The New York/Chicago Corridor: The Starting Itinerary
Below is a sample itinerary designed to inspire your journey. All elements — from accommodations to experiences — can be tailored to match your travel style and preferences.
*AVAILABLE ALSO WITH THE REVERSED ITINERARY
Day 1 — New York City
Arrive in New York City and enjoy a private airport transfer to your hotel. After check-in, the rest of the day is intentionally light—perfect for unwinding, settling in, and easing into the rhythm of the city.
Night: New York City, 4-star superior hotel (preferred network), with an optional upgrade to 5-star luxury.
Day 2–3 — New York City
Enjoy two full days to explore NYC at your own pace. If this is your first time, we can arrange curated touring to help you experience the highlights efficiently. If you already know the city, use these days to discover new openings, visit museums you haven’t seen yet, explore neighborhoods, and enjoy the city’s energy between dining and sightseeing.
Night: New York City, 4-star superior hotel (preferred network), with an optional upgrade to 5-star luxury.
Day 4 — New York City → Philadelphia → Amish Country → Washington, D.C.
Today you’ll pick up your rental SUV and begin heading south. Enjoy a curated stop in
Philadelphia (perfect for a short, efficient historic-core visit), then continue through
Amish Country for a slower-paced,
scenic contrast before arriving in Washington, D.C. in the evening.
Driving guide (approx.):
- New York City → Philadelphia: ~1 hr 45 min (98 mi / 158 km)
- Amish Country visit: allow a couple of hours
- Amish Country → Washington, D.C.: ~2 hr 30 min (119 mi / 192 km)
Night: Washington, D.C., 4-star superior hotel (preferred network), with an optional upgrade to 5-star luxury.
Day 5 — Washington, D.C.
Enjoy a full day exploring the capital. Highlights can include the
National Mall memorials, select Smithsonian museums,
Capitol Hill, views of the White House area, and (if desired)
Arlington National Cemetery—all paced to your interests and comfort level.
Night: Washington, D.C., 4-star superior hotel (preferred network), with an optional upgrade to 5-star luxury.
Day 6 — Washington, D.C. → Shenandoah National Park → Lexington, Virginia
Leave Washington, D.C. and head south for a full day in nature. We recommend entering Shenandoah National Park from the
Front Royal Entrance (North Gate) (approx. 72 miles / 116 km from D.C.) and driving south along
Skyline Drive toward Rockfish Gap (South Entrance)—a spectacular route known for its scenic overlooks, rolling ridgelines, and peaceful viewpoints.
After exiting the park, continue toward Lexington, VA, staying on the
Blue Ridge Parkway for a portion of the drive—one of America’s most iconic scenic roads, stretching through Virginia and North Carolina.
Driving guide (approx.):
- Skyline Drive within the park: ~107 miles / 172 km (around 3 hrs + stops)
- Total day: ~249 miles / 400 km (around 5 hrs driving, plus scenic stops)
Night: Around Lexington, Virginia, 4-star superior hotel (preferred network), with an optional upgrade to a boutique 5-star, if available.
Day 7 — Lexington, Virginia → Lexington, Kentucky
Today you’ll head west into
Kentucky, crossing into the heart of Bluegrass Country. This is a longer drive day, so we recommend a relaxed morning, comfortable pacing, and a few well-timed stops.
Kentucky is celebrated for its
horse heritage,
bourbon culture, and wide-open landscapes—an ideal transition from East Coast history into classic American heartland character.
Driving guide (approx.): ~360 miles / 579 km (about 6 hrs)
Night: Lexington, Kentucky, 4-star hotel (preferred network) or boutique luxury Hotel.
Day 8 — Lexington, Kentucky → Louisville
Enjoy a slower-paced day focused on Lexington, often considered the
heart of American horse country. This is the ideal place to experience the atmosphere of the Bluegrass region, known worldwide for equestrian tradition and refined rural landscapes.
Later, continue to
Louisville—home of the
Kentucky Derby and a natural base for bourbon-country flavor, dining, and city culture.
Driving guide (approx.): Lexington → Louisville is ~1 hr 15 min (traffic-dependent)
Night: Louisville, 4-star superior hotel (preferred network), with an optional upgrade to 5-star luxury.
Day 9 — Louisville → St. Louis, Missouri
Spend the morning enjoying Louisville at your own pace—historic districts, riverfront views, and time for any curated add-ons—then continue west to St. Louis, a
classic Mississippi River city with a strong cultural identity and excellent food scene.
Driving guide (approx.): ~261 miles / 420 km (about 4.5 hrs)
Night: St. Louis, 4-star superior hotel (preferred network) or boutique historic-style property.
Day 10 — St. Louis, Missouri
Enjoy a relaxed day in St. Louis, set along the banks of the
Mississippi River. This is a great moment in the itinerary to slow the pace: explore a few key neighborhoods, enjoy riverfront views, and take advantage of the city’s culinary scene.
Optional curated upgrades (available on request):
- A guided city experience focused on architecture, history, or music culture
- Museum planning and timed-entry support
- A refined food-focused evening (reservations + neighborhood pairing)
Night: St. Louis, 4-star superior hotel (preferred network) or boutique historic-style property.
Day 11 — St. Louis → Chicago, Illinois
Today is the final major drive as you head north to
Chicago. We recommend breaking the journey with a meaningful mid-day stop.
A great option is
Springfield, Illinois—known for its connection to
President Abraham Lincoln—for a cultural pause and lunch. You can also incorporate a nostalgic slice of Americana with a stop at historic
Route 66 points of interest (including the Chain of Rocks Bridge, time permitting).
Arrive in Chicago by late afternoon, check in, and settle in for the final city chapter of the trip.
(Vehicle return/drop-off logistics depend on your rental plan and city routing.)
Driving guide (approx.): ~5 hrs / 298 miles (480 km), plus stops
Night: Chicago, 4-star superior hotel (preferred network), with an optional upgrade to 5-star luxury.
Day 12–13 — Chicago
Two full days to experience Chicago at the pace and style you prefer. We recommend a balanced plan that mixes signature highlights with time to simply enjoy the city’s neighborhoods, dining, and lakeside energy.
Top experiences to consider (available on request):
- Architecture-focused touring (on foot and/or by river cruise)
- Skyline viewpoints and lakefront moments
- Museum priorities based on your interests
- Neighborhood discovery with a curated food angle
Night: Chicago, 4-star superior hotel (preferred network), with an optional upgrade to 5-star luxury.
Day 14 — Chicago departure (End of services)
Enjoy a free morning for a final stroll, a relaxed breakfast, or last-minute shopping. Check out of your hotel and transfer to the airport.
Included: Private airport transfer (as selected)
End of services.
Route overview: New York to Chicago at a glance
Let’s design your New York to Chicago Journey
From skyline icons in New York City to the architectural energy of Chicago, this itinerary is all about contrasts—and the stories that connect them. Along the way, we weave in Philadelphia and Washington, D.C., scenic drives through Shenandoah, and the cultural flavor of the heartland from Kentucky’s Bluegrass region (Lexington & Louisville) to the Mississippi River charm of St. Louis, with the option to add a nostalgic stretch of Route 66 in Illinois.
No two travelers experience this corridor the same way, and that’s exactly how we plan it. With local insight, trusted partners, and a refined approach to pacing, we tailor your route, hotels, and experiences around what matters most to you—history and museums, food and music, scenic drives, or a slower, more comfort-forward rhythm.
Ready to start planning? Send us your preferred dates and travel style, and we’ll craft a personalized New York-to-Chicago road trip designed around your priorities.
