To save up to 91% on this flight, we recommend booking at least 44 days prior to travel. The price may fluctuate and will likely increase closer to your departure date. Users on Cheapflights have found tickets from Anchorage to Chicago Midway Airport from $320 1-2 weeks out and tickets from $320 for flights departing within the next 72 hours.
Our data shows that October tends to be the cheapest month to fly to Chicago Midway Airport from Anchorage. 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.
When flying from Anchorage to Chicago Midway Airport, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.
Fly from
Fly to
Budget
$415 - $588
Route
Depart
Return
Price
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 stops14h 04m
AnchorageChicago Midway
ANC - MDW
ANCMDW
Anchorage
Fri 9/27
1 stop9h 24m
Chicago Midway
Sun 9/29
1 stop8h 43m
AnchorageChicago Midway
ANC - MDW
ANCMDW
Anchorage
Fri 10/11
2 stops14h 16m
Chicago Midway
Tue 10/15
2 stops13h 56m
AnchorageChicago Midway
ANC - MDW
ANCMDW
Anchorage
Sun 7/7
1 stop15h 08m
Chicago Midway
Sun 7/14
1 stop15h 19m
AnchorageChicago Midway
ANC - MDW
ANCMDW
Anchorage
Tue 8/13
2 stops12h 30m
Chicago Midway
Tue 8/27
1 stop8h 23m
AnchorageChicago Midway
ANC - MDW
ANCMDW
Anchorage
Tue 8/13
2 stops12h 30m
Chicago Midway
Tue 8/27
2 stops13h 49m
AnchorageChicago Midway
ANC - MDW
ANCMDW
Anchorage
Fri 10/11
1 stop9h 36m
Chicago Midway
Tue 10/15
1 stop8h 29m
AnchorageChicago Midway
ANC - MDW
ANCMDW
Anchorage
Tue 6/18
1 stop9h 36m
Chicago Midway
Fri 6/21
1 stop12h 08m
No data available for this route at this time. Please check back soon.
Entertainment
Food
Comfort
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
Food
Comfort
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.