Small Towns Near Chicago

About 45 miles as the crow flies · Best for: beach days, boating, an easy escape

New Buffalo is a Lake Michigan resort town of 1,708 at the mouth of the Galien River. Its natural harbor is used mostly by pleasure boats, and it has long drawn visitors from the Chicago area.

Don’t miss: the city beach on Lake Michigan and the municipal harbor, where you can rent a kayak

★ Good to know Beach parking takes a vehicle pass in season, so check the city’s beach parking page before you go.

About 50 miles as the crow flies · Best for: movie fans, theater, a historic square

Woodstock is the McHenry County seat, with about 25,600 people and a turn-of-the-century town square. It stood in for the Pennsylvania town in the 1993 movie Groundhog Day, and plaques mark the filming spots around downtown.

Don’t miss: the Woodstock Opera House, built in 1889 on the Square, and the self-guided Groundhog Day walking tour

★ Good to know Come for Groundhog Days weekend if you want the guided version of the walking tour, led by locals who worked on the film.

About 55 miles as the crow flies · Best for: a distillery, Harbor Country, small-town Michigan

Three Oaks is a village of 1,370 about 5 miles in from the Lake Michigan shore, in the part of southwest Michigan called Harbor Country. E.K. Warren’s old Featherbone factory, which turned turkey feathers into corset stays, is now a distillery.

Don’t miss: Journeyman Distillery in the Featherbone factory, with tours, tastings and the Staymaker restaurant

★ Good to know Pair it with New Buffalo, just to the west, for a full day in Harbor Country.

About 60 miles as the crow flies · Best for: beaches, lighthouses, families

St. Joseph, a city of 7,856, sits on a bluff where the St. Joseph River meets Lake Michigan. Silver Beach below town was an amusement park from 1891 to 1970 and is now a county park with 2,450 feet of lakefront.

Don’t miss: Silver Beach County Park, the view of the St. Joseph Lighthouse from the South Pier, and the Silver Beach Carousel

★ Good to know The beach lot has just over 600 spaces and closes when full on summer days, so get there early.

About 65 miles as the crow flies · Best for: a hometown festival, train trip

Harvard, population 9,469, calls itself the Milk Capital of the World, and a cow statue named Harmilda stands in town. Its Metra station is the farthest in the system, 63 miles from downtown Chicago, so you can come by train.

Don’t miss: Harvard Milk Days in early June, with a long parade, a junior cattle show, an antique tractor show and fireworks

★ Good to know Milk Days is the reason to come; the rest of the year Harvard is a quiet stop.

About 65 miles as the crow flies · Best for: lake views, mansions, a weekend

Lake Geneva, a city of 8,277, sits on the northeastern bay of Geneva Lake in Wisconsin. After the Great Chicago Fire of 1871, wealthy Chicago families built summer estates here, and the place earned the nickname Newport of the West.

Don’t miss: the free Geneva Lake Shore Path, all the way around the lake past the estates, and the Lake Geneva Cruise Line’s mail boat tour, where mail jumpers leap off to deliver to 75 lakeside homes

★ Good to know The mail boat is a seasonal cruise, so check the schedule and reserve early.

About 80 miles as the crow flies · Best for: hiking, waterfalls, a winery

North Utica, usually just called Utica, is a village of 1,323 on the Illinois River and the base for Starved Rock State Park. The park has 18 canyons and more than 13 miles of trails on 2,630 acres.

Don’t miss: Starved Rock State Park and its 1930s Civilian Conservation Corps lodge, plus August Hill Winery’s tasting room on Mill Street

★ Good to know French, LaSalle, Ottawa and St. Louis canyons have the most reliable waterfalls, and in winter many of the falls freeze.

About 90 miles as the crow flies · Best for: art, beaches, a summer weekend

Saugatuck began as a lumber town and port, then became an art colony in the late 1800s. Only 865 people live here year-round, and the town’s economy runs on tourism.

Don’t miss: Oval Beach, the 303 stairs up Mount Baldhead, and the hand-cranked chain ferry, in use since 1857

★ Good to know Oval Beach’s lot often fills on summer afternoons, so arrive early or take the Interurban bus.

About 105 miles as the crow flies · Best for: Amish country, a flea market

Shipshewana is a town of 839 in LaGrange County, at the center of northern Indiana’s Amish country. Its flea market claims the title of the Midwest’s largest, with more than 600 vendor spaces on 40 acres.

Don’t miss: the Shipshewana Flea Market, Tuesdays and Wednesdays from May through September, and Menno-Hof, which covers five centuries of Amish and Mennonite history

★ Good to know Menno-Hof and many Amish-owned shops close on Sundays.

Things to do in Shipshewana →

About 145 miles as the crow flies · Best for: history, art studios, Cornish food

Mineral Point grew on lead mining, and by 1845 about half its people had Cornish roots. Much of the town is on the National Register of Historic Places, and in the 1930s two residents started restoring its stone cottages and drawing artists here.

Don’t miss: Pendarvis, the Wisconsin Historical Society’s 1840s Cornish miners’ cottages; Shake Rag Alley arts center; and a pasty at one of the Cornish-food restaurants

★ Good to know Pendarvis is open Thursday to Sunday from late May into early October.

About 150 miles as the crow flies · Best for: history, shopping, a weekend

Galena, population 3,308, was the center of America’s first major mineral rush, when lead mining boomed in the 1820s. About 85 percent of its buildings are in the Galena Historic District, and it is marking 200 years in 2026.

Don’t miss: Historic Main Street and the Ulysses S. Grant Home, given to Grant by Galena residents in 1865 and furnished with many Grant family pieces

★ Good to know The Grant Home is open Wednesday through Sunday, so skip Monday and Tuesday if it’s your main stop.