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 $606 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 $472. You can even find prices in October for less than $472, 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
$382 - $701
Route
Depart
Return
Price
Chicago MidwayAnchorage
MDW - ANC
MDWANC
Chicago Midway
Thu 5/30
1 stop8h 19m
Anchorage
Sun 6/30
1 stop15h 10m
Chicago MidwayAnchorage
MDW - ANC
MDWANC
Chicago Midway
Tue 5/28
2 stops10h 21m
Anchorage
Sun 6/2
1 stop7h 55m
Chicago MidwayAnchorage
MDW - ANC
MDWANC
Chicago Midway
Wed 5/29
1 stop9h 27m
Anchorage
Sun 6/2
1 stop7h 55m
Chicago MidwayAnchorage
MDW - ANC
MDWANC
Chicago Midway
Sat 6/8
2 stops27h 12m
Anchorage
Sun 6/16
1 stop15h 09m
Chicago MidwayAnchorage
MDW - ANC
MDWANC
Chicago Midway
Sat 9/28
1 stop10h 26m
Anchorage
Tue 10/1
2 stops13h 23m
Chicago MidwayAnchorage
MDW - ANC
MDWANC
Chicago Midway
Sat 6/8
2 stops22h 25m
Anchorage
Sun 6/16
2 stops12h 39m
Chicago MidwayAnchorage
MDW - ANC
MDWANC
Chicago Midway
Sat 6/8
2 stops27h 12m
Anchorage
Thu 6/13
2 stops28h 28m
Chicago MidwayAnchorage
MDW - ANC
MDWANC
Chicago Midway
Thu 6/6
3 stops42h 09m
Anchorage
Thu 6/13
2 stops28h 07m
Chicago MidwayAnchorage
MDW - ANC
MDWANC
Chicago Midway
Thu 7/4
3 stops42h 36m
Anchorage
Sun 7/7
2 stops27h 01m
No data available for this route at this time. Please check back soon.
Crew
Food
Entertainment
Overall
Boarding
Comfort
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.
Crew
Food
Entertainment
Overall
Boarding
Comfort
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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