Route 66 stops in Illinois

170-ft water tower shaped like a ketchup bottle — iconic photo stop.

The official eastern terminus sign where travelers begin Route 66.

Historic Chicago German-American restaurant operating since 1898.

The western terminus marker for Route 66 in downtown Chicago.

World-renowned art museum with an extensive collection including "American Gothic" and more.

A serene 2.5-acre garden in the heart of Millennium Park celebrating Chicago's transformation from marshland to modern city.

Interactive video sculpture in Millennium Park featuring faces of Chicagoans and water features.

Iconic public park home to Cloud Gate, outdoor art, and performances.

Historic marquee theater and one of Chicago’s signature icons.

Major downtown park cluster with fountains, art and skyline views.

Expansive downtown park with gardens, winding paths, play spaces and skyline views.

Scenic urban river promenade lined with views, dining and activity.

Grand historic rail terminal and architectural landmark.

Lakefront museum campus with three world-class cultural attractions.

Historic lakefront planetarium offering astronomy exhibits and some of Chicago’s best skyline views.

Compact urban beach near downtown, favored for swimming, lakefront lounging and dramatic skyline views.

Surviving post-fire landmark anchoring the Magnificent Mile.

Historic lakefront pier with attractions, views and entertainment.

Historic lakefront pier with attractions, views and entertainment.

Navy Pier tribute marking Route 66’s beginning with themed signage, souvenirs and a symbolic Pier-to-Pier connection.

Iconic skyscraper offering dramatic skyline and lake views.

Classic downtown beach framed by high-rises, lakefront paths and some of Chicago’s best skyline views.

Iconic Chicago beach known for skyline views, volleyball, lakefront energy and people watching.

Adaptive reuse concert venue with industrial character and river views.

Historic free zoo set within scenic Lincoln Park.

Scenic harborfront beach with marina access, skyline views, walking paths and a relaxed waterfront setting.

Colorful Route 66-themed mural beside beloved hot dog stand.

Legendary baseball park and beloved Chicago institution.

Retro castle-style mid-century car wash with quirky architecture.

Spacious North Side beach known for sunsets, lakefront recreation, picnic areas and a laid-back local vibe.

Expansive North Side beach popular for recreation, birding, boating access and a relaxed neighborhood feel.

Historic Uptown theater known for concerts and glowing marquee.

Historic South Side beach offering broad sands, cultural history, lake access and beautiful open-water views.

Iconic neon-topped drive-in serving legendary Chicago dogs.

Czech-American eatery with hearty dishes and an old-world lounge.

Legendary hot dog stand famous for Depression dogs and fries.

Restaurant and petting zoo serving fried chicken with Americana décor.

Retro-style ice cream stand near Route 66 Park.

Mini-park with benches, statues, and signs celebrating Route 66 history.

Historic site of one of the earliest Dairy Queens.

Gas station and food stop with Route 66 branding.

Historic section of original Route 66 pavement.

Official Route 66 roadside sign for photos and navigation.

Historic Route 66 ice cream stop in Wilmington.

Tire shop with retro Sinclair Dino statue — quirky Route 66 photo-op.

Small-town garage with vintage vibes and service station throwback feel.

Local gift shop with Route 66 memorabilia, souvenirs, and charm.

Restored streetcar converted into a nostalgic diner on Route 66.

Memorial site honoring the historic Riviera Roadhouse.

Architecturally significant building from the late 1800s still serving customers today.

Restored early 1900s train station in Dwight.

Scenic lake and recreational area near Route 66, good for picnics and photos.

Welcome sign with Route 66 branding popular for selfies.

Local diner serving family meals with Route 66 décor.

Vintage gas station structure, now a preserved Route 66 stop.

Historic pedestrian tunnel beneath Route 66.

Log cabin–style diner known for rustic charm and hearty meals.

Classic roadside motel along Route 66 offering simple accommodations.

Remains of an original Route 66 bridge over the Vermilion River.

Remnant of an early Route 66 bridge and popular photo spot.