Train
Flight
Stamford to Chicago
Updated: 29 May 2026
The distance from Stamford to Chicago is approximately 850 miles. Flying from LGA or JFK to O'Hare (ORD) is the fastest method, taking about 2.5 hours. Alternatively, you can take the train to NYC and then the Amtrak Lake Shore Limited to Chicago, which is a scenic 18-hour journey. Chicago is famous for its architecture, deep-dish pizza, and lakefront parks. Choose the flight for speed or the train for comfort.
Total Distance: 1,350 km driving, 1,200 km air distance.
Fastest Way
Non-stop flight from LGA to ORD.
Cheapest Way
Budget airlines from LGA to ORD.
Compare Stamford to Chicago Routes
|
Direct
|
Direct
|
|
|---|---|---|
| Duration | 18 hours | 2 hours 30 mins |
| Avg Price | $120-$300 | $150-$350 |
| Operator | Amtrak | United Airlines |
| Route | NYC Penn Station to Chicago Union Station | LGA/JFK to ORD |
| Tip | Book a sleeper car for a comfortable overnight trip. | O'Hare is well-connected to downtown via the Blue Line. |
Travel Tips
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Airport AccessThe Blue Line train is the cheapest way to downtown.
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WeatherChicago is the 'Windy City'; dress in layers.
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PizzaTry deep-dish pizza at Lou Malnati's or Giordano's.
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WalkingThe downtown area is very walkable.
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BookingBook flights at least three weeks ahead.
Safety Tips
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Urban SafetyStick to well-populated tourist areas.
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Public TransitThe 'L' train is safe; keep your belongings close.
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EmergencyDial 911 for any assistance.
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Night TravelUse ride-sharing apps late at night.
People Also Ask
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Is the train worth it?Only if you enjoy scenic, slow travel.
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How long is the flight?About 2.5 hours.
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Which airport is best?ORD is the main hub.
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Is Chicago safe?Yes, in the main tourist districts.
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What is the best month?June or September.
Quick Info
- From Stamford, Connecticut, United States
- To Chicago, Illinois, United States
-
Modes
Best Time to Travel
Summer for festivals and lakefront activities.
Things to Do in Chicago
1
Millennium Park
See the famous Cloud Gate sculpture, also known as 'The Bean'.
2
Art Institute of Chicago
Explore one of the oldest and largest art museums in the country.
3
Willis Tower
Step onto the Skydeck for a view from the 103rd floor.
4
Navy Pier
Enjoy the Ferris wheel, shops, and restaurants on the lakefront.
Tags
Stamford to Chicago
flights to Chicago
LGA to ORD
Amtrak to Chicago
Chicago travel
Stamford to IL
fastest way to Chicago
Chicago attractions
