When searching for a good deal, it’s best to be prepared for potential fluctuations in price. We recommend booking at least 46 days in advance, which can save you up to 91% on flights from Alberta to Chicago Midway Airport compared to booking the week you need them. Waiting 46 days out may not be for everyone, so we have options available for flights within the next two weeks, with the lowest price starting at $333. For sooner than that we have options available in the next 3 days from $539.
The best pricing can be found in the month of January. Prices to Chicago Midway Airport from Alberta average $389. You can even find prices in January for less than $389, as users have found deals to Chicago Midway Airport from as low as $215. The month of July appears to be one of the more expensive times to travel to Chicago Midway Airport from Alberta. Flying in the targeted month can save you up to 27%.
When flying from Alberta 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
$223 - $463
Route
Depart
Return
Price
CalgaryChicago Midway
YYC - MDW
YYCMDW
Calgary
Sat 10/26
2 stops9h 13m
Chicago Midway
Tue 10/29
1 stop9h 44m
CalgaryChicago Midway
YYC - MDW
YYCMDW
Calgary
Thu 7/11
1 stop10h 00m
Chicago Midway
Mon 7/15
1 stop11h 32m
CalgaryChicago Midway
YYC - MDW
YYCMDW
Calgary
Wed 9/18
1 stop9h 25m
Chicago Midway
Tue 9/24
1 stop14h 50m
CalgaryChicago Midway
YYC - MDW
YYCMDW
Calgary
Tue 7/23
1 stop8h 50m
Chicago Midway
Fri 8/2
1 stop10h 36m
CalgaryChicago Midway
YYC - MDW
YYCMDW
Calgary
Thu 7/11
2 stops13h 45m
Chicago Midway
Mon 7/15
1 stop11h 32m
CalgaryChicago Midway
YYC - MDW
YYCMDW
Calgary
Tue 8/20
1 stop10h 03m
Chicago Midway
Mon 8/26
1 stop11h 27m
EdmontonChicago Midway
YEG - MDW
YEGMDW
Edmonton
Fri 10/25
2 stops10h 00m
Chicago Midway
Tue 10/29
2 stops13h 09m
EdmontonChicago Midway
YEG - MDW
YEGMDW
Edmonton
Sat 7/27
2 stops10h 17m
Chicago Midway
Sat 8/3
2 stops14h 04m
EdmontonChicago Midway
YEG - MDW
YEGMDW
Edmonton
Thu 7/25
1 stop20h 01m
Chicago Midway
Sat 8/10
1 stop21h 39m
No data available for this route at this time. Please check back soon.
Crew
Boarding
Food
Overall
Entertainment
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
Boarding
Food
Overall
Entertainment
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
Boarding
Food
Overall
Entertainment
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
Boarding
Food
Overall
Entertainment
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.