Bill GadeBill Gade

Looking for a different kind of weekend ride? Try exploring the Illinois section of the legendary Route 66. You can even start at the beginning (which is also the end) of this famous highway, right in downtown Chicago. Then, follow it out of town and downstate for a unique, fascinating ride through history you won't find anywhere else.

Route 66 was created to promote travel and commerce between Chicago and Los Angeles and all points in between. It became famous over the next several decades, appearing in literature, movies, a TV show bearing its name, and even spawning a hit song. Although 66 no longer exists in its entirety, there is enough of "the Mother Road" left to make it worth your riding.

I suggest you start this tour on a weekend or holiday because riding into downtown Chicago during the week can be a real challenge.

A good way to start is with a hearty breakfast at the famous Lou Mitchell's Restaurant and Bakery on West Jackson Boulevard. In fact, many Route 66 tour groups start at Lou Mitchell's because it is a part of 66 history itself, having been there for over 85 years. And you can usually find a place to park across the street early on a weekend morning.

Bill GadeBill Gade

After breakfast, head east to Lake Shore Drive where Route 66 technically starts and ends (although the Route 66 sign is at Jackson and Michigan -- don't ask me why). Head north to Adams, then cut west for a couple of miles to Ogden. Because Route 66 is an old road, you'll often ride through older sections of the cities and towns it passes through, which gives you an interesting perspective on history. Take an easy left onto Ogden, then follow the Route 66 signs out of the city to Harlem, and eventually onto I-55. While much of the original route still exists, some sections of it have been replaced with interstate.

Exit I-55 at Route 53 and follow that through Romeoville and Joliet, to Gardner where much of Route 66 still exists as the frontage road along I-55. Here's where you'll find some great museums, restored gas stations and Route 66 landmarks along the way. Make sure you stop and take a photo by the Gemini Giant next to Wilmington's Launching Pad Drive-In. If you're ready for lunch, this is a great place to stop. The Gemini Giant is the first of three "famous giants" along the Illinois section of Route 66... the other two giants residing in Atlanta (Paul Bunyan) and Springfield (the Lauterbach Giant).

We usually spend the night in Springfield. While that is only 170 miles from the starting point in Chicago, there is so much to stop and see along the way, you will definitely have had a full day of riding. Once you leave Springfield, Route 66 no longer follows I-55, but veers into a very enjoyable ride through small-town central Illinois. We rode through some great small towns that really have not changed much over the years -- you can almost feel yourself riding back in time.

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Continue following Route 66 to where the Illinois part of "the Mother Road" ends -- at the Chain of Rock Bridge, which crosses the Mississippi River between Chouteau Island in Illinois and the north edge of St. Louis in Missouri. Getting to the Chain of Rocks Bridge can be difficult -- ignore the "Road Closed" signs and keep heading toward the river. The bridge is now closed to vehicle traffic but you can cross over it on foot (if you wish) or bicycle (if you packed one).

There's so much to see as you journey along the Illinois section of Route 66 -- you may want to give yourself a couple of days or even more, depending on how much of Route 66 history you wish to immerse yourself in. Check out this link for a map and sights to see along the way:

WARNING: If you plan to ride just the Illinois section of this great old highway, that's terrific, but I will warn you — you're gonna want to hit the road and experience the full two thousand miles of Route 66. And that's not a bad thing... at all!

Ride Safe!


Bill Gade is co-owner and host at Tour on Two, specializing in weekend, 5-day, 8-day and "Ship, Fly and Ride" motorcycle tours around the country.

What is your favorite section of Route 66? Share it in the comments section.

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