Train
Flight
Old Saybrook to Chicago
Updated: 28 May 2026
Traveling from Old Saybrook to Chicago is best accomplished by flying from a nearby airport like Bradley International (BDL) or taking the train from New Haven to New York and then catching a long-distance Amtrak train. Flying is significantly faster, taking about 2.5 hours in the air, while the train journey is a multi-day experience. Chicago is a major cultural and business hub, making it a popular destination from the East Coast.
Total Distance: Driving distance 1,500 km, straight-line air distance 1,300 km.
Fastest Way
Flying from Bradley International (BDL) is the fastest way to reach Chicago.
Cheapest Way
Booking a flight in advance is often cheaper than a sleeper car on the train.
Compare Old Saybrook to Chicago Routes
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Connecting
|
Direct
|
|
|---|---|---|
| Duration | 22 hours | 2 hours 30 mins |
| Avg Price | 150-400 dollars | 200-500 dollars |
| Operator | Amtrak Lake Shore Limited | United, American, Southwest |
| Route | Train to NYC, then Lake Shore Limited to Chicago. | BDL to ORD or MDW. |
| Tip | The train offers a scenic and relaxing way to see the country. | Book flights from Bradley International for the easiest access. |
Travel Tips
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Airport TransitUse the 'L' train to get from O'Hare to downtown Chicago.
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WeatherChicago winters are very cold; pack accordingly.
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DiningTry the famous deep-dish pizza at local restaurants.
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BookingUse flight comparison sites to find the best deals.
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SafetyStay in well-populated areas of the city.
Safety Tips
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City SafetyBe aware of your surroundings in downtown areas.
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Public TransitUse the 'L' train during daylight hours if possible.
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ValuablesKeep your phone and wallet secure in crowded areas.
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EmergencyKnow the location of your hotel and local police stations.
People Also Ask
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Is it better to fly?Yes, flying is much faster and often more affordable.
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How long is the flight?About 2 hours and 30 minutes.
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Is there a direct train?No, you must transfer in New York City.
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What is the best airport?O'Hare (ORD) has more international and domestic flights.
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Is Chicago safe?Yes, stick to the tourist-friendly areas.
Quick Info
- From Old Saybrook, 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.
Things to Do in Chicago
1
Millennium Park
See the iconic Cloud Gate sculpture and enjoy the beautiful gardens.
2
Art Institute of Chicago
Explore one of the oldest and largest art museums in the country.
3
Willis Tower
Take in the views from the Skydeck, one of the tallest buildings in the world.
4
Navy Pier
Walk along the pier for entertainment, dining, and boat tours.
Tags
Old Saybrook to Chicago
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