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Midway

$138+ Cheap flights from Yucatan to Midway (MDW)

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 1/24. Fares are subject to change and may not be available on all flights or dates of travel.
MID — MDW
ene. 14 — ene. 211
mié. 1/14
mié. 1/21
1 adult, Economy
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Cheap flight deals from Yucatan to Midway

Cheapest flights from Yucatan to Midway
Explore the most affordable flight options available from Yucatan to Midway. Find the lowest fares from popular airlines and budget airlines, with prices last updated on diciembre 15, 2025.

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.
lun. 12/228:00 amCUN - MDW
2 stops10h 26mDelta
lun. 1/56:45 amMDW - CUN
1 stop6h 18mDelta
Deal found 12/13$278
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.
jue. 12/2512:05 pmCUN - MDW
2 stops11h 17mDelta
lun. 1/59:32 amMDW - CUN
2 stops10h 39mDelta
Deal found 12/15$279
This Frontier 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 12/302:50 pmCUN - MDW
1 stop8h 22mFrontier
lun. 1/56:12 amMDW - CUN
1 stop6h 28mFrontier
Deal found 12/15$332
This FlightHub 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 12/292:50 pmCUN - MDW
1 stop8h 22mFrontier
sáb. 1/36:12 amMDW - CUN
1 stop6h 25mFrontier
Deal found 12/13$338
This Orbitz 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 12/302:50 pmCUN - MDW
1 stop8h 22mFrontier
dom. 1/410:50 pmMDW - CUN
1 stop17h 22mFrontier
Deal found 12/14$339
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.
lun. 12/151:33 pmCUN - MDW
1 stop11h 14mDelta
jue. 12/186:00 amMDW - CUN
1 stop8h 33mDelta
Deal found 12/15$354
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.
vie. 12/262:50 pmCUN - MDW
1 stop8h 22mFrontier
lun. 1/56:12 amMDW - CUN
1 stop6h 28mFrontier
Deal found 12/13$357
This Frontier 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb. 12/272:50 pmCUN - MDW
1 stop8h 22mFrontier
sáb. 1/36:12 amMDW - CUN
1 stop6h 25mFrontier
Deal found 12/15$358
This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 12/251:45 pmCUN - MDW
Nonstop3h 45mSouthwest
lun. 1/510:40 amMDW - CUN
Nonstop3h 45mSouthwest
Deal found 12/13$360
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.
jue. 12/181:23 pmMID - MDW
2 stops10h 24mDelta
jue. 12/256:00 amMDW - MID
2 stops13h 45mDelta
Deal found 12/13$1,046
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.
vie. 12/266:14 amMID - MDW
2 stops16h 08mDelta
jue. 1/86:45 amMDW - MID
2 stops12h 55mDelta
Deal found 12/14$1,048
This Aeromexico 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 Aeromexico is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 12/186:14 amMID - MDW
2 stops17h 33mAeromexico
jue. 12/256:00 amMDW - MID
2 stops13h 45mAeromexico
Deal found 12/14$1,203

Find flight deals from Yucatan to Midway

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

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$173
(Frontier)

One-way from

$138
(Priceline)

Popular in

April

Cheapest in

February

Average price

$454
Provider with most accurate pricing for Mérida Rejon-Chicago (CHI) flight deals.
Search Deals
Provider most trusted by Cheapflights users for Mérida Rejon-Chicago (CHI) flights.
Search Deals
From Yucatan to Chicago Midway
Search Deals
One-way flight from Yucatan to Chicago Midway
Search Deals
Highest demand for flights based on searches. 3% potential increase in price ($18 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($8 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 Yucatan to Midway 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 diciembre 15, 2025.
Use the filters below to find and compare flights from Yucatan to Chicago Midway Airport that are best for you.

Fly from

Yucatan

Fly to

Midway

Route

Depart

Return

Price

CancúnChicago

CUN - MDW

CUNMDW

Cancun

jue. 1/22

1:45 pm-4:30 pm

Nonstop3h 45m

Chicago Midway

lun. 1/26

9:15 am-1:55 pm

Nonstop3h 40m

$272

CancúnChicago

CUN - MDW

CUNMDW

Cancun

mié. 2/4

4:40 pm-10:22 pm

1 stop6h 42m

Chicago Midway

lun. 2/9

6:00 am-2:03 pm

1 stop7h 03m

$278

CancúnChicago

CUN - MDW

CUNMDW

Cancun

vie. 1/23

8:00 am-5:29 pm

1 stop10h 29m

Chicago Midway

vie. 1/30

6:00 am-3:30 pm

1 stop8h 30m

$278

CancúnChicago

CUN - MDW

CUNMDW

Cancun

mar. 1/27

12:05 pm-10:22 pm

2 stops11h 17m

Chicago Midway

lun. 2/2

10:46 am-9:11 pm

1 stop9h 25m

$278

CancúnChicago

CUN - MDW

CUNMDW

Cancun

mar. 1/27

3:13 pm-10:22 pm

1 stop8h 09m

Chicago Midway

mar. 2/3

6:00 am-3:30 pm

1 stop8h 30m

$278

CancúnChicago

CUN - MDW

CUNMDW

Cancun

vie. 1/23

8:00 am-5:29 pm

1 stop10h 29m

Chicago Midway

vie. 1/30

9:33 am-9:11 pm

2 stops10h 38m

$278

CancúnChicago

CUN - MDW

CUNMDW

Cancun

jue. 1/15

3:13 pm-10:07 pm

1 stop7h 54m

Chicago Midway

mar. 1/27

9:32 am-9:11 pm

2 stops10h 39m

$279

CancúnChicago

CUN - MDW

CUNMDW

Cancun

dom. 1/18

11:05 am-4:29 pm

1 stop6h 24m

Chicago Midway

sáb. 1/24

9:33 am-9:20 pm

2 stops10h 47m

$279

CancúnChicago

CUN - MDW

CUNMDW

Cancun

vie. 1/16

11:05 am-10:07 pm

1 stop12h 02m

Chicago Midway

mié. 2/18

12:46 pm-9:11 pm

1 stop7h 25m

$279

CancúnChicago

CUN - MDW

CUNMDW

Cancun

sáb. 1/17

4:35 pm-10:27 am

2 stops18h 52m

Chicago Midway

vie. 1/23

12:48 pm-9:11 pm

1 stop7h 23m

$279

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/13

Showing 1-10 of 37 results
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Best time to book a flight from Yucatan to Midway

Have a flexible travel schedule? Discover the best time to fly to Midway from Yucatan 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 Yucatan to Chicago Midway Airport
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 Yucatan to Midway. 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 Yucatan to Chicago Midway Airport?

    For as low as $272, Southwest can have you in Chicago Midway Airport from Yucatan in 3h 45m. Airlines will cover a distance of 1434 mi. Both multi-stop and nonstop flights can be found to your destination and back.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Yucatan to Midway 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

Traveling to a place near Chicago Midway Airport?

Book flights to Chicago Midway Airport if you plan to visit one of these locations
Lansing
Merrillville
Hammond
Porter
Benton Harbor

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