Route 66 road trip · Illinois

Illinois Route 66: Chicago to Pontiac day trip

Illinois Route 66: Chicago to Pontiac

The first hundred miles of the Mother Road in its centennial year: a photo at the Begin Route 66 sign in downtown Chicago, Joliet's Route 66 Welcome Center and the 1926 Rialto, the Gemini Giant in Wilmington, burgers at Braidwood's Polk-A-Dot, two restored 1930s gas stations in Dwight and Odell, and the Route 66 Hall of Fame in Pontiac.

Time: 10–11 hour day
Driving: About 200 miles and 4½–5 hours of driving in all, out on old Route 66 and back on I-55
Best time: May to October
Updated: October 13, 2026 at 10:34 PM Pacific

$4 USD

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Two red vintage gas pumps in front of the white clapboard Ambler's Texaco station in Dwight, with a green roof, shuttered window and flower box under a deep blue sky — Gorup de Besanez · CC BY-SA 4.0. May 2017 photograph of Ambler's Texaco in Dwight; resized and displayed with crop.

Suggested times, not bookings

Your day at a glance

8:00 amBegin Route 66 sign
9:30 amJoliet Area Historical Museum and the Rialto
11:30 amGemini Giant, Wilmington
12:15 pmPolk-A-Dot Drive In, Braidwood
1:30 pmAmbler's Texaco, Dwight
2:15 pmStandard Oil station, Odell
2:45 pmRoute 66 Hall of Fame & Museum, Pontiac
4:30 pmReturn to Chicago

Highlights

Worth the trip

A start-line photo at the Begin Route 66 sign across from the Art Institute
The 30-foot Gemini Giant in his new home on a Kankakee River island
Restored 1930s stations in Dwight and Odell, then the Hall of Fame in Pontiac

What’s in the guide

Detailed stop guidance, rules, practical pitfalls, a route map, Google Maps, Waze and Apple Maps links and weather alternatives. Read it online any time, or keep it offline in the Greg’s Guides app for iPhone and iPad. See an example guide →

Plan for the conditions

Expected seasonal weather

From May through October, north-central Illinois usually has warm to hot days, often humid in July and August, with afternoon thunderstorms that can bring heavy rain, lightning and strong wind across the open farmland. May and October are milder and cooler, with crisp mornings in October. There is little shade at the roadside stops. These are seasonal expectations, not a forecast for your travel date; check the NWS forecast the evening before and the morning of your trip.

Admission and parking are separate. Check current conditions before departure.

Another good day

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The wide Illinois River curving past a long wooded bluff in red, orange and gold fall color, with dark green pines at the water's edge and two small motorboats leaving wakes

Canyon hiking & state parks

Chicago → Starved Rock → French & Wildcat canyons → Starved Rock Lodge → St. Louis Canyon → Illinois Waterway Visitor Center → Matthiessen Dells → Utica

Starved Rock & Matthiessen

A canyon-hiking day trip from downtown Chicago to the Illinois River: the sandstone butte and overlooks at Starved Rock, French, Wildcat and St. Louis canyons, lunch at the 1930s Starved Rock Lodge, the lock and dam across the river, and the waterfalls of the Matthiessen Dells, timed around the weekend parking-lot closures.

11–12 hour day·About 4 hours of driving in total

Best: Late March to May, or mid-October

$4 USD

A wide, empty sand beach curving along Lake Michigan under a blue sky, with white-capped waves on the right and a wooded dune in orange and red fall color rising on the left

Dunes, beaches & lakeshore

Chicago → Indiana Dunes State Park → Visitor Center → Chesterton → Century of Progress Homes → West Beach

Indiana Dunes

A lakeshore day from downtown Chicago: the 3 Dune Challenge over the three tallest dunes in Indiana Dunes State Park, passes and maps at the Indiana Dunes Visitor Center, lunch in downtown Chesterton, the 1933 World's Fair houses on Lake Front Drive in Beverly Shores, and the Dune Succession Trail at West Beach, with the Chicago skyline across the water.

9–10 hour day·About 2 hours 30 minutes of driving in total

Best: September to mid-October

$4 USD

The long tile-roofed Riviera building and tour boats at their docks across a calm blue bay, with wooded shoreline and houses behind

Lake town, boat tour & shore walk

Chicago → Riviera Docks cruise → Downtown Lake Geneva → Geneva Lake Shore Path → Yerkes Observatory → Big Foot Beach State Park

Lake Geneva, Wisconsin

A summer day on Geneva Lake, about two hours from downtown Chicago: a morning boat tour from the Riviera Docks past the Gilded Age estates (on the U.S. Mailboat in season), lunch downtown, a walk on the public Shore Path from Library Park, a tour of Yerkes Observatory in Williams Bay and a late swim or walk at Big Foot Beach State Park.

11–12 hour day·About 4 hours of driving in all, most of it the round trip from Chicago

Best: Mid-June to mid-September

$4 USD

A footbridge with black iron railings crossing the grassy levee toward downtown Galena, where brick buildings and church steeples climb a wooded hillside under puffy white clouds

Historic small town & long road trip

Chicago → Horseshoe Mound → U.S. Grant Home → Grant Park → Main Street → Old Blacksmith Shop → Chicago

Galena

A long day from Chicago to Galena, the 1850s lead-mining river town in the far northwest corner of Illinois: a hilltop preserve with views into three states, a tour of the house Galena gave Ulysses S. Grant in 1865, a walk over the river to the brick storefronts of Main Street, and a working 1897 blacksmith shop.

12–13 hour day·About 3 hours each way via Interstate 90 and US 20; little driving once you are in Galena

Best: May to October; best on Friday to Sunday

$4 USD