Best Day Trips from Chicago: Milwaukee, Indiana Dunes and Starved Rock

Chicago’s day-trip menu runs in three directions: north up the lake to Milwaukee, southeast around the lake’s bottom to a national park you can reach by electric commuter train, and southwest into canyon country that nobody expects from Illinois.

For the city itself, see our Chicago guide and things to do in Chicago.

Milwaukee — the easiest second city in the Midwest

Amtrak’s Hiawatha runs seven daily round trips from Union Station to downtown Milwaukee in approximately 90 minutes (around $25–28 each way as of 2026 — book at amtrak.com). One day comfortably covers the Harley-Davidson Museum (approximately $24), the Milwaukee Art Museum with its wing-flapping Calatrava building (approximately $22), and the Historic Third Ward’s Public Market for lunch. Beer is the through-line: Lakefront Brewery’s tour (approximately $15, includes pours) is the canonical stop. Last trains back leave mid-evening — late enough for a fish fry on a Friday.

Indiana Dunes National Park — a national park by commuter train

The South Shore Line from Millennium Station reaches Dune Park or Beverly Shores stations in approximately 70–80 minutes (around $9–10 each way). From Dune Park station you can walk into the state park section and take on the 3 Dune Challenge — 552 vertical feet of sand, approximately 1.5 punishing miles — or head for West Beach’s long sweep of Lake Michigan sand. Summer water temperatures peak in August; the dunes themselves are best in the gold light of September–October. Bring everything you need — concessions are sparse.

Starved Rock State Park — canyons in the cornfields

Approximately 95 miles southwest (1.5–2 hours by car; no practical transit), Starved Rock hides 18 sandstone canyons cut into the Illinois River bluffs. Entry is free, parking approximately $5. After spring rain, St. Louis, French, and Wildcat canyons all run with waterfalls; in deep winter the falls freeze into climbable ice columns and bald eagles fish the river below the dam. Trails are short and interconnected — a 4–5 mile loop hits the highlights. Arrive before 10 am on weekends; the lots fill.

Lake Geneva, Wisconsin — the Gilded Age lake

Approximately 80 miles northwest by car, Lake Geneva has been Chicago money’s summer escape since the 1870s. Walk a stretch of the 21-mile Shore Path, which crosses the manicured lawns of historic mansions at the waterline (public right-of-way, remarkably), or see the same estates from the water on a Lake Geneva Cruise Line boat tour (approximately $35–45 in season). Finish with a Wisconsin supper club — brandy old fashioned, relish tray, prime rib — before the drive home.

New Buffalo and Harbor Country, Michigan — the other side of the lake

Approximately 70 miles around the lake’s southern curve (1.5 hours by car, or Amtrak’s Wolverine to New Buffalo in approximately 70 minutes, around $20–30 each way as of 2026), Harbor Country is a string of low-key Michigan beach towns — New Buffalo, Union Pier, Three Oaks. The draw is the wide, warm-water New Buffalo Public Beach (parking approximately $20 in season), wineries and tasting rooms along the Red Arrow Highway, and Redamak’s, the seasonal burger institution that has anchored New Buffalo summers since 1946. Note Michigan runs an hour ahead of Chicago — build that into the return.

Geneva and the Fox River towns — the Metra escape

Metra’s Union Pacific West line from Ogilvie reaches Geneva in approximately 65–75 minutes (around $7–9 each way as of 2026). The historic downtown sits a short walk from the station: boutiques in century-old houses, the riverside Fox River Trail for a flat walk or bike ride between Geneva, St. Charles, and Batavia, and Fabyan Forest Preserve’s Dutch windmill a couple of miles south along the path. It is the gentlest day trip on this list — lunch on Third Street and an afternoon on the river path, all on a commuter ticket.

Oak Park — the half-day architecture fix

Technically a CTA ride, not a day trip: the Green Line reaches Oak Park in approximately 25 minutes from the Loop. The Frank Lloyd Wright Home and Studio tour (approximately $20) plus the self-guided walk past a dozen Wright houses in the surrounding blocks makes an excellent half day, and Hemingway’s birthplace is around the corner. Pair it with an evening back in the city — our Chicago food guide takes over from there.

Practical tips

• South Shore Line weekend service is less frequent — check the timetable both directions before committing to a beach day
• Starved Rock and the Dunes flip seasons: canyons best in spring, beaches in late summer, both spectacular in October
• Hiawatha tickets are cheapest booked a week or more ahead, and the train beats driving I-94 in any traffic
• Prices as of 2026 — confirm at amtrak.com, mysouthshoreline.com, and venue sites before travelling