route 66 usa travel

Chicago to New York Road Trip


Looking to go on a road trip in the U.S. on your next trip?  We have a sample itinerary for you, that we think that you are going to love!

Trip overview

Travel time: 12-14 hours
Number of days on road: 1-2
Driver skill level: easy

This is a great ‘entry level’ road trip, for those who are unfamiliar with driving on American roads, as most of the road signs are very clearly marked and the roads are easy to drive on.

We recommend renting a mid-size car with an automatic transmission and cruise control, as it will make it much easier for you to adjust to driving on the opposite side of the road.

Although you do not require an international driver’s permit to hire a car in the USA, it is highly recommended, as it will make for an easier overall journey. Click here for more information.

Food and culture

chicago deep dish style pizze







You can’t miss trying some of Chicago’s most famous food, such as their deep dish pizza or a hot dog.

Also, depending on the time of year, you might want to check out one of their live professional sporting teams, such as baseball, ice hockey, basketball or american football.

Once you’re ready to hit the road, your journey begins in Chicago- located on the shores of Lake Michigan and known for being the start of the infamous route 66 (which ends 13,000 km away when it hits the coast, at Los Angeles.)

Although you will be towards the other coast, you will have the pleasure of traveling accross Indiana, Ohio and Pennsylvania before a crossing the New York state line, until you reach the Big Apple.

On the road

route 66






It is recommended to overnight along the way, in order to break up your trip. Cleveland and Pittsburgh are two well-known American cities that offer great places to stay and eat, and experience American culture.

If you choose to stay in Pittsburgh, you can drive across the state to Philadelphia (don’t forget to grab a Philly Cheesesteak for lunch!) before a short drive to New York.

Pro tip!

Most car hire companies charge a ‘one-way’ fee when you pick up your car in one city, and drop it off in another city, especially when it is interstate.

Travel Guru exclusively offer no one-way fees on car hire in the USA! Our USA experts are here to assist you with planning the perfect trip. Contact us at 1300-785-533 or e-mail at and we will be happy to assist!

new york times square







Have you done a USA road trip or are planning to, soon?

We would love to hear from you!

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