HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Yucatan

$111+ 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 7/27. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — MID
Apr 29 — May 61
Tue 4/29
Tue 5/6
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 April 24, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$246
(Southwest)

One-way from

$111
(Southwest)

Popular in

December

Cheapest in

February

Average price

$647
Provider with most accurate pricing for Chicago (CHI)-Mérida Rejon flight deals.
Search Deals
Provider most trusted by Cheapflights users for Chicago (CHI)-Mérida Rejon flights.
Search Deals
From Chicago Midway to Yucatan
Search Deals
One-way flight from Chicago Midway to Yucatan
Search Deals
Highest demand for flights based on searches. 16% potential increase in price ($105 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 4% potential price decrease ($25 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in April 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 April 24, 2025.

This Southwest deal was found by Cheapflights users on 4/23. 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 5/1110:45 amMDW - CUN
Nonstop3h 40mSouthwest
Thu 5/159:00 amCUN - MDW
Nonstop3h 40mSouthwest
Deal found 4/23$246
This Trip.com deal was found by Cheapflights users on 4/22. 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.
Tue 5/66:04 amMDW - CUN
1 stop6h 46mAeromexico
Tue 5/138:00 amCUN - MDW
1 stop7h 30mAeromexico
Deal found 4/22$299
This Delta deal was found by Cheapflights users on 4/23. 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.
Sat 6/712:48 pmMDW - CUN
1 stop7h 32mDelta
Sat 6/148:30 amCUN - MDW
2 stops13h 15mDelta
Deal found 4/23$321
This Kiwi.com deal was found by Cheapflights users on 4/23. 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.
Mon 5/1212:48 pmMDW - CUN
1 stop7h 32mMultiple Airlines
Fri 5/1612:39 pmCUN - MDW
1 stop9h 34mMultiple Airlines
Deal found 4/23$339
This Kiwi.com deal was found by Cheapflights users on 4/23. 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.
Thu 5/152:45 pmMDW - CUN
1 stop19h 13mFrontier
Mon 5/192:31 pmCUN - MDW
1 stop9h 16mFrontier
Deal found 4/23$403
This EaseMyTrip deal was found by Cheapflights users on 4/23. 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 EaseMyTrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/76:00 amMDW - MID
2 stops11h 41mAeromexico
Sat 6/147:53 amMID - MDW
2 stops12h 52mAeromexico
Deal found 4/23$537
This Delta deal was found by Cheapflights users on 4/23. 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.
Sat 6/76:00 amMDW - MID
2 stops13h 53mDelta
Sat 6/1410:15 amMID - MDW
2 stops10h 30mDelta
Deal found 4/23$541
This Cheapflightsfares deal was found by Cheapflights users on 4/23. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/209:59 pmMDW - CUN
1 stop13h 00mVolaris
Wed 8/278:00 amCUN - MDW
1 stop11h 16mVolaris
Deal found 4/23$543
This Kiwi.com deal was found by Cheapflights users on 4/23. 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.
Sun 6/159:12 pmMDW - MID
1 stop21h 48mMultiple Airlines
Fri 6/2011:55 amMID - MDW
1 stop7h 22mMultiple Airlines
Deal found 4/23$562

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 April 24, 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 5/11

10:45 am-2:25 pm

Nonstop3h 40m

Cancun

Thu 5/15

9:00 am-12:40 pm

Nonstop3h 40m

$246

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Tue 5/6

6:04 am-12:50 pm

1 stop6h 46m

Cancun

Tue 5/13

8:00 am-3:30 pm

1 stop7h 30m

$299

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Sat 6/7

6:00 am-5:30 pm

2 stops11h 30m

Cancun

Sat 6/14

9:15 am-9:45 pm

2 stops12h 30m

$321

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Mon 5/12

12:48 pm-8:20 pm

1 stop7h 32m

Cancun

Fri 5/16

12:39 pm-10:13 pm

1 stop9h 34m

$339

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Thu 5/15

2:45 pm-9:58 am

1 stop19h 13m

Cancun

Mon 5/19

2:31 pm-11:47 pm

1 stop9h 16m

$403

ChicagoMérida

MDW - MID

MDWMID

Chicago Midway

Sat 6/7

6:00 am-4:41 pm

2 stops11h 41m

Mérida Rejon

Sat 6/14

7:53 am-9:45 pm

2 stops12h 52m

$537

ChicagoMérida

MDW - MID

MDWMID

Chicago Midway

Sat 6/7

6:00 am-6:53 pm

2 stops13h 53m

Mérida Rejon

Sat 6/14

10:15 am-9:45 pm

2 stops10h 30m

$541

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Wed 8/20

9:59 pm-10:59 am

1 stop13h 00m

Cancun

Wed 8/27

8:00 am-7:16 pm

1 stop11h 16m

$543

ChicagoMérida

MDW - MID

MDWMID

Chicago Midway

Sun 6/15

9:12 pm-6:00 pm

1 stop21h 48m

Mérida Rejon

Fri 6/20

11:55 am-8:17 pm

1 stop7h 22m

$562

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Sun 7/27

5:25 pm-9:00 pm

Nonstop3h 35m

$111

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/23

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 April 24, 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

Comfort

8.0

Entertainment

7.6

Overall

8.0

Boarding

8.2

Food

7.1

Crew

8.6

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!
Southwest
8.0
Very good
4,287 reviews
Southwest
8.0
Very good
4,287 reviews

Comfort

8.0

Entertainment

7.6

Overall

8.0

Boarding

8.2

Food

7.1

Crew

8.6

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!
Delta
8.0
Very good
7,920 reviews
Southwest
8.0
Very good
4,287 reviews

Comfort

8.0

Entertainment

7.6

Overall

8.0

Boarding

8.2

Food

7.1

Crew

8.6

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!
Aeromexico
7.5
Good
1,700 reviews
Southwest
8.0
Very good
4,287 reviews

Comfort

8.0

Entertainment

7.6

Overall

8.0

Boarding

8.2

Food

7.1

Crew

8.6

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!
Volaris
6.7
Okay
1,172 reviews
Southwest
8.0
Very good
4,287 reviews

Comfort

8.0

Entertainment

7.6

Overall

8.0

Boarding

8.2

Food

7.1

Crew

8.6

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!
Frontier
6.0
Okay
3,283 reviews
Southwest
8.0
Very good
4,287 reviews

Comfort

8.0

Entertainment

7.6

Overall

8.0

Boarding

8.2

Food

7.1

Crew

8.6

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!

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 $111 on Southwest. Other airlines that offer cheap prices include Aeromexico from $136 and Delta 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
O'Hare Intl to Guadalajara flights
Midway to Mexico City flights
O'Hare Intl to Mexico City flights
O'Hare Intl to San José del Cabo flights
Midway to Guadalajara flights
O'Hare Intl to Puerto Vallarta flights
O'Hare Intl to Morelia flights
Midway to Morelia flights
O'Hare Intl to León flights
Midway to San José del Cabo flights
Midway to León flights
Midway to Puerto Vallarta flights
O'Hare Intl to Monterrey flights
O'Hare Intl to San Luis Potosí flights
O'Hare Intl to Oaxaca flights
O'Hare Intl to Durango flights
Midway to Aguascalientes flights
O'Hare Intl to Santiago de Querétaro flights
Midway to Monterrey flights
O'Hare Intl to Aguascalientes flights
O'Hare Intl to Mérida flights
Midway to Cozumel flights
O'Hare Intl to Ixtapa flights
Midway to Durango flights
Midway to Oaxaca flights
O'Hare Intl to Veracruz flights
Midway to San Luis Potosí flights
Midway to Zacatecas flights
O'Hare Intl to Mazatlán flights
O'Hare Intl to Tijuana flights
O'Hare Intl to Puerto Escondido flights
Midway to Tijuana flights
O'Hare Intl to Puebla City flights
O'Hare Intl to Zacatecas flights
O'Hare Intl to La Paz flights
Midway to Santiago de Querétaro flights
O'Hare Intl to Hermosillo flights
O'Hare Intl to Acapulco flights
Midway to Veracruz flights
Midway to Mazatlán flights
Midway to Mérida flights
O'Hare Intl to Torreón flights
Midway to Puerto Escondido flights
O'Hare Intl to Chihuahua flights
O'Hare Intl to Manzanillo flights
O'Hare Intl to Santa Maria Huatulco 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.