There are 5 ways to get from Chicago to Sitka by plane, car ferry, or train
Select an option below to see step-by-step directions and to compare ticket prices and travel times in Rome2Rio's travel planner.
Fly Chicago Midway International Airport to Sitka Rocky Gutierrez Airport
best- Fly from Chicago Midway International Airport (MDW) to Sitka Rocky Gutierrez Airport (SIT)plane MDW - SIT
26h 40m$214–907Fly Chicago O'Hare International Airport to Sitka Rocky Gutierrez Airport
cheapest- Fly from Chicago O'Hare International Airport (ORD) to Sitka Rocky Gutierrez Airport (SIT)plane ORD - SIT
11h 2m$154–657Fly Chicago O'Hare International Airport to Juneau International Airport, car ferry
- Fly from Chicago O'Hare International Airport (ORD) to Juneau International Airport (JNU)plane ORD - JNU
- Take the car ferry from Juneau to Ferry Terminal - Sitkacarferry
22h 21m$216–798Train to South Bend, fly to Sitka Rocky Gutierrez Airport
- Take the train from Van Buren St. to South Bend Airporttrain
- Fly from South Bend (SBN) to Sitka Rocky Gutierrez Airport (SIT)plane SBN - SIT
26h 12m$285–1,116Train to General Mitchell International Airport, fly to Sitka Rocky Gutierrez Airport
- Take the train from Chicago Union Station to Milwaukeetrain
- Fly from General Mitchell International Airport (MKE) to Sitka Rocky Gutierrez Airport (SIT)plane MKE - SIT
14h 42m$326–1,420
Chicago Midway International Airport (MDW) to Sitka Rocky Gutierrez Airport (SIT) flights
Questions & Answers
The cheapest way to get from Chicago to Sitka is to fly which costs $150 - $700 and takes 11h 2m.
The fastest way to get from Chicago to Sitka is to fly which takes 11h 2m and costs $150 - $700.
The distance between Chicago and Sitka is 2350 miles.
It takes approximately 26h 40m to get from Chicago to Sitka, including transfers.
Sitka is 3h behind Chicago. It is currently 2:50 PM in Chicago and 11:50 AM in Sitka.
There are two+ hotels available in Sitka.
What companies run services between Chicago, IL, USA and Sitka, AK, USA?
Southwest Airlines, Alaska Airlines, Inc., and Delta fly from Chicago Midway International Airport (MDW) to Sitka Rocky Gutierrez Airport (SIT) 4 times a day.
- Website
- alaskaair.com
Flights from Chicago Midway International Airport to Sitka Rocky Gutierrez Airport via Seattle
- Ave. Duration
- 31h 43m
- When
- Every day
- Estimated price
- $210–900
Flights from Chicago Midway International Airport to Sitka Rocky Gutierrez Airport via Portland, Seattle
- Ave. Duration
- 24h 13m
- When
- Tuesday, Wednesday, Thursday, Friday, and Sunday
- Estimated price
- $220–950
Flights from Chicago Midway International Airport to Sitka Rocky Gutierrez Airport via Omaha, Seattle
- Ave. Duration
- 27h 18m
- When
- Monday, Wednesday, Thursday, Friday, and Sunday
- Estimated price
- $210–900
Flights from Chicago Midway International Airport to Sitka Rocky Gutierrez Airport via Spokane, Seattle
- Ave. Duration
- 27h 58m
- When
- Monday, Thursday, and Friday
- Estimated price
- $210–900
Flights from Chicago Midway International Airport to Sitka Rocky Gutierrez Airport via Bozeman, Seattle
- Ave. Duration
- 28h 48m
- When
- Monday, Thursday, and Friday
- Estimated price
- $210–900
Flights from Chicago Midway International Airport to Sitka Rocky Gutierrez Airport via General Mitchell International Airport, Seattle
- Ave. Duration
- 28h 48m
- When
- Monday, Thursday, and Friday
- Estimated price
- $210–900
Flights from Chicago O'Hare International Airport to Sitka Rocky Gutierrez Airport via Seattle
- Ave. Duration
- 8h 18m
- When
- Every day
- Estimated price
- $150–650
Flights from Chicago O'Hare International Airport to Juneau International Airport via Seattle
- Ave. Duration
- 11h 47m
- When
- Every day
- Estimated price
- $160–650
Flights from Chicago O'Hare International Airport to Juneau International Airport via Anchorage
- Ave. Duration
- 16h 2m
- When
- Every day
- Estimated price
- $200–800
Flights from South Bend to Sitka Rocky Gutierrez Airport via Chicago O'Hare International Airport, Seattle
- Ave. Duration
- 22h 18m
- When
- Monday, Thursday, Friday, and Sunday
- Estimated price
- $270–1,100
Flights from South Bend to Sitka Rocky Gutierrez Airport via Las Vegas, Seattle
- Ave. Duration
- 23h 20m
- When
- Thursday and Sunday
- Estimated price
- $320–1,300
Flights from South Bend to Sitka Rocky Gutierrez Airport via Dallas/Ft.Worth, Seattle
- Ave. Duration
- 23h 35m
- When
- Monday, Thursday, and Friday
- Estimated price
- $320–1,300
Flights from South Bend to Sitka Rocky Gutierrez Airport via Detroit, Seattle
- Ave. Duration
- 26h 43m
- When
- Every day
- Estimated price
- $290–1,200
Flights from South Bend to Sitka Rocky Gutierrez Airport via Atlanta, Seattle
- Ave. Duration
- 27h 13m
- When
- Monday, Tuesday, Wednesday, Thursday, Friday, and Sunday
- Estimated price
- $350–1,400
Flights from South Bend to Sitka Rocky Gutierrez Airport via Charlotte, Seattle
- Ave. Duration
- 27h 50m
- When
- Every day
- Estimated price
- $350–1,400
Flights from South Bend to Sitka Rocky Gutierrez Airport via Washington Dulles, Seattle
- Ave. Duration
- 30h 48m
- When
- Every day
- Estimated price
- $350–1,400
Flights from General Mitchell International Airport to Sitka Rocky Gutierrez Airport via Denver, Seattle
- Ave. Duration
- 10h 43m
- When
- Monday, Thursday, Friday, Saturday, and Sunday
- Estimated price
- $300–1,300
- Website
- delta.com
Flights from Chicago O'Hare International Airport to Juneau International Airport via Seattle
- Ave. Duration
- 13h 37m
- When
- Sunday
- Estimated price
- $160–650
Flights from Chicago O'Hare International Airport to Juneau International Airport via Minneapolis, Seattle
- Ave. Duration
- 12h 17m
- When
- Sunday
- Estimated price
- $160–700
- Phone
- +1 219-926-5744
- Website
- mysouthshoreline.com
Train from Van Buren St. to South Bend Airport
- Ave. Duration
- 1h 58m
- Frequency
- Every 2 hours
- Estimated price
- $13–15
- Schedules at
- mysouthshoreline.com
- Adults 14-64
- $13–15
Rome2Rio's guide to Amtrak
Contact Details
- Phone
- +1 800-872-7245
- Website
- amtrak.com
Train from Chicago Union Station to Milwaukee
- Ave. Duration
- 1h 29m
- Frequency
- Every 4 hours
- Estimated price
- $22–40
- Website
- https://www.amtrak.com/home.html
- Phone
- +1 800-642-0066
- dot.amhs.customer@alaska.gov
- Website
- dot.alaska.gov
Car ferry from Juneau to Ferry Terminal - Sitka
- Ave. Duration
- 9h 45m
- Frequency
- On demand
- Estimated price
- $35–120
- Website
- https://dot.alaska.gov
- Schedules at
- https://dot.alaska.gov/amhs/schedules.shtml
- Adult 12+
- $35–120
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