Is there a direct train?

No, you must transfer in New York City.

How long is the flight?

The flight takes about 2.5 hours.

Where does the train arrive?

Trains arrive at Chicago Union Station.

Tourist areas are generally safe, but always remain aware of your surroundings.

Yes, but it is a very long drive, taking over 14 hours.

Danbury

Chicago

Train Flight

Danbury to Chicago

Updated: 28 May 2026

The distance from Danbury to Chicago is approximately 1,300 kilometers. Flying is the most practical and fastest method, typically involving a trip to a major airport like JFK, LaGuardia, or Bradley International. The flight time is about 2.5 hours. Alternatively, taking the train is a long-distance journey that requires a transfer in New York City and can take over 20 hours. Chicago is a major cultural and economic hub, famous for its architecture, museums, and deep-dish pizza.

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

Fastest Way

Flying is the fastest, taking about 2.5 hours of flight time.

Cheapest Way

Booking flights in advance is often cheaper than long-distance train travel.

Compare Danbury to Chicago Routes

	Train Connecting	Flight Direct
Duration	22 hours	2 hours 30 mins
Avg Price	$150 - $400	$200 - $500
Operator	Amtrak	United Airlines, American Airlines
Route	Metro-North to NYC, then Amtrak Lake Shore Limited to Chicago Union Station.	Flight from JFK/LGA/BDL to Chicago O'Hare (ORD).
Tip	The train journey is scenic but very long; consider a sleeper car for comfort.	Book flights in advance to secure the best rates.

Travel Tips

Airport Transit
Use the CTA Blue Line to get from O'Hare to downtown Chicago quickly and cheaply.
Weather
Chicago weather can change rapidly; dress in layers.
Dining
Try the local deep-dish pizza; it is a must-do experience.
Booking
Use travel aggregators to compare flight prices across different airlines.
Walking
Downtown Chicago is very walkable, but use the 'L' train for longer distances.