Train
Flight
Old Greenwich to Chicago
Updated: 30 May 2026
The journey from Old Greenwich to Chicago covers 1,300 kilometers. The fastest way is to fly from LaGuardia (LGA) or JFK to O'Hare (ORD) or Midway (MDW) airport, taking about 2.5 hours. Alternatively, you can take an Amtrak train from NYC, which is a scenic but long journey. Chicago is famous for its architecture, deep-dish pizza, and lakefront parks.
Total Distance: 1,300 km driving, 1,150 km air distance.
Fastest Way
Flight, 2.5 hours, direct.
Cheapest Way
Flight, if booked in advance.
Compare Old Greenwich to Chicago Routes
|
Direct
|
Direct
|
|
|---|---|---|
| Duration | 20 hours | 2.5 hours |
| Avg Price | 150-300 USD | 150-350 USD |
| Operator | Amtrak | United / American |
| Route | Lake Shore Limited from NYC | LGA/JFK to ORD |
| Tip | A long but comfortable overnight journey. | O'Hare is the most common destination. |
Travel Tips
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AirportO'Hare is well-connected to downtown by the 'L' train.
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TransportThe 'L' train is the best way to get around.
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WeatherChicago winters are very cold; pack accordingly.
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DiningTry authentic deep-dish pizza.
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WalkingDowntown is very walkable.
Safety Tips
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Urban SafetyStay in well-populated tourist areas.
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DrivingParking in downtown is expensive.
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EmergencyDial 911 for immediate help.
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Night TravelUse ride-sharing apps at night.
People Also Ask
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Is there a direct train?Yes, the Lake Shore Limited from NYC.
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How long is the flight?About 2.5 hours.
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What is Chicago known for?Architecture and pizza.
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Is it safe?Generally safe in tourist areas.
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Best way to travel?Flight is the most convenient.
Quick Info
- From Old Greenwich, Connecticut, United States
- To Chicago, Illinois, United States
-
Modes
Best Time to Travel
Summer for festivals and lakefront activities.
Things to Do in Chicago
1
Millennium Park
Home to the famous Cloud Gate sculpture, also known as 'The Bean'.
2
Art Institute of Chicago
A world-renowned art museum with an extensive collection of impressionist works.
3
Willis Tower
Offers incredible views of the city from its Skydeck.
4
Navy Pier
A popular destination with shops, restaurants, and a Ferris wheel.
Tags
Old Greenwich to Chicago
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LGA to ORD
JFK to ORD
Chicago travel guide
Old Greenwich to Illinois
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