HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Yucatan

$124+ 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 8/3. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — MID
ago. 4 — ago. 111
lun. 8/4
lun. 8/11
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 julio 30, 2025.

Round-trip from

$270
(Southwest)

One-way from

$124
(Southwest)

Popular in

December

Cheapest in

February

Average price

$690
From Chicago Midway to Yucatan
Search Deals
One-way flight from Chicago Midway to Yucatan
Search Deals
Highest demand for flights based on searches. 14% potential increase in price ($91 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 6% potential price decrease ($32 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in July 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 julio 30, 2025.

This Southwest deal was found by Cheapflights users on 7/30. 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.
sáb. 11/83:40 pmMDW - CUN
Nonstop3h 45mSouthwest
jue. 11/132:15 pmCUN - MDW
Nonstop3h 45mSouthwest
Deal found 7/30$270
This SmartFares deal was found by Cheapflights users on 7/29. 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 SmartFares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb. 9/66:00 amMDW - CUN
1 stop5h 30mAeromexico
jue. 9/1112:25 pmCUN - MDW
1 stop9h 11mAeromexico
Deal found 7/29$303
This Delta deal was found by Cheapflights users on 7/28. 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.
dom. 10/2610:35 amMDW - CUN
1 stop9h 45mDelta
sáb. 11/11:58 pmCUN - MDW
1 stop8h 16mDelta
Deal found 7/28$324
This Priceline deal was found by Cheapflights users on 7/29. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb. 11/86:00 amMDW - CUN
1 stop14h 20mMultiple Airlines
sáb. 11/152:41 pmCUN - MDW
1 stop9h 28mMultiple Airlines
Deal found 7/29$341
This Frontier deal was found by Cheapflights users on 7/30. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb. 11/86:10 amMDW - CUN
1 stop6h 16mFrontier
sáb. 11/152:41 pmCUN - MDW
1 stop9h 28mFrontier
Deal found 7/30$342
This Delta deal was found by Cheapflights users on 7/30. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 9/196:00 amMDW - MID
2 stops15h 55mDelta
mar. 9/309:00 amMID - MDW
2 stops11h 36mDelta
Deal found 7/30$524
This Kiwi.com deal was found by Cheapflights users on 7/28. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 9/129:48 amMDW - MID
1 stop9h 12mMultiple Airlines
vie. 9/199:05 amMID - MDW
1 stop9h 11mMultiple Airlines
Deal found 7/28$544
This Aeromexico deal was found by Cheapflights users on 7/30. 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 Aeromexico is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 8/216:04 amMDW - MID
2 stops27h 06mAeromexico
lun. 8/258:58 pmMID - MDW
2 stops23h 46mAeromexico
Deal found 7/30$849
This Mytrip deal was found by Cheapflights users on 7/28. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 9/128:39 pmMDW - MID
3 stops25h 56mVolaris
vie. 9/1912:57 pmMID - MDW
3 stops26h 08mVolaris
Deal found 7/28$853

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 julio 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

lun. 10/27

9:40 am-1:15 pm

Nonstop3h 35m

Cancun

dom. 11/2

2:15 pm-5:00 pm

Nonstop3h 45m

$270

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

sáb. 9/6

6:00 am-11:30 am

1 stop5h 30m

Cancun

jue. 9/11

12:25 pm-9:36 pm

1 stop9h 11m

$303

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

dom. 10/26

10:35 am-8:20 pm

1 stop9h 45m

Cancun

sáb. 11/1

1:58 pm-10:14 pm

1 stop8h 16m

$324

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

sáb. 10/4

6:15 am-12:40 pm

1 stop6h 25m

Cancun

sáb. 10/11

10:50 am-12:11 am

1 stop13h 21m

$331

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

jue. 9/11

6:20 am-12:40 pm

1 stop6h 20m

Cancun

jue. 9/18

12:25 pm-9:36 pm

1 stop9h 11m

$351

ChicagoMérida

MDW - MID

MDWMID

Chicago Midway

vie. 9/19

6:00 am-8:55 pm

2 stops15h 55m

Mérida Rejon

mar. 9/30

9:00 am-9:36 pm

2 stops11h 36m

$524

ChicagoMérida

MDW - MID

MDWMID

Chicago Midway

vie. 9/12

9:48 am-6:00 pm

1 stop9h 12m

Mérida Rejon

vie. 9/19

9:05 am-7:16 pm

1 stop9h 11m

$544

ChicagoMérida

MDW - MID

MDWMID

Chicago Midway

jue. 8/21

6:04 am-8:10 am

2 stops27h 06m

Mérida Rejon

lun. 8/25

8:58 pm-9:44 pm

2 stops23h 46m

$849

ChicagoMérida

MDW - MID

MDWMID

Chicago Midway

vie. 9/12

8:39 pm-9:35 pm

3 stops25h 56m

Mérida Rejon

vie. 9/19

12:57 pm-4:05 pm

3 stops26h 08m

$853

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

dom. 8/3

5:25 pm-9:00 pm

Nonstop3h 35m

$124

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/28

Showing 1-10 of 16 results
1
2

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.

Reviews of airlines servicing Yucatan

Get insights into the airlines that provide service to Yucatan. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Yucatan. Reviews last updated julio 30, 2025.
Get a feel of what it's like to fly with Southwest, Delta, and Aeromexico from Chicago Midway Airport to Yucatan by reading reviews from past customers. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,241 reviews

Boarding

8.1

Crew

8.6

Comfort

8.0

Overall

8.0

Food

7.0

Entertainment

7.5

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
Southwest
8.0
Very good
4,241 reviews
Southwest
8.0
Very good
4,241 reviews

Boarding

8.1

Crew

8.6

Comfort

8.0

Overall

8.0

Food

7.0

Entertainment

7.5

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
Delta
8.0
Very good
7,980 reviews
Southwest
8.0
Very good
4,241 reviews

Boarding

8.1

Crew

8.6

Comfort

8.0

Overall

8.0

Food

7.0

Entertainment

7.5

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
Aeromexico
7.5
Good
1,721 reviews
Southwest
8.0
Very good
4,241 reviews

Boarding

8.1

Crew

8.6

Comfort

8.0

Overall

8.0

Food

7.0

Entertainment

7.5

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
Volaris
6.6
Okay
1,164 reviews
Southwest
8.0
Very good
4,241 reviews

Boarding

8.1

Crew

8.6

Comfort

8.0

Overall

8.0

Food

7.0

Entertainment

7.5

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
Frontier
5.9
Fair
3,237 reviews
Southwest
8.0
Very good
4,241 reviews

Boarding

8.1

Crew

8.6

Comfort

8.0

Overall

8.0

Food

7.0

Entertainment

7.5

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.

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.

  • What are the cheapest airlines to fly from Chicago Midway Airport to Yucatan one-way?

    One-way options have recently been found by users for as low as $124 on Southwest. Other airlines that offer cheap prices include Aeromexico from $133 and Frontier from $146 one-way.

  • 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
Midway to Mexico City flights
O'Hare Intl to Mexico City flights
O'Hare Intl to Puerto Vallarta flights
O'Hare Intl to San José del Cabo flights
O'Hare Intl to Guadalajara flights
Midway to Guadalajara flights
Midway to Puerto Vallarta flights
Midway to San José del Cabo flights
Midway to Morelia flights
O'Hare Intl to Morelia flights
O'Hare Intl to León flights
Midway to León flights
O'Hare Intl to Oaxaca flights
O'Hare Intl to Santiago de Querétaro flights
Midway to Cozumel flights
O'Hare Intl to Monterrey flights
O'Hare Intl to Durango flights
O'Hare Intl to Aguascalientes flights
Midway to Aguascalientes flights
Midway to Durango flights
O'Hare Intl to Mérida flights
O'Hare Intl to Ixtapa flights
O'Hare Intl to Zacatecas flights
Midway to Oaxaca flights
O'Hare Intl to Puerto Escondido flights
Midway to Monterrey flights
O'Hare Intl to San Luis Potosí flights
O'Hare Intl to Tepic flights
O'Hare Intl to Veracruz flights
Midway to Santiago de Querétaro flights
O'Hare Intl to Santa Maria Huatulco flights
O'Hare Intl to Tuxtla Gutiérrez flights
O'Hare Intl to Acapulco flights
O'Hare Intl to Tijuana flights
Midway to Mérida flights
Midway to San Luis Potosí flights
Midway to Zacatecas flights
O'Hare Intl to Hermosillo flights
O'Hare Intl to Mazatlán flights
O'Hare Intl to Puebla City flights
O'Hare Intl to Manzanillo flights
O'Hare Intl to La Paz flights
Midway to Tijuana flights
Midway to Ixtapa flights
Midway to Mazatlán 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.