Where Route 66 Begins—Chicago, IL
Chicago is a legendary city for many reasons, from jazz music to Prohibition-era gangsters, baseball, and unique hot dogs. Motorcyclists, however, have a wholly unique reason to ride to the Windy City.
This is where Route 66 begins.
I suppose you could also argue that this is where the Mother Road ends, if you were to ride it the other way around. But the classic way to do it is to head west, and the signs say this is where the route starts.
Oh yes, the signs. The old, classic Begin Historic Route 66 sign is located at the intersection of Adams St and Michigan Ave. These days, it’s been positioned quite a few feet off the ground level, so it just may be (mostly) sticker-free during your visit.
Chicago has also erected additional Route 66 signs around the Mother Road’s starting area in anticipation of the road’s centennial celebrations. No biker should miss snapping a photo of themselves posing next to one (or all) of them.
Right across the road from the Begin Historic Route 66 sign are the Millennium Park and the Art Institute of Chicago. They’re well worth a visit, especially since you’ll be off your bike for the signs anyway. Speaking of being off your bike, there are multiple public garages nearby, so you can easily find a place to stash your motorcycle while you walk around.
That said, you may find a place to park your motorcycle elsewhere as well. Chicago has a vibrant motorcycling culture with many events and meetups over the year, such as the Motoblot and the Chicagoland Vintage and Antique Motorcycle Show. Local restaurants and bars also often arrange bike nights, which are perfect occasions for finding your next best biker buddy.
Riders who really feel the need for speed can head outside Chicago to Joliet and the Chicagoland Speedway. This racetrack frequently hosts motorcycle races, such as the MotoAmerica Championships and Motorcycle Road Racing. Come around during one of the track days, and you can put your own racing skills to the test.
Chicago also offers plentiful opportunities for urban riding (as long as you don’t mind the occasional congestion). You could point your front wheel to the Pilsen neighborhood to explore colorful murals and enjoy delicious Mexican food. Alternatively, head to the Old Town with its cobblestone streets and Victorian buildings—including the St. Michael’s Church, one of the seven existing buildings to survive the Great Chicago Fire.
Baseball fans must visit the iconic Wrigley Field to see the Cubs play. This second-oldest ballpark in America has been home to many memorable baseball moments, such as Babe Ruth’s famous point-and-hit-a-home-run stunt.
Plenty of motorcyclists enjoy blues, and Chicago has plenty to offer them. As a specific highlight, I might mention Buddy Guy’s Legends blues club.
Should the saddle start wearing you down, head on over to the Chicago Riverwalk to stretch your legs. There’s another (often full) parking garage near the walk so you won’t have to go far from your motorcycle.
Lincoln Park is another opportunity to take a stroll in a beautiful setting. That, or you could simply ride around the park to take in the views.
Chicago is your launching point to an unforgettable Route 66 adventure. Don’t be in too much of a rush to hit the road, though, as the Windy City has plenty to keep you occupied.
Facts & Info
Nearby Attractions
- Begin Historic Route 66 Sign
- Chicagoland Speedway
- Wrigley Field
- Buddy Guy’s Legends
- Chicago Riverwalk
Nearby Roads
Lake Shore Drive is a 15-mile span of US 41 that skirts Lake Michigan, passing several piers, beaches, and parks. Traffic on the road can be heavy and the going slow, but that’s alright—you’ll have views over the water for most of the way.
Another riding option within Chicago itself is the Chicago Skyway, elevated section of I-91 that stretches across the city. It’s a toll road, but it’s a good chance for some highway cruising amidst a vista of the Chicago skyline and its famous skyscrapers.
You can also ride around the Chicago Loop, the city’s central business district. This urban route takes you by some of the most iconic buildings in Chicago, like the Willis Tower (ex-Sears Tower) and John Hancock Center. It can have some extremely hectic traffic, though, so smart riders avoid peak rush hours.
And then there’s Route 66, of course. Head southwest out of the city to start your journey on Illinois Route 66.
Recommended Lodging: Holiday Inn Express Chicago North Shore
There are plenty of excellent hotels for virtually any budget (especially higher ones) in central Chicago, but the area poses one problem for motorcyclists—parking. As such, it’s better to get a comfortable hotel a short ways out of the city center, like the Holiday Inn Express Chicago North Shore.
If you’ve ever traveled anywhere, you’ll know what to expect from this chain hotel. It’s nothing fancy, but the rooms are large enough to accommodate you, your pillion rider, and your gear, and you’ll have a good, quiet night’s sleep.
The real kicker, though, is the parking lot. Compared to the prices of overnight or valet parking in central Chicago, being able to park by the hotel makes a world of difference.
The hotel offers a breakfast buffet that will get you on the road with a full belly. For dinner, there are places within a quick ride—or, since you’re still in Chicago, you could order delivery to the hotel door.
Food & Dining
Chicago is particularly renowned for two types of food. The first is the city’s famous deep dish pizza, and the second is the one-of-a-kind Chicago hot dog.
For the pizza, you must visit both Pizzeria Uno and Lou Malnati’s to try two takes on this classic. I’m recommending both because let’s just say that there’s a bit of a rivalry and I don’t want any Chicagoans showing up at my door with torches and pitchforks. What I can say is both are excellent.
As for the hot dogs, you really should grab one from a local street vendor. They’ll do it right with the poppy seed bun, mustard, onions, the neon-green relish, pickle spear, tomatoes, and celery salt. Good luck not making a mess.
Finally, you can’t forget Lou Mitchell’s. This diner is often known as the unofficial first stop on Route 66. It has been getting travelers ready for the road since 1949 with delicious breakfast and lunch (including the RoadRUNNER crew). Find it at 565 W Jackson Blvd, Chicago, IL.
Best Time to Travel
Spring and summer are the best times to visit Chicago, as you get to enjoy warm temperatures and plenty of local events. If you’re planning to stay and ride around Chicago, summer is a good time. Should you be planning to head down on Route 66, though, do your ride in spring, as summer temps in the southern parts of the road get oppressive.