Route 66 Turns 100: Fall in Chicago, the Mother Road and the Great American Road Trip

America’s most iconic highway is celebrating its centennial, and the adventure starts in Chicago. From a historic Art Deco hotel to a new presidential center, an immersive magic experience and the open road beyond the city, there are plenty of reasons to make this fall the time to explore. In America, the road trip is more than a way to get somewhere. It is a promise: a highway stretching toward the horizon, a town you didn’t plan to visit, a roadside sign that makes you pull over and a story you couldn’t have found by staying home. In 2026, one of America’s most famous highways turns 100. Route 66 has carried generations of travelers from Chicago toward the Pacific, earning its nickname, the Mother Road, along the way. You don’t have to drive all 2,448 miles to celebrate. Start in Chicago this fall, explore the history behind the highway and discover a city with plenty of reasons to stay awhile before heading west.

I’ve enjoyed visiting Chicago, including when I spoke at the Travel & Adventure Show, but there is still so much more of this great city I want to explore. As I work toward my goal of 60 new experiences before turning 60, the Route 66 centennial feels like the perfect reason to return. I can’t wait to stay at Pendry Chicago, visit the Obama Presidential Center, experience The Hand & The Eye and discover more of the city before driving a stretch of the legendary Mother Road myself. A road trip doesn’t have to mean weeks away or thousands of miles behind the wheel. Sometimes the best adventure begins with a long weekend, a great hotel and a list of places you’ve been meaning to see. Chicago offers all that and more, with the added excitement of celebrating a century of American travel. Why Route 66 Is Called the Mother Road To understand the fascination with Route 66, go back to the 1920s, when America was falling in love with the automobile. Cars were changing how people lived, worked and traveled, but the nation’s roads were still a patchwork of local and state routes. A connected highway system promised to make longer journeys easier and bring new opportunities to communities along the way. Route 66 was officially designated on November 11, 1926. It brought together existing roads into a route of roughly 2,448 miles from Chicago to Los Angeles, later celebrated at Santa Monica’s Pacific Coast endpoint. Its diagonal path connected the Midwest with the Great Plains and the Southwest, passing through eight states. The road was not fully paved until 1938. The highway offered more than a route west. For towns that had been far from major transportation corridors, it brought the possibility of new customers and commerce. Gas stations, restaurants, motor courts and roadside attractions sprang up to serve the people traveling through. Then history gave the road a much deeper meaning. During the Dust Bowl and the Great Depression, families left devastated farms and struggling communities to search for work and a better future in the West. Many traveled Route 66 toward California. John Steinbeck’s 1939 novel The Grapes of Wrath helped cement the highway’s place in the American imagination, using the nickname “Mother Road.” The name captures the road’s complicated history. For some travelers, Route 66 was a road of escape and survival. For others, it became a road of family vacations, freedom and discovery. After World War II, as car ownership and leisure travel grew, its motels, diners and roadside attractions became symbols of a new era of American mobility. Eventually, the Interstate Highway System diverted traffic away from much of the original route. Route 66 was officially decommissioned as a U.S. highway in 1985, but its story was far from over. Preservation efforts, historic businesses, popular culture and generations of road trippers kept the Mother Road alive. A hundred years after its designation, Route 66 still speaks to something many of us want: the chance to explore at our own pace, find the unexpected and make a journey our own. Chicago: Where the Journey Begins Chicago was a natural starting point for Route 66. In the 1920s, it was a major transportation crossroads, connecting railways, waterways, industry and the expanding automobile network. Travelers heading west could leave the city and follow a route linking urban centers with rural communities across the country. For the traditional Route 66 photo, head to the historic starting-point sign near Adams Street and Michigan Avenue, across from the Art Institute of Chicago. This is the familiar downtown location associated with the route’s beginning for generations of travelers. For the centennial, Chicago is also celebrating a new ceremonial starting point at Navy Pier, which stretches out into Lake Michigan. The pier’s Route 66 marker creates a symbolic “pier-to-pier” connection with Santa Monica Pier at the western end of the journey. Visiting both downtown and Navy Pier offers two different ways to mark the beginning of the Mother Road’s next century. At Navy Pier, walk along the lakefront, enjoy the skyline and explore the attractions. The views of Lake Michigan offer a reminder that Chicago’s identity is tied as much to its waterfront as to its highways and railways. The city is both a destination and a gateway to a much longer adventure. But don’t rush off to the highway just yet. Chicago deserves more than a quick photograph before you leave town.

Art, Architecture and a Little Chicago Wonder Start downtown with a visit to the Art Institute of Chicago, one of the city’s great cultural treasures. While you’re there, look for Edward Hopper’s Nighthawks. The painting’s late-night diner scene evokes a familiar American landscape: the glow of a restaurant after dark, strangers sharing the same space and the feeling that the road outside might lead anywhere. It’s an especially fitting image to encounter before a Route 66 adventure. The highway’s story has always included the places where travelers stop, eat, rest and watch the world go by. Chicago’s architecture deserves time of its own. Take an architecture cruise on the Chicago River to see the city’s extraordinary skyline from the water and hear how its buildings reflect changing ideas about design, engineering and urban life. Or look down on the city from the Skydeck at Willis Tower, where the scale of Chicago’s streets and skyscrapers comes into focus. For another perspective, explore parts of the original Route 66 corridor and seek out the city’s Route 66 murals and public art. The highway was never just a line connecting two distant points. It passed through neighborhoods where people lived and worked, and where local culture shaped the road’s identity. And if your idea of a perfect travel day includes an unexpected twist, save an evening for The Hand & The Eye.

A Historic Mansion Where Magic Happens One of Chicago’s intriguing newer experiences is The Hand & The Eye, a destination for live magic inside the historic McCormick Mansion. Rather than a conventional theater where everyone watches a performance from the same seat, the experience brings magic into intimate spaces throughout the mansion. The setting combines historic architecture, live performances and the thrill of not quite knowing what will happen next. Why include a magic mansion in a story about Route 66? Because the best trips need a little wonder. Road trips are full of moments that cannot be planned: an unexpected view, a hidden gem or a stop that turns out to be the highlight of the day. The Hand & The Eye brings that spirit of discovery to an evening in Chicago. It’s on my list for my next visit, and I can’t wait to experience it for myself.  Adventure doesn’t always require a long drive. Sometimes it begins when you step through an unfamiliar door.

Add a New Chapter at the Obama Presidential Center For travelers interested in American history and contemporary culture, the Obama Presidential Center offers another reason to explore beyond downtown. The campus in Jackson Park on Chicago’s South Side opened to the public in June 2026. Its grounds include gardens, public art, walking paths and community spaces. The museum offers a deeper look at the Obama presidency and the issues that shaped it. The visit adds a different dimension to a Route 66-inspired trip. The Mother Road connects stories of migration, work, community and the pursuit of opportunity. The presidential center offers another place to reflect on the people and events that continue to shape the country. I cannot wait to go.

Check In Somewhere with a Story: Pendry Chicago For a trip celebrating a century of American travel, why not choose a hotel with a history of its own? Pendry Chicago occupies the landmark Carbide & Carbon Building, a striking Art Deco skyscraper completed in 1929. Its dark-green exterior and gold accents make it one of downtown’s distinctive architectural landmarks. Designed by the Burnham Brothers, the building originally housed the regional offices of Union Carbide and Carbon Co. It was designated a Chicago landmark in 1996 and became home to Pendry Chicago in 2021. The timing feels especially fitting: Route 66 was designated in 1926, and this architectural landmark followed just three years later. Both belong to an era when America was looking ahead, embracing new technology and imagining new ways to live and travel. Today, Pendry Chicago combines the building’s historic character with contemporary guest rooms, dining and cocktail venues. Its downtown location on Michigan Avenue makes it a convenient base for exploring the Route 66 starting point, Millennium Park, the Art Institute and the Chicago River. I’m looking forward to staying at Pendry Chicago and experiencing the building for myself. I love discovering the stories behind the places where I stay, and this one has a particularly fitting connection to the Route 66 centennial. The hotel itself is part of the city’s architectural story. Travelers can compare dates, room types and rates on Booking.com, or explore other Chicago accommodations to find a stay that fits their style and budget.

Start Planning Your Route 66 Centennial Getaway You don’t have to wait for the perfect summer road-trip window to start exploring. Fall is an opportunity to plan a Chicago city break, enjoy the city’s architecture and cultural attractions, then decide whether to extend the adventure along historic Route 66. I’m already thinking about how I’d put the trip together: a stay at Pendry Chicago, time to explore the Obama Presidential Center, an evening at The Hand & The Eye and visits to both Route 66 starting-point landmarks. I am going to rent a car and follow the Mother Road, stopping along the way rather than rushing toward the next destination. Booking.com was named the Official Travel Partner of the Route 66 Centennial in 2026, spotlighting the highway and the stays and experiences that make a road trip memorable. Its platform offers travelers a way to compare accommodations, car rentals and travel options while putting together an itinerary. Here are four ways to get started. Find your stay. Compare hotels in downtown Chicago, considering location, amenities and how much time you want to spend exploring on foot. Pendry Chicago is one option for travelers drawn to historic architecture and a central base. Browse Pendry Chicago on Booking.com or search for other stays to compare your options. Book your flight. Chicago is served by O’Hare International Airport and Midway International Airport. Compare arrival times and fares, then choose the airport that works best for your itinerary and budget. If you’re staying downtown, consider the transportation options from the airport before deciding whether you’ll need a car immediately. Choose your experiences. Reserve timed-entry attractions in advance, especially if visiting the Obama Presidential Center museum or The Hand & The Eye. Consider an architecture cruise, a museum visit and a walk along the lakefront, leaving some unplanned time for discoveries. Check official attraction websites for current schedules and ticket availability. Rent a car when you need one. If your trip is focused on Chicago, you may not need a vehicle for the whole visit. The city’s downtown attractions are close enough to explore on foot in many cases, and public transportation and rideshares can help with longer trips. If you’re continuing along historic Route 66, compare rental options and consider picking up a car when you’re ready to leave the city. Booking.com announced its centennial partnership in February 2026, making the milestone an especially timely opportunity to plan a trip around the Mother Road. You can read more in the company’s Route 66 Centennial announcement. The most important part of planning is leaving room for spontaneity. Make reservations for the experiences you don’t want to miss, but don’t fill every hour. The unexpected stop is often the one that becomes your favorite memory. How Far Will You Go? The beauty of Route 66 is that you can make it your own. Maybe you’ll spend three days in Chicago, take photographs at both starting points, discover a new favorite painting, look out over the city from a skyscraper and spend an evening watching magic unfold in a historic mansion. Perhaps you’ll rent a car and follow the original route through Illinois, stopping in communities that still celebrate their place in the Mother Road’s story. Or maybe Chicago will be the beginning of a much longer journey, one that takes you across the plains, through the Southwest and toward the Pacific. You don’t have to complete all 2,448 miles to understand why this highway has inspired travelers for 100 years. You just have to experience a little of its history and imagine the journeys that began before yours. Route 66 has carried families searching for a fresh start, vacationers chasing summer, musicians and artists, curious travelers and people who simply wanted to see what lay beyond the next bend. Its meaning has changed over the decades, but its invitation remains the same: get out there and explore. I’m ready to start planning my own Chicago adventure as part of my 60 Before 60 journey. Between the history of the Mother Road, the architecture of Pendry Chicago, the Obama Presidential Center and the promise of an evening filled with magic, there is plenty to look forward to before even getting behind the wheel. A hundred years after Route 66 first appeared on the map, the invitation still stands. Start in Chicago, follow the stories, take the detour and see where the road leads. You can travel all the way to California or simply begin with a fall weekend in the city where the journey starts. The first mile is waiting.

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