4 Days: Chicago and Illinois

Four days keeps the 3-day plan’s Oak Park and Starved Rock days intact and adds a downstate Route 66 run to Joliet and Pontiac, out and back in a day, no overnight required. Want to stop at three days, or keep driving south to Springfield? See the 3-day or 5-day version.

Book these before you go

Day 1: Land in Chicago, no Illinois day trip yet

Fly into O’Hare or Midway and get downtown on the CTA Blue Line (O’Hare, 24 hours, about 45 minutes) or Orange Line (Midway, faster but with an overnight gap); either way it’s a $2.75 tap with a Ventra card or contactless payment. Check into a Loop or River North hotel and spend the afternoon on Chicago itself; our Chicago guide covers the Riverwalk, Millennium Park and the rest of downtown in depth.

If your visit lands on a Third Thursday or a Summer Thursday (5-8pm, Jun 11-Sep 17, 2026), Illinois residents get into the Art Institute free that evening; it only works with proof of residency, so it changes nothing for an out-of-state visitor.

Day 2: Oak Park, the half-day Frank Lloyd Wright trip

Take the CTA Green Line (Harlem/Lake branch) or Blue Line (Forest Park branch) to Oak Park, 20-25 minutes from the Loop. Book the guided interior tour of Frank Lloyd Wright’s Home and Studio ahead, about $25 per adult, or the “Inside and Out” combo for about $36. The tour runs under two hours; the district walk adds maybe ninety minutes. That’s the whole day trip, so get back on the Green Line by early afternoon and spend the rest of the day inside Chicago.

Day 3: Starved Rock State Park, the car-only day

Rent a car this morning; Starved Rock has no direct train and no realistic rideshare option for a multi-hour hike. Drive 99 miles southwest via I-80, about 1 hour 45 minutes to 2 hours depending on traffic. Entry and parking are both free. Do the fuller multi-canyon loop, 5-6 hours, rather than the quick 2-hour sampler; you didn’t drive two hours each way for the short version. Pack lunch and water. Keep the rental car overnight; tomorrow’s trip needs it too.

Day 4: Route 66 downstate, Joliet and Pontiac, back by dinner

Head south on I-55. Joliet is 45 minutes down, with Route 66-era landmarks in a walkable downtown. Pontiac is another hour beyond that, about 100 miles from Chicago in total, home to the Route 66 Hall of Fame and Museum and a downtown covered in murals. Both towns fit into a single day, down and back, no overnight required. If you’d rather not drive, search Route 66 Illinois tours on Viator for current guided options.

Turn around after Pontiac. Springfield is still 1.5-2 hours further south, and that’s a trip for a longer itinerary, not this one.

Should you drive all the way to Springfield on this trip?

No, not on four days. Springfield needs an overnight of its own; tacking it onto this itinerary as a day trip means ten-plus hours of driving on day 4 alone. Joliet and Pontiac give you the Route 66 flavor without the overnight commitment; see our 5-day version if Springfield is the actual goal.

Do you need a car for all four days?

For two of them. Days 1 and 2 run entirely on the CTA; days 3 and 4 both need the rental car you picked up for Starved Rock. Keep it for both days rather than returning and re-renting, it’s cheaper and it’s one less counter transaction.

The three day trips this itinerary covers

Day trip Distance from Chicago Travel time Cost
Oak Park (Frank Lloyd Wright) ~10 miles west 20-25 min by CTA $25 guided tour, $36 combo
Starved Rock State Park ~99 miles southwest 1h45-2h by car Free entry and parking
Joliet and Pontiac (Route 66) 45 min-1h45 by car Day trip, no overnight Mostly free walking, museum admission varies

Return the rental car with a full tank before you head to the airport; the counter charges more for the privilege of doing it for you.