Chicago Gateway: 5 Days Out and Onward
Five days repeats our 4-day itinerary exactly through day four, then adds a day that isn’t a trip at all: Union Station itself, and the six long-haul routes most Chicago visitors never notice. This same spine extends into our 6-day and 7-day versions.
Book these before you go
- Milwaukee day trip from Chicago : book the morning slot before summer Saturdays fill up.
- Milwaukee brewery and lakefront tour : worth locking in if a guided afternoon beats wandering solo.
- Route 66 road trip experience : a guided taste of the drive if renting a car for one afternoon isn’t worth it.
- Chicago hotel rates near Union Station : stay walkable to the station since every day here starts there.
| Day | Focus | Distance / travel time from Chicago |
|---|---|---|
| 1 | Chicago, the home base | In the city |
| 2 | Milwaukee, WI (Amtrak Hiawatha) | ~90 min one-way, $19-37 |
| 3 | Indiana Dunes National Park, IN (South Shore Line) | ~1.5-2h one-way, verify current schedule |
| 4 | Route 66’s national start (Adams St + Navy Pier) | In the city; the full drive is ~2,448 mi to Santa Monica |
| 5 | Union Station’s long-haul network | In the city; six routes reach beyond it |
Day 1: Chicago, the home base
If you’re flying in, the Blue Line is the only O’Hare rail line running all 24 hours, about 45 minutes to the Loop for $2.75 tapped on a Ventra card or contactless payment. If you’re arriving off one of Union Station’s own long-haul trains, you’re already downtown, no transfer needed. Our Chicago guide covers Millennium Park, the river cruise and the rest of downtown in the depth it deserves; day one here is about getting oriented. Walk the free Riverwalk toward Union Station in the evening.
Day 2: Milwaukee, the one honest day trip
Catch a morning Amtrak Hiawatha from Union Station; the ride to Milwaukee runs about 90 minutes, with 7 weekday and Saturday round trips a day (6 on Sunday) and fares of $19-37 one-way depending on demand. The train stops at Glenview, Sturtevant and General Mitchell Airport along the way. Spend the day at the Harley-Davidson Museum, the Milwaukee Art Museum’s lakefront wing, or wandering the Milwaukee Public Market, then catch an evening train back before dinner in Chicago. Confirm current departure times at visitmilwaukee.org before you lock in a return train.
Day 3: Indiana Dunes National Park, if the trains cooperate
The South Shore Line runs direct from Millennium Station through roughly 20 stops, Hammond, Gary and East Chicago among them, to the dunes. A June 24, 2026 freight derailment near East Chicago forced a weekend-and-holiday-only schedule for several weeks; full weekday service resumed July 9, 2026, but confirm the current timetable at mysouthshoreline.com before you build a day around a specific departure. Once there, Mount Baldy’s shifting dune and the Lake Michigan beaches are the payoff; check current entrance fees and trail closures at nps.gov/indu first.
Day 4: Route 66’s national start, not a day trip in disguise
Route 66’s original “Begin” sign has stood at Adams Street and Michigan Avenue, across from the Art Institute, since roughly 1955, and it hasn’t moved. 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” run toward Santa Monica Pier; the Navy Pier start adds to the original sign rather than replacing it. The actual drive runs roughly 2,448 miles across 8 states, and a driver who wants to see the road properly budgets 10 to 14 days, not a week. A rental car and a single afternoon on the original alignment just outside the city gets you a preview, not the trip.
Day 5: Union Station and the rest of the country
Spend a day inside Union Station itself; the 1925 Beaux-Arts Great Hall is worth an hour on its own, and treat the rest of the day as decision day. Six long-haul Amtrak routes originate here: the California Zephyr toward the San Francisco Bay Area, the Empire Builder toward Seattle and Portland, the Lake Shore Limited toward New York and Boston, the Capitol Limited toward Washington DC, the Texas Eagle toward San Antonio, and the City of New Orleans toward New Orleans. None of them fit into this trip; that’s the point of the day, knowing they exist changes how you plan the next one. Check current routes and frequencies at amtrak.com .
Do you need a car for this trip?
Only for one afternoon. Days one, two, three and five run entirely on the CTA, the Amtrak Hiawatha, the South Shore Line and your own two feet inside Union Station; day four’s Route 66 preview is the only part that benefits from a rental, and only for a few hours.
Getting around this itinerary
CTA rail is $2.75 and bus is $2.50 since the February 2026 fare update (see transitchicago.com for current fares); tap a Ventra card or a contactless bank card directly at the turnstile. For a version that upgrades Milwaukee into an overnight, see our 6-day and 7-day versions. For day trips that stay inside Illinois, see our Chicago, Illinois guide instead.
Concrete tip: don’t skip day five because it doesn’t leave the city. Walking Union Station’s Great Hall and reading the departure board for six routes you didn’t take is the cheapest way to plan your next trip while you’re still on this one.