Award flights from Chicago to Cancun (CUN)
Award space from Chicago to Cancun (CUN)
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AwardTool saw award space on 2 airport pairs between Chicago (ORD, MDW) and Cancun (CUN) in the last 30 days. Lowest economy: 9,500 miles + $62.85 on MDW–CUN (American Airlines AAdvantage). Lowest business class: 20,000 miles + $62.85 on MDW–CUN (American Airlines AAdvantage). Lowest first class: 35,000 points + $82.85 on ORD–CUN (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 + $62.85
- MDW–CUN · AAdvantage
- Lowest premium economy
- 23,061 pts + $136.06
- ORD–CUN · Aeroplan
- Lowest business class
- 20,000 pts + $62.85
- MDW–CUN · AAdvantage
- Lowest first class
- 35,000 pts + $82.85
- ORD–CUN · Atmos
Compare airports
Lowest one-way award AwardTool observed on each airport pair between Chicago and Cancun (CUN), with the program and the number of departure dates seen.
| Airports | Economy | Premium Economy | Business | First |
|---|---|---|---|---|
| Chicago O’Hare (ORD) to Cancun (CUN) | 10,700 pts + $62.85TrueBlue · 313 dates | 23,061 pts + $136.06Aeroplan · 257 dates | 23,000 pts + $62.85AAdvantage · 311 dates | 35,000 pts + $82.85Atmos · 273 dates |
| Chicago Midway (MDW) to Cancun (CUN) | 9,500 pts + $62.85AAdvantage · 8 dates | — | 20,000 pts + $62.85AAdvantage · 8 dates | 46,600 pts + $62.85MileagePlus · 7 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, Chicago to Cancun (CUN)
- Economy: 9,500 miles + $62.85 on Chicago Midway (MDW) to Cancun (CUN) with American Airlines AAdvantage, which showed economy award space there on 8 dates.
- Premium Economy: 23,061 points + $136.06 on Chicago O’Hare (ORD) to Cancun (CUN) with Air Canada Aeroplan, which showed premium economy award space there on 257 dates.
- Business Class: 20,000 miles + $62.85 on Chicago Midway (MDW) to Cancun (CUN) with American Airlines AAdvantage, which showed business-class award space there on 8 dates.
- First Class: 35,000 points + $82.85 on Chicago O’Hare (ORD) to Cancun (CUN) with Alaska Atmos Rewards, which showed first-class award space there on 273 dates.
Points that transfer to these programs
| Program | Amex | Bilt | Capital One | Chase | Citi | Wells Fargo |
|---|---|---|---|---|---|---|
| Air Canada Aeroplan | 1:1 · Instant | 1:1 · Instant | 1:1 · Instant | 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 Chicago to Cancun (CUN) award flights
Which airports had the lowest award prices from Chicago to Cancun (CUN)?
In business class, MDW–CUN with 20,000 miles + $62.85 (American Airlines AAdvantage). In economy, MDW–CUN with 9,500 miles + $62.85 (American Airlines AAdvantage). Prices are the lowest AwardTool observed in the last 30 days; search live before transferring points.
Which airport pairs between Chicago and Cancun (CUN) had award space?
ORD–CUN (economy, premium economy, business class and first class) and MDW–CUN (economy, business class and first class). Airport pairs not listed had no award space AwardTool observed in the last 30 days.