Train
Flight
Malden to Chicago
Updated: 28 May 2026
The journey from Malden to Chicago covers about 980 miles. The fastest way to travel is by flight from Logan Airport to O'Hare or Midway, which takes about 2.5 hours. Alternatively, you can take the Amtrak Lake Shore Limited from South Station, which is a scenic 20-hour journey. Chicago is famous for its architecture, deep-dish pizza, and vibrant lakefront.
Total Distance: Driving distance 1,600 km, straight-line air distance 1,550 km.
Fastest Way
Flight from Logan to O'Hare.
Cheapest Way
Flight if booked in advance.
Compare Malden to Chicago Routes
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Direct
|
Direct
|
|
|---|---|---|
| Duration | 20 hours | 2 hours 30 mins |
| Avg Price | $150 - $500 | $150 - $400 |
| Operator | Amtrak | United / American / JetBlue |
| Route | South Station to Union Station via Lake Shore Limited. | Logan Airport (BOS) to O'Hare (ORD) or Midway (MDW). |
| Tip | The train offers a unique way to see the American landscape. | O'Hare is well-connected to downtown via the Blue Line. |
Travel Tips
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Flight BookingBook your flights at least three weeks in advance.
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Airport TransitUse the CTA trains to get from the airport to downtown.
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Chicago TransitUse a Ventra card for all CTA buses and trains.
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WalkingDowntown Chicago is very walkable and grid-based.
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FoodTry the deep-dish pizza; it is a Chicago staple.
Safety Tips
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Crowd SafetyStay aware of your surroundings in tourist-heavy areas.
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Night TravelStick to well-lit areas in the city at night.
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EmergencyChicago has a large police presence; call 911 for emergencies.
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AwarenessKeep your belongings secure in crowded transit hubs.
People Also Ask
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Is the train better than flying?Flying is much faster; the train is for the experience.
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How do I get to Logan Airport?Take the Blue Line or Silver Line from South Station.
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Is Chicago safe?Yes, it is safe in the tourist and downtown areas.
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Can I drive?Yes, but it is a very long drive (15+ hours).
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What is the best way to travel?Flying is the most practical option.
Quick Info
- From Malden, Massachusetts, United States
- To Chicago, Illinois, United States
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Modes
Best Time to Travel
Summer for the best weather and lakefront activities.
Things to Do in Chicago
1
Millennium Park
Home to the famous Cloud Gate sculpture. It is a must-see in downtown Chicago.
2
Art Institute of Chicago
One of the oldest and largest art museums in the US. It is world-renowned.
3
Willis Tower
Offers incredible views of the city from the Skydeck. It is an iconic skyscraper.
4
Navy Pier
A popular destination with rides, shops, and restaurants. It is great for families.
Tags
Malden to Chicago
flights Boston to Chicago
Amtrak Boston to Chicago
travel to Chicago
Chicago travel guide
train to Chicago
commute to Chicago
Massachusetts to Illinois
