Chicago Day Trips: Go Big, Go Fast
Skip the rental car. Chicago sits on top of a rail network good enough to get you to a national park, a Frank Lloyd Wright district, and a second state’s biggest art museum, all before dinner.
Milwaukee, 89 minutes north
Amtrak’s Hiawatha service runs Chicago Union Station straight to Milwaukee Intermodal Station, seven round trips a day Monday through Saturday, six on Sunday. One-way coach fares run $19 to $37 depending on how early you book. Check current Hiawatha schedules and fares before you commit to a departure time. Once there, Santiago Calatrava’s Milwaukee Art Museum (with its folding brise-soleil wings) is a 15-minute walk from the station, and the Harley-Davidson Museum and Third Ward dining district round out the afternoon. If you’d rather skip the logistics, book a guided Milwaukee day trip on Viator instead.
Indiana Dunes, sand without the drive
The South Shore Line (NICTD) runs from Millennium Station directly to Dunes Park Station in roughly 80 minutes; fares run around $9 each way, though it’s worth confirming the exact current price on their site since fares shift. Following 2026 track upgrades, trains run hourly on weekdays and every two hours on weekends, so check the timetable before you head out. Once there, you get 15 miles of Lake Michigan shoreline, the climb up Mount Baldy, and the 3 Dune Challenge at the state park next door. National park entrance is $25 per vehicle or $15 per walk-in and train passenger, valid for seven days. Prefer a guide who handles the transit for you? Search Indiana Dunes tours on GetYourGuide .
Oak Park, an architecture masterclass in one afternoon
The CTA Green Line runs from the Loop to Harlem/Lake in 22 minutes for the standard $2.75 fare; Metra’s Union Pacific West line from Ogilvie gets you there in 16 minutes for about $4. From either station it’s a ten-minute walk into the Frank Lloyd Wright Historic District. The Frank Lloyd Wright Home and Studio, where Prairie School architecture was essentially invented between 1889 and 1909, runs a 60-minute guided tour for $25; Unity Temple, Wright’s 1908 reinforced-concrete landmark and a UNESCO World Heritage Site, runs $20. Book ahead through the Frank Lloyd Wright Trust : both sell out on weekends.
Starved Rock, canyons without a coastline
This one needs a car: it’s 95 miles southwest via I-80, roughly two hours each way, with no passenger rail connection. Eighteen sandstone canyons carved by glacial meltwater, 13 miles of marked trail, and admission that’s entirely free make it worth the drive, but stick to the marked trails, the cliffs are brittle sandstone and off-trail scrambling causes fatal falls every year. Parking lots fill and gates close by 10:00 am on peak fall-foliage weekends, so get an early start.
Before you go
None of these rail trips require booking a car, but do book museum and tour tickets ahead where they exist (Wright sites especially). If you want the boat-and-skyline version of a Chicago day instead of leaving the city, the attraction tours in Chicago cover the river cruises and observation decks that stay downtown.