Planning a road trip on Route 66 from Chicago

Some of the most iconic images of Route 66 are long stretches of open road flanked by a desert landscape or leading to towering mountains ahead. And because of that, many people are surprised to find out that Route 66 actually starts in downtown Chicago. For the modern-day road tripper, this is ultra convenient since you can fly into one of the city’s two large airports, stock up on supplies at any number of stores and then hop into a rental car mere blocks away from where this historic road begins. But before you do that, start off with a little history and some tips that’ll ensure you’re able to maximize your time — and get your kicks — on Route 66. 

Quick history of Route 66

Route 66 dates back to the 1920s, when it was created to be a direct route that would help speed up the long journey from Chicago to Los Angeles as more Americans bought cars. Mom-and-pop businesses sprouted up along the route to cater to travelers prior to World War II, during which the road served as an important corridor for the military. After the war, Route 66 went through a revival as car ownership grew again and families headed west to enjoy destinations like the Grand Canyon, Disneyland and California’s beaches. 

Starting in the ‘50s, interstates were built as high-speed routes and slowly replaced this once-popular roadway. This eventually led to Route 66 being decommissioned in 1985. Now, instead of being a practical and efficient way to travel from the Midwest to the West Coast, this historic road and all of the interesting attractions along the way are considered to be core pieces of Americana. 

Where Route 66 starts in Chicago

The beginning of historic Route 66 is on E. Adams Street at the intersection with S. Michigan Avenue. These cross streets may not mean much if you don’t know the city very well, so we’ll put it into context. This spot is right downtown in The Loop, which is home to some of Chicago’s most visited attractions like Grant and MIllennium Parks, the Willis Tower and the Art Institute of Chicago, which is directly across the street from where Route 66 starts. E. Adams is a one-way street heading west out of town, which is the perfect metaphor for a westward getaway on Route 66.  

Preparing for a Route 66 road trip

Getting ready for a road trip on Route 66 from Chicago requires a bit of a different approach than if you drove hundreds of miles on the highway. Because of the unique attractions, accommodations and restaurant options, you may want to plan more in advance, and especially if you’re on a tight or fixed schedule. Here are some tips to help you maximize this once-in-a-lifetime trip.

Plan your itinerary

Search for what roadside attractions exist along the stretch of road you’ll be driving on so you can pre-plan your stops. Add in extra time for side trips, like a stop at the Grand Canyon or visits to famous filming locations in Los Angeles, as well as spontaneous detours, since you’ll surely come across attractions you didn’t discover during your research.

Not everyone has the vacation time to drive the entire route, so determine how many miles you can realistically cover in the time you have (taking into account the stops you’d like to make) and if you need to plan for a return trip back to Chicago instead of a one-way drive. 

Pack well

Depending on how much ground you’ll cover, you may encounter long stretches of road without gas stations, cafes, restaurants, etc. Fill your car with plenty of water, snacks and light meals to be prepared for any scenario. Pack necessary road trip accessories, including a first aid kit and an emergency roadside kit. And like any good road trip, go in prepared with car games and a killer playlist or two that you can access without data in case you go through a cellular dead zone. 

Make bookings in advance

Staying in a roadside motel is part of the quintessential Route 66 experience. But quality varies, so book ahead if you want to ensure your top choices aren’t flashing a neon “No vacancy” sign when you arrive.

Of course, you need a reliable car for your trip. There’s nothing more convenient than picking up your rental car downtown instead of driving in from the airport and paying for expensive hotel parking while you take some time to enjoy Chicago’s sights and gather trip supplies. Avail car sharing is your best option for an easy downtown pick-up, with dozens of locations across Chicago that are all self-service. Each booking is protected by Allstate insurance and 24/7 roadside assistance. Even better: There’s no cost to add a second driver, so you can save money while sharing the wheel during this memorable road trip.