Chicago Plus Illinois in 6 Days on a Budget

Six days takes the 5-day plan’s Oak Park, Starved Rock and Springfield run and adds a free day back in Chicago to recover before you leave. Need less time? Drop back to the 3-day or 5-day version. Need more? Nest into the 7-day version of this same route.

Book these before you go

Day Focus Distance/time from Chicago Cost
Day 1 Settle into the Loop, Ventra card, free Riverwalk evening In Chicago $15-25
Day 2 Oak Park Frank Lloyd Wright tour, free Chicago afternoon 20-25 min CTA $25-40
Day 3 Starved Rock State Park, free canyons ~100 mi, 1h45-2h drive $20-45
Day 4 Drive south via Joliet and Pontiac’s Route 66 stops, overnight in Springfield ~200 mi, ~3.5h drive $80-140
Day 5 Free Lincoln Home National Historic Site, drive back ~200 mi, ~3.5h drive $15-35
Day 6 Free Chicago wind-down: Millennium Park, the Riverwalk In Chicago $10-25

Day 1: Settle into Chicago

Morning/afternoon: land, check into a Loop or River North hotel, and pick up a Ventra card ($5, refunded as transit credit if registered online within 90 days) or plan to tap a contactless bank card instead. Rail runs $2.75 a ride; a $6 1-Day pass pays off once you take three rides.

Evening: walk the free Chicago Riverwalk and Millennium Park before dinner. Both cost nothing and put you within a few blocks of tomorrow’s CTA line out to Oak Park. Grab a casual counter meal for $12-20 a person rather than a sit-down dinner tonight; you’ll want the budget for day two’s tour instead.

Day 1 running total: roughly $15-25 per person, transit and food only.

Day 2: Oak Park’s Frank Lloyd Wright half-day

Morning: take the Green or Blue Line 20-25 minutes out to Oak Park for the Frank Lloyd Wright Home and Studio, $25 for the one-hour guided interior tour or $36 for the “Inside and Out” combo with the outdoor district audio walk. Book ahead; this sells out on summer weekends.

Midday: this is genuinely a half-day trip, not a full one, so budget lunch in Oak Park itself, a casual $10-15 plate, before heading back into the city.

Afternoon: back downtown by early afternoon, use the free time on something that costs nothing: the Chicago Cultural Center’s Tiffany dome, or a longer stretch of the Riverwalk you skipped yesterday.

Getting around: $2.75 each way on the CTA rail fare, or use the 1-Day pass from yesterday if you bought one.

Day 2 running total: roughly $25-40 per person, tour and transit and food included.

Day 3: Starved Rock State Park

Early morning: Starved Rock has no train link, so this is a car day, rent one through Discover Cars or split an Uber/Lyft round trip three or four ways with your group; either beats a solo rideshare fare. Leave by 8am for the roughly 1h45-2h drive down I-80.

Midday: entry and parking are both free (current trail status at dnr.illinois.gov , since a 2026 trail project has some paths limited). A 2-hour sampler covers the canyons nearest the visitor center; if you left early, the full multi-canyon loop runs 5-6 hours instead.

Afternoon/evening: drive back to Chicago, budgeting the same 1h45-2h in reverse. Pack a lunch or eat near the visitor center; there’s little else nearby.

Day 3 running total: roughly $20-45 per person, split gas or a day rental plus food, no entry fee at all.

Day 4: South to Springfield via Route 66

Morning: pick up (or keep) the rental car and head south on I-55, the same downstate Route 66 corridor. Stop in Joliet and Pontiac for free roadside Route 66 murals and signage; neither stop needs a ticket.

Afternoon/evening: continue on to Springfield, roughly 3.5 hours of total driving with stops. Check into a budget motel; a night plus gas for the day runs roughly $80-140 depending on group size and how the gas splits.

Day 4 running total: roughly $80-140 per person or per car, gas and lodging combined; splits cheaper across a group.

Day 5: Free Lincoln sites, then back to Chicago

Morning: Lincoln Home National Historic Site is free, but the tour ticket is same-day only, picked up in person at the visitor center starting at 9am. Arrive early in summer before the day’s tickets run out.

Midday: the Old State Capitol and Lincoln’s Tomb round out a free or near-free Lincoln morning if the tour ticket schedule leaves time before the drive back.

Afternoon: drive back to Chicago, the same 3.5-hour stretch in reverse. It’s a long final day; split the driving if you can.

Day 5 running total: roughly $15-35 per person, mostly gas share and a casual lunch, the Lincoln sites themselves free.

Day 6: A free Chicago wind-down

Morning: return the rental car before it starts a new day’s charge. Spend the morning back on foot: Millennium Park and Cloud Gate, free and open 6am-11pm.

Afternoon: walk the rest of the Riverwalk, or the Chicago Cultural Center if you skipped it on day two; both are free. If your dates land on a Third or Summer Thursday, check whether you qualify for the Art Institute’s Illinois-resident evening window , 5-8pm, ID required.

Evening: a final casual dinner, $12-20 a person, before an early night ahead of departure.

Day 6 running total: roughly $10-25 per person, transit and a casual meal, everything else free.

Getting around this itinerary

Oak Park sits on the CTA map; days four and five need the rental car picked up for day three, since neither Starved Rock nor Springfield has a direct train. Check current CTA fares on transitchicago.com before day two.

Is a 6th day worth adding to the Springfield trip?

Yes, if you’d rather not fly out the same day you drive back from Springfield. A full free day back in Chicago on day six also gives the Illinois-resident museum evenings (Art Institute, Adler) a real shot at lining up with your dates, something the tighter 5-day plan doesn’t leave room for.

Get your Lincoln Home tour ticket the moment the visitor center opens on day five; same-day-only tickets are the one part of this trip you can’t book ahead.