Chicago is a young city on old prairie, and its remarkable trees are the prairie's survivors: bur oaks that stood here before the city had a name. One shaded the Midway while the 1893 World's Fair was built around it, a grove on Wooded Island survived the same fair, and a Norwood Park savanna remnant may be older than the United States. The famous zoo oak fell in 2023, which makes the ones still standing worth the trip. Four of the six are free; the two champions stand on public golf courses, where a green fee generally applies.
0 / 6 visitati a Chicago
1
The Bur Oak on the Midway
Bur Oak (Quercus macrocarpa) · roughly 250 to 300+ years · Hyde Park
When the Midway Plaisance was cleared and regraded for the 1893 World's Fair, one tree was left standing, and this is it. By then it was already substantial enough that the ecologist Henry Cowles used it in his 1901 textbook as the example of its kind. Accounts of the fair place it behind the Sitting Bull's Cabin exhibit and the ostrich farm concession, neither of which lasted the year. Sources disagree on how it got here, and it is worth stating both. The University of Chicago Magazine quotes a campus environment official describing it as ostensibly planted as part of a Native American exhibit during the fair itself. The better supported account, from the Hyde Park historian Gary Ossewaarde, from Cowles in 1901 and from a local history record of a 2024 trunk measurement, has it standing long before 1893 and deliberately spared. That measurement reportedly ran past the largest bur oak on the Morton Arboretum's own growth reference chart, which would push it beyond the 250 or so years usually quoted. Bur oak is the tree of the prairie edge in this part of Illinois, corky barked enough to survive the fires that kept the grassland open. This one is the last of that landscape left on the Midway. It stands near Ellis Avenue, in front of the university hospital, on a pin that is close rather than surveyed.
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2
The Bur Oak Grove of Wooded Island
Bur Oak (Quercus macrocarpa) · the grove's oldest survivors are roughly 200 to 300 years · Jackson Park / Hyde Park
One of these oaks blew down around 2016, and its rings were counted back to roughly 1730. It had been standing for nearly three centuries when it fell. The ones still up are of the same generation: DNAinfo reported 250 year old bur oaks across the island, with a red oak of about 150 among them. Wooded Island is the part of the 1893 World's Fair that was deliberately left alone. Frederick Law Olmsted kept buildings off it entirely while the Court of Honor went up in white plaster to the south, and fair era painters kept turning their backs on the architecture to paint these oaks instead. The island sits on an undisturbed sand ridge, which is why the soil under the trees was never scraped and rebuilt the way the rest of Jackson Park was. In 2016 the Army Corps of Engineers spent 8.1 million dollars restoring the habitat here and wrote the old bur oaks into the plan, along with roughly 120 bur oak saplings that had seeded themselves around their parents. An oak stand actually reproducing inside a city is a rare thing to stand in. The place to stand is the path just south of the Osaka Garden, looking into the south end of the island, where the grove reads as one thing rather than as scattered trees.
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3
The Bur Oak Savanna of Union Ridge Cemetery
Bur Oak (Quercus macrocarpa) · the oldest estimated at 325 to 375 years, based on trunk size · Norwood Park
The oldest oak in this grove has been estimated at 325 to 375 years, which would make it roughly two centuries older than the city around it. It was already a mature prairie tree when Chicago was a portage and a fort. The figure comes from Scott Carlini, quoted in a 2016 hunt for the city's oldest tree, and it is based on trunk diameter rather than a ring core, so treat it as directional. We found no second independent estimate, which is why this entry stays flagged. What is solid is the setting. Union Ridge took its first burial in 1841 and is described by the Norwood Park Historical Society as the oldest continuously operating cemetery in Chicago. The ground was open prairie before it was platted, and what stands here is a genuine relict bur oak savanna: widely spaced, heavy limbed trees with daylight between them, which is what oaks look like when they grow up in grassland rather than in forest. Bur oak's thick corky bark let it survive the fires that kept that prairie open, and the graves that arrived in 1841 put an end to both the fires and the plough. It is a working cemetery, so come during posted visiting hours and behave like a guest. The pin is the entrance; the old section and its oaks are inside the grounds.
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4
The Champion Boxelder of Edgebrook
Box Elder (Acer negundo) · not documented · Forest Glen / Edgebrook
Boxelder is the tree nobody wants. It seeds itself into alleys and back lots, drops limbs, hosts the boxelder bugs that get into houses in autumn, and is generally written off as a weed that never lives long enough to get big. This one is the biggest known in Illinois. The state's Big Tree Register, run by University of Illinois Extension, ranks it champion of its species: just over nine feet around the trunk, 55 feet tall, a crown spreading 35 feet, and 172.3 points on the register's scoring formula, ahead of the runner up down in Shawnee National Forest at the far southern end of the state. It was measured and listed in 2026 with a dated photograph, so it is standing now. One honesty note, and it is the reason this entry is flagged: the register is the only source we could find on it. The Sun-Times feature on the state's big trees, the Extension's own announcement and the Forest Preserves champion list all fail to mention it, most likely because the title is very new. No Illinois register carries an age field either, so nobody has dated this tree and we are not going to guess at it. Visiting is a golf question. It stands on Edgebrook Golf Course, a public course run by the Forest Preserves of Cook County, which normally means a green fee to walk the fairways, and whether it can be seen from the perimeter is unconfirmed.
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5
The Champion Red Pine of Indian Boundary
Red Pine (Pinus resinosa) · not documented · Dunning
This is the state champion red pine of Illinois, and it holds the title partly for want of competition. The Illinois Big Tree Register lists exactly one red pine anywhere in the state, and this is the one, standing on the Indian Boundary golf course on Chicago's northwest side. Its 153.52 points come from a trunk 6.8 feet around, a height of 64 feet and a crown spreading 31.5 feet, measured and listed in 2026, which doubles as the freshest evidence that it is alive and thriving. Nobody has dated it. Red pine is a northern species, well outside its natural range down here, so this is a planted tree rather than a relic of anything, and the register carries no age field for any entry. Any figure attached to this tree is worked backwards from its trunk rather than measured, and should be read that way. What is documented is the size, and for Pinus resinosa the giveaway is the needles: paired, three to six inches long, snapping cleanly in half when you bend one. Access is the honest problem. Indian Boundary is a public 18 hole course run by the Forest Preserves of Cook County, so walking the fairways generally means paying a green fee, and whether the tree can be seen or reached from outside the course was not established. Ask at the clubhouse before planning the trip.
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6
The Kenilworth Witness Oak
Bur Oak (Quercus macrocarpa) · roughly 230 to 300 years, sources disagree · Oak Park (day trip from Chicago, not within city limits)
Local history holds that this bur oak was a witness tree, a landmark the Potawatomi used to find the route back to the Des Plaines River after a hunt. Oak Park's own paper, the Wednesday Journal, reported that reading in 2014 along with the claim that it is the oldest parkway tree in the village. Its age depends on which article you open. The 2014 survey puts it at about 230 years. A 2011 piece in the same paper, written when Openlands and the Morton Arboretum gathered its acorns for a historic oak propagation project, calls it three centuries old. That is a gap of seventy years, nobody has resolved it, and both figures stand here rather than one being quietly chosen. There is a harder caveat. No source has confirmed this tree alive since that 2014 article. In October 2025 another Oak Park heritage bur oak of the same generation, over on Forest Avenue, was removed after disease took it. That was a different tree at a different address, but the cohort is visibly failing, so go expecting an oak and not a guarantee. It stands on the parkway, the village-owned strip between sidewalk and street, in front of a private house on North Kenilworth Avenue in the Hemingway district. Public ground, so stay on the pavement. Oak Park is not Chicago but the suburb immediately west, 20 to 25 minutes from the Loop on the Green Line.
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