HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Yucatan

$123+ 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 7/18. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — MID
jun. 17 — jun. 241
mar. 6/17
mar. 6/24
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 junio 12, 2025.

Round-trip from

$269
(Southwest)

One-way from

$123
(Southwest)

Popular in

December

Cheapest in

February

Average price

$498
From Chicago Midway to Yucatan
Search Deals
One-way flight from Chicago Midway to Yucatan
Search Deals
Highest demand for flights based on searches. 17% potential increase in price ($112 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 June 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 junio 12, 2025.

This Southwest deal was found by Cheapflights users on 6/9. 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. 7/104:35 pmMDW - CUN
Nonstop3h 35mSouthwest
mar. 7/158:30 amCUN - MDW
Nonstop3h 35mSouthwest
Deal found 6/9$269
This Priceline deal was found by Cheapflights users on 6/10. 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. 8/236:10 amMDW - CUN
1 stop6h 29mFrontier
sáb. 8/301:54 pmCUN - MDW
1 stop9h 17mFrontier
Deal found 6/10$292
This Trip.com deal was found by Cheapflights users on 6/10. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 6/2412:44 pmMDW - CUN
1 stop7h 36mAeromexico
sáb. 9/612:40 pmCUN - MDW
1 stop8h 32mAeromexico
Deal found 6/10$305
This Trip.com deal was found by Cheapflights users on 6/11. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 6/2412:44 pmMDW - CUN
1 stop7h 36mMultiple Airlines
mié. 6/253:25 pmCUN - MDW
1 stop29h 28mMultiple Airlines
Deal found 6/11$322
This Delta deal was found by Cheapflights users on 6/10. 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. 9/86:00 amMDW - CUN
1 stop8h 10mDelta
sáb. 9/138:15 amCUN - MDW
1 stop7h 15mDelta
Deal found 6/10$323
This Kiwi.com deal was found by Cheapflights users on 6/9. 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.
lun. 8/186:00 amMDW - MID
2 stops14h 00mMultiple Airlines
vie. 8/299:05 amMID - MDW
1 stop9h 11mMultiple Airlines
Deal found 6/9$573
This Delta deal was found by Cheapflights users on 6/9. 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. 8/186:04 amMDW - MID
2 stops16h 00mDelta
vie. 8/296:54 amMID - MDW
2 stops13h 55mDelta
Deal found 6/9$583
This Mytrip deal was found by Cheapflights users on 6/10. 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.
jue. 7/38:39 pmMDW - MID
2 stops16h 46mVolaris
lun. 7/79:09 pmMID - MDW
1 stop21h 07mVolaris
Deal found 6/10$659
This Aeromexico deal was found by Cheapflights users on 6/10. 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.
sáb. 10/256:00 amMDW - MID
2 stops33h 20mAeromexico
sáb. 11/17:03 amMID - MDW
2 stops13h 41mAeromexico
Deal found 6/10$973

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 junio 12, 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

jue. 7/10

4:35 pm-8:10 pm

Nonstop3h 35m

Cancun

mar. 7/15

8:30 am-12:05 pm

Nonstop3h 35m

$269

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

sáb. 8/23

6:10 am-12:39 pm

1 stop6h 29m

Cancun

sáb. 8/30

1:54 pm-11:11 pm

1 stop9h 17m

$292

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

mar. 6/24

12:44 pm-8:20 pm

1 stop7h 36m

Cancun

sáb. 9/6

12:40 pm-9:12 pm

1 stop8h 32m

$305

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

mar. 6/24

12:44 pm-8:20 pm

1 stop7h 36m

Cancun

mié. 6/25

3:25 pm-8:53 pm

1 stop29h 28m

$322

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

lun. 9/8

6:00 am-2:10 pm

1 stop8h 10m

Cancun

sáb. 9/13

8:15 am-3:30 pm

1 stop7h 15m

$323

ChicagoMérida

MDW - MID

MDWMID

Chicago Midway

lun. 8/18

6:00 am-7:00 pm

2 stops14h 00m

Mérida Rejon

vie. 8/29

9:05 am-7:16 pm

1 stop9h 11m

$573

ChicagoMérida

MDW - MID

MDWMID

Chicago Midway

lun. 8/18

6:04 am-9:04 pm

2 stops16h 00m

Mérida Rejon

vie. 8/29

6:54 am-9:49 pm

2 stops13h 55m

$583

ChicagoMérida

MDW - MID

MDWMID

Chicago Midway

jue. 7/3

8:39 pm-12:25 pm

2 stops16h 46m

Mérida Rejon

lun. 7/7

9:09 pm-7:16 pm

1 stop21h 07m

$659

ChicagoMérida

MDW - MID

MDWMID

Chicago Midway

sáb. 10/25

6:00 am-2:20 pm

2 stops33h 20m

Mérida Rejon

sáb. 11/1

7:03 am-9:44 pm

2 stops13h 41m

$973

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

vie. 7/18

4:35 pm-8:10 pm

Nonstop3h 35m

$123

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/10

Showing 1-10 of 17 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

Rainfall in Yucatan by month

Plan your trip to Yucatan by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Yucatan ranges from 0.8 - 6.3 inches per month. September is typically the wettest month, when rainfall can reach 6.3 in. February is typically the driest time to visit Yucatan when rainfall is around 0.8 in.

Temperature in Yucatan by month

Plan your trip to Yucatan by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Yucatan, use this chart to help with planning. For those seeking warmer temperatures, May is the ideal time of year to visit, when temperatures reach an average of 84.2 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 73.4 F).

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 junio 12, 2025.
See what other customers who have flown with Southwest, Delta and Aeromexico from Chicago to Yucatan have to say. 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
4,287 reviews

Boarding

8.2

Comfort

8.0

Entertainment

7.6

Overall

8.0

Food

7.1

Crew

8.6

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
Southwest
8.0
Very good
4,287 reviews
Southwest
8.0
Very good
4,287 reviews

Boarding

8.2

Comfort

8.0

Entertainment

7.6

Overall

8.0

Food

7.1

Crew

8.6

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
Delta
8.0
Very good
7,946 reviews
Southwest
8.0
Very good
4,287 reviews

Boarding

8.2

Comfort

8.0

Entertainment

7.6

Overall

8.0

Food

7.1

Crew

8.6

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
Aeromexico
7.5
Good
1,706 reviews
Southwest
8.0
Very good
4,287 reviews

Boarding

8.2

Comfort

8.0

Entertainment

7.6

Overall

8.0

Food

7.1

Crew

8.6

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
Volaris
6.7
Okay
1,170 reviews
Southwest
8.0
Very good
4,287 reviews

Boarding

8.2

Comfort

8.0

Entertainment

7.6

Overall

8.0

Food

7.1

Crew

8.6

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
Frontier
6.0
Okay
3,295 reviews
Southwest
8.0
Very good
4,287 reviews

Boarding

8.2

Comfort

8.0

Entertainment

7.6

Overall

8.0

Food

7.1

Crew

8.6

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.

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 $123 on Southwest. Other airlines that offer cheap prices include Frontier from $131 and Aeromexico from $132 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 Guadalajara flights
O'Hare Intl to San José del Cabo flights
O'Hare Intl to Puerto Vallarta flights
Midway to Guadalajara flights
Midway to Puerto Vallarta flights
Midway to San José del Cabo flights
O'Hare Intl to Morelia flights
O'Hare Intl to León flights
Midway to Morelia flights
O'Hare Intl to Monterrey flights
Midway to León flights
O'Hare Intl to Oaxaca flights
O'Hare Intl to Durango flights
Midway to Cozumel flights
O'Hare Intl to San Luis Potosí flights
O'Hare Intl to Santiago de Querétaro flights
O'Hare Intl to Zacatecas flights
O'Hare Intl to Aguascalientes flights
Midway to Aguascalientes flights
Midway to Oaxaca flights
Midway to Zacatecas flights
Midway to Durango flights
Midway to Monterrey flights
O'Hare Intl to Mérida flights
O'Hare Intl to Puebla City flights
O'Hare Intl to Puerto Escondido flights
Midway to Santiago de Querétaro flights
O'Hare Intl to Ixtapa flights
O'Hare Intl to Veracruz flights
O'Hare Intl to Santa Maria Huatulco flights
O'Hare Intl to Mazatlán flights
Midway to San Luis Potosí flights
O'Hare Intl to Villahermosa flights
O'Hare Intl to Hermosillo flights
O'Hare Intl to Torreón flights
Midway to Santa Maria Huatulco flights
O'Hare Intl to Acapulco flights
O'Hare Intl to Tijuana flights
Midway to Veracruz flights
O'Hare Intl to Tuxtla Gutiérrez flights
Midway to Mérida flights
O'Hare Intl to Tampico flights
O'Hare Intl to La Paz flights
Midway to Mazatlán 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.