6 Days: Chicago and Downstate

Six days is enough to turn the downstate Route 66 run into a genuine overnight: instead of turning back at Pontiac, keep going to Springfield, sleep there, and see the Lincoln sites before driving home. Only have five days? See the 5-day version, which covers Joliet and Pontiac without the overnight. Want a full extra Chicago day tacked on after the drive back? See the 7-day version.

Book these before you go

Day Focus Distance / Travel Time from Chicago
Day 1 Chicago home base: the Loop, Millennium Park, an architecture cruise Within the city
Day 2 Oak Park half-day (Frank Lloyd Wright) plus a downtown evening 20-25 min by CTA, round trip
Day 3 Starved Rock State Park, canyon hiking About 100 mi / 1h45-2h each way by car
Day 4 Chicago rest day: Museum Campus plus an Illinois-resident evening perk Within the city
Day 5 Downstate Route 66: Joliet, Pontiac, on to Springfield About 200 mi / roughly 3.5h, overnight in Springfield
Day 6 Springfield’s Lincoln sites, then the drive back About 200 mi / roughly 3.5h back to Chicago

Day 1: Chicago Home Base

Morning (8:30 am - 12:00 pm)

  • Millennium Park and Cloud Gate, free, before 9am for a clean photo
  • Walk the free Riverwalk toward Michigan Avenue

Afternoon (12:00 pm - 5:00 pm)

  • Lunch at Portillo’s, $8-13
  • The Chicago Architecture Center river cruise, 90 minutes, book ahead in summer

Evening (5:00 pm - 9:00 pm)

  • Dinner at Lou Malnati’s, deep-dish, $24-30 for a medium
  • Confirm tomorrow’s Oak Park tour time

Day 2: Oak Park and a Downtown Evening

Morning (9:00 am - 1:00 pm)

  • CTA Green Line (Harlem/Lake) or Blue Line (Forest Park branch) to Oak Park, 20-25 minutes
  • Tour the Frank Lloyd Wright Home and Studio, about $25, or the Inside and Out combo for about $36

Afternoon (1:00 pm - 5:00 pm)

  • Back downtown, the Art Institute of Chicago ($32) or Willis Tower Skydeck (from $32)
  • Pick up your rental car this afternoon

Evening (5:00 pm - 9:00 pm)

  • Early dinner, Starved Rock rewards an 8am start

Day 3: Starved Rock State Park

Morning (7:30 am - 12:00 pm)

  • Drive southwest via I-80, about 100 miles, 1h45-2h out of the city
  • Hike French Canyon and St. Louis Canyon, free entry and parking

Afternoon (12:00 pm - 5:00 pm)

  • Continue the full multi-canyon loop for a 5-6 hour day, or head back after a lighter 2-hour sampler
  • Check the Illinois DNR park page for trail conditions

Evening (5:00 pm - 9:00 pm)

  • Drive back to Chicago, 1h45-2h

Day 4: Museum Campus and a Resident-Evening Perk

Morning (9:00 am - 12:30 pm)

  • One Museum Campus anchor: the Field Museum or the Shedd Aquarium, roughly $27-40
  • Walk the free lakefront path between Grant Park and the Museum Campus

Afternoon (12:30 pm - 5:00 pm)

  • Lunch at The Berghoff, a Chicago institution since 1898
  • A slow afternoon around the Loop or a neighborhood you missed on Day 1

Evening (5:00 pm - 9:00 pm)

  • Wednesday: the Adler Planetarium’s free evening window for Illinois residents
  • Early night, tomorrow’s a full driving day

Day 5: Downstate Route 66, on to Springfield

Morning (7:00 am - 12:00 pm)

  • Drive southwest on I-55 to Joliet, about 45 minutes, for the Rialto Square Theatre and Route 66 murals
  • Continue to Pontiac, roughly 1.5-2h from Chicago, for the Route 66 Hall of Fame and Museum

Afternoon (12:00 pm - 5:00 pm)

  • Instead of turning back, keep driving south, Springfield is about 200 miles and 3.5 hours total from Chicago
  • Check in to your Springfield hotel and grab an early dinner before the sites close

Evening (5:00 pm - 9:00 pm)

Day 6: Springfield and the Drive Home

Morning (8:30 am - 12:00 pm)

  • Tour the Lincoln Home National Historic Site, free, ranger-led, check current tour times at nps.gov/liho
  • Walk through the Old State Capitol, where Lincoln served and delivered his “House Divided” speech

Afternoon (12:00 pm - 6:00 pm)

  • Lunch in downtown Springfield, then start the drive back north
  • Budget the full 3.5 hours plus stops, I-55 traffic around Bloomington-Normal can add time on weekends

Evening (arrival varies)

  • Back in Chicago by early evening if you left by early afternoon
  • A quiet last dinner, no more early alarms after this one

Where to Stay

Chicago: the Loop or River North for the fastest exits toward I-55 and I-80. Springfield: stay downtown, walking distance to the Lincoln sites. Compare Springfield rates on Booking.com and Chicago rates here .

Getting Around

CTA rail is $2.75, bus $2.50, confirmed current at transitchicago.com . Keep the rental car from Day 3 through Day 6, there’s no practical reason to return and re-rent between the two road-trip days.

Do You Need a Car for This Trip?

Yes, for three of the six days: Starved Rock and both Route 66 days. Oak Park and the two Chicago-based days run entirely on the CTA.

Things to Know

Gas up before Pontiac on Day 5, stations thin out on I-55 south of there with Springfield still 90 minutes off. The Lincoln Home’s ranger-led tours run on a fixed daily schedule, not walk-up whenever, confirm times before you plan your Day 6 morning around one.

Book the Springfield hotel before you leave Chicago, not after you’re already on I-55, downtown options are limited and fill up during Route 66 season.