Train
Flight
Kittery to Chicago
Updated: 28 May 2026
The distance from Kittery to Chicago is approximately 1,600 kilometers. The most practical way to travel is by flying from Boston Logan International Airport (BOS) to Chicago O'Hare (ORD) or Midway (MDW). Alternatively, you can take the Amtrak Downeaster to Boston and connect to the Lake Shore Limited train to Chicago. Flying takes about 3 hours, while the train journey takes over 20 hours. Chicago is a major cultural and architectural hub.
Total Distance: 1,600 km driving, 1,500 km air distance.
Fastest Way
Flying is significantly faster, taking only 3 hours in the air.
Cheapest Way
Flying is often cheaper than the train if booked in advance.
Compare Kittery to Chicago Routes
|
Connecting
|
Direct
|
|
|---|---|---|
| Duration | 24 hours | 3 hours |
| Avg Price | 180-400 USD | 200-400 USD |
| Operator | Amtrak | United/American/JetBlue |
| Route | Downeaster to Boston, then Lake Shore Limited to Union Station. | BOS to ORD/MDW. |
| Tip | The train offers a scenic, albeit long, journey through the Northeast. | Book flights from Boston Logan for the most direct options. |
Travel Tips
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Airport TransitUse the 'L' train system to get from O'Hare airport to downtown Chicago quickly.
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WeatherChicago weather can change rapidly; pack layers regardless of the season.
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ArchitectureTake an architecture river cruise to see the city's famous skyline from the water.
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DiningTry the famous deep-dish pizza at one of the city's many iconic pizzerias.
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BookingUse flight comparison sites to find the best deals from Boston Logan.
Safety Tips
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City AwarenessStay in well-lit, populated areas, especially at night.
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Public TransitKeep your belongings secure while riding the 'L' train.
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EmergencyKnow the location of your hotel and the nearest police station.
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WalkingBe cautious when crossing busy intersections in the downtown area.
People Also Ask
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Is it better to fly or take the train?Flying is much faster and often cheaper.
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How long is the flight?Approximately 3 hours.
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Is the train scenic?Yes, the Lake Shore Limited offers beautiful views of the Great Lakes.
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How do I get to Boston airport?You can drive or take a bus from Kittery.
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Is Chicago walkable?Yes, the downtown area is very pedestrian-friendly.
Quick Info
- From Kittery, Maine, 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 the city.
Things to Do in Chicago
1
Millennium Park
Home to the iconic Cloud Gate sculpture, also known as 'The Bean'. It is a must-see for every visitor.
2
Art Institute of Chicago
One of the oldest and largest art museums in the country, featuring famous works like 'American Gothic'.
3
Willis Tower
Offers incredible views of the city from the Skydeck. The glass floor is a thrilling experience.
4
Navy Pier
A popular waterfront destination with rides, restaurants, and boat tours of Lake Michigan.
Tags
Kittery to Chicago
flights to Chicago
train to Chicago
travel from Maine to Illinois
Chicago travel guide
Kittery transport
Boston to Chicago flight
Amtrak to Chicago
