One Week in Gateway: An Offbeat Itinerary

A full week revisits Indiana Dunes for the trails Day 3 skipped, on top of the same first six days as the 6-day version . Want the condensed version instead? Start at the 2-day version .

Book these before you go

Chicago’s gateway distances at a glance

Gateway Distance from Chicago Travel time
Milwaukee, WI (Amtrak Hiawatha) ~86 miles ~90 min
Indiana Dunes National Park, IN (South Shore Line) ~46 miles ~66 min
O’Hare International Airport ~17 miles ~45 min (Blue Line)
Route 66 to Santa Monica Pier, CA (by road) ~2,448 miles multi-day drive
Empire Builder to Seattle/Portland (Amtrak) ~2,200 miles ~46 hours
California Zephyr to Emeryville, CA (Amtrak) ~2,438 miles ~52.5 hours

Day 1: Chicago, the crossroads before you leave it

Start downtown, since tomorrow’s train leaves early. Walk the free Riverwalk to Millennium Park for Cloud Gate, the Bean, then head back to the Loop; a CTA 1-Day pass is $6 if today involves more than two rail trips. The deep city sights get one day here; see the Chicago hidden gems guide for the rest. Dinner in the Loop or River North, then an early night.

Day 2: Milwaukee, the easiest state line you’ll cross

Catch one of Amtrak’s Hiawatha trains from Union Station; the roughly 86-mile ride to Milwaukee takes about 90 minutes, one-way fares $19 to $37. Walk the Milwaukee Riverwalk to the Bronze Fonz, a life-size statue of Henry Winkler’s “Happy Days” character installed near Wells Street in 2008, then spend the afternoon at the Harley-Davidson Museum, general admission in the low-to-mid $20s and cheaper booked online ahead. Catch an evening Hiawatha back.

Do you need a car to do Milwaukee as a day trip?

No. The Hiawatha runs directly from Union Station to downtown Milwaukee’s Intermodal Station, and the Riverwalk, the Bronze Fonz, and the Harley-Davidson Museum all sit within walking distance or a short rideshare of that stop.

Day 3: Indiana Dunes, the national park next to a steel mill

Board the South Shore Line at Millennium Station for the roughly 46-mile, 66-minute ride to Dunes Park, one-way fares about $9 to $10. As of today 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 Indiana Dunes National Park is free. West Beach’s trails climb well over 100 feet with US Steel’s Gary Works visible across the water.

Day 4: Route 66, the road you’re not driving today

Walk or ride the L to Adams Street and Michigan Avenue, across from the Art Institute, for the original Route 66 “Begin” sign, standing since roughly 1955 at 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, so see both rather than assuming one.

Does the Navy Pier ceremony replace the original Begin 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.

Day 5: Union Station, pick a direction and go

Spend a slower morning in Union Station’s Beaux-Arts Great Hall, then read the Amtrak departures board the way locals read 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. Standing under the skylight while a board lists six cities a continent apart is the whole point of this family of trips.

Day 6: O’Hare, the busiest hub you’ll never fly out of today

Ride the Blue Line, the only one of Chicago’s two airport rail lines that runs 24 hours, out to 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 and head back without ever showing a boarding pass. Save the airport’s actual hidden gem, an 850-foot neon tunnel and a 72-foot Brachiosaurus skeleton cast between Terminal 1’s Concourses B and C, for next time you’re flying out through United’s side; both sit past security.

Day 7: Indiana Dunes again, the trails Day 3 skipped

Take the South Shore Line back out, this time to a different stretch of the park: Mount Baldy’s shifting dune (check current access; sections close periodically for dune migration) or the Cowles Bog Trail’s wetlands-to-shoreline loop, both longer and quieter than West Beach’s crowds. A guided tour is worth it if you want a naturalist explaining how a national park ended up sandwiched between steel mills, since the visitor center doesn’t always have staff free to do that on demand.

Is a second Indiana Dunes day overkill?

Not really. West Beach on Day 3 is the easy, crowded introduction; Mount Baldy and Cowles Bog on Day 7 are the quieter, more varied sides of the same national park. Seeing both in one trip is unusual, and that’s the appeal of taking a full week.

How many days do you actually need for the whole gateway family?

Four covers the core: Chicago, Milwaukee, Indiana Dunes, and Route 66’s start. Five and six add Union Station and O’Hare’s own angle. Seven is for travelers who want Indiana Dunes twice, not a requirement.

Where to stay: a Loop or River North hotel for all seven nights, since every day trip here returns to Chicago the same evening.

For the interstate day trips in guide form, see the America hidden gems guide , or the in-state alternative at the Illinois hidden gems guide .