‘I did the ultimate US road trip down Route 66 – recreate my journey from Chicago to Madison’

When it comes to road trips, Route 66 is one of the most well-known. As the Main Street of America and the Mother Road, Route 66 goes by many nicknames and holidaymakers from across the globe flock to the US to travel all or part of the route, which spans from Chicago to Los Angeles.

Spanning 2,448 miles from end-to-end, Route 66 is the quintessential American road trip and those wanting to make the trip can expect to see quirky landmarks, antique shops and diners that look frozen in time – as OK! found out earlier this year. From sensational food tours to river dining, here’s why you should consider making the road trip of a lifetime…

Chicago

There’s a multitude of reasons to visit the Windy City, from the mouthwatering food scene and dynamic neighbourhoods to that warm Midwestern welcome. It’s also the start of the iconic Route 66.

Take a boat ride on Lake Michigan, soaking up the city’s bold architecture, before strolling down the Magnificent Mile, home of luxe fashion outlets and fine-dining restaurants.

We loved exploring Millennium Park. Spread over 24 acres, it’s one of the largest green roof parks in the world. Built over parking garages and a rail yard, it’s now buzzing with outdoor music venues, public art, food concessions, theatre and children’s play zones. We also had to grab a mirror-selfie in the reflection of the Bean, a huge quirky sculpture in the city.

Sports fans should head to Wrigley Field for a Chicago Cubs baseball game or visit the United Center atrium to pose by the statue of basketball star Michael Jordan before a Chicago Bulls game.

Our weekend highlight was a food tour with the award-winning Bobby’s Bike Hike. Our guide Nate showed us a combo of Instagram-worthy landscapes and heavenly local delicacies. Our favourite spots were Lou Malnati’s, for the best deep-dish pizza, The Wiener’s Circle, where we stopped for a ketchup-free Chicago hotdog, and Oprah Winfrey’s favourite bakery Bittersweet, for the most delectable chocolate brownie.

Don’t miss Navy Pier’s Centennial Wheel and the incredible views from the 360 Chicago observation deck, and take in the inspiring Van Gogh exhibition at the Art Institute of Chicago.

Joliet and Pontiac

Route 66 travellers should pull off the “Mother Road” to delve into the rich history of Joliet, an all-American city south of Chicago that’s packed with nostalgia.

We booked a guided tour of the fabled Old Joliet Prison. Seen on The Blues Brothers and Prison Break, the former penitentiary is a hot spot for true crime fans, having housed notorious inmates such as John Wayne Gacy and James Earl Ray during its working years. Feeling brave? Opt for a Haunted Tour, a 90-minute dusk trek through the eerie cells and maze-like corridors.

One hour south of Joliet is the charming town of Pontiac, where you can take snaps of an outdoor mural known as the biggest Route 66 shield in the world.

We spent an evening at one of Humiston-Riverside’s weekly music festivals. We brought camping chairs and a cooler of root beer and were entertained by local artists.

Springfield

A place where presidential history meets Americana, the state capital of Illinois is jam-packed with family-friendly activities.

Visit Springfield’s Ace Sign Museum, which features more than 85 historic signs from Springfield and Route 66, including the neon Sonrise Donut sign. Then tuck into a Cozy Dog at the Cozy Dog Drive In, home of the original corn dog on a stick, dipped in batter and deep fried… mmm!

At the Abraham Lincoln Presidential Library and Museum we learned about the life, loves and losses of the 16th US President. Immersive exhibits and tour guides left us feeling like we were walking in Honest Abe’s shoes.

Meanwhile, the chilling Ghosts of the Theatre show helps visitors understand the importance of artefact preservation using dramatic special effects.

And what better way to end the day than with dinner at Motorheads Bar & Grill, a classic car restaurant where you must try its enormous Horseshoe sandwich. The delicacy is piled up with juicy pulled pork topped with French fries and served on Texas toast smothered in a delicious homemade cheese sauce.

Grafton and Madison

Travelling south along the Mississippi River we reached the harbour city of Grafton, recognised for its resort-quality amenities including scenic river dining, an abundance of guest houses and a surplus of outdoor fun.

Our highlight was taking a gondola up to Aerie’s Resort, atop one of the area’s plush green hills, to try ziplining. We also braved Aerie’s new Alpine Coaster, a thrilling downhill ride through the trees.

Later, on the deck of Aerie’s Riverview Winery, we sat back with a cold glass of wine, admiring the breathtaking sunset.

For those visiting Illinois in June (like us), the Enjoy Illinois 300 – a NASCAR Cup Series race at World Wide Technology Raceway in Madison – will blow your socks off. The nail-biting 240-lap race sees 36 fearless drivers attempt to navigate the challenging track in a battle for the No1 spot.

How to book

See choosechicago.com, enjoyillinois.com, hcdestinations.com, visitspringfieldillinois.com and riversandroutes.com

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