Route 66 Leg One: Chicago to St. Louis

Classic motel neon, vintage filling stations, roadside giants, and historic bridges

  • 71
  • 12:60
  • 523 mi
  • $119
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Created by Kelly Pulskamp - December 22nd 2021

The stretch of Route 66 from Chicago, Illinois, to St. Louis, Missouri, is home to aluminum-and-chrome diners, historic, family-owned cafes, bizarre attractions, and other reminders of the route’s charming past. You’ll also see plenty of cornfields and flat prairie land between the bustling cities and sleepy towns along this first leg.

Photo of Indiana Dunes State Park

1600 N. 25 E., Chesterton, IN, US

Indiana Dunes State Park

If you plan on starting your Route 66 adventure in Chicago, this is the perfect campground for tenting, RVing, or cabin camping. The South Shore Line offers rail service directly from the state park to downtown Chicago.

Chicago, Illinois, United States

Start your epic journey at the route’s original 1937 terminus at Lake Shore Drive and E. Jackson Drive in downtown Chicago.

Photo of Route 66 Starts Here Sign

65 E Adams St, Chicago, IL, US

Route 66 Starts Here Sign

Don’t miss the Route 66 Starts Here sign at the corner of S Michigan Avenue and E Adams Street. The sign (along with a handful of replica signs on the same block) is located in a busy section, so you may need to find parking elsewhere and walk to the sign for a photo.

565 W Jackson Blvd, Chicago, IL, US

Lou Mitchell's Restaurant

Lou Mitchell’s is the perfect place to get breakfast—and a cup of the “world’s finest coffee”—before you leave the Windy City. The restaurant has been serving home-cooked comfort food to travelers since 1923, predating the designation of Route 66 by 3 years. Before sitting down, diners are handed a freshly-made donut hole and a miniature box of candy. And because one donut hole is never enough, you can order some to-go.

Photo of Buckingham Fountain

301 S. Columbus Dr, Chicago, IL, US

Buckingham Fountain

Chicago's landmark is considered one of the country's finest fountains due to its Beaux-Arts-style landscape design, finely wrought bronze sculpture, and innovative use of technology.

Photo of The Willis Tower (Sears Tower)

233 S Wacker Dr, Chicago, IL, US

The Willis Tower (Sears Tower)

It's one of the first stops Ferris Bueller makes on his day off, so you know it's an essential Chicago icon. The Skydeck really does offer great views when the weather is good, plus the glass-floored "ledge" is an unforgettable experience for those brave enough to step on to it.

17 W Adams St, Chicago, IL, US

The Berghoff Restaurant

1000 S Leavitt St, Chicago, IL, US

Lulu's Hot Dogs

Photo of Castle Car Wash

3801 W Ogden Ave, Chicago, IL, US

Castle Car Wash

6031 W Ogden Ave, Cicero, IL, US

Henry's Drive-In

Photo of Hofmann Tower

3910 barry point rd., Lyons, IL, US

Hofmann Tower

Tinley Park, Illinois, United States

On a balmy August evening in 2004, Chicago residents reported seeing a series of red or white lights that formed a triangle shape. Several videos captured the light show, and it was even reported by local news outlets. The phenomenon occurred about 45 miles from O’Hare International Airport, but the lights moved too slowly to be a commercial plane. What makes this one of the more significant UFO sightings is that it was investigated by the Mutual UFO Network (MUFON), a non-profit with thousands of civilian volunteers. The mysterious occurrence was also featured on the History Channel’s UFO Hunters.

645 Joliet Rd, Willowbrook, IL, US

Dell Rhea's Chicken Basket

Route 66 is renowned for its classic American cuisine. If you’re not still full of donut holes (or even if you are), visit Dell Rhea's Chicken Basket, just outside Chicago, for some of the best fried chicken you'll ever taste. The roadhouse has been serving its home-cooked goodness since 1946, and even if you’re not ready to eat just yet, the neon sign is a classic photo op.

255 S. Joliet Road, Bolingbrook, IL, US

Montana Charlie’s Little America Flea Market

11mi 00h 19m

920 N Broadway St, Joliet, IL, US

Rich & Creamy

1mi 00h 04m
Photo of Joliet Area Historical Museum

204 N Ottawa St, Joliet, IL, US

Joliet Area Historical Museum

0mi 00h 02m
Photo of Rialto Square Theatre

102 N Chicago St, Joliet, IL, US

Rialto Square Theatre

4mi 00h 10m

500 Speedway Boulevard, Joliet, IL, US

Route 66 Raceway

12mi 00h 16m
Photo of The Gemini Giant

810 E. Baltimore Street, Wilmington, IL, US

The Gemini Giant


The Illinois stretch of Route 66 is home to several great roadside attractions, but nothing shouts "retro kitsch" louder than a massive Muffler Man. Snap a picture with the Gemini Giant the newly-reopened Launching Pad Drive-In in Wilmington. Named for the Gemini space program, he’s one of many similar statues made by International Fiberglass. The giant stands guard over the Launching Pad Drive-in, which also houses a gift shop, a restaurant, and the Mini Americana Museum.

5mi 00h 09m
Photo of The Polk-a-dot Drive In

222 N Front St, Braidwood, IL, US

The Polk-a-dot Drive In


You did it—one leg down, five more to go. As you travel further southwest, the weather will get warmer, the road will get flatter, and the views will only get better. While it’s true that you never forget your first, so much of Route 66 is still in front of you—so keep going and let the Show-Me State show you why almost 100 years after its creation, the Mother Road is still the best place to get your kicks.

Kelly Pulskamp

Born & raised in the Midwest. Lover of food, wine and adventure. Production Manager, Content and Partnerships at Roadtrippers. "Life is meant for good friends and great adventures"