Chicago Plus Illinois in 5 Days on a Budget
Five days builds on the 3-day plan’s Oak Park and Starved Rock days with a genuine overnight south to Springfield for the free Lincoln Home National Historic Site. More trip ideas for the rest of the state sit on enjoyillinois.com . Need less time? Drop back to the 3-day version . Need more? Nest into the 6-day or 7-day version of this same route.
Book these before you go
- Book the Frank Lloyd Wright Home and Studio tour , the day two centerpiece; summer weekend slots sell out.
- Check rates for a Starved Rock and Springfield rental car on Discover Cars ; neither destination has a train.
- Search Springfield hotel rates on Booking.com for the overnight before you drive down.
- Compare Loop and River North hotel rates on Booking.com for the Chicago nights.
| 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 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.
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 the Springfield overnight worth 2 of your 5 days?
Yes, if Lincoln history or Route 66 is the draw, no otherwise. The Lincoln Home tour costs nothing, but the two travel days eat a real chunk of a 5-day trip, roughly 7 hours of driving total. Skip it and stay at the 3-day version instead if Springfield isn’t the priority.
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.