Train
Flight
Allston to Chicago
Updated: 28 May 2026
The distance from Allston to Chicago is approximately 1,500 kilometers. Flying from Logan International Airport (BOS) to O'Hare (ORD) or Midway (MDW) is the most practical method, taking about 2.5 hours. Alternatively, the Amtrak Lake Shore Limited runs from South Station to Chicago Union Station, taking about 22 hours. Chicago is a major cultural and economic hub in the Midwest.
Total Distance: 1,500 km driving, 1,550 km air distance.
Fastest Way
Flight at 2.5 hours.
Cheapest Way
Flight if booked in advance.
Compare Allston to Chicago Routes
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Direct
|
Direct
|
|
|---|---|---|
| Duration | 22 hours | 2 hours 30 mins |
| Avg Price | $150 - $400 | $180 - $350 |
| Operator | Amtrak Lake Shore Limited | United Airlines / American Airlines |
| Route | South Station to Union Station | BOS to ORD |
| Tip | Book a roomette for a more comfortable overnight experience. | O'Hare is well-connected to the city via the Blue Line train. |
Travel Tips
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Airport TransitUse the CTA Blue Line from O'Hare to get downtown cheaply.
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Train StationUnion Station is in the heart of downtown Chicago.
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WalkingChicago is very walkable, especially the downtown Loop area.
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DiningTry the famous deep-dish pizza at local institutions like Lou Malnati's.
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WeatherChicago winters are very cold; pack accordingly if visiting then.
Safety Tips
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General SafetyStay in well-populated areas, especially at night.
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Public TransitThe CTA is generally safe, but stay aware of your surroundings.
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EmergencyDial 911 for any emergencies.
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Tourist AreasBe aware of pickpockets in crowded tourist spots like Navy Pier.
People Also Ask
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Is flying faster?Yes, significantly faster than the train.
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Is the train comfortable?Yes, especially if you book a sleeper car.
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Which airport is best?O'Hare (ORD) has more flight options.
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Do I need a car?No, public transit is excellent in Chicago.
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How do I get to South Station?Take the Green Line to Park Street and transfer to the Red Line.
Quick Info
- From Allston, Massachusetts, United States
- To Chicago, Illinois, United States
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Modes
Best Time to Travel
May to September for pleasant weather and lakefront activities.
Things to Do in Chicago
1
Millennium Park
See the iconic Cloud Gate sculpture, also known as 'The Bean'. It is a must-visit for any tourist.
2
Art Institute of Chicago
Explore one of the oldest and largest art museums in the country. It houses famous works like 'American Gothic'.
3
Navy Pier
Enjoy the lakefront views, rides, and restaurants. It is a popular spot for families.
4
Willis Tower
Go to the Skydeck for incredible views of the city from the 103rd floor.
Tags
Allston to Chicago
flights to Chicago
Amtrak to Chicago
Boston to Chicago travel
cheapest way to Chicago
Chicago travel guide
Lake Shore Limited
Allston transit
