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The highest-performing listings in Wilmington.
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Challenging to Investors
Wilmington, IL allows STRs in general, but no specific local ordinance is provided; investors must verify zoning, permits, fees, caps, and inspections with the city and county and meet Illinois tax and health rules. This reliance on unverified local processes creates uncertainty and a higher compliance burden, making it more challenging to invest confidently.
Local STR Agent
STR specialist · Wilmington, IL
Wilmington is a small village in Will County, Illinois, with a population of roughly 5,700 residents. Situated near the confluence of the Kankakee and Des Plaines Rivers, the community has a relaxed, river-town atmosphere and serves as a popular jumping-off point for paddlers, anglers, and travelers tracing the historic alignment of Route 66. It lies approximately 55 miles southwest of downtown Chicago, putting it within easy striking distance of the metropolitan area while retaining a distinctly rural feel.
Just west of town, Kankakee River State Park covers more than 4,000 acres of wooded terrain and offers hiking, horseback riding, camping, and river access. The park's limestone bluffs and shaded ravines contrast with the surrounding farmland, and its canoe and kayak launches see steady traffic during the warmer months. From central Wilmington, the main park entrances are roughly a 10- to 15-minute drive.
Wilmington sits along the original Illinois alignment of Route 66, and the village retains a handful of mid-century commercial buildings, vintage signage, and the familiar "66" route markers that draw Mother Road enthusiasts. Travelers driving the historic highway between Chicago and central Illinois often stop in town for a meal, a photo, or a quick walk through the small downtown, giving Wilmington a steady stream of nostalgic visitors year-round.
The rivers themselves are central to the town's identity. Where the Kankakee meets the Des Plaines, just south of the village, the slow-moving waterway is a popular destination for smallmouth bass, walleye, and catfish, and local outfitters offer canoe and kayak rentals for paddlers looking to spend a day on the water. The surrounding bottomland also attracts birdwatchers, particularly during spring and fall migration.
A short drive south, Mazonia-Braidwood State Fish and Wildlife Area covers thousands of acres of reclaimed land that now serves as habitat for wildlife and a destination for hunting, fishing, and hiking. Braidwood Lake, one of the area's main features, is roughly 20 minutes from Wilmington and adds another option for outdoor recreation beyond the rivers.
Wilmington makes a compelling base for short-term rental operators looking to serve a mix of Chicago-area weekenders, Route 66 road-trippers, and outdoor enthusiasts heading to the rivers and state-managed lands nearby. Its combination of small-town character, river-based recreation, and proximity to a major metropolitan market gives it a year-round draw that few similarly sized Illinois communities can match.