Is the train worth it?

Yes, for the scenic route along the Great Lakes.

How long is the flight?

Approximately 2.5 hours of flight time.

Are there direct trains?

Yes, the Lake Shore Limited is direct from NYC.

Yes, the downtown area is very pedestrian-friendly.

What is the best time to visit?

Summer offers the best weather for outdoor activities.

New York

Chicago

Train Flight

New York to Chicago

Updated: 28 May 2026

The route from New York to Chicago is a major transit corridor connecting the two largest cities in the US. Flying is the most efficient, with frequent flights from LGA, JFK, and EWR to ORD or MDW taking about 2.5 hours. Amtrak operates the Lake Shore Limited, a scenic 19-hour train journey that follows the Hudson River and the shores of Lake Erie. Driving via I-80 takes approximately 13 hours. Each mode offers a unique way to experience the transition from the East Coast to the Midwest.

Total Distance: Driving distance 1,250 km, straight-line air distance 1,150 km.

Fastest Way

Direct flight from LGA to ORD is the fastest, taking 2.5 hours.

Cheapest Way

Budget airlines often offer flights for under $100 if booked in advance.

Compare New York to Chicago Routes

	Train Direct	Flight Direct
Duration	19 hours	2 hours 30 mins
Avg Price	$120 - $300	$100 - $250
Operator	Amtrak	United Airlines
Route	Penn Station to Union Station Chicago.	LGA to ORD.
Tip	The Lake Shore Limited offers beautiful views of the Hudson River.	Choose O'Hare (ORD) for more flight options and better transit links.

Travel Tips

Airport Transit
Use the 'L' train in Chicago to get from O'Hare to downtown cheaply.
Train Comfort
Bring a neck pillow and blanket for the overnight train journey.
Driving Route
If driving, be prepared for tolls on the Pennsylvania Turnpike.
Packing
Chicago is known as the 'Windy City'; bring a windbreaker or warm coat.
Booking
Book flights at least two weeks ahead for the best prices.

Safety Tips

Urban Safety
Stay in well-lit, populated areas when exploring both cities at night.
Train Safety
Keep your belongings secure while sleeping on the train.
Driving Safety
Avoid driving during heavy snowstorms in the Midwest winter.
Public Transit
Keep your wallet in a front pocket while riding crowded subways.