Pear picking in Chicago, IL
4 farms near Chicago pick pears, running August to October and peaking in September. 4 ask you to check before you drive out.
4
farms
4
towns
4
want a call first
August to October
season
pears near Chicago
J
F
M
A
M
J
J
A
S
O
N
D
farms: Apple Holler picks pears alongside its apples and peaches, R&M Orchards picks apples, pears and grapes, and Homestead Orchard grows fifteen varieties of apple and pear. Prairie Sky was recorded picking Asian pears in the first pass and its own site names no crops at all
Where the pear farms are
4 farms across 4 towns, biggest cluster first.
4 more towns with one each
Every farm near Chicago that picks pears
Each one read against its own website. Where a farm publishes nothing, this says so rather than guessing.
Prairie Sky Orchard
Union4.5
Closed for the 2026 season after spring frosts that, in the orchard's own words, "killed 99% of the blooms". It anticipates reopening in 2027.
August to October(815) 923-4834Farm ShopRead from the farm's own site on 2026-08-21
Apple Holler
Sturtevant4.4
The orchard is open for apple picking. The farm store and bakery run 8:30am to 4pm daily and the Farm Park and Orchard 10am to 4pm, with the last admission at 3pm.
August to October(262) 884-7100CafeFarm ShopFarm AnimalsRead from the farm's own site on 2026-08-21
R&M Orchards
Kenosha4.4
Closed for the season. The orchard picks apples, pears and grapes, with no entry or parking fee and no picking minimum.
August to October(262) 960-1789EFTPOSFarm ShopRead from the farm's own site on 2026-08-21
Homestead Orchard
Woodstock4.3
U-pick McIntosh started on 15 August 2026, with Dutchess and Early Blaze already picking. The orchard grows fifteen varieties of apple and pear and is grafting heirlooms that are not yet bearing.
August to October(815) 338-7443Farm ShopShaded SeatingRead from the farm's own site on 2026-08-21