Train
Flight
Medford to Chicago
Updated: 28 May 2026
The journey from Medford to Chicago is about 1,000 miles. The most practical way is to fly from Boston Logan (BOS) to O'Hare (ORD) or Midway (MDW). This takes about 2.5 hours. You can also take the Amtrak Lake Shore Limited train from Boston South Station, which is a 20-hour journey. Chicago is famous for its architecture, deep-dish pizza, and lakefront parks.
Total Distance: Driving distance 1,600 km, straight-line air distance 1,500 km.
Fastest Way
Direct flight from BOS to ORD takes about 2.5 hours.
Cheapest Way
Budget airlines offer the lowest fares for this route.
Compare Medford to Chicago Routes
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Direct
|
Direct
|
|
|---|---|---|
| Duration | 20 hours | 2 hours 30 mins |
| Avg Price | $100 - $300 | $150 - $400 |
| Operator | Amtrak | United Airlines |
| Route | Boston South Station to Chicago Union Station. | BOS to ORD. |
| Tip | The train is a long but scenic journey. | Direct flights are frequent and fast. |
Travel Tips
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CTAUse the 'L' train to get around; it is very efficient.
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WalkingDowntown is very walkable; wear comfortable shoes.
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BookingBook architecture tours in advance.
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AppsUse the Ventra app for transit payments.
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DiningTry the local deep-dish pizza.
Safety Tips
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Urban SafetyStay aware of your surroundings in tourist areas.
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L-Train SafetyStay in well-lit areas on platforms.
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WeatherBe prepared for cold winters; pack warm gear.
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EmergencyDial 911 for any emergency.
People Also Ask
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Is the train better than flying?Flying is much faster and often cheaper.
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How long does it take?About 2.5 hours by flight.
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Is Chicago walkable?Yes, the downtown area is very walkable.
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What is the best way to get around?The 'L' train is the most efficient method.
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Do I need a car?No, a car is not necessary in Chicago.
Quick Info
- From Medford, Massachusetts, United States
- To Chicago, Illinois, United States
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Modes
Best Time to Travel
May to September for pleasant weather and festivals.
Things to Do in Chicago
1
Millennium Park
See the Bean sculpture. Enjoy the park's events.
2
Art Institute
Tour the world-class museum. See famous paintings.
3
Willis Tower
Go to the Skydeck. See the city from above.
4
Navy Pier
Walk the pier. Enjoy the rides and views.
Tags
Medford to Chicago flight
Boston to Chicago travel
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Medford travel
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