Title: Chicago to Cancun cheap flights from $103 (MDW to CUN) - Expedia.com ![Resort area in Cancun](https://images.trvl-media.com/place/179995/a32e040e-98f8-4322-aa10-770d06e97a6f.jpg?impolicy=fcrop&w=1200&h=500&q=medium) ![](https://images.trvl-media.com/place/179995/a32e040e-98f8-4322-aa10-770d06e97a6f.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # $103 Cheap Flights from Chicago (MDW) to Cancun (CUN) [View $103 flight on Sat, Apr 11, 2026](https://expedia.com/Flights-Search?trip=oneway&leg1=from:MDW,to:CUN,departure:4/11/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:103.00&airProductToken=AQowCi4IxnISAzIzNRjssAEggm0oioiKAzDwiYoDOEVAAFgBagRQQ18xcgdLMDBTTU4yEgwIARABGAEqAkY5MgAYASIECAEQASgCKAMwDQ) ## Popular airlines from Chicago Midway Airport (MDW) to Cancun Intl. Airport (CUN) - ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/09/23/landing_airline_sq_logo_WN.svg) Southwest Airlines [](https://www.expedia.com/Flights-Search?leg1=from:MDW,to:CUN,departure:4/22/2026TANYT&leg2=from:CUN,to:MDW,departure:4/29/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"WN"}}]) - ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/09/23/landing_airline_sq_logo_Y4.svg) Volaris [](https://www.expedia.com/Flights-Search?leg1=from:MDW,to:CUN,departure:4/22/2026TANYT&leg2=from:CUN,to:MDW,departure:4/29/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"Y4"}}]) - ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/09/23/landing_airline_sq_logo_AM.svg) Aeromexico [](https://www.expedia.com/Flights-Search?leg1=from:MDW,to:CUN,departure:4/22/2026TANYT&leg2=from:CUN,to:MDW,departure:4/29/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"AM"}}]) - ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/09/23/landing_airline_sq_logo_DL.svg) Delta [](https://www.expedia.com/Flights-Search?leg1=from:MDW,to:CUN,departure:4/22/2026TANYT&leg2=from:CUN,to:MDW,departure:4/29/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"DL"}}]) - ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/09/23/landing_airline_sq_logo_F9.svg) Frontier Airlines [](https://www.expedia.com/Flights-Search?leg1=from:MDW,to:CUN,departure:4/22/2026TANYT&leg2=from:CUN,to:MDW,departure:4/29/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"F9"}}]) - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__notification.svg) ### Be in the know Get alerts if flight prices drop or rise\* - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__deals.svg) ### Book smarter Save up to 30% on select hotels after you book a flight\* - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__trophy.svg) ### Earn twice Earn your airline miles on top of our OneKeyCash [Learn about One Key](https://www.expedia.com/welcome-one-key) ## Cheap Flights from Chicago to Cancun (MDW-CUN) Prices were available within the past 7 days and start at $103 for one-way flights and $244 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply. All deals One way Roundtrip ![Frontier Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/F9.gif) Sat, Apr 11 - Sat, Apr 25 MDW Chicago CUN Cancun $244 Roundtrip found 1 day ago [](https://expedia.com/Flights-Search?trip=roundtrip&leg1=from:MDW,to:CUN,departure:4/11/2026TANYT&leg2=from:CUN,to:MDW,departure:4/25/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:243.93&airProductToken=AQowCi4IxnISAzIzNRjssAEggm0oioiKAzDwiYoDOEVAAFgBagRQQ18xcgdLMDNTTU4yCmAKLQjGchIDMTAyGIJtIOBcKPGniwMwnqmLAzhFQABYAWoEUENfMXIHSzE0UE1DNAovCMZyEgQyNzc5GOBcIOywASiGq4sDMIKsiwM4RUAAWAFqBFBDXzFyB0sxNFBNQzQSCggBEAEYASoCRjkYASIECAEQASgCKAMwDQ) ![Frontier Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/F9.gif) Thu, Apr 30 - Sat, May 2 MDW Chicago CUN Cancun $270 Roundtrip found 14 hours ago [](https://expedia.com/Flights-Search?trip=roundtrip&leg1=from:MDW,to:CUN,departure:4/30/2026TANYT&leg2=from:CUN,to:MDW,departure:5/2/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:269.05&airProductToken=AQpeCi4IxnISBDIyOTIY7LABIOBcKNTciwMw292LAzhLQABYAWoDRUNPcgdLMjFQTUM0CiwIxnISAzE1MxjgXCCCbSi734sDMOzgiwM4S0ABWAFqA0VDT3IHSzIxUE1DNApeCiwIxnISAzEwMhiCbSDgXCj99osDMKv4iwM4S0AAWAFqA0VDT3IHSzIxUE1DNAouCMZyEgQyNzc5GOBcIOywASjm-YsDMOL6iwM4S0ABWAFqA0VDT3IHSzIxUE1DNBIMCAEQARgBKgJGOTIAGAEiBAgBEAEoAigDKAQwAQ) ![Frontier Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/F9.gif) Mon, Apr 27 - Sat, May 2 MDW Chicago CUN Cancun $271 Roundtrip found 6 hours ago [](https://expedia.com/Flights-Search?trip=roundtrip&leg1=from:MDW,to:CUN,departure:4/27/2026TANYT&leg2=from:CUN,to:MDW,departure:5/2/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:270.92&airProductToken=AQpgCi8IxnISBDIyOTIY7LABIOBcKPS6iwMw-7uLAzhFQABYAWoEUENfMXIHSzE0UE1DNAotCMZyEgMxNTMY4Fwggm0o272LAzCMv4sDOEVAAFgBagRQQ18xcgdLMTRQTUM0CmAKLQjGchIDMTAyGIJtIOBcKP32iwMwq_iLAzhFQABYAWoEUENfMXIHSzIxUE1DNAovCMZyEgQyNzc5GOBcIOywASjm-YsDMOL6iwM4RUAAWAFqBFBDXzFyB0syMVBNQzQSDAgBEAEYASoCRjkyABgBIgQIARABKAIoAzAN) ![Frontier Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/F9.gif) Thu, Apr 30 - Mon, May 4 MDW Chicago CUN Cancun $273 Roundtrip found 5 hours ago [](https://expedia.com/Flights-Search?trip=roundtrip&leg1=from:MDW,to:CUN,departure:4/30/2026TANYT&leg2=from:CUN,to:MDW,departure:5/4/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:272.98&airProductToken=AQpgCi8IxnISBDIyOTIY7LABIOBcKNTciwMw292LAzhFQABYAWoEUENfMXIHSzIxUE1DNAotCMZyEgMxNTMY4Fwggm0ou9-LAzDs4IsDOEVAAFgBagRQQ18xcgdLMjFQTUM0EgoIARABGAEqAkY5GAEiBAgBEAEoAigDMA0) ![Frontier Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/F9.gif) Sat, Apr 11 - Tue, Apr 21 MDW Chicago CUN Cancun $276 Roundtrip found 1 day ago [](https://expedia.com/Flights-Search?trip=roundtrip&leg1=from:MDW,to:CUN,departure:4/11/2026TANYT&leg2=from:CUN,to:MDW,departure:4/21/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:275.14&airProductToken=AQowCi4IxnISAzIzNRjssAEggm0oioiKAzDwiYoDOEVAAFgBagRQQ18xcgdLMDNTTU4yEgoIARABGAEqAkY5GAEiBAgBEAEoAigDMA0) ![Frontier Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/F9.gif) Thu, Apr 30 - Mon, May 4 MDW Chicago CUN Cancun $282 Roundtrip found 5 hours ago [](https://expedia.com/Flights-Search?trip=roundtrip&leg1=from:MDW,to:CUN,departure:4/30/2026TANYT&leg2=from:CUN,to:MDW,departure:5/4/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:281.55&airProductToken=AQpeCi4IxnISBDI3ODAY7LABIOBcKMPgiwMwweGLAzhLQABYAWoDRUNPcgdLMjFQTUM0CiwIxnISAzE1MxjgXCCCbSjb6osDMIzsiwM4S0ABWAFqA0VDT3IHSzIxUE1DNApeCiwIxnISAzE1MhiCbSDgXCizjowDMNuPjAM4S0AAWAFqA0VDT3IHSzIxUE1DNAouCMZyEgQyMjkxGOBcIOywASitlowDMKmXjAM4S0ABWAFqA0VDT3IHSzIxUE1DNBIKCAEQARgBKgJGORgBIgQIARABKAIoAygEMAE) ![Southwest Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/wn.gif) Sun, May 10 - Thu, May 14 MDW Chicago CUN Cancun $313 Roundtrip just found [](https://expedia.com/Flights-Search?trip=roundtrip&leg1=from:MDW,to:CUN,departure:5/10/2026TANYT&leg2=from:CUN,to:MDW,departure:5/14/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:312.45&airProductToken=AQowCi4I15wBEgMyMTgY7LABIIJtKMDPjAMwl9GMAzhWQABYAWoDV0dBcgdWQ05WUjJGCjAKLgjXnAESAzIxNxiCbSDssAEo9v6MAzDSgI0DOFZAAFgBagNXR0FyB1ZDTlZSMkYSDAgBEAEYASoCV04yABgBIgQIARABKAIoAygEMAE) ![Delta](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/DL.gif) Sat, Apr 25 - Wed, Apr 29 MDW Chicago CUN Cancun $358 Roundtrip found 9 hours ago [](https://expedia.com/Flights-Search?trip=roundtrip&leg1=from:MDW,to:CUN,departure:4/25/2026TANYT&leg2=from:CUN,to:MDW,departure:4/29/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:357.05&airProductToken=AQpuCjYIxJgBEgQzNzk5GOywASDMfCjQqosDMLiriwM4RUAAWAFqCU1BSU5CQVNJQ3IIVk5YSjBTQk0KNAjEmAESAzE5ORjMfCCCbSi6sIsDMK2yiwM4RUABWAFqCU1BSU5CQVNJQ3IIVk5YSjBTQk0Kbgo0CMSYARIDNTk3GIJtIOBcKIrViwMwr9aLAzhFQABYAWoJTUFJTkJBU0lDcghWTlhKMFNCTQo2CMSYARIEMTA3NhjgXCDssAEontiLAzCQ2YsDOEVAAVgBaglNQUlOQkFTSUNyCFZOWEowU0JNEgoIARABGAEqAkRMGAEiBAgBEAEoAigDKAQwAQ) ![Aeromexico](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/am.gif) Sun, May 10 - Thu, May 14 MDW Chicago CUN Cancun $398 Roundtrip just found [](https://expedia.com/Flights-Search?trip=roundtrip&leg1=from:MDW,to:CUN,departure:5/10/2026TANYT&leg2=from:CUN,to:MDW,departure:5/14/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:397.05&airProductToken=AQppCjMIwZoBEgQ0NDMwGOywASDgXCirzYwDMKbOjAM4VkAAWAFqBkJBU0lDQXIIRU5OTDBTQk0KMgjBmgESBDUzMTkY4Fwggm0ohs-MAzCk0IwDOFZAAVgBagZCQVNJQ0FyCEVOTkwwU0JNCmkKMgjBmgESBDMxNjQYgm0g4Fwosv6MAzDU_4wDOFZAAFgBagZCQVNJQ0FyCEVOTkwwU0JNCjMIwZoBEgQzNzYzGOBcIOywASiqgI0DMKGBjQM4VkABWAFqBkJBU0lDQXIIRU5OTDBTQk0SDAgBEAEYASoCQU0yABgBIgQIARABKAIoAygEMAE) ![Volaris](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/Y4.gif) Sun, May 3 - Wed, May 6 MDW Chicago CUN Cancun $420 Roundtrip found 6 hours ago [](https://expedia.com/Flights-Search?trip=roundtrip&leg1=from:MDW,to:CUN,departure:5/3/2026TANYT&leg2=from:CUN,to:MDW,departure:5/6/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:419.22&airProductToken=AQpfCi4I2WgSBDE4NDEY7LABIOZYKJOFjAMwm4eMAzhMQABYAWoEWmVyb3IGTExDU1MyCi0I2WgSBDEwNTIY5lgggm0oooqMAzC_i4wDOExAAVgBagRaZXJvcgZMTENTUzIKXwotCNloEgQxMDQ5GIJtIOZYKKyijAMw2KOMAzhOQABYAWoEWmVyb3IGTkxDU1MxCi4I2WgSBDE4NDAY5lgg7LABKLmkjAMwpKaMAzhOQAFYAWoEWmVyb3IGTkxDU1MxEgwIARABGAEqAlk0MgAYASIECAEQASgCKAMoBDAN) ## Alternative airports near Cancun Prices were available within the past 7 days. Prices and availability are subject to change. [](https://www.expedia.com/Flights-Search?leg1=from:MDW,to:CUN,departure:4/22/2026TANYT&leg2=from:CUN,to:MDW,departure:4/24/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&sortOrder=INCREASING&sortType=PRICE) CUN Cancun Intl. CheapestClosest 18 min [Flights from $436 ](https://www.expedia.com/Flights-Search?leg1=from:MDW,to:CUN,departure:4/22/2026TANYT&leg2=from:CUN,to:MDW,departure:4/24/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&sortOrder=INCREASING&sortType=PRICE) ## Frequently asked questions ### How much does a flight from Chicago, IL (MDW-Midway Intl.) to Cancun, Quintana Roo (CUN-Cancun Intl.) cost? ### What is the cheapest month to fly from Chicago, IL (MDW-Midway Intl.) to Cancun, Quintana Roo (CUN-Cancun Intl.)? ### Which airlines fly direct from Chicago, IL (MDW-Midway Intl.) to Cancun, Quintana Roo (CUN-Cancun Intl.)? ### What is the cheapest airline that flies from Chicago, IL (MDW-Midway Intl.) to Cancun, Quintana Roo (CUN-Cancun Intl.)? ### How do I find cheap flights from Chicago, IL (MDW-Midway Intl.) to Cancun, Quintana Roo (CUN-Cancun Intl.)? ### What is the best airline to fly with from Chicago, IL (MDW-Midway Intl.) to Cancun, Quintana Roo (CUN-Cancun Intl.)? ### What is the best time to fly from Chicago, IL (MDW-Midway Intl.) to Cancun, Quintana Roo (CUN-Cancun Intl.)? ### How many flights per day from Chicago, IL (MDW-Midway Intl.) to Cancun, Quintana Roo (CUN-Cancun Intl.)? ### What is the earliest flight from Chicago, IL (MDW-Midway Intl.) to Cancun, Quintana Roo (CUN-Cancun Intl.)? ### What are the most popular departure times for flights from Chicago, IL (MDW-Midway Intl.) to Cancun, Quintana Roo (CUN-Cancun Intl.)? ### How long does it take to fly from Chicago, IL (MDW-Midway Intl.) to Cancun, Quintana Roo (CUN-Cancun Intl.)? ### Can you fly business or first class from Chicago, IL (MDW-Midway Intl.) to Cancun, Quintana Roo (CUN-Cancun Intl.)? ### How do I earn miles on a Chicago, IL (MDW-Midway Intl.) to Cancun, Quintana Roo (CUN-Cancun Intl.) flight with Expedia? ### What airports do you fly into for Cancun from Midway Intl. (MDW)? ### Is it cheaper to buy a plane ticket from Chicago, IL (MDW-Midway Intl.) to Cancun, Quintana Roo (CUN-Cancun Intl.) at the last minute? ### Is it cheaper to book a Chicago, IL (MDW-Midway Intl.) to Cancun, Quintana Roo (CUN-Cancun Intl.) flight and hotel package? ### Can I cancel or change the date of my flight from Chicago, IL (MDW-Midway Intl.) to Cancun, Quintana Roo (CUN-Cancun Intl.)? ## Travel information | Origin airport | Midway Intl. | | ------------------- | ----------------------------------------------------------------- | | Destination airport | Cancun Intl. | | Airlines serving | Aeromexico, Delta, Frontier Airlines, Southwest Airlines, Volaris | | Roundtrip price | $236 | | Distance | 1434 mi | | Average flight time | 3 hours 40 mins | \*Flight schedules are subject to change. \*Available to One Key members. ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Vacation Rentals - Other - [All-Inclusive Resorts in Cancun ](https://www.expedia.com/Cancun-Hotels-All-Inclusive-Hotel.0-0-d179995-tAllinclusiveHotel.Travel-Guide-Filter-Hotels) - [Hotels near El Tinto Golf Course ](https://www.expedia.com/El-Tinto-Golf-Course-Hotels.0-l6242262-0.Travel-Guide-Filter-Hotels) - [B&B in Alfredo V. 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