5 Days: Chicago and the Midwest

Five days adds a full day on Chicago’s own national-gateway mythology: the 1955 Route 66 Begin sign, its new 2026 Navy Pier centennial start, and Union Station’s long-haul Amtrak network. Shorter trip? See 2 , 3 , or 4 days . More time? Step up to 6 or 7 days .

Book these before you go

Day Focus Distance / travel time from Chicago
Day 1 Arrival, Millennium Park, Cloud Gate, the Riverwalk, architecture cruise In Chicago
Day 2 Skydeck or 360 CHICAGO, Navy Pier, the Art Institute In Chicago
Day 3 Milwaukee day trip ~90 min each way, Amtrak Hiawatha
Day 4 Indiana Dunes National Park ~1-1.5 hr each way, South Shore Line
Day 5 Route 66 Begin sign, Navy Pier centennial start, Union Station In Chicago

Day 1: Arrival and the Loop

  • Land at O’Hare and ride the Blue Line downtown, about 45 minutes and the only one of Chicago’s two airport rail lines that runs 24 hours a day; landing at Midway instead, the Orange Line is faster at 25-30 minutes but has a real overnight service gap, so don’t count on it for a very early or very late arrival
  • Check into a hotel in the Loop or River North, both put you inside a short walk of Union Station and the Magnificent Mile
  • Walk Millennium Park, free, and photograph Cloud Gate (“the Bean”), then follow the Riverwalk south toward the Loop
  • Book the Chicago Architecture Center’s river cruise for late afternoon if you haven’t already, popular slots sell out May through November
  • Dinner in the Loop or River North; save a full deep-dish meal for a group, it’s not really a solo-portion dish

Day 2: Skyline and the lakefront

  • Morning at the Willis Tower Skydeck (from $32 adult, access to The Ledge glass balconies included) or 360 CHICAGO (from $30 weekday, $35 weekend); pick one, not both, they show the same skyline from opposite ends of it
  • CTA or walk to Navy Pier, free to enter; individual rides, boat tours, and the new-for-2026 Summer Skate lakefront rink are ticketed separately
  • Afternoon at the Art Institute of Chicago ($32 adult, $26 senior/student/teen), home to American Gothic and a genuinely deep Impressionist collection
  • Evening back in the Loop or River North

Day 3: Milwaukee, the easiest interstate day trip

  • Catch an early Amtrak Hiawatha from Union Station, about 90 minutes direct, 7 weekday and Saturday round trips a day (6 on Sunday), fares $19-37 one-way depending on demand, check current times on amtrak.com
  • Spend the day in Milwaukee’s Historic Third Ward or along the lakefront; a short brewery tour fits comfortably between trains
  • Full event calendars and neighborhood detail sit at visitmilwaukee.org
  • Catch an evening train back to Chicago; book the return leg the same day you book the outbound one, since fares climb as departure gets closer

Day 4: Indiana Dunes National Park

  • Ride the South Shore Line direct from Millennium Station, about 20 stops through Hammond, Gary, and East Chicago to Dunes Park; full weekday service only just resumed July 17, 2026, after a June 24 derailment near East Chicago knocked the line onto a reduced weekend-only schedule for weeks, check current departures at mysouthshoreline.com before building the day around one specific train
  • Hike the dunes themselves; Mount Baldy and the 3 Dune Challenge are the two most-photographed options, both free once you’re inside the park, full trail and seasonal hours at nps.gov/indu
  • Pack a lunch or eat in Chesterton before the return train, food options directly at Dunes Park are limited
  • Catch the South Shore Line back into Chicago by early evening; budget extra buffer time given the corridor’s recent disruption history

Day 5: Route 66 and Union Station, Chicago’s national-gateway day

  • Photograph the historic Route 66 “Begin” sign at Adams Street and Michigan Avenue, in place since roughly 1955, directly across from the Art Institute
  • Walk to Navy Pier for the newer 2026 centennial ceremonial starting point, dedicated March 25, 2026; it adds a second “pier-to-pier” framing toward Santa Monica Pier, roughly 2,448 miles away, and it does not replace the original Adams Street sign
  • Tour Union Station’s Great Hall, a few blocks south of the Loop, and check the departure boards for the long-haul network: the California Zephyr toward San Francisco, 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
  • If an actual Route 66 drive is on the radar for a future trip, search current Route 66 tour options on Viator to test a shorter guided leg first

Does Route 66 start at Navy Pier now? No. The 2026 Navy Pier dedication added an extra ceremonial starting point for the highway’s centennial year. The actual historic “Begin” sign at Adams Street and Michigan Avenue has stood since 1955 and remains the official start; treat Navy Pier as a second photo stop, not a relocation of the original.

Do I need a rental car for the Route 66 day? No, this fifth day stays entirely inside Chicago on foot and CTA: the Begin sign, Navy Pier, and Union Station all sit within a few miles of the Loop. A rental car only enters the picture if you’re extending past this itinerary into an actual multi-state Route 66 drive.

One concrete tip: do the Route 66 photo stop at Adams Street early, before the Art Institute’s lines form across the street, then work outward to Navy Pier and Union Station as the day warms up.