Chicago isn't just the beginning or end of Route 66, or your adventure with Route 66 Tours, it's also a major American destination located right in the middle of the country and brimming with culture, food, sights and sports. Whether you plan to stay for a day or a week, Chicago is a city deserving of your attention. Follow this guide to see the Windy City's best and most famous sights, then tack on a few more discoveries of your own.
This behemoth of a building was, until recently, the tallest in the world. Today, it remains the second tallest building in North America, at a whopping 443 metres. Ride the elevator up 103 floors and take in an unmatched view of Chicago in the world famous Skydeck. On a clear day, viewers can see as far as 50 miles out.
If a trip to the Skydeck isn't triggering any fears, step out onto the Ledge, an enclosure that sticks out from the Skydeck and is transparent all the way around. It doesn't get closer to a bird's-eye view than this. Not for the faint of heart!
In addition to being a must-see destination, the Willis Tower sits right by the very beginning of Route 66, making it an easy stop before or after your tour.
Prefer to stay closer to the ground? Chicago is home to an incredible system of urban green spaces, and Millennium Park is its crown jewel. The park packs greenery, public art and a world-class concert venue in 25 acres. The entire thing sits right by downtown and is open to the public, completely free of charge. Since opening in 2004, Millennium Park has quickly become a Chicago icon, delighting visitors and locals alike.
The Park is filled with highlights and includes a little bit of something for everyone. Jay Pritzker Pavilion, which hosts everything from major events like the Chicago Jazz Festival, to community summer film series and plays. It is known for its distinct band-stand and world-class sound system. Art lovers will be overjoyed to get up close to The Bean, a massive, stainless steel sculpture that reflects the Chicago skyline. Once you're done taking in the park's man-made achievements, take a minute to reflect in the Lurie Garden, an oasis of natural plant life that still grants views of the Chicago skyline. Come in the Fall to enjoy the park's changing colours before embarking on your American adventure.
The Art Institute of Chicago
On the other side of Monroe Street from Millennium Park sits the Art Institute of Chicago, one of the premier art museums in America. Whatever kind of art speaks to you, the Art Institute has you covered. Pieces in its enormous collection include paintings by masters like Picasso, Van Gogh, Andy Warhol and Salvador Dali. The art comes from every corner of the globe, including several by Australian artists. If you can't find something in the Art Institute of Chicago that will take your breath away, you're not looking hard enough!
The Museum Campus
If the Art Institute of Chicago isn't enough for your museum fix, make your way further south to the Museum Campus, a 57-acre space on the shores of Lake Michigan that hosts a variety of museums, as well as an American Football stadium. Check out the Field Museum of Natural History and stand in awe of Sue, the largest Tyrannosaurus Rex fossilised skeleton ever discovered and Maximo, the single largest dinosaur ever discovered, at almost 9 metres tall and 37 metres long. In addition to its famous dinosaurs, the Field Museum boasts exhibits on planetary history, Ancient Egypt and a special section just for kids.
Just steps away from the Field Museum are the Adler Planetarium and the Shedd Aquarium. The Adler includes a telescope that's available to the public, as well as a variety of special events and exhibits. The Shedd, meanwhile, is home to a wide array of critters that call the sea home, including sharks, beluga whales, penguins and octopi. Seeing the stars and distant planets, then exploring the world's oceans right after has never been so convenient. Three great museums in one park isn't enough for you? Don't worry! There are great museums all the way through your Route 66 journey.
Also located on the Museum Campus is Soldier Field, home of The Bears, Chicago's professional American Football team. The stadium boasts a capacity of over 60,000 people and holds events on over 200 days of the year. Go on a tour or take in a game when you're in town!
No trip to Chicago is complete without a visit to the famous Navy Pier. Once used to house warships, and as a military training centre during World War II, the pier of today is a much friendlier place, filled with shops, restaurants and events. More than 2 million visitors pass through the Pier every year – and for good reason. Attractions include amusement park rides at the Navy Pier Park, the Chicago Children's Museum and a one-acre botanical garden. History buffs can take a ride in Tall Ship Windy, a historic boat modelled after the trading vessels of old. If your tour is in the summer, the Pier will have fireworks every week.
Sightseeing Boat Tour
Chicago is a city defined by its waterways and its buildings. Experience both with a guided boat tour down the Chicago River. Boat tours come in a variety of lengths and sizes, and offer a range of amenities including, on some, gourmet dinners. Educational guided tours cover a variety of themes, including the city's architecture and history. River boat rides offer a great way to see as many of Chicago's sights and famous skyscrapers as possible.
Your Chicago adventure is just one of many reasons to travel Route 66, and take in the very best of America. From major cities to endless miles of country road, our tours have it all. Our Fall Route 66 Tour currently still has a few spaces available so reach out to us today to save yourself a spot or enquire about a different tour that you are interested in!