5 Days: Chicago and Illinois

Five days keeps the 4-day plan’s Oak Park, Starved Rock and Route 66 days intact, then keeps driving from Pontiac to Springfield for the overnight the map keeps tempting you to skip. Want to stop at four days, or add a return morning in Springfield instead of a same-day turnaround? See the 4-day or 6-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; either way, this is the day the Route 66 corridor turns from a day trip into the start of an overnight one.

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, this is not a Chicago hotel night, book it separately, and spend the afternoon at the Lincoln Home National Historic Site , free admission, and the Old State Capitol downtown.

This is the day that proves Springfield isn’t a day trip. Add up the driving on both ends and a same-day round trip runs seven-plus hours in a car; staying over turns that into an actual visit instead of a windshield tour.

Is Springfield really worth an overnight?

Yes, if Lincoln’s Illinois sites interest you at all. The Home, the Old State Capitol and Lincoln’s Tomb are spread across a walkable downtown, and none of them rush well after a 3.5-hour drive. Skip it only if you’d rather spend that extra day and hotel night back in Chicago instead; Springfield is genuinely optional on a shorter Illinois trip.

What should you cut if five days feels tight?

Drop Joliet and Pontiac, not Springfield or Starved Rock. Driving straight from Chicago to Springfield in one push (3.5 hours) frees up most of a day compared with stopping at both Route 66 towns first, and you still get the state’s two headline day trips plus the overnight without losing a full day to the drive.

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

Book the Springfield hotel before you leave Chicago, not from the road. Weekend rooms near the Lincoln sites sell out faster than the drive time suggests they should.