Travelers have found it’s best to book a flight 42 days in advance to save up to 27% compared to booking the same week of travel. As your travel date approaches, the cost of this flight route may potentially increase. While opting to book 42 days out may not be an option for all, there are still additional ways to secure a deal in the near future. You might find a flight from Chicago Midway Airport to Alaska 1-2 weeks in advance for as low as $322, or $600 for flights within the next 24 hours.
The best pricing can be found in the month of October. Prices to Alaska from Chicago Midway Airport average $471. You can even find prices in October for less than $471, as users have found deals to Alaska from as low as $196. The month of June appears to be one of the more expensive times to travel to Alaska from Chicago Midway Airport. Flying in the targeted month can save you up to 33%.
Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Chicago Midway Airport to Alaska as you normally would.
Fly from
Fly to
Budget
$404 - $753
Route
Depart
Return
Price
Chicago MidwayFairbanks
MDW - FAI
MDWFAI
Chicago Midway
Mon 8/19
1 stop9h 53m
Fairbanks
Thu 8/29
1 stop7h 27m
Chicago MidwayFairbanks
MDW - FAI
MDWFAI
Chicago Midway
Tue 8/20
2 stops14h 08m
Fairbanks
Thu 8/29
1 stop7h 27m
Chicago MidwayAnchorage
MDW - ANC
MDWANC
Chicago Midway
Sat 6/22
1 stop12h 20m
Anchorage
Fri 6/28
1 stop14h 19m
Chicago MidwayFairbanks
MDW - FAI
MDWFAI
Chicago Midway
Tue 8/20
2 stops17h 43m
Fairbanks
Mon 8/26
2 stops11h 56m
Chicago MidwayAnchorage
MDW - ANC
MDWANC
Chicago Midway
Thu 7/4
2 stops12h 56m
Anchorage
Fri 7/12
1 stop14h 05m
Chicago MidwayAnchorage
MDW - ANC
MDWANC
Chicago Midway
Sat 8/24
1 stop12h 15m
Anchorage
Fri 8/30
2 stops15h 26m
Chicago MidwayAnchorage
MDW - ANC
MDWANC
Chicago Midway
Sat 8/24
2 stops11h 45m
Anchorage
Sun 9/1
2 stops13h 37m
Chicago MidwayAnchorage
MDW - ANC
MDWANC
Chicago Midway
Thu 6/27
3 stops42h 09m
Anchorage
Sun 7/7
2 stops27h 01m
Chicago MidwayAnchorage
MDW - ANC
MDWANC
Chicago Midway
Thu 6/27
3 stops42h 09m
Anchorage
Sun 7/7
3 stops27h 01m
No data available for this route at this time. Please check back soon.
Boarding
Entertainment
Food
Comfort
Overall
Crew
Reviews
When I was going to board, one of the staff members told me that I could not board with my passport bag because it was tree items and I would need to check a bag. This was so stupid ! The bag was small. So I had to put my things in my pockets, put the funny bag inside the other bag. Then go throw it. Then in the plane put everything back again in my funny bag.
Boarding
Entertainment
Food
Comfort
Overall
Crew
Reviews
When I was going to board, one of the staff members told me that I could not board with my passport bag because it was tree items and I would need to check a bag. This was so stupid ! The bag was small. So I had to put my things in my pockets, put the funny bag inside the other bag. Then go throw it. Then in the plane put everything back again in my funny bag.
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