Chicago, which is located in Illinois on the banks of beautiful Lake Michigan, is the third-largest city in the U.S. and one of our favorite cities! It is known for its jaw-dropping, modern architecture, vibrant music scene, amazing food (including its deep-dish pizza) and iconic neighborhoods. It was also voted the second most fun city in the world and the third friendliest city.Chicago is one of the Midwestern cities that enjoys the waters of Lake Michigan, which is among the largest and deepest freshwater lakes in the world. In fact, Chicago’s nickname, the ‘Windy City’, comes from the breezes that blow off Lake Michigan and sweep through the city’s streets and skyscrapers.
Imagine that gentle cool breeze against your face, as you cruise on your motorcycle down Lake Shore Drive, the multilevel expressway that runs alongside the shoreline of Lake Michigan in Chicago. It’s a warm summer’s day, the sunlight is reflecting on the water, and Chicago-based funk band Earth, Wind & Fire is playing out on your bike’s headset – life is good! Or follow in the footsteps of Bruce Wayne in ‘Batman’, and ride your motorcycle across the Marshall Suloway Bridge in Downtown Chicago.
Getting motorcycle rentals in Chicago couldn’t be easier. If you are flying into Chicago, you could check out Explorify Motorcycle Rentals Chicago at O’Hare Int. Airport. Chicago Harley-Davidson®, which has a range of models to choose from. Just select your time and date to collect.
Of course, what Chicago is perhaps most well-known for in the world of motorcycling, is the iconic Route 66. If there’s one dream ride on the bucket list of every motorcyclist around the world, there’s no doubt it has to be Route 66.
“It has always been a lifelong dream of mine to one-day ride Route 66. I traveled over to the US back in 1975 to ride around Yonkers in New York for two weeks and my experience was indescribable. Touring the US on a motorcycle is an experience like no other, and I can almost taste the sense of freedom and ecstasy that riding Route 66 can bring.”
Motorcyclist Hugh Walsh from Dublin
Everyone is familiar with the iconic Route 66 Begin Sign, marking the starting point of one of the most famous highways in the world. The sign has become a historic landmark that signifies the beginning of a journey through the heart of America: from Chicago, Illinois to Santa Monica, California. Kick off your adventure on the Mother Road with a photo at the Route 66 Begin sign! (You can read more about it here)
The route itself is 2,448 miles and you can complete the journey in approximately two weeks. Or you can simply ride along the stretch of Route 66 that covers Illinois. But if you plan on sticking around Chicago, there are some other excellent shorter motorcycle roads nearby worth checking out too – all in Illinois. Here are some top suggestions:
This route is a 180-mile loop through the Midwestern portions of Illinois and neighboring Wisconsin. Start in the village of Schaumburg, then join Route 72 and travel west all the way through the towns of Genoa, Kirkland, Davis, Junction, and Byron. You’ll head towards Rockford, and on up to Janesville, Wisconsin before looping back to Schaumburg, by taking US Route 14 west to State Route 11. Enjoy miles of pasture and riverside views en route, with small towns, fuel stops and other amenities spread evenly along the way. The trip can be easily done in one day.
This 42-mile stretch of asphalt runs south of Rockford and follows part of the winding Rock River – which is a tributary of the Mississippi in Wisconsin and Illinois – until you reach Dixon. It’s approximately a 1.5-hour ride, and has some gentle curves that even a beginner rider can be at ease with. You’ll be astonished by the route’s impressive rock formations and serene riverside views. Read more about the Rock River Run here.
Taking you through some of the most scenic farmland in Illinois and many small rural towns, this route begins in the Bolingbrook-Naperville-Romeoville area and takes you west towards Galena and the town of Scales Mound. You’ll experience gentle curves and excellent sweeping corners, and the road is very light on traffic. This trip can take between 4-6 hours.
If you find yourself near the town of Elizabeth, you certainly can get some great riding in. As it stands, the ride from Mount Carroll to Elizabeth is one of the most scenic roads in Illinois. The pathway has a ton of trees and rolling hills, with a couple of sharp curves which can get intense, but provide some additional fun. While there isn’t much to stop for along the way, Elizabeth has plenty of diversions and great food options.
U.S. Highway 6 is an east–west arterial surface road that runs 179.88 miles (289.49 km) from the city of Moline to Lansing at the Indiana state line. You can do a one-day trip (33 miles) by beginning in Woodfield, Indiana (55 minutes outside Chicago proper) and riding all the way to Walkerton. The trip is filled with countryside, and cornfields and follows a flat, two-lane highway, so don’t expect any extreme turns.
Spanning 71 miles, beginning in Big Rock and ending at Starved Rock Park, this is a classic ride and it wouldn’t be an Illinois motorcycle ride list without it! The route can take anywhere between 2-4 hours, depending on how many stops you make along the way. It’s a great run anytime in the summer, but certainly, as fall approaches, the scenery is amazing when the trees and foliage change color.
Illinois’ national forest offers some of the most beautiful forestry and natural scenery in the state. And you can expect a challenging, yet rewarding ride from Chicago, starting from Murphysboro or Carbondale in southern Illinois. And check the Garden of the Gods, which allows visitors the opportunity to view miles of scenic Shawnee Forest woodlands from a historic viewpoint. A perfect day-trip loop, with plenty of sightseeing, snacking, and intense riding opportunities.
During, or after, your explorations of the many motorcycle routes, there are plenty of activities and attractions to discover within the city of Chicago in your free time. Here are some of our must-visits:
The 50-acre Navy Pier is undeniably one of Chicago’s top attractions. Located on the shoreline of Lake Michigan, in Downtown Chicago, the scenic waterfront destination is home to an epic Ferris wheel, countless cafés and restaurants, entertainment, accommodation, shops and more – it’s like another city within the city!
More than 180 million guests have come to enjoy Navy Pier, also known as the ‘People’s Pier’. And the waterfront truly comes to life in the summer, with fireworks displays, live music, theatre and cruises setting sail daily. There’s a dedicated motorcycle parking area located at Riva/Entrance 1, just past the West Garage, so park up, explore the area and take in the buzzing atmosphere.
The Art Institute of Chicago in Chicago’s Grant Park is one of the oldest and largest art museums in the world. It houses the largest collection of Impressionist and Post-Impressionist art on the planet outside the Louvre. It’s also home to more than 300,000 pieces of art, including some of the world’s most revered masterpieces. Some outstanding pieces include ‘Two Sisters’ by Pierre-Auguste Renoir, ‘The Bedroom’ by Vincent Van Gogh and ‘Water Lilies’ by Claude Monet.
General admission is $25 for an adult ticket, $19 for seniors, $19 for students and teens (14-17) are $19. Children are free and there is a discounted price for Chicago and Illinois residents. Advanced ticket purchase is advised.
Many people will recognize the distinctive, shiny, bean-shaped sculpture on arrival at Millennium Park. Officially titled Cloud Gate, it is one of the world’s largest permanent outdoor art installations designed by Indian-born British sculptor Anish Kapoor. Its polished exterior reflects the people moving around the park, the lights of Michigan Avenue, the surrounding skyline and the greenery of Millennium Park.
Known as the ‘front lawn of Chicago’, Millennium Park is also home to three more artistic highlights: the Jay Pritzker Pavilion, the Crown Fountain and the Lurie Garden. Locals and visitors alike gather in the Park to enjoy free concerts and movie screenings, explore the beauty of the grounds and enjoy a picnic.
You’ll already have experienced a variety of thrills riding your motorcycle through Chicago and the surrounding areas. But for another thrill at a height of 1,000ft, check out the 360 CHICAGO Observation Deck. Breathtaking 360-degree views across the city await from the top of the former John Hancock Center – it’s an impressive 94 floors up!
You can try out the Tilt ride as an optional add-on to your ticket (which grants access to the observation deck). ‘Tilt’ is an enclosed, glass-and-steel platform, which slowly tilts you outward to an adventurous angle, providing downward views of Chicago. Then sit back with a drink, and admire the views, in 360 CHICAGO’s CloudBar. Open daily from 9 am-11 am (last entry is one hour prior to closing). Tickets start at $30 for adults (12 years old and above) and $20 for youth (3-11 years old).
Another amazing viewing deck is the Willis Tower Skydeck. At 1,353ft and based on the 103rd floor, it’s the tallest building in Chicago. The viewing tower offers spectacular views spanning up to four states, but if you’re brave enough, you can also step out into The Ledge, which is a glass balcony extending 4ft outside the building.
Check out the website for opening hours, as they vary depending on the month you visit. General adult admission is between $30-$44 and youth tickets are $22-36. This includes access to the elevator ride to the Skydeck and The Ledge.
Sometimes referred to as The Mag Mile, this is one of the most iconic shopping districts in Chicago. It encompasses the 13-block stretch of North Michigan Avenue that runs from the banks of the Chicago River to the south, to Oak Street to the north.
There are approximately 430 stores, as well as many fine dining spots and entertainment options. Visit a museum such as the Chicago Sports Museum, Prince: The Immersive Experience or the Art Institute of Chicago. Catch a theater show, get refreshed at one of the many relaxing spas, or simply rest up for the night at one of over 70 luxurious hotels located along The Magnificent Mile.
Chicago-style pizza, which is a deep-dish pizza with inverted layers of ingredients (compared with thin-crust pizza), was developed in Chicago, Illinois, in the 1940s. It’s one of the culinary hallmarks of the city. And pizza lovers will be in heaven on a Chicago Pizza Tour, where trained guides take you to popular, historic pizzerias around the city and you can eat lots of pizza to your heart’s content! Book your tickets in advance online. Ticket prices start from $40 each, depending on the type of tour booked.
This 20-acre park is a Chicago favorite, offering a climbing wall, miniature golf, playground, picnic area, tennis courts and an ice-skating rink. There’s an on-site café, offering some lunch options and beverages too.
Maggie Daley Park also includes a Cancer Survivors’ Garden, which is a beautiful garden designed to be a celebration of life.
Did you know that Chicago has the only river in the world that flows backward? After huge rainfall in 1885 carried sewage from the Chicago River to Lake Michigan and resulted in waterborne illnesses from Chicago’s primary source of drinking water, engineers reversed the direction of its river away from the lake.
Today, there are plenty of activities and attractions to enjoy along the Chicago River, from kayaking and boat tours to sipping wine at the City Winery!
The Second City Theater is one of the most influential and prolific comedy theaters in the world. It’s the oldest ongoing improvisational theater troupe to be continually based in Chicago. Enjoy an evening of laughs, with a range of shows to choose from. Check out the website for specific show details, depending on when you travel to Chicago.
Or, check out The Chicago Theater, which offers a range of shows from comedy to arts and music.
During the Great Migration, African Americans flocked to Chicago from the South, bringing age-old jazz and blues traditions with them. The city soon became the jazz capital of the world, attracting legendary musicians like King Oliver, Jelly Roll Morton, and Louis Armstrong.
Visit one of many of the jazz clubs in the city, such as Jazz Showcase, Chicago’s oldest jazz club. And if you want to pick up your own vintage jazz record, stop by the Dusty Groove store on Ashland Ave, where you can score super-rare records.
In the roaring twenties, Chicago was home to well-known gangster Al Capone, and you can discover all about life during those days. You can take in the sights like Cicero Restaurant, where Capone had a speakeasy, Al Capone’s brewery and the Blackstone Hotel, which was apparently also a haunt of Capone’s. It was in the hotel’s Crystal Ballroom where the iconic baseball bat scene from The Untouchables was filmed.
North Avenue Beach in Lincoln Park is one of Chicago’s most popular beaches with the most picturesque views. The beach is perfect for a day spent lounging shoreside or taking a dip in the water. There are vendors to rent kayaks, lounge chairs, and more.
Stop by Castaways Bar and Grill to cool off with an icy drink or something tasty to eat, before you set off on your motorcycle for the day!
If you’re not traveling around Chicago on your own bike, there are plenty of motorcycle rentals in Chicago available, such as Explorify Motorcycle Rentals. Just speak to the experts.
“People don’t take trips, trips take people.”
Whether you end up riding down Route 66 or find yourself traveling one of the city’s other hidden gems, Chicago and its surrounding areas are sure to evoke a feeling of pure joy, nostalgia and freedom. From tree-lined countryside roads and scenic waterfront views to quaint small towns and city gems, it’s all waiting to be explored.