Are there direct flights from Maui to Chicago?

Yes, United Airlines offers direct flights from OGG to ORD.

How do I get from ORD to downtown?

The CTA Blue Line train is the most convenient and affordable option.

What is the best time to visit Chicago?

Summer months offer the best weather for outdoor activities.

Do I need a car in Chicago?

No, public transit is excellent and parking is expensive.

How long is the flight from Kihei?

The flight time is approximately 9 hours.

Kihei

Chicago

Flight

Kihei to Chicago

Updated: 01 Jun 2026

To reach Chicago from Kihei, fly from Kahului Airport (OGG) to O'Hare International Airport (ORD). The air distance is approximately 6,800 km. Upon arrival, the CTA Blue Line train provides a direct connection to downtown Chicago. This route takes you from the tropical Pacific to the heart of the Midwest.

Total Distance: Driving distance N/A; Air distance 6,800 km.

Fastest Way

Direct flight from OGG to ORD taking 9 hours.

Cheapest Way

Flight via United Airlines booked in advance.

Compare Kihei to Chicago Routes

Flight

Direct

Duration

9 hours

Avg Price

$350 - $800

Operator

United Airlines

Route

OGG to ORD

The Blue Line train is the most cost-effective way to reach the city.

Travel Tips

Public Transit
Use the CTA 'L' train system to get around the city easily.
Weather
Chicago winters are very cold; pack appropriately if visiting during that time.
Dining
Try the famous deep-dish pizza; it is a Chicago staple.
Walking
Chicago is a very walkable city; wear comfortable shoes.
Architecture
Take an architecture boat tour on the Chicago River for a unique perspective of the city.

Safety Tips

General Safety
Chicago is generally safe, but stay aware of your surroundings in urban areas.
Night Safety
Avoid walking alone in isolated areas at night.
Emergency
Dial 911 for any emergency assistance.
Public Transit
Stay alert when using public transportation late at night.