HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Midway

$149+ 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 2/26. Fares are subject to change and may not be available on all flights or dates of travel.
MID — MDW
Feb 28 — Mar 71
Sat 2/28
Sat 3/7
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Yucatan to Midway with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

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 January 29, 2026.

This Delta deal was found by Cheapflights users on 1/28. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/121:40 pm
CUN
-
MDW
1 stop9h 51m
Delta
Tue 2/1712:45 pm
MDW
-
CUN
1 stop7h 26m
Delta
Deal found 1/28$281
This Delta deal was found by Cheapflights users on 1/27. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 1/304:40 pm
CUN
-
MDW
1 stop6h 42m
Delta
Mon 2/26:00 am
MDW
-
CUN
1 stop9h 35m
Delta
Deal found 1/27$282
This Aeromexico deal was found by Cheapflights users on 1/28. 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 Aeromexico is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 2/68:00 am
CUN
-
MDW
1 stop10h 29m
Aeromexico
Mon 2/96:00 am
MDW
-
CUN
1 stop9h 35m
Aeromexico
Deal found 1/28$283
This Priceline deal was found by Cheapflights users on 1/26. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/2311:30 am
CUN
-
MDW
1 stop10h 51m
Frontier
Mon 4/276:00 am
MDW
-
CUN
1 stop8h 56m
Frontier
Deal found 1/26$287
This Frontier deal was found by Cheapflights users on 1/27. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/1911:48 am
CUN
-
MDW
1 stop10h 24m
Frontier
Mon 2/236:00 am
MDW
-
CUN
1 stop6h 37m
Frontier
Deal found 1/27$305
This Southwest deal was found by Cheapflights users on 1/27. 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.
Fri 1/301:45 pm
CUN
-
MDW
Nonstop3h 45m
Southwest
Mon 2/29:15 am
MDW
-
CUN
Nonstop3h 40m
Southwest
Deal found 1/27$306
This CheapOair deal was found by Cheapflights users on 1/28. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 3/143:07 pm
CUN
-
MDW
Nonstop4h 06m
Multiple Airlines
Sat 3/217:54 pm
MDW
-
CUN
1 stop13h 54m
Multiple Airlines
Deal found 1/28$310
This Frontier deal was found by Cheapflights users on 1/27. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/1610:34 am
CUN
-
MDW
2 stops21h 30m
Frontier
Tue 4/216:00 am
MDW
-
CUN
1 stop8h 56m
Frontier
Deal found 1/27$317
This Southwest deal was found by Cheapflights users on 1/28. 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.
Thu 2/193:00 pm
CUN
-
MDW
Nonstop3h 45m
Southwest
Mon 2/2310:35 am
MDW
-
CUN
Nonstop3h 40m
Southwest
Deal found 1/28$332
This Southwest deal was found by Cheapflights users on 1/28. 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.
Fri 2/133:40 pm
CUN
-
MDW
Nonstop3h 40m
Southwest
Mon 2/1610:45 am
MDW
-
CUN
Nonstop3h 40m
Southwest
Deal found 1/28$337
This Delta deal was found by Cheapflights users on 1/28. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/168:00 am
CUN
-
MDW
1 stop8h 29m
Delta
Tue 4/219:27 am
MDW
-
CUN
2 stops10h 47m
Delta
Deal found 1/28$339
This Delta deal was found by Cheapflights users on 1/28. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/165:45 am
MID
-
MDW
2 stops9h 44m
Delta
Tue 4/2110:43 am
MDW
-
MID
2 stops14h 12m
Delta
Deal found 1/28$395

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 January 29, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$281
(Delta)

One-way from

$149
(Southwest)

Popular in

April

Cheapest in

February

Average price

$496
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. 2% potential increase in price ($11 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($6 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in January 2026
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 January 29, 2026.
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

Fri 2/13

11:00 am-5:45 pm

1 stop7h 45m

Chicago Midway

Mon 2/16

6:00 am-4:45 pm

1 stop9h 45m

$281

CancúnChicago

CUN - MDW

CUNMDW

Cancun

Thu 2/12

1:40 pm-10:31 pm

1 stop9h 51m

Chicago Midway

Tue 2/17

12:45 pm-9:11 pm

1 stop7h 26m

$281

CancúnChicago

CUN - MDW

CUNMDW

Cancun

Thu 4/23

11:30 am-10:21 pm

1 stop10h 51m

Chicago Midway

Mon 4/27

6:00 am-2:56 pm

1 stop8h 56m

$283

CancúnChicago

CUN - MDW

CUNMDW

Cancun

Thu 2/12

3:40 pm-6:20 pm

Nonstop3h 40m

Chicago Midway

Tue 2/17

10:35 am-3:15 pm

Nonstop3h 40m

$306

CancúnChicago

CUN - MDW

CUNMDW

Cancun

Thu 2/19

3:00 pm-5:45 pm

Nonstop3h 45m

Chicago Midway

Mon 2/23

10:35 am-3:15 pm

Nonstop3h 40m

$332

CancúnChicago

CUN - MDW

CUNMDW

Cancun

Fri 2/13

3:40 pm-6:20 pm

Nonstop3h 40m

Chicago Midway

Mon 2/16

10:45 am-3:25 pm

Nonstop3h 40m

$337

CancúnChicago

CUN - MDW

CUNMDW

Cancun

Thu 5/14

11:30 am-8:04 am

2 stops20h 34m

Chicago Midway

Tue 5/19

6:00 am-2:56 pm

1 stop8h 56m

$339

CancúnChicago

CUN - MDW

CUNMDW

Cancun

Fri 4/17

10:00 am-4:29 pm

1 stop6h 29m

Chicago Midway

Wed 4/22

10:43 am-8:14 pm

1 stop9h 31m

$341

CancúnChicago

CUN - MDW

CUNMDW

Cancun

Thu 4/23

8:05 am-10:28 pm

2 stops14h 23m

Chicago Midway

Mon 4/27

6:00 am-4:40 pm

2 stops10h 40m

$341

MéridaChicago

MID - MDW

MIDMDW

Mérida Rejon

Thu 4/16

5:45 am-4:29 pm

2 stops9h 44m

Chicago Midway

Tue 4/21

10:43 am-11:55 pm

2 stops14h 12m

$395

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/28

Showing 1-10 of 35 results
1
2
3
4

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 $306, Delta can have you in Chicago Midway Airport from Yucatan in 3h 40m. 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

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Yucatan to Midway

See prices for flight routes from nearby airports that may be better suited for you.
Mexico City to O'Hare Intl flights
Mexico City to Midway flights
Cancún to O'Hare Intl flights
Monterrey to O'Hare Intl flights
Guadalajara to O'Hare Intl flights
Cancún to Midway flights
Mexico City to O'Hare Intl flights
Mexico City to Midway flights
Monterrey to Midway flights
Cozumel to O'Hare Intl flights
Guadalajara to Midway flights
León to O'Hare Intl flights
Santiago de Querétaro to O'Hare Intl flights
Morelia to O'Hare Intl flights
León to Midway flights
Santiago de Querétaro to Midway flights
Morelia to Midway flights
Aguascalientes to O'Hare Intl flights
San José del Cabo to O'Hare Intl flights
Puerto Vallarta to O'Hare Intl flights
Aguascalientes to Midway flights
San Luis Potosí to O'Hare Intl flights
Mérida to O'Hare Intl flights
San Luis Potosí to Midway flights
San José del Cabo to Midway flights
Durango to Midway flights
Durango to O'Hare Intl flights
Chihuahua to O'Hare Intl flights
Zacatecas to Midway flights
Veracruz to O'Hare Intl flights
Tijuana to O'Hare Intl flights
Puerto Vallarta to Midway flights
Puebla City to O'Hare Intl flights
Tijuana to Midway flights
Zacatecas to O'Hare Intl flights
Oaxaca to O'Hare Intl flights
Torreón to O'Hare Intl flights
Culiacán to O'Hare Intl flights
Ciudad Juárez to O'Hare Intl flights
Villahermosa to O'Hare Intl flights
Acapulco to O'Hare Intl flights
Saltillo to O'Hare Intl flights

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.