Train
Flight
Greenwich to Chicago
Updated: 30 May 2026
The journey from Greenwich to Chicago covers approximately 800 miles. The most practical way to travel is by flying from LaGuardia (LGA) or JFK to O'Hare (ORD) or Midway (MDW). Alternatively, you can take an Amtrak train from NYC, but it is a long, overnight journey. Flying takes about 2.5 hours, while the train takes 18+ hours. Flying is the standard choice for this route.
Total Distance: 1,300 km driving distance; 1,150 km straight-line air distance.
Fastest Way
Flying is the fastest method, taking only 2.5 hours.
Cheapest Way
Flying is usually cheaper and much faster than the train.
Compare Greenwich to Chicago Routes
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Direct
|
Direct
|
|
|---|---|---|
| Duration | 19 hours | 2 hours 30 minutes |
| Avg Price | $100-$200 | $150-$300 |
| Operator | Amtrak | United / American / Delta |
| Route | Penn Station to Union Station | LGA/JFK to ORD/MDW |
| Tip | Consider a sleeper car for the overnight journey. | Book flights in advance for the best rates. |
Travel Tips
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Airport ChoiceLGA and JFK are both accessible; check flight times and prices for both.
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TrafficTraffic to NYC airports can be heavy; allow extra time for your commute.
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PackingPack light for your flight to avoid baggage fees.
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TransportationUse the 'L' train system to get around Chicago easily.
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WeatherChicago can be very cold in the winter; dress accordingly.
Safety Tips
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Airport SafetyStay alert in busy airports and keep your belongings secure.
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Train SafetyIf taking the train, keep your belongings secure and be aware of your surroundings.
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Personal BelongingsKeep your valuables in a secure place while traveling.
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Night TravelStick to well-lit, populated areas when exploring Chicago at night.
People Also Ask
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Is there a direct flight?Yes, there are many direct flights from NYC airports to Chicago.
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How long is the flight?The flight takes about 2.5 hours.
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Is the train better?The train is only better if you enjoy scenic, long-distance travel.
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Are there tolls?Yes, there are many tolls on the driving route.
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What is the best way to travel?Flying is the most convenient and fastest option.
Quick Info
- From Greenwich, Connecticut, United States
- To Chicago, Illinois, United States
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Modes
Best Time to Travel
Late spring or early autumn for pleasant weather in Chicago.
Things to Do in Chicago
1
Millennium Park
See the iconic 'Bean' sculpture and enjoy the beautiful gardens and architecture.
2
Art Institute of Chicago
Explore one of the oldest and largest art museums in the country.
3
Willis Tower Skydeck
Get a stunning view of the city from the observation deck of one of the tallest buildings in the world.
4
Navy Pier
Enjoy the amusement park, restaurants, and boat tours on the shores of Lake Michigan.
Tags
Greenwich to Chicago flight
LGA to ORD
Chicago travel
Greenwich to Chicago train
Amtrak Lake Shore Limited
Midwest travel
Chicago vacation
flight to Chicago
