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16 Day Route 66 Self-Drive Eastern Adventure, Chicago to Grapevine, TX, via St Louis, Tulsa, Oklahoma City + more.

16 Day Route 66 Self-Drive Eastern Adventure, Chicago to Grapevine, TX, via St Louis, Tulsa, Oklahoma City + more.

16 Days

Kickstart the Mother Road as you zoom out of Chicago on a self-drive adventure on world-famous Route 66. Deep-dive into the heart of American culture, from Chicago to Grapevine, TX, driving cross-country through big-name cities & its fascinating lesser-known gems.

  • 16-Day Unforgettable Self-Drive Tour Of Route 66
  • 15 Nights In Modern Accommodations
  • 14-Day Car Hire
  • Breakfast Is Included Every Day

About This Trip

The Mother Road. The route to end all routes. While it is just a number, as soon as it is mentioned, images of freedom, endless skies and opportunity spring to mind. Route 66 winds from Chicago in the northeast, to Los Angeles on the west coast and on this self-drive trip, you will be exploring the eastern half. 


Dropping south from the skyscrapers of Chicago, you are heading into America’s heartland, a land with a rich and tumultuous history. Stopping off for some classic Americana, your route is dotted with aluminium-clad, neon lit diners, complete with pastel-padded booths and jukeboxes on the table. Many of those jukeboxes will be lined up with St Louis favourites and your exploration of this incredibly vibrant city will more than likely include music. Packed with venues, some of the greatest stars in history got their start in St Louis and the city still jams as hard as it did back then. 


From Missouri, you cross into your third State, Oklahoma where you have a couple of outstanding cities to explore. Often ignored by tourists, purely because of its location, Oklahoma is an incredible state and definitely one of the up-and-coming lists of travel sites worldwide. Tulsa has a smoking blend of barbeque, performing arts and social history and you should dive into each of these with equal relish. Oklahoma City is where the old world meets the new. With a cowboy heart and a large Native American population, this city is not to be missed. 


And as you speed into Texas on the final leg of your Route 66 adventure, your mind will be filled with a thousand images of the hidden American you have just discovered.


What's Included
16-Day Unforgettable Self-Drive Tour Of Route 66

Experience the freedom of this thrilling part of America as you explore hidden corners, marvel at stunning vistas and soak in every little bit of Americana.

15 Nights In Modern Accommodations

We have sourced the very best accommodation along Route 66 to ensure you have a comfortable bed at the end of your day's adventure.

14-Day Car Hire

From Chicago to Grapevine, TX you will be driving yourself along the famous Route 66, with daily instructions supplied, you can’t go wrong.

Breakfast Is Included Every Day

Start off your day with the famous all-American breakfasts served in your hotel. Usually enough to see you through to dinner time!

24/7 Passenger Service

No matter where you are or what you are stuck with, you can call our local, on-the-ground agent and they will help you with whatever you need.

Top Local Experiences

Included in your deal

Trip Itinerary


Where You'll Stay

Included in your deal

3* Accommodation - Twin/Double Share Basis

All hotels are subject to availability, the final hotel list will be provided to you 2-4 weeks prior to your departure. In the event that any of the hotels are unavailable, we will accommodate you in a hotel of a similar or higher standard, in a similar location to ensure your itinerary is able to run smoothly. Example hotels:


3* Chicago Whitehall - Chicago

3* St. Louis Hampton Inn - St. Louis 

3* Springfield Best Western Coach House - Springfield

3* Tulsa Hilton Garden Inn - Tulsa 

3* Oklahoma City Hilton Garden Inn - Oklahoma City 

3* Sulphur Best Western Plus - Chickasaw Inn

3* Grapevine Hyatt Place - Grapevine

A general list of amenities across all of our hotels is as follows:


  • Private double/twin share room with ensuite
  • Complimentary Wi-Fi
  • 24-hour reception
  • Bar
  • Restaurant
  • Pool
Single supplementNo
Max occupancy2 Adults
ShareableNot available
Bedding arrangementDouble/Twin Room
Other Info

There is nothing quite like a road trip. If discovery is your thing, then this is the only way to travel, especially in the USA. Route 66 is a bit of a conundrum. Its name is known all around the world, yet when you look at the places it visits, not many of them jump out as must-see destinations. There is no New York, Las Vegas or San Francisco. There is no Yellowstone, Yosemite or Great Lakes. So what makes this route so special?


The answer lies in the detail. This trip is not about ticking off the big showstoppers of America, this is about actually discovering what America is really like. Route 66 is not a tourist attraction, it is a stunning route that winds through some of the greatest landscapes in the country and visits the heart of real America. 


While your big cities on this trip, Chicago, St Louis, and Oklahoma City are all incredible, it is those lesser-known cities, Tulsa, Springfield and Sulphur that make the most memories. Here, you’ll feel like an explorer, but in a very odd way. While these are huge, wonderful cities, so few tourists ever come to this part of America, you feel like you are discovering the real country, actually seeing how people live, work and enjoy themselves. New York and LA are great, but this is the route to take if you want to see America at its most splendid.



This is a long trip, covering almost half of the USA. You start off by flying into The Windy City, Chicago. After a few days of exploring here, you will jump in your car and start heading down Route 66. Heading out of Illinois, you will enter Missouri and stop for a few nights in St Louis and a couple in Springfield. Then you are into Oklahoma, visiting Tulsa, Oklahoma City and Sulphur, before heading into Texas to spend your final nights in Grapevine before flying home from Dallas Fort Worth airport.



The hotels included in our Route 66 Adventure feature the following facilities:


  • 24-Hour Reception Desk
  • Complimentary Wi-Fi
  • Air conditioning
  • Restaurant
  • Wellness Centre
  • & Many More!

important info

Important Info.


  • Return international flights
  • Visas
  • International Driver's License
  • Any applicable rental car one-way drop fee
  • Optional activities/tours, personal expenses/transfers not mentioned
  • Travel Insurance
  • Tips & gratuities

Age restrictions

  • The minimum age for this tour is 20 years old


  • The minimum number for this tour to commence is two people
  • Double/twin share basis

Passport & visa requirements

  • All visitors require a passport with a minimum validity of 3 months beyond your return travel date is required for all passengers (including children and infants)
  • It is the visitor's responsibility to ensure they are holding the correct and current visa for the countries they are visiting
  • If the visitor is a non-Australian passport holder, a valid re-entry visa may be required
  • Important: Please start arranging your visa at least 6-8 weeks prior to departure to account for any delays due to consulate operating hours and processing times

Travel Insurance

  • We recommend you purchase travel insurance as soon as possible after purchasing this package

Health & vaccination

  • As border restrictions for countries begin to ease, being fully vaccinated against COVID-19 will maximise the number of locations you can visit. So whilst you are not legally required to be vaccinated, and it’s also not a requirement to travel with us, it will limit some of the countries that you can visit and may make it harder to travel for the next 12-18 months.
  • We highly recommend our travellers to look at the current travel restrictions of their destination, speak with a medical professional at least 30 days before departure or get in touch with our team for travel advice.
  • Health care such as a doctor’s surgery, dentist and optometrists may not always be accessible on this tour
  • It is advised that you ensure you have adequate health insurance cover as part of your travel insurance


  • Porterage is not included on this trip.


  • Tipping and gratuities are not included in the package and are at your own discretion

Fitness requirements

  • Travellers should have a good level of physical fitness and mobility. They must be able to partake unaided in their chosen activities/package tours/cruise etc. as outlined in the itinerary

Dietary requirements

  • Any dietary requirements must be received by DealsAway at least 30 days prior to your scheduled departure date. Failure to provide these details by this date may result in an inability to cater for your requirements
  • In most cases DealsAway can cater for special dietary requirements but please note that on occasion, this may not be possible due to location, lack of availability of ingredients, and other extenuating circumstances. It is always advised to carry supplies with you


  • As this is a self-drive tour, no transfers are necessary.


  • Any applicable pre-trip or tour documentation will be emailed to you prior to travelling. Should you have any queries regarding this please feel free to contact us directly via email at

DealsAway savings

  • The value and comparative savings have been determined based on published rack rates and the value of inclusions. Please be advised that rack rates may not be reflective of actual rates being charged, dependent on the timing and manner of your booking and therefore are only indicative of the level of saving

Itinerary amendments & changes

  • Occasionally our itineraries are updated prior to departure to incorporate improvements stemming from past travellers’ feedback as well as updates from our ground operators. Please note that while we operate successful tours in this region throughout the year, some changes may be necessary due to inclement weather, public holidays, common seasonal changes to timetables and transport routes, and unforeseen circumstances. This can happen with little notice so please be prepared for modifications to the route. The order and timing of included activities may also vary from time to time


  • All DealsAway trips are available on a request-only basis and are subject to availability. Once booked you should receive a payment confirmation and receipt via email, followed by a booking confirmation normally within 72hrs of making a booking, sometimes this can take a little longer subject to supplier delay
  • If you have not received your confirmation within 5 business days of payment confirmation please contact us immediately by email at
  • In the event that your trip is unavailable on the dates you have chosen, we will contact you by telephone to advise the next available dates


  • Any prices quoted exclude specific costs/measures which may be introduced at a later stage as a result of Government changes due to COVID-19 health and safety restrictions. DealsAway will inform its guests of these changes as soon as possible, these additional charges will be passed on by DealsAway to the guest



Name change or corrections

  • Name corrections may incur a fee
  • Name changes are not permitted
  • After bookings are fully paid, any amendment has to be requested in writing and incurs a $69 fee per person from our supplier, plus any additional costs and administrative expenses incurred in arranging the amendment

Date changes

  • Date changes are not permitted


  • Please refer to our booking conditions for all information on refunds

DealsAway reserves the right to modify prices for marketing and commercial reasons. Please note that full terms and conditions apply. Refer to the website's terms and conditions.


Car Hire


Each daily hire is based on a period of 24hrs rental, for example, a 2-day hire is the equivalent of 48hrs hire starting at the time the vehicle is picked up. If you require a longer rental time due to flight times or for any other reason then we advise you to purchase another day of rental hire. This can be added on request for an additional fee 

If you are late returning the vehicle this may result in a fee being charged to you from the car hire supplier directly

DealsAway takes no responsibility for any additional fees incurred to the customer by the car hire supplier


Minimum Driver Age

  • 20 years old
  • YOUNG DRIVER FEE - Where a renter is aged between 20-24 a young driver fee may apply  


One Way Drop Off

  • One-way fees/charges are not included and can vary depending on the provider
  • Applicable one-way fees/charges will be charged directly to the customer's nominated credit card by the car rental company
  • A one-way rental is the collection and return of a rental vehicle from one retail location to another.
  • One-way rentals are subject to availability and a service fee applies. This fee will vary depending on the class of vehicle and the pick-up and drop-off locations required


Additional Drivers

  • Additional Drivers are subject to availability and may incur an additional driver fee. 
  • Any additional driver fee will be charged directly to the customer's nominated credit card by the car rental company
  • Additional authorised drivers must be registered upon pick up of rental vehicle by the rental car team.


Car hire rates do not include:

  • One-way drop off fees
  • Additional driver fees
  • Out of hours pick up
  • Delivery & collection fees
  • Fuel purchase options
  • Additional equipment: child seats
  • Road tolls
  • Personal accident and effects cover
  • Premium roadside assist
  • Private parking charges

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