestern islands which harbour these pineyards and absent from central, eastern and southern islands such as Eleuthera.

[7] A detailed study by Wunderle et al. (2010) using a much larger sample size of new data from 153 capture sites and 499 observations, and investigations of the diet, found that Sykes and Clench had been correct, and there was no validity to the assertions of Lee, Walsh-McGehee and Haney.

[24] Jones et al. (2013), researching the warbler on an island where pineyards had never grown, hypothesized that a sampling bias for birds in pineyards had skewed the results of the research presented by Haney et al.[25] Despite the evidence, Birdlife International, which performs the IUCN Red List assessments, has consistently shown preference for the Haney et al. interpretation, stating that the conclusion that "changes in population have occurred contemporaneously with the degradation and recovery of the north Bahamas pine ecosystem" is more compelling than that the recovery efforts in Michigan were having effects on the population size.

[7] However, in 2007, Wunderle et al. pointed out that hurricanes might produce such young successional habitat, albeit with no empirical evidence; they theorized that perhaps this warbler species had specifically evolved to take advantage of such weather phenomena.

[1] It depends heavily during overwintering on the berries of Lantana involucrata, which is a very common successional shrub a few years after agriculture has been abandoned in a particular field.

[24] Of 331 observations of two warblers on Eleuthera in 1986, 76% were of foraging on Lantana, 8% were in Tournefortia volubilis, 4% in snowberry, 3.5% in Acacia rigens, 3.3% in Erithalis, 1.8% in Zanthoxylum fagara, and 1% Casuarina equisetifolia.

[31] As global climate changed after the ice age through the last 10 millennia or so, jack pine, and consequently also Kirtland's warbler, shifted their habitat north.

One theory is that during the ice ages, which lasted much longer than interglacials, Kirtland's warbler had a more stable distribution and habitat; i.e. the species exists as a glacial relict during geologically brief periods of warming global temperatures.

Most of the Lower Peninsula of Michigan was once covered in vast tracts of old growth white pine (Pinus strobus), the final stage of succession in the woodlands of that region, but these were all harvested by the early 19th century for construction in the growing cities and towns around the Great Lakes and along the East Coast.

This period coincides with the era where most Kirtland's warbler specimens were collected, reflecting a possible peak in population size.

[7] In July 1903, the taxidermist Norman Asa Wood was presented with a specimen by a student at the University of Michigan, and promptly travelled to the area it was killed, where he found the first nest ever recorded for the species near the banks of the Au Sable River.

Adams used dates of records of this bird in different states to show it migrated according to a very tight schedule, but used quite a broad route north spanning from the Mississippi River to South Carolina.

One was that the age of the jack pines in a stand is the most pertinent determinant in the suitability of a particular terrain as a breeding habitat for the species, and another discovery was that the population was subject to a deleterious brood parasitism by the brown-headed cowbird.

Development and fragmentation of forests in the eastern United States have allowed brown-headed cowbirds to greatly expand their range eastward.

Some 76,000 hectares are reserved for this purpose on the Lower Peninsula of Michigan, of which some 15,000 are maintained as young jack pine breeding habitat for the bird.

In 2007 three Kirtland's warbler nests were discovered in central Wisconsin[43] and one at CFB Petawawa in Ontario,[44] providing a sign that they are recovering and expanding their range once again.

[22] A new mixed red and jack pine stand was planted at a location in Simcoe County in 2018 in the hopes of attracting the warbler,[51] of which a sighting in the area had earlier been reported.