Trains, boats and the big wheel with kids around Chicago
Chicago is the railroad capital of the country, and for a train-loving kid it has everything: bi-level Metra commuter trains, the L curving between skyscrapers, century-old trolleys, the largest railway museum in America, and a water taxi down the river.
The simplest day starts at the Naperville station: a $7 weekend pass with kids free, the upper deck to Union Station, a walk to the old Quincy station for a lap of the Loop on the L, then the water taxi from under the Michigan Avenue bridge to Chinatown for dim sum. For old equipment, the Fox River Trolley in South Elgin runs 4 miles along the river, and admission to the Illinois Railway Museum in Union includes unlimited rides on streetcars and old trains, with barns full of retired L cars to climb aboard. The Centennial Wheel and carousel at Navy Pier count as riding too.
- 6 places
- 6 stroller-friendly
- closest is 5 min away
6 places
Drive times from Naperville

Metra train ride downtown (BNSF line)
5.0Naperville · 5 min drive
3 h · stroller-friendly
$ · Parking: Free weekend parking at the Naperville station lot (permit required weekdays); same at Route 59

Fox River Trolley Museum
5.0South Elgin · 30 min drive
2 h · stroller-friendly
$ · Parking: Free museum lot (365 S LaFox St)

Riding the L around the Loop
5.0Chicago · 45 min drive
1.5 h · stroller-friendly
$ · Parking: Metra to Union Station, then a 10-minute walk to Quincy; Loop garages are $15–30 on weekends if you drive

Chicago Water Taxi
5.0Chicago · 45 min drive
1.5 h · stroller-friendly
$ · Parking: Michigan Ave dock is below the Wrigley Building; from Metra at Union Station you can board directly at the Ogilvie / Union dock

Illinois Railway Museum
5.0Union · 65 min drive
4 h · stroller-friendly
$$ · Parking: Large free museum lot (7000 Olson Rd)

Navy Pier Centennial Wheel and carousel
4.0Chicago · 50 min drive
3 h · stroller-friendly
$$ · Parking: Two Navy Pier garages ($30–40 on weekends, very expensive); bus 124 direct from Union Station / Ogilvie
💡 Good to know
- On weekends up to three kids 11 and under ride Metra free with each fare-paying adult, and kids under 7 ride the CTA free; one Ventra account buys everything.
- The Fox River Trolley and the Illinois Railway Museum are volunteer-run and operate only on certain weekends; check the day's schedule before you leave.