Chicago Gateway on a Budget: 4 Cheap Day Trips
Chicago’s cheapest trips all leave by train
Chicago earns its “crossroads of America” reputation on price, not just geography. The Amtrak Hiawatha reaches Milwaukee in 90 minutes from $19 one-way, the South Shore Line reaches a genuinely free national park in about an hour, and the same Wisconsin line has a cheaper, quieter stop most visitors never try. None of these four trips needs a car, an overnight, or more than a single day, and every one of them starts a few blocks from the 1955 Route 66 “Begin” sign that opens the 2,448-mile run to Santa Monica.
Chicago’s cheapest interstate day trips, at a glance
| Trip | Time and cost from Chicago | Best months | Booking note |
|---|---|---|---|
| Milwaukee, WI (Amtrak Hiawatha) | ~90 min, $19-37 one-way | May-Oct | book a summer Saturday run a few days ahead |
| Indiana Dunes National Park, IN (South Shore Line) | ~1h to Dunes Park, ~$9-10 one-way | Jun-Sep | check mysouthshoreline.com for current schedule first |
| Racine, WI (Hiawatha to Sturtevant, then a local bus) | ~70 min train plus a 20-min bus, ~$25-35 one-way | May-Sep | confirm the Racine bus times before you leave Union Station |
| South Bend, IN (South Shore Line, full route) | ~2h, $14.25 one-way | Apr-Oct | book ahead on a Notre Dame home game weekend |
Budget $40-90 per person for any single one of these, train fare plus food plus one paid activity, all in US dollars. Book a Milwaukee brewery or architecture tour on GetYourGuide before a summer weekend fills up.
Milwaukee on $19 and 90 minutes: the easiest escape
The Amtrak Hiawatha runs seven weekday and Saturday round trips between Chicago’s Union Station and downtown Milwaukee (six on Sunday), stopping at Glenview, Sturtevant, and Milwaukee’s Mitchell Airport along the way. Advance fares run $19-37 one-way depending on demand, and the ride itself takes about 90 minutes, no security line, no parking. In Milwaukee , the Public Market covers lunch on a pay-per-vendor basis, and the Lakefront Brewery tour ($13 weekday, $16 weekend, two pours and a souvenir glass included) is one of the better-value brewery tours in the Midwest. The Milwaukee Art Museum is free on first Thursdays if a visit lines up with one.
Indiana Dunes National Park: the free park at the end of a cheap train ride
The South Shore Line runs direct from Millennium Station through around 20 stops, including Hammond, Gary, and East Chicago, to Dunes Park, roughly an hour away for about $9-10 one-way. Entry and parking at the national park are both free; pick a lakefront beach or a dune trail depending on how much walking the day calls for. As of this writing, check the current schedule at mysouthshoreline.com before you go: a June 24, 2026 freight derailment near East Chicago cut weekday service to a weekend-only pattern for several weeks, with full Monday-Friday service only resuming July 17, 2026.
Is Racine or South Bend worth the extra stop?
Yes, both, if a Chicago trip runs past three or four days. Racine, Wisconsin’s official state pastry (the kringle, since 2013) draws day-trippers to O&H Danish Bakery, and the Hiawatha gets you most of the way there even though it doesn’t stop in Racine itself; you get off one stop early at Sturtevant and finish the trip on RYDE Racine’s Route 20 bus , a roughly 20-minute connection. South Bend, Indiana sits at the far end of the South Shore Line’s full route, about two hours and $14.25 one-way, and it’s a different stop entirely from Indiana Dunes, worth it for Notre Dame’s free-to-walk campus and, budget allowing, the Studebaker National Museum or the College Football Hall of Fame.
Where Route 66 actually starts (both signs)
The historic “Begin” sign at Adams Street and Michigan Avenue, across from the Art Institute, has stood since roughly 1955, marking the start of the 2,448-mile drive to Santa Monica across eight states. For the road’s 2026 centennial, the city added a second, ceremonial starting point at Navy Pier, dedicated March 25, 2026, framing a “pier-to-pier” version of the same journey. The Navy Pier marker adds to the story; it doesn’t replace or relocate the original Adams Street sign, and both are free photo stops with no ticket required. Book a Route 66 tour on Viator if the drive itself is the goal rather than just the photo stop. The downstate Illinois leg through Joliet and Pontiac toward Springfield gets its own coverage in the Chicago to Illinois day trips guide ; this guide sticks to the national jumping-off point.
Union Station and O’Hare: Chicago’s exits to the rest of the country
Chicago Union Station , the 1925 Beaux-Arts landmark at 225 S Canal St, is Amtrak’s Midwest hub and the departure point for six long-haul routes: the California Zephyr to the Bay Area, the Empire Builder to Seattle and Portland, the Lake Shore Limited to New York and Boston, the Capitol Limited to Washington DC, the Texas Eagle to San Antonio, and the City of New Orleans. O’Hare backs up the same “national crossroads” claim in the air: it ranked first in the world for aircraft movements in 2025 and sixth globally by passenger count, with 84.8 million travelers. The Blue Line runs the 45-minute trip downtown 24 hours a day for a $2.75 CTA fare, the only one of Chicago’s two airport rail lines that never stops overnight.
Is Megabus or FlixBus cheaper than the train to Milwaukee?
In raw dollars, sometimes. FlixBus runs Chicago-Milwaukee from roughly $14-18 one-way, undercutting the Hiawatha’s $19 floor, but the ride runs closer to two to two and a half hours against the train’s 90 minutes. Megabus has served the same corridor historically, but its US operations went through a 2024 bankruptcy and a change of ownership, so treat current Megabus availability on this route as something to verify at booking time rather than a given; FlixBus is the safer first check.
Do you need a car for any of this?
No. Every trip in this guide runs on a train that starts in downtown Chicago, and the one bus connection (Sturtevant to Racine) is a scheduled public route, not a rental. Skip the rental car entirely unless a side trip beyond this list specifically calls for one.
Where to stay in Chicago for these trips
Base yourself in the Loop or River North for easy walks to both Union Station and the Route 66 sign; compare rates on Booking.com before locking in a neighborhood. A same-day Milwaukee return means no second hotel night is required, though Milwaukee hotel rates on Booking.com are worth a glance if a trip runs long enough to justify splitting it into an overnight instead.
For the city itself, without any of these interstate trips, see the Chicago on a budget guide ; for in-state day trips instead of interstate ones, see Chicago to Illinois on a budget . The 2-day through 7-day versions of this itinerary lay out exactly which day gets which trip.
Book the Hiawatha to Milwaukee before anything else on this list; it’s the one trip with genuine weekend sell-out risk, and every other stop nests around it.