Lewiston
Lewiston
Chicago
Chicago
Flight Driving

Lewiston to Chicago

Updated: 28 May 2026

The journey from Lewiston to Chicago covers approximately 1,100 miles. Driving involves taking I-95 South to I-90 West (the New York State Thruway and then the Indiana Toll Road). You will pass through Albany, Buffalo, Cleveland, and South Bend before reaching Chicago. Alternatively, you can fly from Portland (PWM) to Chicago O'Hare (ORD) or Midway (MDW). Driving is a long but straightforward trip across the Midwest. Be prepared for tolls on the Thruway and Toll Road.

Total Distance: 1,770 km driving distance, 1,500 km straight-line air distance.
Fastest Way
Flying is the fastest, taking about 6 hours including layovers.
Cheapest Way
Driving is the most cost-effective for groups, while bus travel is the cheapest for solo travelers.
Compare Lewiston to Chicago Routes
Flight
Connecting
Driving
Direct
Duration 6 hours 18 hours
Avg Price 250-450 USD 200-300 USD
Operator United/American Personal Vehicle
Route PWM to ORD/MDW via a hub like Newark or Philadelphia. I-95 S to I-90 W (New York State Thruway and Indiana Toll Road).
Tip Chicago airports are well-connected to the city via the CTA 'L' train system. The Thruway and Toll Road are toll roads; use E-ZPass for convenience.
Travel Tips
  • Driving
    The I-90 is a major highway; watch for speed traps near small towns.
  • Parking
    Chicago has ample parking; street parking is often free on weekends.
  • Transit
    The CTA 'L' train system covers the city and surrounding suburbs effectively.
  • Weather
    Chicago experiences significant snowfall; avoid driving during winter storms.
  • Booking
    Book your flight at least 3 weeks in advance for the best rates.
Safety Tips
  • Winter Driving
    If driving in winter, ensure your car is equipped with snow tires and an emergency kit.
  • Vehicle Prep
    Check your fluid levels and tire pressure before starting the long drive.
  • Emergency Kit
    Carry a blanket, flashlight, and water in case of a breakdown on the Toll Road.
  • Navigation
    Use a GPS with real-time traffic updates to avoid construction delays on I-90.
People Also Ask
  • Is Chicago safe?
    Yes, Chicago is generally safe, especially in the tourist-friendly areas like downtown.
  • How long is the drive?
    The drive is approximately 18 hours depending on traffic and stops.
  • Do I need a car in Chicago?
    A car is not recommended for downtown; public transit is excellent.
  • What is the best way to travel?
    Flying is the fastest, but driving is more flexible for sightseeing.
  • Are there direct trains?
    No, there is no direct train service from Lewiston to Chicago.
Quick Info
  • From Lewiston, Maine, United States
  • To Chicago, Illinois, United States
  • Modes
Best Time to Travel

May to September for pleasant weather and outdoor activities.

Things to Do in Chicago
1
Millennium Park
Home to the famous Cloud Gate sculpture (The Bean) and beautiful gardens.
2
Art Institute of Chicago
A world-class art museum with a vast collection of global art.
3
Navy Pier
A popular waterfront destination with shops, restaurants, and a Ferris wheel.
4
Willis Tower Skydeck
Enjoy panoramic views of the city from one of the tallest buildings in the world.
Tags
Lewiston to Chicago Maine to Illinois travel flight to Chicago driving to Chicago I-90 route travel tips Maine to Chicago fastest way to Chicago cheapest travel Maine