5 Days: Chicago and Downstate

Five days adds the downstate Route 66 corridor, Joliet and Pontiac, as a long single-day round trip that gets you back to Chicago the same night. Push it further into a Springfield overnight and you’ll want 6 or 7 days instead. Shorter trip? See 2 through 4 days .

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 and Pontiac, round trip About 200 mi round trip / 3-4h driving

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 near the visitor center, 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 first

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: the Riverwalk, Grant Park, or a neighborhood you missed on Day 1

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

  • Wednesday: use the Adler Planetarium’s free evening window for Illinois residents
  • Early night, Day 5 is a long drive

Day 5: Downstate Route 66, Joliet and Pontiac

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

  • Drive southwest on I-55 to Joliet, about 45 minutes, for the Rialto Square Theatre and a run of Route 66 murals downtown
  • Continue on to Pontiac, roughly 1.5-2h total from Chicago, for the Route 66 Hall of Fame and Museum, which covers the full Chicago-to-Santa Monica story

Afternoon (12:00 pm - 4:00 pm)

  • Lunch in Pontiac, then browse the town’s small Route 66 murals and shopfronts before the drive back
  • If you’re tempted to push on to Springfield instead, that’s another 2 hours each way, save it for the 6 or 7-day version of this trip

Evening (4:00 pm - 8:00 pm)

  • Drive back to Chicago, roughly 1.5-2h, arriving in time for a final dinner in the Loop or River North

Where to Stay

Base yourself in the Loop or River North, close to Museum Campus and the fastest exit toward I-55 and I-80. Check current rates on Booking.com .

Getting Around

CTA rail is $2.75, bus $2.50, confirmed current at transitchicago.com . Days 3 and 5 both need the rental car; keep it for the whole back half of the trip rather than returning and re-renting.

Do You Need a Car for This Trip?

Yes, for two of the five days. Starved Rock and the downstate Route 66 run both sit outside any train network. Oak Park and the two city days run entirely on the CTA.

Things to Know

Gas up in the city before Day 5, stations thin out south of Joliet. The Art Institute’s Illinois-resident evening window is Third and Summer Thursdays 5-8pm, and the Adler’s is Wednesday evenings, confirm both at artic.edu and adlerplanetarium.org .

Five days is the last version of this trip that avoids an overnight outside Chicago entirely, decide before you book whether Springfield belongs on this trip or the next one.