Ogilvie Transportation Center
(131 N Clinton St) Start the day at the bustling Chicago French Market inside the station, which has 30 food stalls offering everything from crêpes to fresh produce. Kid-friendly snacks for the ride include übercrisp Belgium frites with housemade mayo and ketchup ($4) at Frietkoten and flaky croissants ($3) at the petite Vanille Patisserie.
Hop off here for a half-mile walk to Beat Street (930 Green Bay Rd, Winnetka; 847-441-8580), an edgy, eclectic, filled-to-the-brim shop with the feel of an old-timey five-and-dime. Dig around for treasures among more than 40,000 toys, jewelry and household items, plus a humongous candy selection featuring retro treats such as Zots ($1 for four pieces) and Razzles (15 cents) and current faves such as Harry Potter Chocolate Frogs ($5). Miyazaki fans will dig the grinning Totoro wallet ($16).
Step off the train and into bucolic small-town America just across the street from the station at charming Village Green Park, which has shade, a pretty gazebo and a Friday-morning farmers’ market. It’s a perfect spot for a game of Frisbee. Then stroll the shops on nearby Scranton Avenue and duck into Wisma (24 E Scranton Ave, 847-234-1805), a bright, inviting café where everything’s made with locally sourced ingredients. Grown-ups can have a glass of wine or a craft beer (someone else is doing the driving, right?) while the kids cool off with a pink lemonade sorbet ($3).
Metra stops 1.8 miles from Illinois State Beach Park (Sheridan and Wadsworth Rds, 847-662-4811), which offers six and a half miles of uninterrupted shoreline with no admission fee. Metra allows bikes (up to 20 per train), so bring yours for a breezy ride to the beach along the Zion Bike Path.
It’s the end of the line, which means everyone’s got to be hungry. From the station, take a half-mile walk to Franks Diner (508 58th St, 262-657-1017), a popular local treasure housed in an old diner car. Breakfast is served all day, so the kids can enjoy fluffy French toast made from housemade bread ($5.95) and you can tuck into one of its famous Garbage Plates: a combo of hash browns, eggs, peppers and the meat of your choice. ($8.55). But when a diner has the motto, “Be nice or leave!” you know you’re in good hands.
From Franks, walk two blocks over to 56th Street to hop on one of the city’s restored electric streetcars ($1 for 13 and over, 50 cents for ages 5–12, under 4 free) and take it to the Kenosha Public Museum (5500 First Ave, 262-653-4140, $2 suggested donation), a combo of a natural science and fine arts museum. Check out the impressive woolly mammoth specimen on display, discovered in Kenosha County in 1994 and the largest ever found in North America. If you’ve got time for more fossil hunting, hop back on a streetcar to the Dinosaur Discovery Museum (5608 Tenth Ave, 262-653-4450). It houses the nation’s largest display of meat-eating theropods, plus bones from the Institute’s most recent excavation, a juvenile T. Rex called “Little Clint.”