Is the train faster than flying?

No, flying from HPN to ORD takes approximately 2.5 hours compared to 19 hours by train.

Where does the train arrive in Chicago?

The Amtrak Lake Shore Limited arrives at Chicago Union Station.

Do I need a car in Chicago?

No, Chicago has an extensive public transit system that covers most tourist destinations.

What is the best airport for downtown?

O'Hare (ORD) is connected via the Blue Line, while Midway (MDW) is connected via the Orange Line.

Are there direct flights from HPN?

Yes, American Airlines operates direct flights from Westchester County Airport to Chicago O'Hare.

Mount Kisco

Chicago

Train Flight

Mount Kisco to Chicago

Updated: 31 May 2026

The journey from Mount Kisco to Chicago spans approximately 1,300 kilometers. You can take the Metro-North Railroad to Grand Central Terminal, then transfer to Penn Station for the Amtrak Lake Shore Limited. Alternatively, fly from Westchester County Airport to O'Hare International Airport for a faster transit. The train route follows the historic New York Central Railroad corridor along the Hudson River. Expect scenic views of the Finger Lakes region if traveling by rail during daylight hours.

Total Distance: Driving distance 1,300 km, straight-line air distance 1,150 km.

Fastest Way

Flight from Westchester County Airport (HPN) to O'Hare (ORD) taking 2.5 hours.

Cheapest Way

Amtrak coach seating booked at least three weeks in advance.

Compare Mount Kisco to Chicago Routes

	Train Direct from NYC Penn Station	Flight Direct
Duration	19 hours	2 hours 30 mins
Avg Price	$120 - $350	$150 - $400
Operator	Amtrak Lake Shore Limited	American Airlines
Route	Empire Corridor to Chicago Union Station	HPN to ORD
Tip	Book a roomette for overnight comfort on this long-haul route.	Use the Westchester County Airport to avoid JFK or LaGuardia traffic.

Travel Tips

Transit Cards
Purchase a Ventra card for seamless access to the CTA 'L' trains and buses.
Airport Access
The Blue Line train provides direct, affordable access from O'Hare to the downtown Loop.
Dining
Try deep-dish pizza at Lou Malnati's or Giordano's for an authentic Chicago culinary experience.
Weather Prep
Chicago is known as the Windy City; always carry a windbreaker or layers regardless of the season.
Station Arrival
Arrive at Union Station at least 45 minutes before your train departure to navigate the terminal.

Safety Tips

Stay Aware
Stick to well-lit, populated areas in the downtown Loop and River North districts.
Public Transit
Keep your belongings secure and in front of you while riding crowded CTA trains.
Emergency Numbers
Dial 911 for any immediate emergency assistance within city limits.
Navigation
Use reputable ride-sharing apps rather than hailing street cabs late at night.