Award flights from Chicago Midway (MDW) to Calgary (YYC)

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In the last 30 days AwardTool saw award space on 5 programs for MDW→YYC. Lowest economy: 10,000 miles + $5.60 (American Airlines AAdvantage). Lowest business class: 20,500 miles + $5.60 (American Airlines AAdvantage). Lowest first class: 35,000 miles + $5.60 (American Airlines AAdvantage).

In economy, the lowest award seen was 10,000 miles + $5.60 with American Airlines AAdvantage, against 11,700 miles + $5.60 with Delta SkyMiles, the next-lowest program. With American Airlines AAdvantage, business class started at 20,500 miles + $5.60, about 2.1 times the points of its lowest economy award (10,000 miles + $5.60).

Every airport: Chicago to Calgary (YYC) award flights.

Prices observed Oct 13 – Nov 12, 2026; newest observation Nov 11, 2026, 23:39 UTC.

Page regenerated from the Nov 12, 2026 data snapshot (normally daily). Summary last changed Nov 12, 2026. Seats change quickly.

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Compare programs by cabin

The lowest one-way award each program showed in each cabin, sorted by points.

Economy

Program	Points + taxes	Stops	Airlines seen	Seats	Dates seen	Newest observation
American Airlines AAdvantageLowest observed	10,000 pts + $5.60	1 stopNonstop from 15,500 pts + taxes vary	AAAS	—	63	Nov 7, 2026, 05:30 UTC	See dates
Delta SkyMiles	11,700 pts + $5.60	2 stops	DLWS	2	76	Nov 11, 2026, 00:30 UTC	See dates
United MileagePlus	17,500 pts + $13.70	1 stopNonstop from 25,400 pts + taxes vary	ACUA	8	68	Nov 7, 2026, 05:30 UTC	See dates
Air France/KLM Flying Blue	18,000 pts + $21.80	1 stop	DLWS	4	68	Nov 11, 2026, 23:39 UTC	See dates
Qantas Frequent Flyer	20,700 pts + $5.60	Nonstop	AAASWS	1	41	Nov 7, 2026, 05:30 UTC	See dates

Business Class

Program	Points + taxes	Stops	Airlines seen	Seats	Dates seen	Newest observation
American Airlines AAdvantageLowest observed	20,500 pts + $5.60	1 stopNonstop from 38,000 pts + taxes vary	AA	—	63	Nov 7, 2026, 05:30 UTC	See dates
Qantas Frequent Flyer	43,600 pts + $5.60	Nonstop	AAWS	1	40	Nov 7, 2026, 05:30 UTC	See dates
United MileagePlus	45,000 pts + $13.70Mixed cabin	1 stopNonstop from 59,400 pts + taxes vary	ACUA	4	68	Nov 7, 2026, 05:30 UTC	See dates
Air France/KLM Flying Blue	55,000 pts + $31.70	1 stop	DL	2	3	Nov 11, 2026, 23:39 UTC	See dates

Not seen in business class: Delta SkyMiles.

First Class

Program	Points + taxes	Stops	Airlines seen	Seats	Dates seen	Newest observation
American Airlines AAdvantageLowest observed	35,000 pts + $5.60	1 stop	AAAS	—	63	Nov 7, 2026, 05:30 UTC	See dates
Delta SkyMiles	41,100 pts + $5.60	2 stops	DL	2	76	Nov 11, 2026, 00:30 UTC	See dates
United MileagePlus	61,000 pts + $5.60	1 stop	UA	9+	68	Nov 7, 2026, 05:30 UTC	See dates

Not seen in first class: Air France/KLM Flying Blue and Qantas Frequent Flyer.

Premium economy: not seen in the last 30 days.

Not seen means AwardTool hasn't observed this cabin on this route in the last 30 days. It doesn't mean the airline has no seats. Dates seen counts departure dates with an open award in that cabin at any price; newest observation is the latest time AwardTool saw one of them. Seats is the count the program reported when we observed it; some programs report at most 9.

Chicago Midway (MDW) to Calgary (YYC) at a glance

From: Chicago Midway International, Chicago, Illinois, United States (MDW)
To: Calgary International, Calgary, Canada (YYC)
Programs with award space seen: 5 of 5 programs tracked on this route
Nonstop award space seen: Yes, in economy and business class, via American Airlines AAdvantage, Qantas Frequent Flyer and United MileagePlus
Airlines seen on these awards: American Airlines (AA), Air Canada (AC), Alaska Airlines (AS), Delta Air Lines (DL), United Airlines (UA), WestJet (WS)
Departures with open awards: Nov 2026 to Aug 2027
Most dates with space: 76 of 76 departure dates checked (Delta SkyMiles, economy)
Latest departure with space: Aug 20, 2027
Observation window: Awards observed in the last 30 days
Distance: 1,396 miles (2,247 km), great-circle
Destination guide: Award flights to Calgary (YYC)

Observed award examples

Awards AwardTool observed for departures in the next 60 days (one way, per traveler)
Departure	Cabin	Program	Points + taxes	Seats	Stops	Observed (UTC)
Nov 25, 2026	Economy	Delta SkyMiles	11,700 pts + $5.60	2	2 stops	Nov 1, 2026, 20:56 UTC	Check this date
Dec 9, 2026	Business	Air France/KLM Flying Blue	55,000 pts + $31.70	2	1 stop	Nov 11, 2026, 23:39 UTC	Check this date
Nov 25, 2026	First	Delta SkyMiles	41,100 pts + $5.60	2	2 stops	Nov 1, 2026, 20:56 UTC	Check this date

Prices are one-way per traveler: the program's points or miles plus taxes and carrier fees in USD, as AwardTool observed them in the observation window. Award space changes constantly. A seat we saw may be gone, and space we haven't seen may exist. Always confirm with a live search before transferring points; most transfers can't be reversed.

Nonstop award space

Economy: nonstop from 15,500 miles via American Airlines AAdvantage, which showed nonstop space on 63 dates (3 programs had nonstop space).
Business class: nonstop from 38,000 miles via American Airlines AAdvantage, which showed nonstop space on 63 dates (3 programs had nonstop space).

Best months to fly from Chicago Midway (MDW) to Calgary (YYC) on points

Lowest prices among the dates we observed, by departure month. A record, not a forecast.
Month	Economy	Business	First
Nov 2026	11,700 pts + $5.60 (2 dates)SkyMiles	—	41,100 pts + $5.60 (2 dates)SkyMiles
Dec 2026	17,900 pts + $5.60 (2 dates)SkyMiles	55,000 pts + $31.70 (2 dates)Flying Blue	71,400 pts + $5.60 (2 dates)SkyMiles
Feb 2027	20,500 pts + taxes not reported (3 dates)Flying Blue	—	66,700 pts + taxes not reported (1 date)SkyMiles
Mar 2027	18,000 pts + taxes not reported (2 dates)SkyMiles	55,000 pts + taxes not reported (1 date)Flying Blue	53,900 pts + taxes not reported (2 dates)SkyMiles
May 2027	20,500 pts + taxes not reported (1 date)Flying Blue	—	—
Jun 2027	10,000 pts + taxes not reported (17 dates)AAdvantage	20,500 pts + taxes not reported (17 dates)AAdvantage	35,000 pts + taxes not reported (17 dates)AAdvantage
Jul 2027	10,000 pts + taxes not reported (30 dates)AAdvantage	20,500 pts + taxes not reported (30 dates)AAdvantage	35,000 pts + taxes not reported (30 dates)AAdvantage
Aug 2027	10,000 pts + taxes not reported (16 dates)AAdvantage	20,500 pts + taxes not reported (16 dates)AAdvantage	35,000 pts + taxes not reported (16 dates)AAdvantage

A month's taxes are those of an award AwardTool recorded at that month's lowest price for a departure that month. “Taxes not reported” means the data has none for that month; the award still has taxes and fees.

Points that transfer to these programs

US card points to program miles or points: ratio and typical transfer time
Program	Amex	Bilt	Capital One	Chase	Citi	Wells Fargo
Air France/KLM Flying Blue	1:1 · Instant	1:1 · Instant	1:1 · Instant	1:1 · Instant	1:1 · Instant	1:1 · Instant
American Airlines AAdvantage	—	—	—	—	1:1 · Instant	—
Delta SkyMiles	1:1 · Instant	—	—	—	—	—
Qantas Frequent Flyer	1:1 · Instant	—	1:1 · ~1-2 days	—	1:1 · Instant	—
United MileagePlus	—	1:1 · Instant	—	1:1 · Instant	—	—

Check current transfer bonuses. Most transfers can't be reversed.

Search, calendar and alerts from Chicago Midway (MDW) to Calgary (YYC)

Route calendar

Every departure date with open award seats on MDW→YYC for United MileagePlus and the other programs: a limited window on the free plan and 365 days with Pro.

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How many miles you need from Chicago Midway (MDW) to Calgary (YYC)

In economy, American Airlines AAdvantage had the lowest observed award, 10,000 miles + $5.60; see how many miles you need with American Airlines AAdvantage.
In business class, American Airlines AAdvantage had the lowest observed award, 20,500 miles + $5.60; see how many miles you need with American Airlines AAdvantage.
In first class, American Airlines AAdvantage had the lowest observed award, 35,000 miles + $5.60; see how many miles you need with American Airlines AAdvantage.

Questions about award flights from Chicago Midway (MDW) to Calgary (YYC)

How many points does it take to fly from Chicago Midway (MDW) to Calgary (YYC)?

The lowest economy award AwardTool has seen was 10,000 miles + $5.60 with American Airlines AAdvantage. American Airlines AAdvantage showed economy award space on 63 departure dates at any price (newest observation Nov 7, 2026, 05:30 UTC). The lowest business-class award AwardTool has seen was 20,500 miles + $5.60 with American Airlines AAdvantage. American Airlines AAdvantage showed business-class award space on 63 departure dates at any price (newest observation Nov 7, 2026, 05:30 UTC). Search live before transferring points.

Which loyalty programs had award space from Chicago Midway (MDW) to Calgary (YYC)?

5 programs in the last 30 days: American Airlines AAdvantage (economy 63 dates, business class 63 dates, first class 63 dates); Delta SkyMiles (economy 76 dates, first class 76 dates); Air France/KLM Flying Blue (economy 68 dates, business class 3 dates); Qantas Frequent Flyer (economy 41 dates, business class 40 dates); United MileagePlus (economy 68 dates, business class 68 dates, first class 68 dates). Dates count departure dates with an open award.

Can you fly nonstop from Chicago Midway (MDW) to Calgary (YYC) on points?

Yes. AwardTool observed nonstop award space in economy and business class, bookable via American Airlines AAdvantage, Qantas Frequent Flyer and United MileagePlus. The lowest nonstop award in economy was 15,500 miles with American Airlines AAdvantage.

How much are taxes and fees on award flights from Chicago Midway (MDW) to Calgary (YYC)?

Taxes and fees on each program's lowest award ranged in economy from $5.60 with AAdvantage (10,000 miles + $5.60) to $21.80 with Flying Blue (18,000 miles + $21.80); in business class from $5.60 with AAdvantage (20,500 miles + $5.60) to $31.70 with Flying Blue (55,000 miles + $31.70). Amounts are one way per traveler in USD and can differ on other dates and routings.

Which credit card points can book awards from Chicago Midway (MDW) to Calgary (YYC)?

American Express Membership Rewards: Delta SkyMiles (1:1), Air France/KLM Flying Blue (1:1), Qantas Frequent Flyer (1:1). Bilt Rewards: Air France/KLM Flying Blue (1:1), United MileagePlus (1:1). Capital One Miles: Air France/KLM Flying Blue (1:1), Qantas Frequent Flyer (1:1). Chase Ultimate Rewards: Air France/KLM Flying Blue (1:1), United MileagePlus (1:1). Citi ThankYou Points: American Airlines AAdvantage (1:1), Air France/KLM Flying Blue (1:1), Qantas Frequent Flyer (1:1). Wells Fargo Rewards: Air France/KLM Flying Blue (1:1). These are US card programs; ratios come from AwardTool's transfer partner list. Check current bonuses first.

What's the best month to fly from Chicago Midway (MDW) to Calgary (YYC) on points?

Counting only month prices from programs with award space on 2 or more dates that month, and leaving out unusually low outliers: in economy, the lowest award was for Jul 2027 departures, 10,000 miles + taxes not reported with AAdvantage (30 dates); in business class, the lowest award was for Jul 2027 departures, 20,500 miles + taxes not reported with AAdvantage (30 dates). The month table shows every lowest price, including those. Based on dates we observed, not a forecast.

When do award seats open for flights from Chicago Midway (MDW) to Calgary (YYC)?

Booking windows before departure published by the programs with award space here (AwardTool's program data, reviewed Nov 6, 2026): Air France/KLM Flying Blue about 359 days, Qantas Frequent Flyer about 353 days, United MileagePlus about 337 days and 2 other programs. AwardTool saw award space on this route for departures as late as Aug 20, 2027; seats can open earlier or later, and released seats may already be booked. See award release dates by program.