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$104+ 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 1/12. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — MID
Jan 14 — Jan 211
Wed 1/14
Wed 1/21
1 adult, Economy
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Cheap 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 December 15, 2025.

This Frontier deal was found by Cheapflights users on 12/13. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/316:12 amMDW - CUN
1 stop6h 28mFrontier
Thu 1/154:12 pmCUN - MDW
1 stop7h 07mFrontier
Deal found 12/13$269
This Frontier deal was found by Cheapflights users on 12/14. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/316:12 amMDW - CUN
1 stop6h 28mFrontier
Thu 1/83:14 pmCUN - MDW
1 stop8h 03mFrontier
Deal found 12/14$277
This Delta deal was found by Cheapflights users on 12/13. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/1612:50 pmMDW - CUN
1 stop7h 30mDelta
Sat 12/202:56 pmCUN - MDW
1 stop8h 26mDelta
Deal found 12/13$327
This Delta deal was found by Cheapflights users on 12/13. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/179:34 amMDW - CUN
2 stops10h 46mDelta
Sun 12/218:00 amCUN - MDW
1 stop9h 20mDelta
Deal found 12/13$331
This Delta deal was found by Cheapflights users on 12/14. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/319:29 amMDW - CUN
2 stops10h 51mDelta
Thu 1/811:05 amCUN - MDW
1 stop12h 02mDelta
Deal found 12/14$341
This Frontier deal was found by Cheapflights users on 12/14. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/306:14 amMDW - CUN
1 stop6h 25mFrontier
Thu 1/83:14 pmCUN - MDW
1 stop8h 03mFrontier
Deal found 12/14$347
This Delta deal was found by Cheapflights users on 12/14. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/1710:49 amMDW - CUN
1 stop9h 31mDelta
Wed 12/248:00 amCUN - MDW
2 stops10h 26mDelta
Deal found 12/14$351
This Delta deal was found by Cheapflights users on 12/13. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/146:00 amMDW - CUN
1 stop5h 23mDelta
Sun 12/214:30 pmCUN - MDW
1 stop6h 52mDelta
Deal found 12/13$354
This Delta deal was found by Cheapflights users on 12/15. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/156:40 pmMDW - CUN
2 stops15h 15mDelta
Thu 12/181:33 pmCUN - MDW
1 stop11h 14mDelta
Deal found 12/15$358
This Southwest deal was found by Cheapflights users on 12/12. 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 12/1410:40 amMDW - CUN
Nonstop3h 45mSouthwest
Tue 12/161:45 pmCUN - MDW
Nonstop3h 45mSouthwest
Deal found 12/12$359
This Southwest deal was found by Cheapflights users on 12/15. 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 12/1511:25 amMDW - CUN
1 stop7h 20mSouthwest
Thu 12/182:15 pmCUN - MDW
Nonstop3h 45mSouthwest
Deal found 12/15$364
This Kiwi.com deal was found by Cheapflights users on 12/14. 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.
Sat 12/209:15 amMDW - MID
2 stops12h 00mMultiple Airlines
Fri 12/2612:05 pmMID - MDW
1 stop9h 53mMultiple Airlines
Deal found 12/14$1,399

Find flight deals from Midway to Yucatan

Keep the following information in mind while searching for Midway to Yucatan flight deals. Data was last updated December 15, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$228
(Super.com)

One-way from

$104
(Super.com)

Popular in

April

Cheapest in

September

Average price

$629
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
High demand for flights, 2% potential price rise
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($11 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 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 December 15, 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

ChicagoMérida

MDW - MID

MDWMID

Chicago Midway

Mon 1/19

7:20 pm-5:45 pm

1 stop22h 25m

Mérida Rejon

Fri 1/23

12:05 pm-7:52 pm

1 stop7h 47m

$296

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Tue 2/10

5:00 am-1:55 pm

1 stop7h 55m

Cancun

Sat 2/14

11:00 am-1:35 pm

Nonstop3h 35m

$323

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Fri 1/9

6:45 am-4:35 pm

1 stop8h 50m

Cancun

Wed 1/14

4:40 pm-10:07 pm

1 stop6h 27m

$333

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Tue 1/13

6:45 am-4:35 pm

1 stop8h 50m

Cancun

Thu 2/19

8:00 am-5:45 pm

1 stop10h 45m

$333

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Fri 2/20

10:53 am-9:11 pm

1 stop9h 18m

Cancun

Wed 2/25

12:05 pm-10:42 pm

2 stops11h 37m

$338

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Mon 3/2

6:00 am-8:02 pm

2 stops13h 02m

Cancun

Sat 3/7

12:05 pm-10:42 pm

2 stops11h 37m

$338

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Sat 1/10

6:45 am-4:35 pm

1 stop8h 50m

Cancun

Tue 1/13

12:05 pm-10:07 pm

2 stops11h 02m

$338

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Fri 1/23

6:00 am-4:35 pm

1 stop9h 35m

Cancun

Tue 1/27

12:05 pm-10:22 pm

2 stops11h 17m

$338

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Mon 1/5

6:45 am-4:35 pm

1 stop8h 50m

Cancun

Thu 1/15

12:05 pm-10:07 pm

2 stops11h 02m

$338

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Fri 2/20

9:30 am-7:45 pm

1 stop9h 15m

Cancun

Thu 2/26

4:10 pm-6:50 pm

Nonstop3h 40m

$363

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/14

Showing 1-10 of 45 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 7h 55m. Fly via Southwest, Delta, or Aeromexico 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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