Is there a direct flight?

No, you will need to connect through a hub like Juneau or Seattle.

How long does it take?

About 10 hours including layovers.

Yes, flights from Alaska can be costly.

What is the best way?

Flying into ORD is the most convenient.

Do I need a passport?

No, both are in the United States.

Skagway

Chicago

Flight

Skagway to Chicago

Updated: 28 May 2026

Traveling from Skagway to Chicago is a long-distance journey that requires flying. You will typically fly from Skagway to Juneau, then connect to a flight to O'Hare International Airport (ORD). This journey takes you from the northern wilderness to the bustling city of Chicago.

Total Distance: Straight-line air distance 4,000 km.

Fastest Way

Flying is the only practical way to complete this journey in one day.

Cheapest Way

Flying into ORD is the most efficient and cost-effective method.

Compare Skagway to Chicago Routes

Flight

Connecting

Duration

10 hours

Avg Price

$600-$1,000

Operator

Alaska Airlines

Route

Skagway to Juneau (flight) then Juneau to Chicago (flight).

O'Hare International Airport (ORD) is well-connected to downtown via the Blue Line train.

Travel Tips

Airport Choice
Fly into O'Hare International Airport (ORD) for the best access to the city.
Transport
Use the Blue Line train to get from the airport to downtown Chicago.
Weather
Chicago is known for its cold winters; bring a warm coat and boots.
Booking
Book flights well in advance to secure the best rates.
Packing
Bring comfortable walking shoes for exploring the city.

Safety Tips

Flight Safety
Follow all airline safety protocols during your flight.
City Safety
Chicago is generally safe, but use standard precautions in urban areas.
Emergency
Keep your identification and travel documents accessible.
Road Safety
If driving in the city, be aware of heavy traffic on the expressways.