Few drives feel as timeless as the first stretch of Route 66 in Illinois. From Chicago’s lakefront to Springfield’s historic core, the Mother Road serves up neon signs, classic diners, small‑town museums and photo‑ready murals. Before you hit the road, line up your car rental so you can cruise straight from the terminal to the “Begin Route 66” sign downtown. If you prefer UK‑style terminology, explore car hire in Chicago for the same great selection with familiar wording.
Chicago to Joliet
Start the morning near Adams Street to snap the iconic marker, then roll past city neighborhoods toward Joliet. Detour for breakfast at a vintage diner or a roadside bakery, and drop by a local visitor center for maps and stamp books that track your stops. If you’re flying into O’Hare, an easy O’Hare Airport car hire keeps pick‑up quick and predictable.
Joliet to Pontiac
South of Joliet, communities celebrate their Route 66 heritage with murals, museums and lovingly restored filling stations. Stretch your legs at small parks, browse antique shops, and keep an eye out for quirky fiberglass giants along the roadside. Families often split this section into multiple short stops to avoid back‑seat boredom and to make space for photos.
Bloomington–Normal to Springfield
As you glide toward the state capital, you’ll find more interpretive signs and classic eateries. Springfield pairs Route 66 nostalgia with presidential history, so add time for landmark neighborhoods and a lively food scene. Prefer extra luggage space for souvenirs? Check local SUV hire in Chicago before departure to enjoy a more relaxed cruise.
Essential tips
- How long? A relaxed one‑to‑two‑day drive covers most highlights without rushing.
- When to go: Late spring to early autumn offers mild weather and longer daylight.
- Navigation: Old alignments diverge from the interstate—download offline maps and watch signage.
- Etiquette: Support small businesses and ask before entering private property for photos.
Why book with Hola Car Rentals
- Free Cancellation up to 48 hours before pick‑up.
- All‑Inclusive+ Rate with maximum coverage.
- Transparent pricing—no surprise fees, save up to 60%.
- Cashback on tolls and free travel insurance up to US$150,000.
FAQ
Is Route 66 well signed in Illinois? Generally yes, but older segments zig‑zag through towns—keep a printed map or offline app as backup.
What car is best? Any modern compact or midsize works. If you want more comfort for four travelers, consider an upgrade via our partner network, such as Alamo car hire in Chicago.
Can I return the car in Springfield? Many itineraries are round‑trips via Chicago. One‑way options vary by season; check availability during booking.
Bring your road‑trip playlist—and let Hola Car Rentals help you compare vehicles, pick extras, and set off down the Mother Road with confidence.
Photo stops & small towns
Between Chicago and Springfield you’ll find classic murals, small local museums and retro service stations that have been lovingly preserved by volunteers. Many sites are free with donation boxes; a few keep limited hours—arrive earlier in the day to avoid disappointment and to leave time for unexpected roadside gems.
Fuel, food & music
Fill up before rural stretches and keep snacks and water handy. Part of Route 66’s magic is the soundtrack—queue oldies, jazz and blues as you glide past fields and water towers. If you’re traveling with kids, plan short hops with frequent breaks; couples often opt for a late start to enjoy golden‑hour photos in Springfield.
Sample timeline
Day 1: Morning pick‑up in Chicago, breakfast near the “Begin” sign, then meander to Joliet and Pontiac with museum stops and mural photos. Overnight near Bloomington–Normal.
Day 2: Easy cruising to Springfield, lunch at a classic drive‑in, then downtown landmarks before a relaxed return to Chicago via the interstate or a one‑way drop depending on your plans.
Whichever pace you choose, Hola Car Rentals gives you transparent pricing, strong coverage options and the freedom to focus on the Mother Road—not the paperwork.
