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Chicago to Cancún Flights — Fares from $1,294.00 | MDW–CUN

Compare the cheapest Chicago (MDW) to Cancún (CUN) fares found by our live flight search, then book online or over the phone with our travel experts.

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Adults
12+
1
Children
2–11
0
Infants
Under 2
0
Cabin
🏷️
Save up to 40% with unpublished phone fares
Consolidator deals on selected Chicago → Cancún flights that do not appear in online search results. The live fares below are bookable right now — or call to check for an unpublished fare on your dates.
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One-way fares Chicago → Cancún

showing indicative fares · loading live prices…
Southwest
Southwest CHEAPEST
MDW → CUN · Economy
lowest fare seen on this route
$2,157.00
$1,294.20
Select
Frontier
Frontier
MDW → CUN · Economy
lowest fare seen on this route
$2,349.00
$1,409.40
Select
Aeromexico
Aeromexico
MDW → CUN · Economy
lowest fare seen on this route
$3,752.91
$2,251.75
Select
Delta Air Lines
Delta Air Lines
MDW → CUN · Economy
lowest fare seen on this route
$3,752.91
$2,251.75
Select
See all flights & times → Prices per adult, one way, incl. taxes & fees. Availability changes constantly.
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Live fares we can book on MDW–CUN

Lowest fare found per airline on the MDW → CUN route, with our discounted phone-deal price.

AirlineCabin Found fareOur discounted fare Fare found on
Southwest Southwest Economy $2,157.00 $1,294.20 Aug 14, 2026 Book
Frontier Frontier Economy $2,349.00 $1,409.40 Aug 14, 2026 Book
Aeromexico Aeromexico Economy $3,752.91 $2,251.75 Aug 14, 2026 Book
Delta Air Lines Delta Air Lines Economy $3,752.91 $2,251.75 Aug 14, 2026 Book

Discounted fares are negotiated phone deals from our vendor network and may not appear in online search results — call 765-995-0868 to lock one in. Fares were found on the dates shown, are per person in USD, and change with availability.

More routes we cover

Chicago to Atlanta Chicago to Charlotte Chicago to Los Angeles Chicago to Oakland Chicago to Ontario Chicago to Orlando Charleston to Cancún Chicago to Cancún Dallas-Fort Worth to Cancún Dallas to Cancún Guadalajara to Cancún Indianapolis to Cancún All routes →

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FlyLemo is an independent travel agency — call 765-995-0868 or use the search above to compare live fares on this route. See our terms, privacy policy, refund policy and service fees for full details, or contact us any time.

Page updated August 16, 2026 · fare data refreshed automatically from live flight searches.