To save on the cost of your flight from Calgary to Chicago Midway Airport, book at least 21 days before your planned departure. Booking around this time can save you about 49% on the cost of this flight compared to booking a flight leaving this week. We have found prices from C$ 624 if you need a flight within two weeks. For flights within the next 72 hours, you can find tickets from as low as C$ 830.
Our data shows that November tends to be the cheapest month to fly to Chicago Midway Airport from Calgary. Users have commonly found prices around C$ 603 for the month, but tickets can be as low as C$ 289. Due to multiple factors, prepare for potentially higher prices in December.
Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Calgary to Chicago Midway Airport as you normally would.
Fly from
Fly to
Budget
C$ 379 - C$ 566
Route
Depart
Return
Price
CalgaryChicago Midway
YYC - MDW
YYCMDW
Calgary
Thu 23/5
1 stop9h 12m
Chicago Midway
Thu 30/5
2 stops14h 27m
CalgaryChicago Midway
YYC - MDW
YYCMDW
Calgary
Mon 3/6
1 stop8h 27m
Chicago Midway
Thu 13/6
1 stop17h 37m
CalgaryChicago Midway
YYC - MDW
YYCMDW
Calgary
Mon 3/6
1 stop8h 27m
Chicago Midway
Wed 12/6
2 stops11h 58m
CalgaryChicago Midway
YYC - MDW
YYCMDW
Calgary
Wed 5/6
1 stop15h 32m
Chicago Midway
Thu 13/6
1 stop17h 37m
CalgaryChicago Midway
YYC - MDW
YYCMDW
Calgary
Mon 3/6
1 stop8h 27m
Chicago Midway
Tue 11/6
1 stop16h 56m
CalgaryChicago Midway
YYC - MDW
YYCMDW
Calgary
Mon 3/6
1 stop8h 27m
Chicago Midway
Thu 13/6
2 stops18h 45m
CalgaryChicago Midway
YYC - MDW
YYCMDW
Calgary
Mon 3/6
1 stop8h 27m
Chicago Midway
Wed 12/6
1 stop16h 00m
CalgaryChicago Midway
YYC - MDW
YYCMDW
Calgary
Sun 19/5
1 stop9h 12m
Chicago Midway
Sat 25/5
2 stops12h 14m
CalgaryChicago Midway
YYC - MDW
YYCMDW
Calgary
Sat 11/5
1 stop8h 00m
Chicago Midway
Tue 14/5
2 stops16h 12m
No data available for this route at this time. Please check back soon.
Entertainment
Overall
Comfort
Crew
Food
Boarding
Reviews
Terrible flight crew that skipped our row for service multiple times.
Entertainment
Overall
Comfort
Crew
Food
Boarding
Reviews
Terrible flight crew that skipped our row for service multiple times.
Entertainment
Overall
Comfort
Crew
Food
Boarding
Reviews
Terrible flight crew that skipped our row for service multiple times.
Entertainment
Overall
Comfort
Crew
Food
Boarding
Reviews
Terrible flight crew that skipped our row for service multiple times.
Deals for Calgary to Midway flights are sourced from 900+ travel sites when you use Cheapflights. When all flight results come back, Cheapflights lets you sort and filter flights using different criteria to choose better, like price, airport, cabin class, and plenty of other options.
By finding flights from multiple airlines and providers at completely no cost, Cheapflights helps millions of users like you annually find the best flights to Midway from Calgary.
Yes, we can. To see specific flights from Calgary to Midway with no change fees, users can toggle flexible booking options after using the search form above to find flights.
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