A colorful tribute to the Mother Road in the heart of Pontiac, IL.
Illinois Office of Tourism
As the birthplace of the skyscraper, Michael Jordan’s former playground and home of delectable deep dish pizza, Chicago is no Second City when it comes to its world-renowned brand recognition. The nickname “Second City” was coined after Chicago rebuilt itself after the Great Chicago Fire of 1871. Today, a different kind of fire rages in the city as a diverse, multinational population is fiercely passionate about their sports teams, soul-stirring food, the city's world-class skyline and its robust cultural output.
A few rules to start: Here are a few important things to note if this is your first visit to Chicago: Never put ketchup on your Chicago hot dog, never refer to the “L” (short for “elevated train”) as the subway and always pack a layer (the Lake Michigan wind can cast a chill at a moment’s notice). Stick to those essential tips and you’ll fit right in, enjoying everything this glorious city has to offer.
The beginning of a perfect road trip: Did you know that the legendary Route 66 begins right in the heart of downtown Chicago? Marked by the iconic “Route 66 Begin” sign (122 S. Michigan Ave.), this spot is where countless road trips and Americana dreams have launched for nearly a century. As Route 66 prepares to celebrate its 100th anniversary in 2026, there’s no better time to start your journey at its historic beginning. Spanning 2,448 miles from Chicago to Santa Monica, California, the road is living American history. Delight in the charm of the road with every turn leading to retro diners, iconic landmarks and photo-worthy pit stops. It all starts here, in the Windy City.
The ideal destination and starting place for adventure, Chicago eagerly welcomes curious travelers of all ages. Whether you’re on the hunt for elevated dining, legendary sporting events or immersing yourself in the arts and culture, Chicago is a city where excellence comes standard.
