Route 66 Leg One: Chicago to St. Louis

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

  • 41
  • 09:30
  • 480 mi
  • $45
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.

Route 66 Starts Here Sign
3.2

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.

Lulu's Hot Dogs
3.8

1000 S Leavitt St, Chicago, IL, US

Lulu's Hot Dogs

Two-Cell Jail
4.4

E Mazon St, Gardner, IL, US

Two-Cell Jail

Castle Car Wash
3.8

3801 W Ogden Ave, Chicago, IL, US

Castle Car Wash

Henry's Drive-In
4.7

6031 Ogden Ave, Cicero, IL, US

Henry's Drive-In

Hofmann Tower
4.0

3910 barry point rd., Lyons, IL, US

Hofmann Tower

Dell Rhea's Chicken Basket
4.1

645 Joliet Rd (Historic Rt 66), 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

Rich & Creamy
4.0

920 N Broadway St, Joliet, IL, US

Rich & Creamy

Joliet Area Historical Museum
4.5

204 N Ottawa St, Joliet, IL, US

Joliet Area Historical Museum

Rialto Square Theatre
4.5

102 N Chicago St, Joliet, IL, US

Rialto Square Theatre

1
12mi 00h 19m
The Gemini Giant
4.0

810 E. Baltimore Street, Wilmington, IL, US

The Gemini Giant

1

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.

2
5mi 00h 08m
The Polk-a-dot Drive In
4.5

222 N Front St, Braidwood, IL, US

The Polk-a-dot Drive In

2
3
17mi 00h 24m
Old Route 66 Family Restaurant
4.5

105 South Old 66, Dwight, IL, US

Old Route 66 Family Restaurant

3
4
15mi 00h 20m
Illinois Route 66 Mining Museum
4.0

150 S Kankakee St, Godley, IL, US

Illinois Route 66 Mining Museum

4

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.

5
14mi 00h 19m
Ambler's Texaco Gas Station
4.5

W Waupansie St, Dwight, IL, US

Ambler's Texaco Gas Station

5

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.

6
8mi 00h 11m
The Standard Oil Gas Station
4.3

400 S West St, Odell, IL, US

The Standard Oil Gas Station

6
7
10mi 00h 14m
Illinois Route 66 Hall of Fame and Museum
4.5

110 W Howard St, Pontiac, IL, US

Illinois Route 66 Hall of Fame and Museum

7

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.

8
1mi 00h 03m
Old Log Cabin Inn
4.0

18700 Old Route 66, Pontiac, IL, US

Old Log Cabin Inn

8
9
1mi 00h 04m
International Walldog Mural & Sign Art Museum
4.4

217 N Mill St, Pontiac, IL, US

International Walldog Mural & Sign Art Museum

9

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.