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The Ultimate Route 66 Road Trip

The ultimate guide to seeing the best of Route 66 in one week.

  • 123
  • 36:54
  • 1,718 mi
  • $285
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Created by ladijane - March 11th 2018

Route 66, and its 2,500 miles, is known affectionately as "The Mother Road." It's the quintessential cross-country road trip experience. From Chicago through the beating heart of America and down to Los Angeles, the route officially ends at the Santa Monica Pier. The road reached peak popularity in the late 40's and early 50's before being officially removed from the US Highway System in 1985. After a few years, travelers from America and beyond started feeling tinges of nostalgia, and by the end of the 1980's it was fast becoming one of the most popular road trip routes once more.

645 Joliet Rd, Willowbrook, IL, US

Dell Rhea's Chicken Basket

The Illinois stretch of Route 66 is home to some pretty good eats, especially if you like classic American cuisine. Before you hit the road, visit Dell Rhea's Chicken Basket, just outside Chicago, for some of the best fried chicken you'll ever have. They've been serving the home-cooked goodness since 1946.

Photo of Illinois Route 66 Mining Museum
4.0

150 S Kankakee St, Godley, IL, US

Illinois Route 66 Mining Museum

Photo of Two-Cell Jail
4.2

E Mazon St, Gardner, IL, US

Two-Cell Jail

Photo of Ambler's Texaco Gas Station
4.5

W Waupansie St, Dwight, IL, US

Ambler's Texaco Gas Station

Old Route 66, Odell, Illinois

Old Route 66, Odell, Illinois

18700 Old Rt 66, Pontiac, IL, US

Old Log Cabin Inn

Old Route 66 & Aurora St, Pontiac, IL, US

Old Log Cabin Restaurant, Bar & Catering

Historic Highway 66, Pontiac, IL, US

La Mex / Pontiac, Illinois

Po Box 21824, Lexington, KY, US

The Best Of Lexington, Kentucky

Lexington, IL, US

John Patton Log Cabin

Old US South Route 66, Normal, Illinois

Historic US 66, Shirley, Illinois

5257 Old Rte 66, McLean, IL, US

Funks Grove Pure Maple Sirup

For those of you with a sweet tooth, Funks Grove Pure Maple Sirup in Shirley, IL produces over 1,800 gallons of maple syrup using old-fashioned techniques, and it's all bottled in beautiful, vintage-looking bottles.

Photo of Bunyon With a Hotdog
4.3

110 Southwest Arch Street, Atlanta, IL, US

Bunyon With a Hotdog

114 SW Arch St, Atlanta, IL, US

Route 66 Arcade Museum

The Illinois stretch of Route 66 is also home to loads of great roadside attractions, but none shout "retro-kitsch" louder than the massive muffler men statues! The Gemini Giant in Wilmington and Bunyon With a Hotdog in Atlanta, IL are two of the best for photo-ops of this iconic vestige of Americana. While you're in Atlanta, which is a ridiculously charming little town in Illinois, visit the Route 66 Arcade Museum: it's a fantastic hidden gem that features tons of vintage arcade machines you can play.

Photo of Smiley Water Tower
4.4

503 SW Second St, Atlanta, IL, US

Smiley Water Tower

Frontage Road, Lincoln, Illinois

Frontage Road/Route 66, Elkhart, Illinois

Old United States Route 66, Elkhart, Illinois

Best time of year to travel along Route 66: The best time to road trip down Route 66 is between late April and early July, as well as late August through late October. The worst times to visit would be July and August, this is when the temperature is sweltering and all the kids are out of school, which means you'll come across some crowds along the route. In addition, July and August is considered high season, so you're going to be paying higher rates for lodging.