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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 7/14. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — MID
may. 5 — may. 121
lun. 5/5
lun. 5/12
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 abril 30, 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.
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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 ($105 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 abril 30, 2025.

This Southwest deal was found by Cheapflights users on 4/28. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
dom. 5/1110:45 amMDW - CUN
Nonstop3h 40mSouthwest
jue. 5/159:00 amCUN - MDW
Nonstop3h 40mSouthwest
Deal found 4/28$246
This SmartFares deal was found by Cheapflights users on 4/29. 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. 7/512:44 pmMDW - CUN
1 stop7h 36mAeromexico
jue. 7/1011:00 amCUN - MDW
1 stop7h 02mAeromexico
Deal found 4/29$306
This Delta deal was found by Cheapflights users on 4/29. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 5/66:04 amMDW - CUN
1 stop7h 57mDelta
sáb. 5/1012:35 pmCUN - MDW
1 stop8h 39mDelta
Deal found 4/29$321
This Kiwi.com deal was found by Cheapflights users on 4/29. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
dom. 6/89:12 pmMDW - CUN
1 stop11h 04mMultiple Airlines
vie. 6/1312:35 pmCUN - MDW
1 stop11h 16mMultiple Airlines
Deal found 4/29$368
This Frontier deal was found by Cheapflights users on 4/29. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 6/36:40 amMDW - CUN
1 stop6h 20mFrontier
sáb. 6/79:09 amCUN - MDW
1 stop10h 16mFrontier
Deal found 4/29$417
This Delta deal was found by Cheapflights users on 4/28. 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.
mar. 6/310:25 amMDW - MID
2 stops13h 38mDelta
mar. 6/107:53 amMID - MDW
2 stops12h 52mDelta
Deal found 4/28$501
This Kiwi.com deal was found by Cheapflights users on 4/29. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 6/136:00 amMDW - MID
2 stops14h 00mMultiple Airlines
vie. 6/2011:55 amMID - MDW
1 stop7h 22mMultiple Airlines
Deal found 4/29$574
This Aeromexico deal was found by Cheapflights users on 4/29. 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 Aeromexico is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 6/1310:26 amMDW - MID
2 stops13h 38mAeromexico
vie. 6/209:20 amMID - MDW
2 stops11h 25mAeromexico
Deal found 4/29$666

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 abril 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

dom. 5/11

10:45 am-2:25 pm

Nonstop3h 40m

Cancun

jue. 5/15

9:00 am-12:40 pm

Nonstop3h 40m

$246

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

sáb. 7/5

12:44 pm-8:20 pm

1 stop7h 36m

Cancun

jue. 7/10

11:00 am-6:02 pm

1 stop7h 02m

$306

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

mar. 5/6

6:04 am-2:01 pm

1 stop7h 57m

Cancun

sáb. 5/10

12:35 pm-9:14 pm

1 stop8h 39m

$321

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

dom. 6/8

9:12 pm-8:16 am

1 stop11h 04m

Cancun

vie. 6/13

12:35 pm-11:51 pm

1 stop11h 16m

$368

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

jue. 5/29

6:20 am-12:55 pm

1 stop6h 35m

Cancun

dom. 6/8

1:47 pm-11:18 pm

1 stop9h 31m

$417

ChicagoMérida

MDW - MID

MDWMID

Chicago Midway

mar. 6/3

10:25 am-11:03 pm

2 stops13h 38m

Mérida Rejon

mar. 6/10

7:53 am-9:45 pm

2 stops12h 52m

$501

ChicagoMérida

MDW - MID

MDWMID

Chicago Midway

vie. 6/13

6:00 am-7:00 pm

2 stops14h 00m

Mérida Rejon

vie. 6/20

11:55 am-8:17 pm

1 stop7h 22m

$574

ChicagoMérida

MDW - MID

MDWMID

Chicago Midway

vie. 6/13

10:26 am-11:04 pm

2 stops13h 38m

Mérida Rejon

vie. 6/20

9:20 am-9:45 pm

2 stops11h 25m

$666

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

lun. 7/14

4:35 pm-8:10 pm

Nonstop3h 35m

$111

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

mar. 6/10

10:26 am-8:20 pm

1 stop9h 54m

$141

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/29

Showing 1-10 of 17 results
1
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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 abril 30, 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
4,295 reviews

Crew

8.6

Entertainment

7.6

Boarding

8.2

Comfort

8.0

Food

7.1

Overall

8.0

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
4,295 reviews
Southwest
8.0
Very good
4,295 reviews

Crew

8.6

Entertainment

7.6

Boarding

8.2

Comfort

8.0

Food

7.1

Overall

8.0

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
7,936 reviews
Southwest
8.0
Very good
4,295 reviews

Crew

8.6

Entertainment

7.6

Boarding

8.2

Comfort

8.0

Food

7.1

Overall

8.0

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
1,698 reviews
Southwest
8.0
Very good
4,295 reviews

Crew

8.6

Entertainment

7.6

Boarding

8.2

Comfort

8.0

Food

7.1

Overall

8.0

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!
WestJet
7.2
Good
2,823 reviews
Southwest
8.0
Very good
4,295 reviews

Crew

8.6

Entertainment

7.6

Boarding

8.2

Comfort

8.0

Food

7.1

Overall

8.0

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
1,174 reviews
Southwest
8.0
Very good
4,295 reviews

Crew

8.6

Entertainment

7.6

Boarding

8.2

Comfort

8.0

Food

7.1

Overall

8.0

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 $134 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

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