America Hidden Gems: 7 Unusual Things to Do
Chicago is a fine city to sightsee, and a better one to leave from. Union Station’s Great Hall lists departures for cities two time zones away, the Blue Line runs a straight 45-minute shot to one of the busiest airports on the planet, and a $19 train ticket gets you to a different state before lunch. Treat Chicago as the crossroads it actually is and these 7 things open up, none of them inside the city limits everyone else writes about.
The gateway trip at a glance
| Days needed | Best months | Daily budget (non-lodging) | Booking warning |
|---|---|---|---|
| 1 (Milwaukee alone) up to 4 (add Indiana Dunes, Route 66’s start, and Union Station) | May to October | $40-90 per person, plus $19-37 for the Milwaukee train | Book the Harley-Davidson Museum slot ahead and confirm the South Shore Line’s current schedule before you go; both shifted more than once in 2026. |
Base yourself in the Loop or River North for all of this; check Chicago hotel rates before booking the Milwaukee train, since every trip here is a same-day round trip and you only need the one room.
1. Ride an actual interstate train for a $19 lunch date
Amtrak’s Hiawatha leaves Union Station up to seven times on a weekday (six on Sunday) and covers the roughly 86 miles to Milwaukee in about 90 minutes, one-way fares $19 to $37 depending on how early you book. No other day trip on this list crosses a state line this fast or this cheaply. Read the full 2-day version of this trip if a single Wisconsin afternoon sounds like enough.
2. Meet the Bronze Fonz before the motorcycles
Milwaukee’s Riverwalk runs past the Bronze Fonz, a life-size statue of Henry Winkler’s “Happy Days” character installed near Wells Street in 2008, on the way to the Harley-Davidson Museum , general admission in the low-to-mid $20s and cheaper booked online ahead. Both sit an easy walk from the Amtrak stop, so no rental car changes anything about this afternoon.
3. Hike a national park with a steel mill for scenery
Indiana Dunes National Park is a straight shot on the South Shore Line from Millennium Station, about 46 miles and 66 minutes to the Dune Park stop, one-way fares roughly $9 to $10. As of this writing the line is back on its full weekday schedule after a June 24 freight derailment forced a reduced timetable for three weeks; check mysouthshoreline.com before you leave in case that changes again. Entry to the park is free. The dunes at West Beach climb well over 100 feet with US Steel’s Gary Works visible across the water, a pairing no other national park offers.
4. Find Route 66’s real starting line before the new one
The original Route 66 “Begin” sign has stood at Adams Street and Michigan Avenue, across from the Art Institute, since roughly 1955, marking the start of the 2,448-mile road to Santa Monica Pier. For the highway’s 2026 centennial, the city added a ceremonial second starting point at Navy Pier, dedicated March 25. It did not replace or relocate the Adams Street sign. See both, in that order, and a guided Route 66 tour covers the Illinois stretch of the highway if the mythology has you hooked and you would rather not drive it yourself today.
5. Watch a departures board name six cities you didn’t fly to
Spend twenty free minutes in Union Station’s Beaux-Arts Great Hall reading the Amtrak board like a menu: the Empire Builder runs about 46 hours to Seattle or Portland, the California Zephyr about 52.5 hours across 2,438 miles to the San Francisco Bay Area, and the Lake Shore Limited about 20 hours to New York or Boston, alongside the Capitol Limited to Washington, the Texas Eagle to San Antonio, and the City of New Orleans. None of that is today’s plan. Standing under the skylight while a board lists six cities a continent apart is the whole point of Chicago being a rail hub at all.
6. Ride the one CTA line that never sleeps, straight to a major US hub
The Blue Line is the only one of Chicago’s two airport rail lines that runs 24 hours, and it ends at O’Hare, still one of the busiest airports in the world by traffic. The free ATS people-mover loops between terminals and the parking structures before security, so you can ride the whole system, watch a hub this size move a full day’s connections, and head back without ever showing a boarding pass.
7. Know where O’Hare hides its weirdest exhibit, if you’re actually flying today
The airport’s genuine hidden gem sits past security in Terminal 1: an 850-foot tunnel between Concourses B and C lit by 466 neon tubes in a reflected light show, next to a 72-foot Brachiosaurus skeleton cast on loan from the Field Museum. Neither is visible without a ticket, so file this one under “next time you connect through United’s side of O’Hare,” not under today’s itinerary.
Do you need a car for any of this?
No. Every stop here runs on Amtrak, the CTA, or the South Shore Line: the Hiawatha reaches Milwaukee, the South Shore Line reaches Indiana Dunes, and the Blue Line reaches O’Hare. A car only matters if you extend past Chicago into the full Route 66 drive, and even the version of that stop covered here is a five-minute walk to a sign, not a road trip.
Does the Navy Pier ceremony replace the original Route 66 sign?
No. The Navy Pier starting point, dedicated March 25, 2026, is an added ceremonial bookend for the highway’s centennial year. The 1955 sign at Adams Street and Michigan Avenue still marks the historic start and has not been relocated or removed.
How much of a genuine day is Indiana Dunes?
A flexible one. The West Beach loop alone fills 3 to 4 hours including the South Shore Line ride each way; add a Mount Baldy or Cowles Bog detour and it stretches into a full day. Either way, budget the 66 minutes each direction on top of time actually spent in the park.
CTA fares apply on the Blue Line legs of this itinerary: $2.75 rail, or a $6 1-Day pass if you are stacking multiple rides around O’Hare and downtown. The 3-Day pass was eliminated in 2026’s fare restructuring.
For the day-by-day version of all this, see the 2-day through 7-day itineraries. Staying inside city limits instead? See Chicago’s own hidden gems . Want the in-state day trips (Starved Rock, Oak Park, downstate Route 66) rather than the interstate ones? That’s the Illinois hidden gems guide .
Authority sources: Amtrak , Indiana Dunes National Park , Visit Milwaukee , South Shore Line , Choose Chicago .
The one-line version: bring $19 for Milwaukee, bring water for the dunes, and bring a boarding pass if you actually want to see O’Hare’s dinosaur.