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Truly iconic – driving Route 66 is perhaps the most famous of road trips.

We took our road trip along Route 66 in September 2014. This guide is dedicated to all the people who live and work along the mother road.

Completed in 1926, the mother road crosses three time zones and eight states, stretching 2,448 miles from Chicago to Santa Monica in Los Angeles. Nothing symbolizes the American Dream more than Route 66, used by many during the great depression to head west in search of the ‘land of promise’

Before I start, I have a little confession to make. We drove Route 66 the wrong way round – from Los Angeles to Chicago. A crime I know, but unfortunately it was the only way round I could do it.

If you find yourself in a similar position, I can assure you that it makes no difference, other than tradition. You will still drive through the same magnificent landscapes, see the same kitsch roadside attractions and eat in the same classic diners.

However, as most travel east to west starting in Chicago, I’ve listed it in that order.

Using the guide

This handy guide is useful to print off and take with you. Whilst plugging addresses into your sat nav will keep the trip efficient, don’t be afraid of getting a little lost along the way – you never know what you might find.

Many of the motels and hotels listed are popular with other roadies and get booked up well in advance so don’t leave it until you arrive, book reservations in advance.

Day 1 – Chicago

Welcome to Chicago, the beginning of Route 66. Today we’re going to assume that you arrived in the morning and you have most of the day to explore. Chicago has world class eateries, attractions and shopping so if you can spare a few more days, you should.

Superdawgs in Chicago

Flickr: dirt

After you’ve arrived in O’Hare airport and picked up your hire car, you’re most likely going to be hungry. Drive the twenty minutes or so north to Superdawg Drive-In for a spot of lunch. Although this road isn’t part of Route 66, Superdawgs has been there almost as long – and the all-beef hotdogs, diner experience and huge rooftop hot-dog figures will certainly give you a taste for things to come.
333 S Milwaukee Ave, +1 847-459-1900, superdawg.com

Essex Inn Chicago

When you arrive in the city there is plenty of accommodation to choose from. A favourite for many roadies is the Essex Inn. Although it’s large and modern, it close to the start of Route 66 and overlooks Grant Park.
800 S Michigan Ave, +1 312-939-2800, essexinn.com

Chicago bean or Cloud GateChicago bean or

Luke Charny

In the afternoon take a walk in Millennium Park. Located in the centre of the city, it’s a good place to start, particularly on a sunny summer afternoon. Admire the fantastic sculptures, including the famous Chicago Bean (Cloud Gate), whose mirrored sides reflect the city skyline and people that surround it, creating wonderful photo opportunities.
201 E Randolph St, millenniumpark.org

Willis Tower the ledge

Luke Charny

Afterwards head over to Willis Tower. This vast 108 floor skyscraper is still referred to by its original name – the Sears Tower. For twenty five years after it was constructed in 1973 it held the title of the world’s tallest building. It’s now dropped to twelve, but it’s still seriously impressive. Take the elevator up to the 103rd floor to stand on ‘the ledge’, one of the glass boxes that protrude out 412 metres above the street below. Probably best missed for those who are scared of heights.
233 S Wacker Dr, willistower.com

Other than hot dogs, Chicago is known (and loved) for its deep-dish pizzas. The joint serving the best pizza in town is a hot topic, but you can’t go wrong with a visit to Uno’s.
29 East Ohio, unos.com

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