To save on the cost of your flight from Alaska to Chicago Midway Airport, book at least 44 days before your planned departure. Booking around this time can save you about 91% on the cost of this flight compared to booking a flight leaving this week. We have found prices from $320 if you need a flight within two weeks. For flights within the next 72 hours, you can find tickets from as low as $320.
Our data shows that October tends to be the cheapest month to fly to Chicago Midway Airport from Alaska. Users have commonly found prices around $481 for the month, but tickets can be as low as $167. Due to multiple factors, prepare for potentially higher prices in February.
Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Alaska to Chicago Midway Airport as you normally would.
Fly from
Fly to
Budget
$410 - $509
Route
Depart
Return
Price
AnchorageChicago Midway
ANC - MDW
ANCMDW
Anchorage
Wed 8/14
1 stop9h 38m
Chicago Midway
Wed 8/28
1 stop8h 23m
AnchorageChicago Midway
ANC - MDW
ANCMDW
Anchorage
Mon 8/12
2 stops9h 42m
Chicago Midway
Tue 8/27
1 stop8h 23m
AnchorageChicago Midway
ANC - MDW
ANCMDW
Anchorage
Mon 8/12
2 stops9h 42m
Chicago Midway
Tue 8/27
2 stops13h 49m
AnchorageChicago Midway
ANC - MDW
ANCMDW
Anchorage
Fri 6/21
1 stop9h 36m
Chicago Midway
Mon 6/24
1 stop9h 51m
AnchorageChicago Midway
ANC - MDW
ANCMDW
Anchorage
Tue 8/13
1 stop8h 15m
Chicago Midway
Tue 8/27
2 stops13h 49m
AnchorageChicago Midway
ANC - MDW
ANCMDW
Anchorage
Fri 6/21
1 stop9h 36m
Chicago Midway
Mon 6/24
1 stop9h 51m
AnchorageChicago Midway
ANC - MDW
ANCMDW
Anchorage
Fri 10/11
2 stops13h 45m
Chicago Midway
Wed 10/16
1 stop8h 29m
FairbanksChicago Midway
FAI - MDW
FAIMDW
Fairbanks
Sat 8/31
1 stop10h 24m
Chicago Midway
Thu 9/5
1 stop14h 36m
FairbanksChicago Midway
FAI - MDW
FAIMDW
Fairbanks
Sat 8/31
2 stops13h 52m
Chicago Midway
Thu 9/5
1 stop14h 36m
No data available for this route at this time. Please check back soon.
Entertainment
Comfort
Food
Boarding
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.
Entertainment
Comfort
Food
Boarding
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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