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$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 4/6. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — MID
Apr 7 — Apr 141
Mon 4/7
Mon 4/14
1 adult, Economy
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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 2, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$246
(Southwest)

One-way from

$111
(Southwest)

Popular in

December

Cheapest in

February

Average price

$640
Provider with most accurate pricing for Chicago (CHI)-Mérida Rejon flight deals.
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Provider most trusted by Cheapflights users for Chicago (CHI)-Mérida Rejon flights.
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From Chicago Midway to Yucatan
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One-way flight from Chicago Midway to Yucatan
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Highest demand for flights based on searches. 16% potential increase in price ($107 potential increase over avg. RT price).
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Cheapest flight prices on average. 4% potential price decrease ($26 potential savings vs. average RT price).
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Average for round-trip flights in April 2025
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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 2, 2025.

This Southwest deal was found by Cheapflights users on 4/1. 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.
Wed 7/94:30 pmMDW - CUN
Nonstop3h 35mSouthwest
Tue 7/158:30 amCUN - MDW
Nonstop3h 35mSouthwest
Deal found 4/1$246
This eDestinos deal was found by Cheapflights users on 4/1. 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/1212:48 pmMDW - CUN
1 stop7h 32mAeromexico
Wed 5/1411:00 amCUN - MDW
1 stop10h 28mAeromexico
Deal found 4/1$276
This Kiwi.com deal was found by Cheapflights users on 4/1. 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 4/195:10 pmMDW - CUN
1 stop15h 05mMultiple Airlines
Sat 4/2611:05 amCUN - MDW
1 stop9h 34mMultiple Airlines
Deal found 4/1$317
This Delta deal was found by Cheapflights users on 4/1. 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.
Mon 5/1212:48 pmMDW - CUN
1 stop7h 32mDelta
Wed 5/1411:00 amCUN - MDW
1 stop10h 28mDelta
Deal found 4/1$321
This Travelocity deal was found by Cheapflights users on 4/1. 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 Travelocity is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/116:44 pmMDW - CUN
1 stop13h 01mFrontier
Tue 4/1512:40 pmCUN - MDW
1 stop7h 05mFrontier
Deal found 4/1$374
This Cheapflightsfares deal was found by Cheapflights users on 4/1. 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.
Sat 4/510:41 pmMDW - CUN
1 stop14h 21mVolaris
Sat 4/128:00 amCUN - MDW
1 stop11h 06mVolaris
Deal found 4/1$465
This Delta deal was found by Cheapflights users on 3/31. 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 5/176:00 amMDW - MID
2 stops14h 47mDelta
Tue 6/36:53 amMID - MDW
2 stops13h 34mDelta
Deal found 3/31$520
This SmartFares deal was found by Cheapflights users on 4/1. 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.
Wed 5/2112:48 pmMDW - MID
2 stops12h 11mAeromexico
Wed 5/286:49 amMID - MDW
2 stops13h 38mAeromexico
Deal found 4/1$531
This Kiwi.com deal was found by Cheapflights users on 4/1. 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.
Fri 5/163:49 pmMDW - MID
2 stops33h 35mMultiple Airlines
Fri 5/2312:00 pmMID - MDW
1 stop7h 17mMultiple Airlines
Deal found 4/1$533
This Mytrip deal was found by Cheapflights users on 4/1. 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.
Fri 5/168:39 pmMDW - MID
3 stops35h 01mVolaris
Fri 5/2310:33 pmMID - MDW
2 stops19h 33mVolaris
Deal found 4/1$704

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 2, 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

Mon 5/12

12:48 pm-8:20 pm

1 stop7h 32m

Cancun

Wed 5/14

11:00 am-9:28 pm

1 stop10h 28m

$276

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Sat 4/19

5:10 pm-8:15 am

1 stop15h 05m

Cancun

Sat 4/26

11:05 am-8:39 pm

1 stop9h 34m

$317

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Mon 5/12

12:48 pm-8:20 pm

1 stop7h 32m

Cancun

Wed 5/14

11:00 am-9:28 pm

1 stop10h 28m

$321

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Tue 6/10

4:30 pm-8:05 pm

Nonstop3h 35m

Cancun

Tue 6/17

10:40 am-4:40 pm

1 stop6h 00m

$336

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Fri 4/11

6:44 pm-7:45 am

1 stop13h 01m

Cancun

Tue 4/15

12:40 pm-7:45 pm

1 stop7h 05m

$374

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Sat 4/5

10:41 pm-1:02 pm

1 stop14h 21m

Cancun

Sat 4/12

8:00 am-7:06 pm

1 stop11h 06m

$465

ChicagoMérida

MDW - MID

MDWMID

Chicago Midway

Sat 5/17

6:00 am-7:47 pm

2 stops14h 47m

Mérida Rejon

Tue 6/3

6:53 am-9:27 pm

2 stops13h 34m

$520

ChicagoMérida

MDW - MID

MDWMID

Chicago Midway

Wed 5/21

12:48 pm-11:59 pm

2 stops12h 11m

Mérida Rejon

Wed 5/28

6:49 am-9:27 pm

2 stops13h 38m

$531

ChicagoMérida

MDW - MID

MDWMID

Chicago Midway

Fri 5/16

3:49 pm-12:24 am

2 stops33h 35m

Mérida Rejon

Fri 5/23

12:00 pm-8:17 pm

1 stop7h 17m

$533

ChicagoMérida

MDW - MID

MDWMID

Chicago Midway

Fri 5/16

8:39 pm-6:40 am

3 stops35h 01m

Mérida Rejon

Fri 5/23

10:33 pm-7:06 pm

2 stops19h 33m

$704

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/1

Showing 1-10 of 19 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 2, 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
4,272 reviews

Comfort

8.0

Entertainment

7.6

Overall

8.0

Boarding

8.2

Food

7.1

Crew

8.6

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
Southwest
8.0
Very good
4,272 reviews
Southwest
8.0
Very good
4,272 reviews

Comfort

8.0

Entertainment

7.6

Overall

8.0

Boarding

8.2

Food

7.1

Crew

8.6

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
Delta
8.0
Very good
7,898 reviews
Southwest
8.0
Very good
4,272 reviews

Comfort

8.0

Entertainment

7.6

Overall

8.0

Boarding

8.2

Food

7.1

Crew

8.6

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
Aeromexico
7.5
Good
1,700 reviews
Southwest
8.0
Very good
4,272 reviews

Comfort

8.0

Entertainment

7.6

Overall

8.0

Boarding

8.2

Food

7.1

Crew

8.6

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
WestJet
7.2
Good
2,789 reviews
Southwest
8.0
Very good
4,272 reviews

Comfort

8.0

Entertainment

7.6

Overall

8.0

Boarding

8.2

Food

7.1

Crew

8.6

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
Volaris
6.7
Okay
1,170 reviews
Southwest
8.0
Very good
4,272 reviews

Comfort

8.0

Entertainment

7.6

Overall

8.0

Boarding

8.2

Food

7.1

Crew

8.6

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.

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 $133 and Frontier from $142 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

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