6 Days: Chicago and Illinois

Six days keeps the 5-day plan intact and gives Springfield a real second morning instead of a same-day turnaround, Lincoln’s Tomb and the Illinois State Capitol before the drive back to Chicago. Want to stop at five days, or add a buffer day at the end? See the 5-day or 7-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 and Millennium Park 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 changes nothing for an out-of-state visitor, but it’s worth knowing.

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. 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. Keep the rental car; the rest of this itinerary needs it.

Day 4: Route 66 downstate, Joliet and Pontiac

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, home to the Route 66 Hall of Fame and Museum and a mural-covered downtown. Overnight in Pontiac or push on toward Springfield this evening if you’d rather split the drive.

Day 5: South to Springfield, the drive that isn’t a day trip

Keep driving south from Pontiac, another 1.5-2 hours, or drive the full 200 miles and 3.5 hours from Chicago directly if you skipped the Route 66 towns. Check into a Springfield hotel, book it separately from your Chicago nights, and spend the afternoon at the Lincoln Home National Historic Site , free admission, and the Old State Capitol downtown.

Day 6: Lincoln’s Tomb, then back to Chicago

Spend the morning at Lincoln’s Tomb in Oak Ridge Cemetery and, if you have another hour, the Illinois State Capitol nearby. Check out of the Springfield hotel by midday and drive the 3.5 hours back to Chicago, arriving in time for dinner. This closes the downstate leg; everything on this trip has now come back to the Chicago-and-Illinois spine you started with.

Is six days enough to do all of this without rushing?

Yes, and it’s genuinely the version that doesn’t rush Springfield. The 5-day plan does Springfield as a single overnight with a next-morning drive back baked into the same day; six days gives Lincoln’s Tomb and the State Capitol a proper unhurried morning instead of a checklist sprint before a 3.5-hour drive.

Do you need to keep the rental car the whole week?

From day 3 through day 6, yes. Days 1 and 2 run entirely on the CTA, but once you pick the car up for Starved Rock, keep it through the Route 66 and Springfield legs rather than returning and re-renting; one rental spanning four days beats three separate transactions.

The three day trips (plus the Springfield overnight) 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
Springfield (Lincoln sites) ~200 miles south ~3.5h by car Overnight required; sites mostly free-$20

Return the rental car with a full tank once you’re back in Chicago; the downtown counters charge more for the privilege of doing it for you.