Tour Duration
Tour Type

What to expect from the NYC to Chicago Corridor OTR

Visit two of the most beautiful cities of the US -- Chicago and New York City! Especially if you love the contrast between modern v. old pre-war architecture, colorful skylines, Blues & Jazz Music, ethnic cuisines ... these two cities will know how to entertain you!

Why New York?

Whether this is your first time in the Big Apple, or you are a true "aficionado", returning every year, you will have 3 days in the city to explore what you haven't seen before or update yourself with the latest news, happenings and most recent openings. 

Why Chicago?

The capital of the Midwest overlooking the immense Michigan Lake that at times looks more like an ocean than a lake. A city famous for its music tradition, its peculiar architecture, Al Capone and much history of the early 20th century.

These two cities "fight" over many things -- the best pizza, the best music, the best skyline, the best sporting teams ... you get where I'm going? Thanks to this itinerary you will be able to experience both cities first-hand and decide for yourself who wins what!

In between these 2 great cities, a vast land, small towns, scenic routes, BBQ and lots of "Americana". This is a great Itinerary to explore the US beyond the Big Metropolis and experience the different cultures.

This itinerary is planned so you visit the region in 14 days.

When to plan your NYC to Chicago Vacation?

Since this Itinerary covers a vast area, and mostly up North  which is subjected to many Winter Storms and heavy Snowfalls, we recommend the Mid- Seasons -- Spring, especially late Spring and Fall.
Simply because you should have fewer chances to encounter snow and road closures, and because most of the territory you will explore will have mild-temperatures.

Summer is also a good option, of course, you will have to suffer the heat especially when you reach Kentucky & Missouri. Winter is simply not recommended for this itinerary.

Medical Insurance

International Travelers? We certainly recommend adding a Medical Insurance while traveling in the US as medical bills are quite expenses. When picking a company, check that there is a 24/7 costumer service and compare the prices of the various policies and the limitations.

International Flights

International flights are not included in the price of this package - we can help you book international and domestic flights.

Book your spot now

Book your spot now
See the available options by selecting a date from the calendar.




Day 1: NYC

Arrival in New York and Airport Transfer.

Check-in Hotel. Free time at your disposal.

Night: New York City Watson Hotel *** or similar

Day 2 & 3: NYC

Enjoy 2 full days to explore NYC. Depending on whether this is your first time in the city, or not, you might want to organize a couple of tours to be more effective with the time at your disposal.

On the other hand, if you are familiar with the city, you can enjoy these 2 days to visit new openings, maybe check out a couple of museums you haven't visited before or simply walk around and enjoy the city-scape.

Night: New York City Watson Hotel *** or similar

Day 4: NYC > Philadelphia (PA)

Today, you will pick-up your rental car and start heading South to visit Philadelphia and Amish County before proceeding towards the capital Washington DC for an evening arrival.

From New York to Philadelphia you have to drive for 1 hour and 45 minutes (98 miles (ca. 158 km)). For visiting the Amish county reckon a couple of Hours, then from there to Washington a 2 hours and half drive (119 miles (ca. 192 km))

Night: Washington, DC Washington Hampton Inn Union Station*** or similar

Day 5: Washington, District of Columbia

Enjoy a full day to visit DC with all the Memorials, Museums, Capitol Hill, the White House, and Arlington National Cemetery.

Night: Washington, DC Washington Hampton Inn Union Station*** or similar

Day 6: DC > Shenandoah National Park

Leave DC and head south towards the beautiful Shenandoah National Park. Today will be a day to be "lost" in mother nature. We recommend starting your visit from the "Front Royal Entrance" (North Gate) located approx. 72 miles (ca. 116 km) from DC and drive south within the park along the Skyline Drive to Rockfish Gap entrance Station (South Entrance) for approx. 3h09 and 107 miles (ca. 172 km) of scenic drives, look-out-points, and beautiful landscapes.

Once you exit the park, continue south for another 70 miles (ca. 113 km) staying right on the Blue Ridge Parkway to reach Lexington (VA). The Blue Ridge Parkway is considered one of the most beautiful scenic roads in the US, it extends for over 450 miles (ca. 724 km) from Virginia to North Carolina.

Today, your total drive will be approx. 249 miles (ca. 400 km) and a total of 5-hour behind the wheel.

Night: around Lexington (VA) Motel 6** or similar

Day 7: Lexington VA > Lexington, Kentucky

Today, you will start heading towards the State of Kentucky and the town of Lexington. There is a bit of road to cover, approx 360 miles (ca. 579 km) which will require about 6 hours.

Kentucky not only is the home state of 2 Presidents -- Lincoln and Bill Monroe, but it's also a great state for all outdoor adventure lovers, especially rafting, and known for its amazing Bourbon and BBQ.

Night: Lexington (KY) Hilton Garden Inn*** or similar

Day 8: Lexington (KY)

Take a day "off" from driving and go explore Lexington, also known as the "Capital of Horses" -- ever heard of the Kentucky Derby? The Derby takes place in Louisville (next stop) but Lexington brings on the tradition.

Night: Louisville Hilton Garden inn Louisville/northeast*** or similar

Day 9: Louisville > St. Louis, Missouri

Spend your morning in Louisville to visit the historic center, and continue towards St. Louis, Missouri. You will have approx. 4.30 hours (261 miles (ca. 420 km))

Night: St. Louis Red Lion Hotel *** or similar

Day 10: St. Louis, Missouri

Relax visiting the city of St. Louis right on the banks of the Mississippi River.

Night: St. Louis Red Lion Hotel *** or similar

Day 11: St. Louis > Chicago, Illinois

Today will be the last big "stretch' of driving that you will have to do. You will leave St. Louis to head towards Chicago. 5 hours (298 miles (ca. 480 km))

During your drive, we recommend stopping for lunch and for a visit to Springfield (IL), located approx. 100 miles (ca. 161 km) from St. Louis, and home of President Lincoln. Here, you can do a tour to learn more about President Lincoln.

Also, you can take the opportunity and stop by some historic and original sites of the iconic Route 66 including the famous Chain of Rocks Bridge.

Arrive in Chicago by late afternoon, check-in in Hotel and drop off car.

Night: Chicago Crowne Plaza Chicago West Loop*** or similar

Day 12 & 13: Chicago

Two full days to discover the beautiful Chicago.

You will have many attractions and things to do to choose from -- Panoramic Terraces, Museums, Architecture River Cruises, Walking Tours and more.

Night: Chicago Crowne Plaza Chicago West Loop*** or similar

Day 14: Chicago > End of Service

Free morning & Hotel Check-out,
Airport Transfer

End of Service.


    • 3 nights in Hotel in New York (central area) overnight stay only
    • 3 nights in Hotel in Chicago (central area) overnight stay only
    • 7 nights in Hotels On the Road (some with breakfast included)
    • Rental Car for 9 days. Type Buick Lacroix or similar - Unlimited mileage - CDW insurance


    • International/Domestic Flights
    • Park Admission / Attractions
    • Extended Car Insurance
    • Food and Drink
    • Everything not expressly indicated in "The Price Includes"


Price in Double Room
Starting at $ 1980.00 per person
Price in Triple Room
Starting at $ 1400.00 per person
Price in Quadruple Room
Starting at $ 1120.00 per person

Quote on request. Please use the Form below to send in a request. 

HOTEL ROOM: Single Rooms also available. Ask for the price!


  • Tipping in the United States is standard practice.
  • Generally, in the United States, accommodation in triple rooms is composed of two large beds or a large bed and a small bed and quadruple accommodation is decorated with two large beds.
  • Driving in the United States:
  • 1. Passing on the right is allowed and everyone does it, don't be intimidated by roads with more than five lanes.
  • 2.It is authorized (and obligatory) to turn right at a red light when there is a signal indicating it.
  • 3. As far as parking is concerned, check the times when you can leave your car there, never park in front of a fire hydrant (although there is no sign expressly prohibiting it). If the parking spaces have markings painted on the ground to delimit them, leave the car in the middle, even if the space seems huge. on your parking meter (check before paying as there are days of the week or times when it is not necessary to pay).
  • 4.Beware of tolls. They may be marked with the words toll or turnpike and usually have no barrier, so it is possible to pass the tolls without realizing it and be fined a few weeks later. Do not stay on the lanes indicated as reserved for “Fastrak” and have cash on hand, as in some tolls you can only pay in this way.
  • 5.Unless you want to have a fine and an awkward conversation with a Highway Patrol officer, it's best not to drive more than 5 or 10 miles above the speed limit. If the police end up stopping you despite everything, always keep your hands on the steering wheel and visible and don't even think about making jokes.
  • 6.We advise you to use a roadside assistance service and have a GPS.


Inclusions: As outlined in the "Included in the Price"
Exclusions: Everything else not specifically outlined in the "Included in the Price"
Discounted Rates: Baby, Kid, Senior and any other discounted Rate only applies to the specified Age-Limit. National ID required at Voucher Exchange as proof of Age.
Please Note:

Supplier & Local Operator Guarantee

“When purchasing your vacation activities don’t take a guess!”
Our team  carefully selected all local operators we collaborate with to ensure that our clients get the best possible service. All products we advertised in our website are offered by reliable suppliers that have been in business for several years and that are recognized to be leaders of excellence in the travel industry. In your travel documents, you will find complete information on the local operator, including contact numbers in case of an emergency. If you need additional help our customer service will be happy to further assist you, contact us!!

How to
get there


 Click on Map: Sample Itinerary - The New York/Chicago Corridor On The Road
We are your local Tour Agency in New York City
Tailored Vacations
Secure Bookings
Your peers love it!
Your vacation, your way!
Free cancellation

Planning a vacation shouldn't be stressful. We all know plans might change, that is why we offer free cancellation for most of our services and tours. *

*exclusions may apply, please refer to each tour.
be free!
Testimonials & Reviews
"Excellent firms don’t believe in excellence – only in constant improvement and constant change." – TOM PETERS
Based on 250 reviews
What They
Devonnec770 | TripAdvisor
5-Star Review on TripAdvisor
I’m the biggest fan of Fall activities, but haven’t had a chance to do anything beyond Apple Picking in NJ. I decided to take a last minute 2 day trip with a friend in Hudson Valley, but didn’t know where to start [...] Thankfully I was able to use New York Welcome to do the hard work for us [...]

From TripAdvisor - October 2021
Breanna A. | TripAdvisor
5-Star Review on TripAdvisor
Irene was a FANTASTIC tour guide! She was so knowledgeable about the area and was so patient with all our questions. We stopped to use the bathroom and we got coffee halfway through, she was so kind! It was a pleasure learning about Brooklyn from you!

From TripAdvisor - April 2022
We are social Join our community of over 350K Followers!
Manhattan - NYC
New York, NY 10029
My Cart
Secure Checkout in a few steps
Item cart added