Is it better to fly or take the train to Chicago?

Flying is significantly faster, while the train offers a scenic, relaxed experience.

How far is Tarrytown from Chicago?

It is approximately 800 miles by road.

Does Amtrak go directly to Chicago?

Yes, the Lake Shore Limited runs directly from New York Penn Station to Chicago Union Station.

What is the best airport for Tarrytown residents?

Westchester County Airport (HPN) is the most convenient local option.

Are there direct flights to Chicago from HPN?

Yes, United Airlines operates direct flights from HPN to O'Hare.

Tarrytown

Chicago

Train Flight

Tarrytown to Chicago

Updated: 29 May 2026

The journey from Tarrytown to Chicago spans approximately 800 miles. You can take the Metro-North to Grand Central, then the subway to Penn Station for the Amtrak Lake Shore Limited. Alternatively, fly from Westchester County Airport (HPN) directly to O'Hare (ORD). The train route follows the scenic Hudson River line before heading west through the Mohawk Valley. Flights offer the fastest transit, while the train provides a classic American rail experience. Expect varied weather patterns when crossing from the Hudson Valley into the Great Lakes region.

Total Distance: 1,280 km driving; 1,150 km air distance.

Fastest Way

Direct flight from Westchester County Airport to O'Hare International Airport takes roughly 3 hours.

Cheapest Way

Amtrak coach seating is the most economical if booked at least three weeks in advance.

Compare Tarrytown to Chicago Routes

	Train Direct	Flight Direct
Duration	20 hours	3 hours
Avg Price	$120 - $300	$200 - $500
Operator	Amtrak	United Airlines
Route	Penn Station to Union Station via Lake Shore Limited	HPN to ORD
Tip	Book a roomette for overnight comfort on this long-haul route.	Arrive at HPN 90 minutes early as security lines can fluctuate.

Travel Tips

Transit Card
Purchase a Ventra card immediately upon arrival for easy access to the CTA 'L' trains and buses.
Dress in Layers
Chicago's lakefront winds can make temperatures feel significantly colder than the forecast suggests.
Dining Reservations
Book tables for popular West Loop restaurants at least two weeks in advance.
Walking Shoes
Chicago is a very walkable city, especially in the Loop and along the Magnificent Mile.
Airport Transport
Use the Blue Line train from O'Hare to reach downtown Chicago for a fraction of the cost of a taxi.

Safety Tips

Stay Aware
Keep your belongings secure in crowded tourist areas like Navy Pier.
Stick to Well-Lit Areas
Avoid walking alone in unfamiliar neighborhoods late at night.
Use Official Taxis
Only use licensed ride-share apps or marked taxi cabs from designated stands.
Emergency Numbers
Save the local non-emergency police line in your phone for quick reference.