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Midway

$149+ 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 10/31. Fares are subject to change and may not be available on all flights or dates of travel.
MID — MDW
ago. 5 — ago. 121
mar. 8/5
mar. 8/12
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 julio 31, 2025.

Round-trip from

$273
(Southwest)

One-way from

$149
(Southwest)

Popular in

October

Cheapest in

February

Average price

$449
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. 3% potential increase in price ($17 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 July 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 julio 31, 2025.

This Delta deal was found by Cheapflights users on 7/31. 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.
vie. 10/248:00 amCUN - MDW
2 stops10h 25mDelta
vie. 10/3110:35 amMDW - CUN
1 stop9h 45mDelta
Deal found 7/31$276
This Aeromexico deal was found by Cheapflights users on 7/31. 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 Aeromexico is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 10/93:14 pmCUN - MDW
1 stop7h 00mAeromexico
dom. 10/126:00 amMDW - CUN
2 stops11h 45mAeromexico
Deal found 7/31$287
This Southwest deal was found by Cheapflights users on 7/31. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb. 9/61:15 pmCUN - MDW
1 stop7h 30mSouthwest
mar. 9/99:55 amMDW - CUN
Nonstop3h 35mSouthwest
Deal found 7/31$289
This Frontier deal was found by Cheapflights users on 7/31. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb. 10/181:41 pmCUN - MDW
1 stop9h 28mFrontier
sáb. 10/256:10 amMDW - CUN
1 stop6h 16mFrontier
Deal found 7/31$296
This Flightnetwork deal was found by Cheapflights users on 7/31. 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 Flightnetwork is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 10/88:00 amCUN - MDW
1 stop11h 16mMultiple Airlines
jue. 10/97:23 pmMDW - CUN
1 stop17h 03mMultiple Airlines
Deal found 7/31$431
This Aeromexico deal was found by Cheapflights users on 7/31. 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 Aeromexico is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 10/27:50 amMID - MDW
2 stops12h 46mAeromexico
lun. 10/66:00 amMDW - MID
2 stops15h 55mAeromexico
Deal found 7/31$449
This Delta deal was found by Cheapflights users on 7/31. 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.
mié. 10/15:50 amMID - MDW
2 stops14h 46mDelta
vie. 10/36:00 amMDW - MID
2 stops14h 56mDelta
Deal found 7/31$566

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 julio 31, 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

vie. 10/24

8:00 am-6:25 pm

2 stops10h 25m

Chicago Midway

vie. 10/31

10:35 am-8:20 pm

1 stop9h 45m

$276

CancúnChicago

CUN - MDW

CUNMDW

Cancun

jue. 10/9

3:14 pm-10:14 pm

1 stop7h 00m

Chicago Midway

dom. 10/12

6:00 am-5:45 pm

2 stops11h 45m

$287

CancúnChicago

CUN - MDW

CUNMDW

Cancun

sáb. 9/6

1:15 pm-8:45 pm

1 stop7h 30m

Chicago Midway

mar. 9/9

9:55 am-1:30 pm

Nonstop3h 35m

$289

CancúnChicago

CUN - MDW

CUNMDW

Cancun

sáb. 10/18

1:41 pm-11:09 pm

1 stop9h 28m

Chicago Midway

sáb. 10/25

6:10 am-12:26 pm

1 stop6h 16m

$296

CancúnChicago

CUN - MDW

CUNMDW

Cancun

mié. 10/8

8:00 am-7:16 pm

1 stop11h 16m

Chicago Midway

jue. 10/9

7:23 pm-12:26 pm

1 stop17h 03m

$431

MéridaChicago

MID - MDW

MIDMDW

Mérida Rejon

jue. 10/2

7:50 am-9:36 pm

2 stops12h 46m

Chicago Midway

lun. 10/6

6:00 am-8:55 pm

2 stops15h 55m

$449

MéridaChicago

MID - MDW

MIDMDW

Mérida Rejon

sáb. 1/24

10:33 am-9:46 pm

2 stops11h 13m

Chicago Midway

sáb. 1/31

6:00 am-6:50 pm

2 stops12h 50m

$533

CancúnChicago

CUN - MDW

CUNMDW

Cancun

vie. 10/31

3:15 pm-6:50 pm

Nonstop3h 35m

$149

CancúnChicago

CUN - MDW

CUNMDW

Cancun

vie. 9/5

8:00 am-9:26 pm

1 stop13h 26m

$175

CancúnChicago

CUN - MDW

CUNMDW

Cancun

sáb. 10/4

7:05 am-9:10 pm

2 stops14h 05m

$185

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/30

Showing 1-10 of 15 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
No data available for this route at this time. Please check back soon.

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 julio 31, 2025.
See what other customers who have flown with Southwest, Delta, and Aeromexico from Yucatan to Chicago Midway Airport have to say. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,246 reviews

Entertainment

7.5

Boarding

8.1

Food

7.0

Overall

8.0

Crew

8.6

Comfort

8.0

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
Southwest
8.0
Very good
4,246 reviews
Southwest
8.0
Very good
4,246 reviews

Entertainment

7.5

Boarding

8.1

Food

7.0

Overall

8.0

Crew

8.6

Comfort

8.0

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
Delta
8.0
Very good
7,981 reviews
Southwest
8.0
Very good
4,246 reviews

Entertainment

7.5

Boarding

8.1

Food

7.0

Overall

8.0

Crew

8.6

Comfort

8.0

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
Aeromexico
7.5
Good
1,721 reviews
Southwest
8.0
Very good
4,246 reviews

Entertainment

7.5

Boarding

8.1

Food

7.0

Overall

8.0

Crew

8.6

Comfort

8.0

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
Volaris
6.6
Okay
1,164 reviews
Southwest
8.0
Very good
4,246 reviews

Entertainment

7.5

Boarding

8.1

Food

7.0

Overall

8.0

Crew

8.6

Comfort

8.0

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
Frontier
5.9
Fair
3,239 reviews
Southwest
8.0
Very good
4,246 reviews

Entertainment

7.5

Boarding

8.1

Food

7.0

Overall

8.0

Crew

8.6

Comfort

8.0

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.

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 $149. Users have also found prices from $175 and $179 on Delta and Aeromexico, 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 Chicago Midway Airport?

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

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