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Midway

$148+ Cheap flights from Yucatan to Midway (MDW)

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 7/12. Fares are subject to change and may not be available on all flights or dates of travel.
MID — MDW
Jun 17 — Jun 241
Tue 6/17
Tue 6/24
1 adult, Economy
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Cheap flight deals from Yucatan to Midway

Keep the following information in mind while searching for Yucatan to Midway flight deals. Data was last updated June 12, 2025.

Round-trip from

$275
(Delta)

One-way from

$148
(Southwest)

Popular in

October

Cheapest in

February

Average price

$478
From Yucatan to Chicago Midway
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One-way flight from Yucatan to Chicago Midway
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Highest demand for flights based on searches. 1% potential increase in price ($7 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease ($6 potential savings vs. average RT price).
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Average for round-trip flights in June 2025
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Find flight deals from Yucatan to Midway

Cheapest flights from Yucatan to Midway
Explore the most affordable flight options available from Yucatan to Midway. Find the lowest fares from popular airlines and budget airlines, with prices last updated on June 12, 2025.

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.
Thu 9/251:45 pmCUN - MDW
1 stop7h 59mDelta
Tue 9/301:05 pmMDW - CUN
1 stop6h 57mDelta
Deal found 6/10$275
This Priceline deal was found by Cheapflights users on 6/12. 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.
Sat 7/129:09 amCUN - MDW
1 stop11h 13mFrontier
Mon 7/146:20 amMDW - CUN
1 stop6h 07mFrontier
Deal found 6/12$290
This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/118:30 amCUN - MDW
Nonstop3h 35mSouthwest
Mon 7/144:35 pmMDW - CUN
Nonstop3h 35mSouthwest
Deal found 6/11$361
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.
Sat 9/1311:10 amCUN - MDW
1 stop10h 34mAeromexico
Sat 9/2010:35 amMDW - CUN
1 stop9h 27mAeromexico
Deal found 6/10$367
This Delta deal was found by Cheapflights users on 6/12. 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 9/45:50 amMID - MDW
2 stops14h 36mDelta
Tue 9/96:00 amMDW - MID
2 stops13h 20mDelta
Deal found 6/12$448
This Aeromexico 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 Aeromexico is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/187:57 amMID - MDW
2 stops12h 47mAeromexico
Mon 9/226:00 amMDW - MID
2 stops13h 20mAeromexico
Deal found 6/11$449
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.
Sat 7/1912:26 pmCUN - MDW
2 stops10h 09mMultiple Airlines
Sat 8/29:12 pmMDW - CUN
1 stop11h 05mMultiple Airlines
Deal found 6/9$505
This Mytrip 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/249:14 pmMID - MDW
1 stop21h 02mVolaris
Mon 6/309:59 pmMDW - MID
2 stops15h 26mVolaris
Deal found 6/11$592
This Kiwi.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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/38:00 amCUN - MDW
1 stop11h 16mVolaris
Mon 7/78:39 pmMDW - CUN
1 stop13h 09mVolaris
Deal found 6/11$636
This eDestinos deal was found by Cheapflights users on 6/12. 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 6/242:05 pmMID - MDW
1 stop28h 11mMultiple Airlines
Mon 6/306:25 amMDW - MID
2 stops25h 45mMultiple Airlines
Deal found 6/12$664

Cheapflights Fare Finder

Customize your flight search to find flights from Yucatan to Midway 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 June 12, 2025.
Use the filters below to find and compare flights from Yucatan to Chicago Midway Airport that are best for you.

Fly from

Yucatan

Fly to

Midway

Route

Depart

Return

Price

CancúnChicago

CUN - MDW

CUNMDW

Cancun

Thu 9/25

1:45 pm-9:44 pm

1 stop7h 59m

Chicago Midway

Tue 9/30

1:05 pm-8:02 pm

1 stop6h 57m

$275

CancúnChicago

CUN - MDW

CUNMDW

Cancun

Sat 7/12

9:09 am-8:22 pm

1 stop11h 13m

Chicago Midway

Mon 7/14

6:20 am-12:27 pm

1 stop6h 07m

$290

CancúnChicago

CUN - MDW

CUNMDW

Cancun

Fri 7/11

8:30 am-12:05 pm

Nonstop3h 35m

Chicago Midway

Mon 7/14

4:35 pm-8:10 pm

Nonstop3h 35m

$361

CancúnChicago

CUN - MDW

CUNMDW

Cancun

Sat 9/13

11:10 am-9:44 pm

1 stop10h 34m

Chicago Midway

Sat 9/20

10:35 am-8:02 pm

1 stop9h 27m

$367

MéridaChicago

MID - MDW

MIDMDW

Mérida Rejon

Thu 9/4

5:50 am-9:26 pm

2 stops14h 36m

Chicago Midway

Tue 9/9

6:00 am-6:20 pm

2 stops13h 20m

$448

MéridaChicago

MID - MDW

MIDMDW

Mérida Rejon

Thu 9/18

7:57 am-9:44 pm

2 stops12h 47m

Chicago Midway

Mon 9/22

6:00 am-6:20 pm

2 stops13h 20m

$449

CancúnChicago

CUN - MDW

CUNMDW

Cancun

Sat 7/19

12:26 pm-10:35 pm

2 stops10h 09m

Chicago Midway

Sat 8/2

9:12 pm-8:17 am

1 stop11h 05m

$505

MéridaChicago

MID - MDW

MIDMDW

Mérida Rejon

Tue 6/24

9:14 pm-7:16 pm

1 stop21h 02m

Chicago Midway

Mon 6/30

9:59 pm-12:25 pm

2 stops15h 26m

$592

CancúnChicago

CUN - MDW

CUNMDW

Cancun

Thu 7/3

8:00 am-7:16 pm

1 stop11h 16m

Chicago Midway

Mon 7/7

8:39 pm-9:48 am

1 stop13h 09m

$636

MéridaChicago

MID - MDW

MIDMDW

Mérida Rejon

Tue 6/24

2:05 pm-7:16 pm

1 stop28h 11m

Chicago Midway

Mon 6/30

6:25 am-7:10 am

2 stops25h 45m

$664

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/9

Showing 1-10 of 18 results
1
2

Best time to book a flight from Yucatan to Midway

Have a flexible travel schedule? Discover the best time to fly to Midway from Yucatan 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 Yucatan to Chicago Midway Airport

Rainfall in Midway by month

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

In terms of precipitation, rainfall in Chicago Midway Airport ranges from 1.7 - 4.9 inches per month. August is typically the wettest month, when rainfall can reach 4.9 in. January is typically the driest time to visit Chicago Midway Airport when rainfall is around 1.7 in.

Temperature in Midway by month

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

If weather is an important factor for your trip to Chicago Midway Airport, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 73.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 23.0 F).

Reviews of airlines servicing Midway

Get insights into the airlines that provide service to Midway. 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 Midway. Reviews last updated June 12, 2025.
Peruse reviews from past customers who have flown with Southwest, Delta and Air Transat from Yucatan to Chicago to help guide your decision. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,287 reviews

Boarding

8.2

Food

7.1

Crew

8.6

Comfort

8.0

Overall

8.0

Entertainment

7.6

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

Food

7.1

Crew

8.6

Comfort

8.0

Overall

8.0

Entertainment

7.6

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
7,950 reviews
Southwest
8.0
Very good
4,287 reviews

Boarding

8.2

Food

7.1

Crew

8.6

Comfort

8.0

Overall

8.0

Entertainment

7.6

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.
Air Transat
7.8
Good
396 reviews
Southwest
8.0
Very good
4,287 reviews

Boarding

8.2

Food

7.1

Crew

8.6

Comfort

8.0

Overall

8.0

Entertainment

7.6

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

Food

7.1

Crew

8.6

Comfort

8.0

Overall

8.0

Entertainment

7.6

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

Food

7.1

Crew

8.6

Comfort

8.0

Overall

8.0

Entertainment

7.6

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 Yucatan to Midway. 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 Yucatan to Chicago Midway Airport one-way?

    For one-way options, check prices for Southwest. According to our data, you can fly for as low as $148. Users have also found prices from $164 and $175 on Frontier and Delta, respectively.

  • Can I find deals for flights from Yucatan to Midway that include hotel bookings?

    Yes. In addition to deals on Yucatan to Midway flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Yucatan to Midway?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Yucatan to Midway.

  • Can I find deals for business class flights from Yucatan to Midway?

    Yes. Cheapflights offers flight deals from Yucatan to Midway 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 Yucatan to Chicago Midway Airport?

    Currently, April is the cheapest month in which you can book a flight from Yucatan to Chicago Midway Airport (average of $160). Flying from Yucatan to Chicago Midway Airport in November is currently the most expensive (average of $249). 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

Traveling to a place near Yucatan?

Book flights to Yucatan if you plan to visit one of these locations
Merrillville
Lansing
Benton Harbor
Porter
Hammond
Valparaiso
Chesterton

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