Train
Flight
Herndon to Chicago
Updated: 28 May 2026
The journey from Herndon to Chicago spans over 700 miles. The most practical way to travel is by flying from Dulles International Airport (IAD) to O'Hare International Airport (ORD), which takes about 2 hours. Alternatively, you can take the Amtrak Capitol Limited from Union Station in D.C. for a long-distance rail experience. Chicago is famous for its architecture, deep-dish pizza, and lakefront parks.
Total Distance: 1,100 km driving, 950 km air distance.
Fastest Way
Flying from IAD to ORD is the fastest, taking 2 hours in the air.
Cheapest Way
Flying on a budget carrier is usually the most cost-effective option.
Compare Herndon to Chicago Routes
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Direct
|
Direct
|
|
|---|---|---|
| Duration | 16 hours | 2 hours |
| Avg Price | $150-$400 | $180-$350 |
| Operator | Amtrak Capitol Limited | United Airlines |
| Route | Union Station to Union Station | IAD to ORD |
| Tip | Book a sleeper car for a more comfortable overnight journey. | O'Hare is well-connected to downtown via the Blue Line train. |
Travel Tips
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Public TransitThe 'L' train system is the best way to navigate Chicago; get a Ventra card.
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WeatherChicago is known as the 'Windy City'; dress in layers regardless of the season.
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DiningTry deep-dish pizza at Lou Malnati's or Giordano's.
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WalkingThe downtown area is very walkable, especially along the Chicago Riverwalk.
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Airport AccessThe Blue Line train runs 24/7 from O'Hare to downtown.
Safety Tips
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General SafetyStick to well-populated tourist areas, especially at night.
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Public TransitKeep your belongings secure on the 'L' trains.
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Night TravelUse rideshare services if traveling late at night in unfamiliar areas.
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EmergencyDial 911 for any emergency.
People Also Ask
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Is it better to fly or take the train?Flying is much faster, but the train is a unique experience.
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How long is the flight?The flight is about 2 hours.
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Where does the train arrive?The train arrives at Union Station in downtown Chicago.
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Is Chicago safe?Like any major city, stay aware of your surroundings and stick to tourist areas.
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Do I need a car?No, public transit is excellent and parking is expensive.
Quick Info
- From Herndon, Virginia, United States
- To Chicago, Illinois, United States
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Modes
Best Time to Travel
Late spring or early autumn to enjoy the city's outdoor spaces.
Things to Do in Chicago
1
Millennium Park
See the iconic Cloud Gate sculpture, also known as 'The Bean'.
2
Art Institute of Chicago
View world-class collections including Grant Wood's 'American Gothic'.
3
Willis Tower Skydeck
Step onto the glass ledge 103 floors up for a view of the entire city.
4
Navy Pier
Enjoy the Ferris wheel, boat tours, and lakefront views at this popular destination.
Tags
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