Award flights from Cancun (CUN) to Chicago Midway (MDW)
Search flights from Cancun (CUN) to Chicago Midway (MDW)
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In the last 30 days AwardTool saw award space on 4 programs for CUN→MDW. Lowest economy: 9,500 miles + $73.98 (American Airlines AAdvantage). Lowest business class: 20,000 miles + $73.98 (American Airlines AAdvantage). Lowest first class: 35,000 miles + $86.13 (United MileagePlus).
Prices observed – ; newest observation .
Page regenerated from the Oct 19, 2026 data snapshot (normally daily). Summary last changed . Seats change quickly.
Cancun (CUN) to Chicago Midway (MDW) at a glance
- From
- Cancun International, Cancun, Mexico (CUN)
- To
- Chicago Midway International, Chicago, Illinois, United States (MDW)
- 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, Qantas Frequent Flyer and United MileagePlus
- Airlines seen on these awards
- American Airlines (AA), Air Canada (AC), Alaska Airlines (AS), JetBlue (B6), Delta Air Lines (DL), United Airlines (UA)
- Departures with open awards
- Nov 2026 to Mar 2027
- Most dates with space
- 11 of 11 departure dates checked (American Airlines AAdvantage, economy)
- Latest departure with space
- Observation window
- Awards observed in the last 30 days
- Destination guide
- Award flights to Chicago Midway (MDW)
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 + $73.98 | 1 stopNonstop from 11,500 pts | American Airlines (AA), Alaska Airlines (AS) | — | 11 | See dates | |
| Air France/KLM Flying Blue | 19,500 pts + $116.63 | 1 stop | Delta Air Lines (DL) | 9+ | 8 | See dates | |
| United MileagePlus | 20,000 pts + $80.79 | Nonstop | Air Canada (AC), JetBlue (B6), United Airlines (UA) | 9+ | 11 | See dates | |
| Qantas Frequent Flyer | 20,700 pts + $103.93 | Nonstop | American Airlines (AA), Alaska Airlines (AS) | 1 | 5 | See dates |
Business Class
| Program | Points + taxes | Stops | Airlines seen | Seats | Dates seen | Newest observation | |
|---|---|---|---|---|---|---|---|
| American Airlines AAdvantageLowest observed | 20,000 pts + $73.98 | 1 stopNonstop from 23,000 pts | American Airlines (AA) | — | 11 | See dates | |
| United MileagePlus | 36,000 pts + $80.79 | Nonstop | United Airlines (UA) | 9+ | 11 | See dates | |
| Qantas Frequent Flyer | 43,600 pts + $103.93 | Nonstop | American Airlines (AA) | 1 | 5 | See dates | |
| Air France/KLM Flying Blue | 51,000 pts + $123.43 | 1 stop | Delta Air Lines (DL) | 1 | 6 | See dates |
First Class
| Program | Points + taxes | Stops | Airlines seen | Seats | Dates seen | Newest observation | |
|---|---|---|---|---|---|---|---|
| United MileagePlus | 35,000 pts + $86.13 | 1 stop | JetBlue (B6), United Airlines (UA) | 9+ | 11 | See dates |
Not seen in first class: American Airlines AAdvantage, 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.
Observed award examples
| Departure | Cabin | Program | Points + taxes | Seats | Stops | Observed (UTC) | |
|---|---|---|---|---|---|---|---|
| Economy | American Airlines AAdvantage | 9,500 pts + $86.13 | — | 1 stop | Check this date | ||
| Economy | Qantas Frequent Flyer | 20,700 pts + $103.93 | 1 | Nonstop | Check this date | ||
| Business | American Airlines AAdvantage | 20,000 pts + $86.13 | — | 1 stop | Check this date | ||
| Business | Qantas Frequent Flyer | 43,600 pts + $103.93 | 1 | Nonstop | Check this date | ||
| Business | Air France/KLM Flying Blue | 51,000 pts + $123.43 | 1 | 1 stop | Check this date | ||
| First | United MileagePlus | 35,000 pts + $86.13 | 9+ | 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 11,500 miles via American Airlines AAdvantage, which showed nonstop space on 11 dates (3 programs had nonstop space).
- Business class: nonstop from 23,000 miles via American Airlines AAdvantage, which showed nonstop space on 11 dates (3 programs had nonstop space).
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 | — |
| 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 Cancun (CUN) to Chicago Midway (MDW)
Route calendar
Every departure date with open award seats on CUN→MDW for United MileagePlus and the other programs: a limited window on the free plan and 365 days with Pro.
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Search one date across programs to see current flights, seats and taxes before you transfer points.
Search Cancun (CUN) to Chicago Midway (MDW)How many miles you need from Cancun (CUN) to Chicago Midway (MDW)
- In economy, American Airlines AAdvantage had the lowest observed award, 9,500 miles + $73.98; see how many miles you need with American Airlines AAdvantage.
- In business class, American Airlines AAdvantage had the lowest observed award, 20,000 miles + $73.98; see how many miles you need with American Airlines AAdvantage.
- In first class, United MileagePlus had the lowest observed award, 35,000 miles + $86.13; see how many miles you need with United MileagePlus.
Questions about award flights from Cancun (CUN) to Chicago Midway (MDW)
What's the lowest Cancun (CUN) to Chicago Midway (MDW) award price AwardTool has seen?
In economy, 9,500 miles + $73.98 with American Airlines AAdvantage. Seen Sep 24, 2026, 14:18 UTC for a Nov 4, 2026 departure. American Airlines AAdvantage showed economy award space on 11 departure dates at any price (newest observation Oct 16, 2026, 22:11 UTC). In business class, 20,000 miles + $73.98 with American Airlines AAdvantage. Seen Sep 24, 2026, 14:18 UTC for a Nov 4, 2026 departure. American Airlines AAdvantage showed business-class award space on 11 departure dates at any price (newest observation Oct 16, 2026, 22:11 UTC). Search live before transferring points.
Which loyalty programs had award space from Cancun (CUN) to Chicago Midway (MDW)?
4 programs in the last 30 days: American Airlines AAdvantage (economy 11 dates, business class 11 dates); Air France/KLM Flying Blue (economy 8 dates, business class 6 dates); Qantas Frequent Flyer (economy 5 dates, business class 5 dates); United MileagePlus (economy 11 dates, business class 11 dates, first class 11 dates). Dates count departure dates with an open award.
Is there nonstop award space from Cancun (CUN) to Chicago Midway (MDW)?
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 11,500 miles with American Airlines AAdvantage.
Which credit card points can book awards from Cancun (CUN) to Chicago Midway (MDW)?
American Express Membership Rewards: 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). Ratios come from AwardTool's transfer partner list; check current bonuses first.