HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Yucatan

$119+ 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 10/20. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — MID
Oct 14 — Oct 211
Tue 10/14
Tue 10/21
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Midway to Yucatan 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 Midway to Yucatan

Keep the following information in mind while searching for Midway to Yucatan flight deals. Data was last updated September 14, 2025.

Round-trip from

$261
(Southwest)

One-way from

$119
(Southwest)

Popular in

December

Cheapest in

September

Average price

$331
From Chicago Midway to Yucatan
Search Deals
One-way flight from Chicago Midway to Yucatan
Search Deals
Highest demand for flights based on searches. 13% potential increase in price ($76 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 4% potential price decrease ($23 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in September 2025
Search Deals

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 September 14, 2025.

This Southwest deal was found by Cheapflights users on 9/14. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/2810:35 amMDW - CUN
Nonstop3h 35mSouthwest
Fri 10/33:20 pmCUN - MDW
Nonstop3h 35mSouthwest
Deal found 9/14$261
This Southwest deal was found by Cheapflights users on 9/13. 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.
Tue 9/309:55 amMDW - CUN
Nonstop3h 35mSouthwest
Sat 10/412:00 pmCUN - MDW
Nonstop3h 35mSouthwest
Deal found 9/13$266
This Southwest deal was found by Cheapflights users on 9/14. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/63:40 pmMDW - CUN
Nonstop3h 45mSouthwest
Fri 12/122:15 pmCUN - MDW
Nonstop3h 45mSouthwest
Deal found 9/14$270
This Southwest deal was found by Cheapflights users on 9/13. 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.
Sat 12/63:40 pmMDW - CUN
Nonstop3h 45mSouthwest
Sat 12/1311:55 amCUN - MDW
Nonstop3h 50mSouthwest
Deal found 9/13$271
This Southwest deal was found by Cheapflights users on 9/14. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/111:45 amMDW - CUN
1 stop8h 05mSouthwest
Thu 11/62:15 pmCUN - MDW
Nonstop3h 45mSouthwest
Deal found 9/14$280
This Southwest deal was found by Cheapflights users on 9/13. 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.
Sat 9/276:35 amMDW - CUN
1 stop7h 15mSouthwest
Sat 10/412:00 pmCUN - MDW
Nonstop3h 35mSouthwest
Deal found 9/13$285
This Southwest deal was found by Cheapflights users on 9/12. 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.
Tue 10/215:35 amMDW - CUN
1 stop6h 30mSouthwest
Fri 10/313:15 pmCUN - MDW
Nonstop3h 35mSouthwest
Deal found 9/12$288
This Southwest deal was found by Cheapflights users on 9/12. 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 12/75:30 amMDW - CUN
1 stop9h 30mSouthwest
Thu 12/111:45 pmCUN - MDW
Nonstop3h 45mSouthwest
Deal found 9/12$292
This Southwest deal was found by Cheapflights users on 9/12. 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 11/305:20 amMDW - CUN
1 stop10h 05mSouthwest
Thu 12/41:45 pmCUN - MDW
Nonstop3h 45mSouthwest
Deal found 9/12$293
This Southwest deal was found by Cheapflights users on 9/12. 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 10/2610:40 amMDW - CUN
Nonstop3h 35mSouthwest
Thu 10/302:15 pmCUN - MDW
2 stops9h 00mSouthwest
Deal found 9/12$299
This Southwest deal was found by Cheapflights users on 9/13. 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.
Mon 9/229:55 amMDW - CUN
Nonstop3h 35mSouthwest
Thu 9/253:10 pmCUN - MDW
Nonstop3h 40mSouthwest
Deal found 9/13$301
This Kiwi.com deal was found by Cheapflights users on 9/13. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/156:30 amMDW - MID
2 stops11h 05mMultiple Airlines
Sun 11/309:35 pmMID - MDW
1 stop19h 59mMultiple Airlines
Deal found 9/13$478

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 September 14, 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

Sun 9/28

10:35 am-2:10 pm

Nonstop3h 35m

Cancun

Fri 10/3

3:20 pm-6:55 pm

Nonstop3h 35m

$261

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Sat 12/6

3:40 pm-8:25 pm

Nonstop3h 45m

Cancun

Fri 12/12

2:15 pm-5:00 pm

Nonstop3h 45m

$270

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Sat 10/18

6:00 am-4:05 pm

1 stop10h 05m

Cancun

Sat 11/1

11:55 am-8:20 pm

2 stops8h 25m

$310

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Tue 10/21

6:15 am-1:40 pm

1 stop7h 25m

Cancun

Fri 10/31

1:00 pm-8:20 pm

1 stop7h 20m

$322

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Sun 11/9

10:47 am-9:20 pm

1 stop9h 33m

Cancun

Wed 11/12

8:00 am-4:39 pm

1 stop9h 39m

$326

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Sat 1/31

6:00 am-4:31 pm

1 stop9h 31m

Cancun

Sat 2/7

11:15 am-9:46 pm

1 stop11h 31m

$326

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Sat 1/17

10:35 am-9:10 pm

1 stop9h 35m

Cancun

Wed 1/21

12:15 pm-6:34 pm

1 stop7h 19m

$326

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Wed 1/28

10:35 am-9:10 pm

1 stop9h 35m

Cancun

Sat 2/7

4:25 pm-9:46 pm

1 stop6h 21m

$326

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Sat 1/17

10:35 am-9:10 pm

1 stop9h 35m

Cancun

Fri 1/23

12:25 pm-9:46 pm

1 stop10h 21m

$326

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Sat 11/15

11:05 am-9:20 pm

1 stop9h 15m

Cancun

Wed 11/19

1:32 pm-11:32 pm

1 stop11h 00m

$326

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/11

Showing 1-10 of 35 results
1
2
3
4

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 3h 35m. Fly via Southwest 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.

  • What is the cheapest month to book a flight from Chicago Midway Airport to Yucatan?

    Currently, June is the cheapest month in which you can book a flight from Chicago Midway Airport to Yucatan (average of $499). Flying from Chicago Midway Airport to Yucatan in December is currently the most expensive (average of $667). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

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 Midway to Yucatan

See prices for flight routes from nearby airports that may be better suited for you.
O'Hare Intl to Cancún flights
O'Hare Intl to Mexico City flights
Midway to Cancún flights
O'Hare Intl to Cozumel flights
O'Hare Intl to Puerto Vallarta flights
Midway to Mexico City flights
O'Hare Intl to San José del Cabo flights
O'Hare Intl to Guadalajara flights
O'Hare Intl to Mexico City flights
O'Hare Intl to Morelia flights
Midway to San José del Cabo flights
Midway to Puerto Vallarta flights
Midway to Morelia flights
Midway to Guadalajara flights
O'Hare Intl to León flights
O'Hare Intl to Monterrey flights
Midway to Cozumel flights
Midway to León flights
O'Hare Intl to Santiago de Querétaro flights
O'Hare Intl to Oaxaca flights
O'Hare Intl to Durango flights
Midway to Monterrey flights
O'Hare Intl to Ixtapa flights
O'Hare Intl to Mérida flights
O'Hare Intl to Aguascalientes flights
Midway to Santiago de Querétaro flights
Midway to Zacatecas flights
Midway to Oaxaca flights
O'Hare Intl to Zacatecas flights
O'Hare Intl to Puerto Escondido flights
O'Hare Intl to San Luis Potosí flights
O'Hare Intl to Acapulco flights
Midway to Aguascalientes flights
Midway to Durango flights
O'Hare Intl to Veracruz flights
O'Hare Intl to Mazatlán flights
O'Hare Intl to Santa Maria Huatulco flights
O'Hare Intl to La Paz flights
O'Hare Intl to Puebla City flights
Midway to San Luis Potosí flights
Midway to Mazatlán flights
Midway to Ixtapa flights
O'Hare Intl to Tijuana flights
O'Hare Intl to Tuxtla Gutiérrez flights
Midway to Veracruz flights
Midway to Mérida flights
O'Hare Intl to Chihuahua flights
O'Hare Intl to Tampico flights
O'Hare Intl to Manzanillo flights
O'Hare Intl to Torreón 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.