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$110+ 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
Feb 28 — Mar 71
Fri 2/28
Fri 3/7
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 February 23, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$292
(Kiwi.com)

One-way from

$110
(Southwest)

Popular in

December

Cheapest in

February

Average price

$416
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. 18% potential increase in price ($120 potential increase over avg. RT price).
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Cheapest flight prices on average. 5% potential price decrease ($27 potential savings vs. average RT price).
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Average for round-trip flights in February 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 February 23, 2025.

This Kiwi.com deal was found by Cheapflights users on 2/21. 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.
Tue 4/14:40 pmMDW - CUN
1 stop15h 33mMultiple Airlines
Tue 4/810:40 amCUN - MDW
1 stop9h 11mMultiple Airlines
Deal found 2/21$292
This Southwest deal was found by Cheapflights users on 2/20. 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 5/78:45 amMDW - CUN
1 stop6h 05mSouthwest
Wed 5/149:00 amCUN - MDW
Nonstop3h 40mSouthwest
Deal found 2/20$307
This Mytrip deal was found by Cheapflights users on 2/22. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/86:45 amMDW - CUN
1 stop30h 43mFrontier
Tue 4/1512:40 pmCUN - MDW
1 stop7h 05mFrontier
Deal found 2/22$321
This eDestinos deal was found by Cheapflights users on 2/22. 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 2/2510:57 amMDW - CUN
1 stop9h 08mAeromexico
Mon 3/33:03 pmCUN - MDW
1 stop8h 17mAeromexico
Deal found 2/22$370
This Delta deal was found by Cheapflights users on 2/21. 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.
Thu 3/612:44 pmMDW - CUN
1 stop7h 21mDelta
Thu 3/1311:05 amCUN - MDW
1 stop6h 57mDelta
Deal found 2/21$390
This Kiwi.com deal was found by Cheapflights users on 2/22. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 3/98:39 pmMDW - CUN
1 stop22h 19mVolaris
Fri 3/148:00 amCUN - MDW
1 stop11h 10mVolaris
Deal found 2/22$392
This Kiwi.com deal was found by Cheapflights users on 2/22. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/47:25 amMDW - MID
1 stop11h 05mMultiple Airlines
Wed 3/129:07 pmMID - MDW
1 stop21h 03mMultiple Airlines
Deal found 2/22$467
This Delta deal was found by Cheapflights users on 2/22. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/181:05 pmMDW - MID
2 stops11h 50mDelta
Tue 9/237:57 amMID - MDW
2 stops12h 50mDelta
Deal found 2/22$500
This Aeromexico deal was found by Cheapflights users on 2/22. 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 Aeromexico is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/236:00 amMDW - MID
2 stops13h 20mAeromexico
Wed 8/279:50 amMID - MDW
2 stops10h 57mAeromexico
Deal found 2/22$665

Find flights from Midway to Yucatan within your budget

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 February 23, 2025.

Fly from

Midway

Fly to

Yucatan

Route

Depart

Return

Price

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Tue 4/1

4:40 pm-8:13 am

1 stop15h 33m

Cancun

Tue 4/8

10:40 am-7:51 pm

1 stop9h 11m

$292

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Wed 5/7

8:45 am-2:50 pm

1 stop6h 05m

Cancun

Wed 5/14

9:00 am-12:40 pm

Nonstop3h 40m

$307

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Tue 4/8

6:45 am-1:28 pm

1 stop30h 43m

Cancun

Tue 4/15

12:40 pm-7:45 pm

1 stop7h 05m

$321

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Tue 2/25

10:57 am-9:05 pm

1 stop9h 08m

Cancun

Mon 3/3

3:03 pm-10:20 pm

1 stop8h 17m

$370

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Sun 3/9

8:39 pm-6:58 pm

1 stop22h 19m

Cancun

Fri 3/14

8:00 am-7:10 pm

1 stop11h 10m

$392

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Sun 3/2

9:33 am-9:05 pm

2 stops10h 32m

Cancun

Tue 3/4

8:00 am-6:11 pm

2 stops11h 11m

$395

ChicagoMérida

MDW - MID

MDWMID

Chicago Midway

Tue 3/18

6:00 am-7:15 pm

2 stops14h 15m

Mérida Rejon

Tue 3/25

6:53 am-10:23 pm

2 stops14h 30m

$590

ChicagoMérida

MDW - MID

MDWMID

Chicago Midway

Sat 3/8

7:25 am-6:30 pm

1 stop11h 05m

Mérida Rejon

Wed 3/12

7:51 am-7:10 pm

2 stops10h 19m

$596

ChicagoMérida

MDW - MID

MDWMID

Chicago Midway

Sat 5/17

6:00 am-6:20 pm

2 stops13h 20m

Mérida Rejon

Wed 5/21

10:57 am-3:30 pm

2 stops27h 33m

$765

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Sun 4/6

4:30 pm-8:25 pm

Nonstop3h 55m

$110

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/21

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.

Travel insights for flights from Midway to Yucatan

Get recent, data-driven insights about flights from Midway to Yucatan including ideal travel times, pricing trends, and more.

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 February 23, 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
8.1
Very good
4,395 reviews

Boarding

8.2

Comfort

8.1

Food

7.1

Crew

8.7

Entertainment

7.6

Overall

8.1

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Southwest
8.1
Very good
4,395 reviews
Southwest
8.1
Very good
4,395 reviews

Boarding

8.2

Comfort

8.1

Food

7.1

Crew

8.7

Entertainment

7.6

Overall

8.1

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Delta
8.0
Very good
8,203 reviews
Southwest
8.1
Very good
4,395 reviews

Boarding

8.2

Comfort

8.1

Food

7.1

Crew

8.7

Entertainment

7.6

Overall

8.1

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Aeromexico
7.5
Good
1,767 reviews
Southwest
8.1
Very good
4,395 reviews

Boarding

8.2

Comfort

8.1

Food

7.1

Crew

8.7

Entertainment

7.6

Overall

8.1

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Volaris
6.7
Okay
1,206 reviews
Southwest
8.1
Very good
4,395 reviews

Boarding

8.2

Comfort

8.1

Food

7.1

Crew

8.7

Entertainment

7.6

Overall

8.1

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Frontier
6.0
Okay
3,352 reviews
Southwest
8.1
Very good
4,395 reviews

Boarding

8.2

Comfort

8.1

Food

7.1

Crew

8.7

Entertainment

7.6

Overall

8.1

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

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 $110 on Southwest. Other airlines that offer cheap prices include Frontier from $111 and Volaris from $168 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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