The New York/Chicago Corridor:
2 Weeks Through the MidWest

The New York/Chicago Corridor:
2 Weeks Through the MidWest

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Location: East Coast & The Midwest
Tour: Leisure
From: New York (or Chicago)
To: Chicago (or New York)
By: Private Car
New York City, Philadelphia, Washington DC, Shenandoah National Park, Kentucky, Missouri, Chicago
Tour Duration
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Why This Region?

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.




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.


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!

Map: Itinerary - The New York/Chicago Corridor On The Road

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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, but we can provide all the information and advice on the best and most convenient flights. We are here to help you in the search for international flights or if you need further help.