First-class award flights from Chicago Midway (MDW) to Calgary (YYC)
In the last 30 days AwardTool saw first-class award space on 3 programs for MDW→YYC. Lowest: 35,000 miles + $5.60 with American Airlines AAdvantage, which showed first-class award space on 63 dates. No nonstop first-class award was seen in the last 30 days.
Every airport: Chicago to Calgary (YYC) award flights.
Prices observed – ; newest observation .
Page regenerated from the Nov 12, 2026 data snapshot (normally daily). Summary last changed . Seats change quickly.
- Lowest observed
- 35,000 miles + $5.60
- American Airlines AAdvantage
- Programs with space
- 3 of 5
- programs seen on this route
- Most dates seen
- 76 of 76
- dates checked · Delta SkyMiles
- Nonstop
- Not seen
- in the last 30 days
In first class, the lowest award seen was 35,000 miles + $5.60 with American Airlines AAdvantage, against 41,100 miles + $5.60 with Delta SkyMiles, the next-lowest program. With American Airlines AAdvantage, first class started at 35,000 miles + $5.60, about 3.5 times the points of its lowest economy award (10,000 miles + $5.60).
Compare programs for first class
The lowest one-way first-class award each program showed on MDW→YYC, sorted by points.
| Program | Points + taxes | Stops | Airlines seen | Seats | Dates seen | Newest observation | |
|---|---|---|---|---|---|---|---|
| American Airlines AAdvantageLowest observed | 35,000 pts + $5.60 | 1 stop |  AA AS | — | 63 | See dates | |
| Delta SkyMiles | 41,100 pts + $5.60 | 2 stops |  DL | 2 | 76 | See dates | |
| United MileagePlus | 61,000 pts + $5.60 | 1 stop |  UA | 9+ | 68 | See dates |
Not seen in first class: Air France/KLM Flying Blue and Qantas Frequent Flyer.
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.
Observed first-class award examples
| Departure | Program | Points + taxes | Seats | Stops | Observed (UTC) | |
|---|---|---|---|---|---|---|
| Delta SkyMiles | 41,100 pts + $5.60 | 2 | 2 stops | Check this date | ||
| Delta SkyMiles | 71,400 pts + $5.60 | 3 | 1 stop | 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.
How often first-class award space showed up
Departure dates in the next 365 days that AwardTool checked for each program in the last 30 days, how many had first-class award space at any price, and the latest departure with space.
| Program | Dates with space | Share of dates checked | Latest departure with space |
|---|---|---|---|
| American Airlines AAdvantage | 63 of 68 | 92% | |
| Delta SkyMiles | 76 of 76 | 100% | |
| United MileagePlus | 68 of 68 | 100% |
First class compared with economy, by program
Each program's lowest one-way first-class and economy awards on MDW→YYC, in its own points or miles, and how many times the economy points the first-class award needed. — in the last column means one of the two is a mixed-cabin award or was not seen on 2 or more dates.
| Program | First | Economy | First ÷ economy points |
|---|---|---|---|
| American Airlines AAdvantage | 35,000 miles + $5.60 | 10,000 miles + $5.60 | 3.5× |
| Delta SkyMiles | 41,100 miles + $5.60 | 11,700 miles + $5.60 | 3.5× |
| United MileagePlus | 61,000 miles + $5.60 | 17,500 miles + $13.70 | 3.5× |
Best months for first class from Chicago Midway (MDW) to Calgary (YYC)
| Month | Lowest observed | Program | Dates |
|---|---|---|---|
| 41,100 pts + $5.60 | Delta SkyMiles | 2 | |
| 71,400 pts + $5.60 | Delta SkyMiles | 2 | |
| 66,700 pts + taxes not reported | Delta SkyMiles | 1 | |
| 53,900 pts + taxes not reported | Delta SkyMiles | 2 | |
| 35,000 pts + taxes not reported | American Airlines AAdvantage | 17 | |
| 35,000 pts + taxes not reported | American Airlines AAdvantage | 30 | |
| 35,000 pts + taxes not reported | American Airlines AAdvantage | 16 |
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.
Lowest first class award by month and program
Each program's lowest one-way first-class award by departure month, in its own points or miles, with the taxes of that month's lowest award and the program's open dates that month under it. A price without taxes had none reported for that month. — means the program showed no first-class space that month.
| Program | |||||||
|---|---|---|---|---|---|---|---|
| American Airlines AAdvantagemiles | — | — | — | — | 35,00017 dates | 35,00030 dates | 35,00016 dates |
| Delta SkyMilesmiles | 41,100+ $5.60 · 2 dates | 71,400+ $5.60 · 2 dates | 66,7001 date | 53,9002 dates | 55,40018 dates | 47,90031 dates | 62,40020 dates |
| United MileagePlusmiles | — | — | — | — | 63,80017 dates | 63,80031 dates | 61,000+ $5.60 · 20 dates |
Airlines seen in first class
Airlines that appeared on the award itineraries AwardTool observed, and the programs that showed them.
- American Airlines (AA): American Airlines AAdvantage
- Alaska Airlines (AS): American Airlines AAdvantage
- Delta Air Lines (DL): Delta SkyMiles
- United Airlines (UA): United MileagePlus
First class on nearby routes
The lowest first-class award AwardTool observed on related routes, as each route's page shows it: the return direction, other airports in the same cities, and more routes from Chicago Midway (MDW) and to Calgary (YYC). One way, in the program's points or miles, with that award's taxes when the data has them.
| Route | Lowest observed | Program | Dates seen |
|---|---|---|---|
| Chicago O’Hare (ORD) to Calgary (YYC)Another Chicago airport | 25,000 miles + $5.60 | American Airlines AAdvantage | 324 |
| Chicago Midway (MDW) to Minneapolis (MSP)Also from MDW | 12,600 miles + $5.60Nonstop | Delta SkyMiles | 310 |
| Chicago Midway (MDW) to Detroit (DTW)Also from MDW | 14,400 miles + $5.60Nonstop | Delta SkyMiles | 319 |
| Chicago Midway (MDW) to Atlanta (ATL)Also from MDW | 24,400 miles + $5.60Nonstop | Delta SkyMiles | 309 |
| Chicago Midway (MDW) to Orlando (MCO)Also from MDW | 18,000 miles + $5.60 | American Airlines AAdvantage | 44 |
| Minneapolis (MSP) to Calgary (YYC)Also to YYC | 25,000 points + $5.60 | Alaska Atmos Rewards | 322 |
| Honolulu (HNL) to Calgary (YYC)Also to YYC | 50,000 points + $5.60 | Alaska Atmos Rewards | 330 |
| Dallas-Fort Worth (DFW) to Calgary (YYC)Also to YYC | 25,000 miles + $5.60 | American Airlines AAdvantage | 310 |
Points that transfer to these programs
| Program | Amex | Bilt | Capital One | Chase | Citi | Wells Fargo |
|---|---|---|---|---|---|---|
| American Airlines AAdvantage | — | — | — | — | 1:1 · Instant | — |
| Delta SkyMiles | 1:1 · Instant | — | — | — | — | — |
| United MileagePlus | — | 1:1 · Instant | — | 1:1 · Instant | — | — |
Check current transfer bonuses. Most transfers can't be reversed.
Questions about first-class award flights from Chicago Midway (MDW) to Calgary (YYC)
How many points for first class from Chicago Midway (MDW) to Calgary (YYC)?
The lowest first-class award AwardTool has seen was 35,000 miles + $5.60 with American Airlines AAdvantage. American Airlines AAdvantage showed first-class award space on 63 departure dates at any price (newest observation Nov 7, 2026, 05:30 UTC). Search live before transferring points.
Which programs had first-class award space from Chicago Midway (MDW) to Calgary (YYC)?
American Airlines AAdvantage (63 dates), Delta SkyMiles (76 dates) and United MileagePlus (68 dates), in the last 30 days.
Can you fly first class nonstop from Chicago Midway (MDW) to Calgary (YYC) on points?
AwardTool hasn't observed nonstop first-class award space on this route in the last 30 days. That doesn't mean nonstop space never appears.
What's the best month to fly first class 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, the lowest first-class award AwardTool observed was for Jul 2027 departures: 35,000 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.