How long is the flight?

The flight time is approximately 2 hours and 15 minutes.

Is the train ride worth it?

Yes, if you enjoy scenic travel and have the time to spare.

What is the best way to get to HPN?

A ride-share or taxi is the most convenient way from Westport.

Like any major city, it has safe areas and areas to avoid; stay in tourist zones.

Do I need a car in Chicago?

No, the public transit system is excellent.

Westport

Chicago

Train Flight

Westport to Chicago

Updated: 31 May 2026

The journey from Westport to Chicago covers nearly 800 miles. The most practical way to travel is by flying from Westchester County Airport (HPN) to Chicago O'Hare (ORD), which takes about 2 hours in the air. Alternatively, you can take the Amtrak Lake Shore Limited from New York City for a long-distance rail experience. Chicago is a major cultural and culinary hub in the Midwest. This route transitions you from the Atlantic coast to the shores of Lake Michigan.

Total Distance: 1,300 km driving, 1,150 km air distance.

Fastest Way

Flying is significantly faster than any other mode of transport.

Cheapest Way

Budget airlines often offer the cheapest fares if booked well in advance.

Compare Westport to Chicago Routes

	Train Direct	Flight Direct
Duration	20 hours	2 hours 15 mins
Avg Price	$120 - $300	$150 - $400
Operator	Amtrak	United Airlines / American Airlines
Route	Amtrak Lake Shore Limited from NYC Penn Station to Chicago Union Station.	Flight from HPN to ORD.
Tip	Consider booking a sleeper car for a more comfortable overnight journey.	Book your flight at least three weeks in advance for the best rates.

Travel Tips

CTA Ventra Card
Use the Ventra card for easy access to the city's extensive 'L' train system.
Deep Dish Pizza
Try authentic Chicago-style deep dish pizza at a local institution like Lou Malnati's.
Lakefront Trail
Rent a bike and ride along the 18-mile trail for great views of Lake Michigan.
Weather
Chicago is known as the Windy City; dress in layers regardless of the season.
Architecture Tour
Take a river cruise to learn about the city's famous architectural history.

Safety Tips

Stay in Busy Areas
Stick to well-populated tourist districts like the Loop and River North.
Public Transit
Be aware of your surroundings when using the 'L' trains late at night.
Valuables
Keep your bags close and avoid displaying expensive items in public.
Emergency
Know the location of your hotel and keep a map of the city handy.