Route 66 Leg One: Chicago to St. Louis

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

  • 41
  • 09:30
  • 480 mi
  • $56
Take This Trip

Created by robmccauley - July 26th 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 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.

1000 S Leavitt St, Chicago, IL, US

Lulu's Hot Dogs

Photo of Two-Cell Jail

E Mazon St, Gardner, IL, US

Two-Cell Jail

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

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

920 N Broadway St, Joliet, IL, US

Rich & Creamy

Photo of Joliet Area Historical Museum

204 N Ottawa St, Joliet, IL, US

Joliet Area Historical Museum

Photo of Rialto Square Theatre

102 N Chicago St, Joliet, IL, US

Rialto Square Theatre

12mi 00h 19m
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 08m
Photo of The Polk-a-dot Drive In

222 N Front St, Braidwood, IL, US

The Polk-a-dot Drive In

17mi 00h 24m

105 S Old Rte 66, Dwight, IL, US

Old Route 66 Family Restaurant

15mi 00h 20m
Photo of Illinois Route 66 Mining Museum

150 S Kankakee St, Godley, IL, US

Illinois Route 66 Mining Museum


The Illinois Route 66 Mining Museum chronicles the significant role the coal industry played in the development of Route 66. Coal mining was the lifeblood of several small towns along the route, and this is a great place to learn how the industry impacted the people and economy along what was once considered America’s Main Street.

14mi 00h 19m
Photo of Ambler's Texaco Gas Station

W Waupansie St, Dwight, IL, US

Ambler's Texaco Gas Station


The route is dotted with old service stations, many of which have been beautifully restored and repurposed as photo ops. The first one you’ll encounter is Ambler's Texaco Gas Station in Dwight. In continuous use for 66 years, from 1933 until 1999, it was one of the longest operating gas stations on the Mother Road. Today it serves as a visitor center.

8mi 00h 11m
Photo of The Standard Oil Gas Station

400 S West St, Odell, IL, US

The Standard Oil Gas Station

10mi 00h 14m
Photo of Illinois Route 66 Hall of Fame and Museum

110 W Howard St, Pontiac, IL, US

Illinois Route 66 Hall of Fame and Museum


The Route 66 Association Hall of Fame and Museum is full of fascinating, family-friendly exhibits, and the staff’s love of the route is infectious. Don’t miss the wall art and wishing well in the museum’s backyard.

1mi 00h 03m

18700 Old Rt 66, Pontiac, IL, US

Old Log Cabin Inn

1mi 00h 04m

321 N. Main Street, Pontiac, IL, US

International Walldog Mural & Sign Art Museum


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.