So you think you might want to drive Route 66?

Well, buckle up because it’s going to be a seriously long road trip, spanning thousands of miles.

thumbnail for post ID 6999866 Route 66 – Chicago, Illinois: Where to eat, what to see and what to do

But this most iconic American road trip will not disappoint – you will have many places to stop and hidden gems to discover along the way, and you definitely won’t get bored (unless you hate driving obviously, in which case this is probably not the journey of a lifetime for you).

Like the historic route, my journey along the Mother Road started in Chicago – the biggest city on my itinerary.

From there on, it’s all about small towns, middle America and the cities you’ve probably heard of but never thought to visit.

Pontiac, Illinois

If you’re short on time, you will probably miss Pontiac – but it’s certainly worth a visit if you have a couple of hours spare.

There are perhaps thousands of Route 66 murals to be found along the way but Pontiac claims to have one of the most photographed.

https://www.instagram.com/p/BZa-VivFgQR/?hl=en&taken-by=qinxiesays

It’s right outside the Illinois Route 66 Hall of Fame and Museum, which houses memorabilia from different states along the Route. And the brick road just beneath the mural are actually original.

Perhaps most famously though, it’s home to Bob Waldmire’s VW van and his ‘road yacht’.

Waldmire, as you’ll discover along the Route, is a bit of a Route 66 legend.

Historic Route 66 Association Hall of Fame & and Museum exhibit of Bob Waldmire 1972 VW Microbus camper
Waldmire’s 1972 VW Microbus camper (Picture: Jeffrey Greenberg/UIG via Getty Images)

The hippie artist spent much of his life travelling up and down the Route in his van and drew incredibly intricate maps of the journey.

In fact, his van was the inspiration for the character of Fillmore in Pixar’s Cars, though it wasn’t officially credited.

Stop in Edinger’s Filling Station for lunch – it looks like a 50s diner but it’s so souped up that your orders are taken with an iPad.

The Firebird Custom (Picture: Qin Xie)

Their fried chicken is delicious and you can get it several ways.

Springfield, Illinois

Springfield, the capital of Illinois, was home to Abraham Lincoln.

https://www.instagram.com/p/BZbrXinlcHo/?hl=en&taken-by=qinxiesays

You can visit his original home in the city for free, but you might also want to check out the Abraham Lincoln Presidential Library and Museum to learn about his life and how he came to be the 16th US president. Entry to the museum is $15 for adults.

I timed my trip to coincide with the International Route 66 Mother Road Festival, which takes place towards the end of September each year.

It’s every petrolhead’s dream.

https://www.instagram.com/p/BZZqr7rl1Wb/?hl=en&taken-by=qinxiesays

Thousands of American muscle cars are driven in from around the country to compete for the best in show.

Many of these vehicles are restored vintages and feature custom body and art work – they’re quite a sight to behold.

Food-wise, the cozy dog, known as corn dog elsewhere in the country, was invented in Springfield so that’s definitely worth trying.

You should also pop into Maldaner’s, even if it’s just for a drink, as it’s the oldest restaurant in the city, having been in continuous operation since 1884.

The Horseshoe is absolutely huge (Picture: Qin Xie)

For something more casual, try Obed & Isaac’s Microbrewery and Eatery.

The Horseshoe – an open sandwich with two burger patties and a mountain of chips – is its most famous creation. It is also huge and you will definitely want to share it with someone with an appetite to match.

St Louis, Missouri

After Springfield, I headed for St Louis in Missouri.

Split down the middle by the Mississippi River, St Louis’ history is intertwined with that of slavery.

https://www.instagram.com/p/BZdxprkFxlN/?hl=en&taken-by=qinxiesays

It was on the steps of the Old Courthouse that slaves were once sold. Many years later, slaves were also able to use the same courthouse to sue for their freedom.

Explore some of the free exhibits there and you will begin to understand America’s long struggle with racial tensions.

It’s also from the steps of the Old Courthouse that you will get one of the best views of the Gateway Arch – the city’s architectural icon.

https://www.instagram.com/p/BZcSA3uF1Di/?hl=en&taken-by=qinxiesays

Take the Gateway Arch Tram Tour – it’s $13 and takes you to the top where you get to see miles of the city in either direction.

St Louis has its own style of barbecue (tender spare ribs bathed in an abundance of BBQ sauce) and pizza (topped with Provel – a blend of cheddar, Swiss, and provolone cheese) – and there are plenty of spots downtown where you can try these.

My pick of the city, though, is Ted Drewes Frozen Custard, a popular drive through that’s been going strong since the 1930s and one of the places recommended in The Route 66 Cookbook by Marian Clark.

https://www.instagram.com/p/BZegnCIlIjd/?hl=en&taken-by=qinxiesays

You’ll be spoilt for choice when it comes to the toppings and people drive through to buy them by the tubs.

Cuba, Missouri

One of the tiny cities you will pass on the road west is Cuba, which has a population of less than 4,000.

The Historic Route 66 passes through the heart of the city, and on the buildings lining either side are colourful Mother Road murals.

Cuba, Missouri, known as the Route 66 Mural City (Picture: Carol M. Highsmith/Buyenlarge/Getty Images)
Cuba, Missouri, known as the Route 66 Mural City (Picture: Carol M. Highsmith/Buyenlarge/Getty Images)

It’s definitely worth stopping here to stretch your legs and take a couple of selfies with all the artwork.

Springfield, Missouri

I once heard a rumour that Springfield was picked for the setting of The Simpsons because there’s one in every state.

It’s not true, but there are definitely plenty of Springfields in the US and Springfield in Missouri is the second one on Route 66.

It’s also said that this Springfield was where Route 66 was first named on April 30, 1926. That one is true.

You’ll have to look hard for signs of the old route though, as most of it has disappeared.

https://www.instagram.com/p/BZgMTHGlM6p/?taken-by=qinxiesays

The Best Western Route 66 Rail Haven is one. It was one of the original motels on the Route, known as the Rail Haven Motor Court, and has since been added to the National Registry of Historic Places.

There’s also an old Steak n’ Shake restaurant on East St. Louis Street that’s on the Registry.

On the way out of town, you will find Gary’s Gay Parita on the old Route.

(Picture: Qin Xie)

While not original, the recreation of a classic Sinclair petrol station will give you a flavour of what life was like in the hey day of Route 66.

And from there, it’s onto Oklahoma.

What you need to know about driving Route 66:

Before you start, it’s worth knowing that just about every town and city along the way has some sort of Route 66 relic.

Since the interstates were introduced, most of the small towns were bypassed. Some have become ghost towns while others have thrived.

(Picture: Qin Xie)

The easiest way to explore the Route, if you have limited time, is to drive along the interstate and exit at the places you want to stop.

You’ll miss a lot, and it’s sort of cheating, but unless you have a month or more, it’s the fastest way to do the Route.

The thing about the Route is that the road quality is not always great – sometimes it’s so bumpy, you’ll think your tyres have burst (that said, some sections of the interstate are not much better).

There are also more twists and turns, which means the speed limit is generally much lower than the interstate.

While a move has been made to preserve the original Route in recent years, there are some areas where it’s essentially impassible, especially after bad weather, so always have a plan B.

How to get there and where to stay:

I started my journey in Chicago, which is served by daily flights from London. Several airlines have direct flights from London to Chicago but indirect flights tend to be cheaper. The cost of a return fare will vary greatly depending on where you end your journey.

For car hire, I went with Alamo, who have a rental office in Downtown Chicago. Rentals start from £78 per day, £833 per week and £1,123 for two weeks, including a free additional driver, taxes, and collision damage waiver for Chicago to LAX.

Be aware that as well as the hire fee, you may also have to pay a one-way drop off fee if you finish your journey in Santa Monica.

https://www.instagram.com/p/BZcSA3uF1Di/?taken-by=qinxiesays

In Springfield, Illinois, I stayed at The State House Inn, which is within walking distance to the main attractions. Rooms there start from $69.

My hotel in St Louis, Missouri, was Drury Plaza Hotel St. Louis at the Arch. It’s just a few minutes walk from both the Old Courthouse and the Gateway Arch. Rooms there start from $106 and they do daily Kickbacks where you get free food and drinks, as well as free popcorn.

And in Springfield, Missouri, I stayed at the Best Western Route 66 Rail Haven, where rooms start from $56.

For more travel ideas, check out Visit The USA, Enjoy Illinois and Visit Missouri.

This is part of a series of posts on Route 66. Check back next Tuesday for the section from Oklahoma to Texas.

MORE : From breakfast to dinner: Here are the best budget-friendly places to eat in Copenhagen

MORE : 5 reasons why a cookery course is the perfect mini-break (even if you can’t cook)

MORE : Why Seville not Madrid or Barcelona should be your next city break