Is there a direct flight?

No, there are no direct flights from Maui to Chicago.

Which airport is better?

O'Hare (ORD) is the main hub, while Midway (MDW) is closer to downtown.

How do I get to downtown?

Take the Blue Line from O'Hare or the Orange Line from Midway.

What is the time difference?

Chicago is 5 hours ahead of Hawaii.

No, public transportation is excellent in Chicago.

Lahaina

Chicago

Flight

Lahaina to Chicago

Updated: 28 May 2026

To reach Chicago from Lahaina, you must fly from Kahului Airport (OGG) to O'Hare International Airport (ORD). The journey involves a connection on the mainland, typically in cities like Denver or Los Angeles. You will travel across the Pacific and the entire width of the United States. The total travel time is approximately 11 hours. Chicago serves as a major hub for the Midwest.

Total Distance: Driving distance 0 km (island); Air distance 6,800 km.

Fastest Way

Flight with a single connection, total time approximately 10 hours.

Cheapest Way

Flight via United or American Airlines with a connection.

Compare Lahaina to Chicago Routes

Flight

Connecting

Duration

11 hours

Avg Price

450-900 USD

Operator

United Airlines

Route

OGG to ORD via DEN or LAX.

Check for flights into Midway (MDW) if you prefer a smaller airport.

Travel Tips

CTA Trains
Use the 'L' train system to navigate the city efficiently.
Deep Dish Pizza
Try a slice of authentic Chicago deep-dish pizza at a local institution.
Lakefront Trail
Rent a bike and ride along the shores of Lake Michigan.
Weather
Be prepared for cold winters and windy conditions near the lake.
Architecture Tour
Take a boat tour on the Chicago River to see the city's famous architecture.

Safety Tips

Neighborhoods
Research neighborhoods before visiting, as some areas have higher crime rates.
Public Transit
Stay aware of your surroundings on the 'L' trains, especially late at night.
Emergency Services
Dial 911 for any emergency.
Pedestrian Safety
Follow traffic signals, as downtown intersections can be very busy.