Route 66 Begin Sign (Adams St.): Snap a family photo at the official starting point of Route 66 in downtown Chicago.
Lou Mitchell’s Restaurant: A beloved diner serving massive breakfasts since 1923—kids get Milk Duds with their meals!
Millennium Park: While not Route 66-specific, this iconic park with “The Bean” (Cloud Gate), splash fountains, and green space is a great family pit stop before hitting the road.

Old Joliet Prison (exterior or tour): A great spot for older kids/teens interested in film history (The Blues Brothers was filmed here). Guided tours are available if your crew is into spooky stories.
Route 66 Welcome Center at the Joliet Area Historical Museum: Interactive exhibits and a Blues Brothers photo-op car for the whole family.
Rich & Creamy Ice Cream Stand: Fun roadside stop with a large ice cream cone sign, statue of Jake & Elwood, and sweet treats.
Pilcher Park Nature Center: A nice detour for families who want to stretch their legs and explore animals and nature trails.

Gemini Giant at the Launching Pad: A towering “Muffler Man” statue dressed as a space explorer—perfect quirky photo stop.
Midewin National Tallgrass Prairie: A short drive from Wilmington, this protected prairie area offers hiking, biking, and a bison-viewing area! Great for outdoor-loving families.

Polk-a-Dot Drive-In (Braidwood): A colorful diner with life-sized figures of Elvis, Betty Boop, and Marilyn Monroe—kids love the theme, and the food is classic Americana.
Two-Cell Jail (Gardner): A quirky, tiny roadside jail that's fun and quick to explore.
Historic Streetcar Diner: A preserved 1930s diner in Gardner, fun for a quick look and some history.

Route 66 Hall of Fame & Museum: A must-stop with tons of memorabilia, vintage cars, and great exhibits. Don’t miss the giant Route 66 mural for a photo op!
Pontiac-Oakland Auto Museum: Car-loving kids (and adults) will love this free museum full of vintage Pontiacs.
Wall Murals Walking Tour: Over 20 colorful murals throughout downtown—fun to explore on foot, with plenty of places to stop for snacks.
Livingston County War Museum: A unique collection of artifacts and veteran stories that older kids and adults can appreciate.

Children’s Discovery Museum (Normal): An excellent indoor stop with hands-on science, art, and building exhibits. Great for younger kids needing a play break.
Cruisin’ with Lincoln on 66 Visitors Center: Combines Abraham Lincoln history with Route 66—family-friendly exhibits with interactive features.

Tall Paul Bunyan Muffler Man: Another great Muffler Man statue, this time holding a giant hot dog!
Route 66 Park: Great for kids to stretch their legs and see Route 66 memorabilia. There's also a library and small museum in town for a quiet stop.

World’s Largest Covered Wagon (with Lincoln reading a book): Fun photo op and quick history lesson in one.
Postville Courthouse: A reconstructed 1840s courthouse where Abraham Lincoln once practiced law.
Lincoln Heritage Museum: Offers hands-on, interactive exhibits about Abraham Lincoln’s early years—great for families interested in history.

Abraham Lincoln Presidential Library & Museum: One of the best family-friendly museums in the U.S.—with immersive exhibits, holograms, and even a ghost show!
Lincoln Home National Historic Site: Walk through the preserved neighborhood where Lincoln lived. Ranger-led tours make it accessible and engaging for families.
Cozy Dog Drive-In: Birthplace of the corn dog on a stick (Cozy Dog!). Great Route 66 nostalgia and a fun place for lunch.
Illinois State Museum: Has a hands-on kids' discovery area along with cool exhibits on Illinois wildlife and geology.

Litchfield Museum and Route 66 Welcome Center: A quick but informative stop for the whole family.
Ariston Café: One of the oldest continually operating restaurants on Route 66. Family-friendly, classic diner vibe.
Sky View Drive-In Theater: Catch a movie under the stars—great fun for families, especially in summer.

Henry’s Rabbit Ranch (Staunton): A quirky stop with live rabbits, VW Rabbits, and Route 66 fun. Kids love it!
Route 66-themed playgrounds & roadside kitsch: Several small towns have themed parks and rest stops perfect for little legs needing to run.

Walk or bike across the Mississippi River via this historic bridge that once carried Route 66 travelers into Missouri.
Scenic views and photo opportunities, especially during sunset!

Mix indoor & outdoor stops: Museums for learning, roadside attractions for photos, and parks for play.
Snack often: Classic diners, drive-ins, and ice cream stands are part of the charm—and keep everyone happy.
Don’t rush: Allow time for unplanned roadside stops—the weirdest places are often the most memorable!
Travel games: Bring Route 66 bingo cards, scavenger hunts, or maps for the kids to track progress.

Wandering Souls