East Stroudsburg
East Stroudsburg
Chicago
Chicago
Flight Driving

East Stroudsburg to Chicago

Updated: 28 May 2026

The distance from East Stroudsburg to Chicago is approximately 780 miles. Driving takes about 12 to 13 hours via I-80 West. Alternatively, you can drive to Newark Liberty International Airport and take a direct flight to Chicago O'Hare or Midway. This is a significant journey crossing multiple states, making flying the most practical option for most travelers.

Total Distance: 1,250 km driving distance; 1,050 km straight-line air distance.
Fastest Way
Flying is significantly faster, taking only a few hours compared to a full day of driving.
Cheapest Way
Flying can often be cheaper than the cost of fuel, tolls, and overnight lodging for a long drive.
Compare East Stroudsburg to Chicago Routes
Flight
Direct
Driving
Direct
Duration 2 hours 30 mins 12 hours
Avg Price $200 - $400 $150 in fuel and tolls
Operator United Airlines / American Airlines Personal Vehicle
Route Fly from Newark (EWR) to Chicago (ORD/MDW). I-80 West across PA, OH, and IN.
Tip Book flights at least 3 weeks in advance for the best prices. This is a long drive; plan for an overnight stop if necessary.
Travel Tips
  • Airport Transit
    Use the 'L' train to get from O'Hare to downtown Chicago.
  • Traffic
    Chicago traffic can be very heavy; use public transit whenever possible.
  • Parking
    Parking in downtown Chicago is very expensive; use public transit.
  • Food
    Don't leave without trying authentic Chicago-style deep-dish pizza.
  • Planning
    Check the weather before you go; Chicago winters can be very harsh.
Safety Tips
  • Awareness
    Stay alert in busy tourist areas and on public transit.
  • Vehicle Safety
    If driving, park in secure garages and keep valuables out of sight.
  • Emergency
    Keep your phone charged and have a roadside assistance plan.
  • Navigation
    Use GPS to navigate the city's grid system.
People Also Ask
  • How long is the flight to Chicago?
    Approximately 2.5 hours.
  • Is there a train to Chicago?
    You can take Amtrak from NYC, but it is a very long journey.
  • What is the best way to get there?
    Flying is the most efficient and practical method.
  • Are there tolls?
    Yes, expect tolls on the I-80 route if driving.
  • Is Chicago safe?
    Yes, tourist areas are generally safe and well-patrolled.
Quick Info
  • From East Stroudsburg, Pennsylvania, United States
  • To Chicago, Illinois, United States
  • Modes
Best Time to Travel

Late spring and early autumn offer the best weather for exploring the city.

Things to Do in Chicago
1
Millennium Park
Visit the iconic Cloud Gate sculpture and enjoy the beautiful gardens.
2
Art Institute of Chicago
Explore one of the oldest and largest art museums in the United States.
3
Willis Tower
Take in the panoramic views of the city from the Skydeck.
4
Navy Pier
Enjoy the rides, shops, and restaurants along the shores of Lake Michigan.
Tags
East Stroudsburg to Chicago flight to Chicago driving to Chicago Poconos to Chicago Chicago travel guide Illinois travel East Stroudsburg transit Midwest travel