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$115+ Cheap flights from Midway (MDW) to Yucatan

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 11/30. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — MID
Nov 29 — Dec 61
Sat 11/29
Sat 12/6
1 adult, Economy
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Find flight deals from Midway to Yucatan

Cheapest flights from Midway to Yucatan
Explore the most affordable flight options available from Midway to Yucatan. Find the lowest fares from popular airlines and budget airlines, with prices last updated on October 30, 2025.

This Southwest deal was found by Cheapflights users on 10/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/153:40 pmMDW - CUN
Nonstop3h 45mSouthwest
Fri 11/212:15 pmCUN - MDW
Nonstop3h 45mSouthwest
Deal found 10/29$262
This Southwest deal was found by Cheapflights users on 10/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/153:40 pmMDW - CUN
Nonstop3h 45mSouthwest
Sat 11/224:25 pmCUN - MDW
Nonstop3h 45mSouthwest
Deal found 10/29$272
This Southwest deal was found by Cheapflights users on 10/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/1610:40 amMDW - CUN
Nonstop3h 45mSouthwest
Sat 11/224:25 pmCUN - MDW
Nonstop3h 45mSouthwest
Deal found 10/30$282
This Southwest deal was found by Cheapflights users on 10/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/83:40 pmMDW - CUN
Nonstop3h 45mSouthwest
Sat 11/151:00 pmCUN - MDW
1 stop6h 55mSouthwest
Deal found 10/28$287
This Southwest deal was found by Cheapflights users on 10/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/38:40 amMDW - CUN
Nonstop3h 45mSouthwest
Fri 11/72:15 pmCUN - MDW
Nonstop3h 45mSouthwest
Deal found 10/28$292
This Southwest deal was found by Cheapflights users on 10/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/18:20 amMDW - CUN
1 stop11h 30mSouthwest
Sat 11/81:50 pmCUN - MDW
1 stop6h 15mSouthwest
Deal found 10/27$296
This Southwest deal was found by Cheapflights users on 10/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/47:00 amMDW - CUN
1 stop9h 00mSouthwest
Thu 11/62:15 pmCUN - MDW
Nonstop3h 45mSouthwest
Deal found 10/27$301
This Southwest deal was found by Cheapflights users on 10/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/210:40 amMDW - CUN
Nonstop3h 45mSouthwest
Thu 11/612:55 pmCUN - MDW
2 stops8h 35mSouthwest
Deal found 10/28$302
This Southwest deal was found by Cheapflights users on 10/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/159:20 amMDW - CUN
1 stop10h 05mSouthwest
Thu 12/182:15 pmCUN - MDW
Nonstop3h 45mSouthwest
Deal found 10/30$304
This Kiwi.com deal was found by Cheapflights users on 10/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/244:00 pmMDW - MID
2 stops18h 55mMultiple Airlines
Sun 11/308:17 pmMID - MDW
1 stop21h 17mMultiple Airlines
Deal found 10/29$570
This Kiwi.com deal was found by Cheapflights users on 10/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/236:54 pmMDW - MID
1 stop13h 26mMultiple Airlines
Thu 12/46:00 amMID - MDW
2 stops15h 53mMultiple Airlines
Deal found 10/30$571
This Gotogate deal was found by Cheapflights users on 10/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/16:54 pmMDW - MID
1 stop13h 51mVolaris
Sat 12/139:29 amMID - MDW
1 stop10h 11mVolaris
Deal found 10/30$581

Cheap flight deals from Midway to Yucatan

Keep the following information in mind while searching for Midway to Yucatan flight deals. Data was last updated October 30, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$252
(Southwest)

One-way from

$115
(Southwest)

Popular in

December

Cheapest in

September

Average price

$539
Provider with most accurate pricing for Chicago (CHI)-Mérida Rejon flight deals.
Search Deals
Provider most trusted by Cheapflights users for Chicago (CHI)-Mérida Rejon flights.
Search Deals
From Chicago Midway to Yucatan
Search Deals
One-way flight from Chicago Midway to Yucatan
Search Deals
Highest demand for flights based on searches. 10% potential increase in price ($58 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($16 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in October 2025
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Midway to Yucatan that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated October 30, 2025.
Use the filters below to find and compare flights from Chicago Midway Airport to Yucatan that are best for you.

Fly from

Midway

Fly to

Yucatan

Route

Depart

Return

Price

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Tue 11/11

5:25 am-3:25 pm

1 stop9h 00m

Cancun

Sat 11/15

8:10 am-4:40 pm

1 stop9h 30m

$306

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Tue 1/20

10:05 am-7:45 pm

2 stops8h 40m

Cancun

Thu 1/29

1:45 pm-4:30 pm

Nonstop3h 45m

$311

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Sat 11/15

6:40 am-2:20 pm

1 stop6h 40m

Cancun

Fri 11/21

2:15 pm-5:00 pm

Nonstop3h 45m

$319

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Sat 2/7

6:00 am-3:30 pm

1 stop8h 30m

Cancun

Tue 2/10

8:00 am-5:32 pm

1 stop10h 32m

$326

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Sun 1/11

6:45 am-9:11 pm

1 stop13h 26m

Cancun

Fri 1/16

4:40 pm-10:09 pm

1 stop6h 29m

$326

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Fri 2/6

6:00 am-4:45 pm

1 stop9h 45m

Cancun

Tue 2/10

12:05 pm-10:26 pm

2 stops11h 21m

$331

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Thu 1/8

9:34 am-9:11 pm

2 stops10h 37m

Cancun

Thu 1/15

12:15 pm-10:09 pm

1 stop10h 54m

$331

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Wed 12/10

12:50 pm-9:20 pm

1 stop7h 30m

Cancun

Fri 12/12

12:00 pm-11:47 pm

1 stop12h 47m

$344

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Wed 11/12

9:20 am-8:25 pm

1 stop10h 05m

Cancun

Sat 11/15

11:20 am-7:05 pm

2 stops8h 45m

$346

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Fri 2/20

10:35 am-9:10 pm

1 stop9h 35m

Cancun

Wed 2/25

1:40 pm-9:46 pm

1 stop9h 06m

$346

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/29

Showing 1-10 of 39 results
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Best time to book a flight from Midway to Yucatan

Have a flexible travel schedule? Discover the best time to fly to Yucatan from Midway with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from Chicago Midway Airport to Yucatan
No data available for this route at this time. Please check back soon.

Related info for your journey

Find useful and relevant information for your journey from Midway to Yucatan. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • How long is the flight from Chicago Midway Airport to Yucatan?

    There are many flights that can get you from Chicago Midway Airport to Yucatan in 8h 30m. Fly via Southwest, Delta, or Volaris to get the fastest option. Chicago Midway Airport and Yucatan are separated by a distance of 1434 mi. This flight may include one or multiple stops.

  • Can I find deals for flights from Midway to Yucatan that include hotel bookings?

    Yes. In addition to deals on Midway to Yucatan flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Midway to Yucatan?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Midway to Yucatan.

  • Can I find deals for business class flights from Midway to Yucatan?

    Yes. Cheapflights offers flight deals from Midway to Yucatan by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

See more FAQs

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Alternative routes for Midway to Yucatan

See prices for flight routes from nearby airports that may be better suited for you.
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Midway to Mazatlán flights
O'Hare Intl to Culiacán flights

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