Award flights from Chicago Midway (MDW) to Cancun (CUN)
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In the last 30 days AwardTool saw award space on 4 programs for MDW→CUN. Lowest economy: 9,500 miles + $62.85 (American Airlines AAdvantage). Lowest business class: 20,000 miles + $62.85 (American Airlines AAdvantage). Lowest first class: 46,600 miles + $62.85 (United MileagePlus).
Prices observed – ; newest observation .
Page regenerated from the Oct 19, 2026 data snapshot (normally daily). Summary last changed . Seats change quickly.
Chicago Midway (MDW) to Cancun (CUN) at a glance
- From
- Chicago Midway International, Chicago, Illinois, United States (MDW)
- To
- Cancun International, Cancun, Mexico (CUN)
- Programs with award space seen
- 4 of 4 programs tracked on this route
- Nonstop award space seen
- Yes, in economy and business class, via American Airlines AAdvantage and United MileagePlus
- Airlines seen on these awards
- American Airlines (AA), Air Canada (AC), Delta Air Lines (DL), United Airlines (UA)
- Departures with open awards
- Oct 2026 to Apr 2027
- Most dates with space
- 9 of 21 departure dates checked (Air France/KLM Flying Blue, economy)
- Latest departure with space
- Observation window
- Awards observed in the last 30 days
- Destination guide
- Award flights to Cancun (CUN)
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 | 9,500 pts + $62.85 | 1 stopNonstop from 20,000 pts | American Airlines (AA) | — | 8 | See dates | |
| Delta SkyMiles | 14,000 pts + $62.85 | 1 stop | Delta Air Lines (DL) | 9+ | 7 | See dates | |
| Air France/KLM Flying Blue | 19,500 pts + $95.48 | 1 stop | Delta Air Lines (DL) | 9+ | 9 | See dates | |
| United MileagePlus | 20,000 pts + $62.85 | Nonstop | Air Canada (AC), United Airlines (UA) | 4 | 7 | See dates |
Business Class
| Program | Points + taxes | Stops | Airlines seen | Seats | Dates seen | Newest observation | |
|---|---|---|---|---|---|---|---|
| American Airlines AAdvantageLowest observed | 20,000 pts + $62.85 | 1 stopNonstop from 52,000 pts | American Airlines (AA) | — | 8 | See dates | |
| United MileagePlus | 39,900 pts + $63.08 | 1 stopNonstop from 44,300 pts | United Airlines (UA) | 9+ | 7 | See dates | |
| Air France/KLM Flying Blue | 51,000 pts + $95.48 | 1 stop | Delta Air Lines (DL) | 4 | 4 | See dates |
Not seen in business class: Delta SkyMiles.
First Class
| Program | Points + taxes | Stops | Airlines seen | Seats | Dates seen | Newest observation | |
|---|---|---|---|---|---|---|---|
| United MileagePlusLowest observed | 46,600 pts + $62.85 | 1 stop | United Airlines (UA) | 9+ | 7 | See dates | |
| Delta SkyMiles | 69,700 pts + $63.08 | 1 stop | Delta Air Lines (DL) | 6 | 7 | See dates |
Not seen in first class: American Airlines AAdvantage and Air France/KLM Flying Blue.
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.
Observed award examples
| Departure | Cabin | Program | Points + taxes | Seats | Stops | Observed (UTC) | |
|---|---|---|---|---|---|---|---|
| Economy | American Airlines AAdvantage | 9,500 pts + $63.08 | — | 1 stop | Check this date | ||
| Business | American Airlines AAdvantage | 20,000 pts + $63.08 | — | 1 stop | Check this date | ||
| Business | Air France/KLM Flying Blue | 51,000 pts + $95.48 | 4 | 1 stop | Check this date | ||
| First | United MileagePlus | 56,200 pts + $63.08 | 9+ | 1 stop | Check this date | ||
| First | Delta SkyMiles | 69,700 pts + $63.08 | 6 | 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.
Nonstop award space
- Economy: nonstop from 20,000 miles via American Airlines AAdvantage, which showed nonstop space on 8 dates (2 programs had nonstop space).
- Business class: nonstop from 44,300 miles via United MileagePlus, which showed nonstop space on 7 dates (2 programs had nonstop space).
Best months to fly from Chicago Midway (MDW) to Cancun (CUN) on points
| Month | Economy | Business | First |
|---|---|---|---|
| 11,500 · AAdvantage (1 date) | 23,000 · AAdvantage (1 date) | 56,400 · MileagePlus (1 date) | |
| 9,500 · AAdvantage (1 date) | 20,000 · AAdvantage (1 date) | 56,200 · MileagePlus (1 date) | |
| 19,000 · AAdvantage (4 dates) | 36,500 · AAdvantage (4 dates) | 72,300 · MileagePlus (4 dates) | |
| 9,500 · AAdvantage (1 date) | 20,000 · AAdvantage (1 date) | 46,600 · MileagePlus (1 date) | |
| 20,000 · Flying Blue (1 date) | 52,000 · Flying Blue (1 date) | — | |
| 9,500 · AAdvantage (1 date) | 20,000 · AAdvantage (1 date) | — |
Points that transfer to these programs
| 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 | — | — | — | — | — |
| 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 Cancun (CUN)
Route calendar
Every departure date with open award seats on MDW→CUN for United MileagePlus and the other programs: a limited window on the free plan and 365 days with Pro.
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Search Chicago Midway (MDW) to Cancun (CUN)How many miles you need from Chicago Midway (MDW) to Cancun (CUN)
- In economy, American Airlines AAdvantage had the lowest observed award, 9,500 miles + $62.85; see how many miles you need with American Airlines AAdvantage.
- In business class, American Airlines AAdvantage had the lowest observed award, 20,000 miles + $62.85; see how many miles you need with American Airlines AAdvantage.
- In first class, United MileagePlus had the lowest observed award, 46,600 miles + $62.85; see how many miles you need with United MileagePlus.
Questions about award flights from Chicago Midway (MDW) to Cancun (CUN)
What's the lowest Chicago Midway (MDW) to Cancun (CUN) award price AwardTool has seen?
In economy, 9,500 miles + $62.85 with American Airlines AAdvantage. Seen Sep 30, 2026, 15:46 UTC for a Nov 13, 2026 departure. American Airlines AAdvantage showed economy award space on 8 departure dates at any price (newest observation Oct 19, 2026, 15:34 UTC). In business class, 20,000 miles + $62.85 with American Airlines AAdvantage. Seen Sep 30, 2026, 15:46 UTC for a Nov 13, 2026 departure. American Airlines AAdvantage showed business-class award space on 8 departure dates at any price (newest observation Oct 19, 2026, 15:34 UTC). Search live before transferring points.
Which loyalty programs had award space from Chicago Midway (MDW) to Cancun (CUN)?
4 programs in the last 30 days: American Airlines AAdvantage (economy 8 dates, business class 8 dates); Delta SkyMiles (economy 7 dates, first class 7 dates); Air France/KLM Flying Blue (economy 9 dates, business class 4 dates); United MileagePlus (economy 7 dates, business class 7 dates, first class 7 dates). Dates count departure dates with an open award.
Is there nonstop award space from Chicago Midway (MDW) to Cancun (CUN)?
Yes. AwardTool observed nonstop award space in economy and business class, bookable via American Airlines AAdvantage and United MileagePlus. The lowest nonstop award in economy was 20,000 miles with American Airlines AAdvantage.
Which credit card points can book awards from Chicago Midway (MDW) to Cancun (CUN)?
American Express Membership Rewards: Delta SkyMiles (1:1), Air France/KLM Flying Blue (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). 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). Wells Fargo Rewards: Air France/KLM Flying Blue (1:1). Ratios come from AwardTool's transfer partner list; check current bonuses first.
Which months had the lowest award prices from Chicago Midway (MDW) to Cancun (CUN)?
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 Dec 2026 departures, 19,000 miles with AAdvantage (4 dates); in business class, the lowest award was for Dec 2026 departures, 36,500 miles with AAdvantage (4 dates). The month table shows every lowest price, including those. Based on dates we observed, not a forecast.