Award flights from Cancun (CUN) to Chicago
Award space from Cancun (CUN) to Chicago
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AwardTool saw award space on 2 airport pairs between Cancun (CUN) and Chicago (ORD, MDW) in the last 30 days. Lowest economy: 9,500 miles + $73.98 on CUN–MDW (American Airlines AAdvantage). Lowest business class: 20,000 miles + $73.98 on CUN–MDW (American Airlines AAdvantage). Lowest first class: 35,000 points + $106.39 on CUN–ORD (Alaska Atmos Rewards).
Prices observed – .
Page regenerated from the Oct 19, 2026 data snapshot (normally daily). Summary last changed . Seats change quickly.
- Lowest economy
- 9,500 pts + $73.98
- CUN–MDW · AAdvantage
- Lowest premium economy
- 22,700 pts + $98.48
- CUN–ORD · Club Premier
- Lowest business class
- 20,000 pts + $73.98
- CUN–MDW · AAdvantage
- Lowest first class
- 35,000 pts + $106.39
- CUN–ORD · Atmos
Compare airports
Lowest one-way award AwardTool observed on each airport pair between Cancun (CUN) and Chicago, with the program and the number of departure dates seen.
| Airports | Economy | Premium Economy | Business | First |
|---|---|---|---|---|
| Cancun (CUN) to Chicago O’Hare (ORD) | 10,200 pts + $91.29TrueBlue · 295 dates | 22,700 pts + $98.48Club Premier · 48 dates | 23,000 pts + $80.79AAdvantage · 328 dates | 35,000 pts + $106.39Atmos · 284 dates |
| Cancun (CUN) to Chicago Midway (MDW) | 9,500 pts + $73.98AAdvantage · 11 dates | — | 20,000 pts + $73.98AAdvantage · 11 dates | 35,000 pts + $86.13MileagePlus · 11 dates |
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.
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.
Lowest observed by cabin, Cancun (CUN) to Chicago
- Economy: 9,500 miles + $73.98 on Cancun (CUN) to Chicago Midway (MDW) with American Airlines AAdvantage, which showed economy award space there on 11 dates.
- Premium Economy: 22,700 points + $98.48 on Cancun (CUN) to Chicago O’Hare (ORD) with Aeromexico Club Premier, which showed premium economy award space there on 48 dates.
- Business Class: 20,000 miles + $73.98 on Cancun (CUN) to Chicago Midway (MDW) with American Airlines AAdvantage, which showed business-class award space there on 11 dates.
- First Class: 35,000 points + $106.39 on Cancun (CUN) to Chicago O’Hare (ORD) with Alaska Atmos Rewards, which showed first-class award space there on 284 dates.
Points that transfer to these programs
| Program | Amex | Bilt | Capital One | Chase | Citi | Wells Fargo |
|---|---|---|---|---|---|---|
| Aeromexico Club Premier | 1:1.6 · ~2 days | — | 1:1 · Instant | — | — | — |
| Alaska Atmos Rewards | — | 1:1 · ~1 day | — | — | — | — |
| American Airlines AAdvantage | — | — | — | — | 1:1 · Instant | — |
| JetBlue TrueBlue | 5:4 · Instant | — | 1:0.6 · Instant | 1:1 · Instant | 1:1 · Instant | 1:1 · Instant |
| United MileagePlus | — | 1:1 · Instant | — | 1:1 · Instant | — | — |
Check current transfer bonuses. Most transfers can't be reversed.
Questions about Cancun (CUN) to Chicago award flights
Which airports had the lowest award prices from Cancun (CUN) to Chicago?
In business class, CUN–MDW with 20,000 miles + $73.98 (American Airlines AAdvantage). In economy, CUN–MDW with 9,500 miles + $73.98 (American Airlines AAdvantage). Prices are the lowest AwardTool observed in the last 30 days; search live before transferring points.
Which airport pairs between Cancun (CUN) and Chicago had award space?
CUN–ORD (economy, premium economy, business class and first class) and CUN–MDW (economy, business class and first class). Airport pairs not listed had no award space AwardTool observed in the last 30 days.