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$161+ 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 6/26. Fares are subject to change and may not be available on all flights or dates of travel.
MID — MDW
Apr 5 — Apr 121
Sat 4/5
Sat 4/12
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 March 31, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$275
(Aeromexico)

One-way from

$161
(lastminute.com)

Popular in

July

Cheapest in

February

Average price

$371
Provider with most accurate pricing for Mérida Rejon-Chicago (CHI) flight deals.
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Provider most trusted by Cheapflights users for Mérida Rejon-Chicago (CHI) flights.
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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. 7% potential increase in price ($33 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease ($8 potential savings vs. average RT price).
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Average for round-trip flights in March 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 March 31, 2025.

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.
Wed 4/212:40 pmCUN - MDW
1 stop9h 43mDelta
Tue 4/86:00 amMDW - CUN
1 stop6h 50mDelta
Deal found 3/31$275
This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/302:00 pmCUN - MDW
1 stop8h 00mSouthwest
Fri 6/64:35 pmMDW - CUN
Nonstop3h 35mSouthwest
Deal found 3/31$341
This Expedia 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/73:56 pmCUN - MDW
1 stop27h 12mMultiple Airlines
Mon 5/1212:48 pmMDW - CUN
1 stop7h 32mMultiple Airlines
Deal found 3/31$367
This Flightnetwork 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 Flightnetwork is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/1110:50 amCUN - MDW
1 stop11h 42mFrontier
Sun 4/206:45 amMDW - CUN
1 stop30h 43mFrontier
Deal found 3/31$377
This Aeromexico 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 Aeromexico is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/306:07 amCUN - MDW
2 stops15h 20mAeromexico
Fri 6/612:48 pmMDW - CUN
2 stops10h 42mAeromexico
Deal found 3/31$409
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 5/105:47 amMID - MDW
2 stops14h 27mDelta
Wed 5/2110:25 amMDW - MID
2 stops14h 34mDelta
Deal found 3/31$472
This eDestinos deal was found by Cheapflights users on 3/30. 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 8/251:57 pmCUN - MDW
1 stop7h 29mVolaris
Sat 8/3010:44 pmMDW - CUN
1 stop14h 18mVolaris
Deal found 3/30$543
This WestJet deal was found by Cheapflights users on 3/30. 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 WestJet is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/251:10 pmCUN - MDW
2 stops20h 41mWestJet
Tue 7/291:05 pmMDW - CUN
2 stops20h 18mWestJet
Deal found 3/30$1,305
This LATAM Airlines 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 LATAM Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/83:45 pmCUN - MDW
2 stops17h 55mLATAM Airlines
Tue 5/134:15 pmMDW - CUN
2 stops24h 05mLATAM Airlines
Deal found 3/31$2,977

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 March 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

Wed 4/23

3:11 pm-10:22 pm

1 stop7h 11m

Chicago Midway

Tue 4/29

6:04 am-2:01 pm

1 stop7h 57m

$275

CancúnChicago

CUN - MDW

CUNMDW

Cancun

Thu 4/17

8:15 am-6:20 pm

2 stops10h 05m

Chicago Midway

Sun 4/20

6:04 am-12:50 pm

1 stop6h 46m

$315

CancúnChicago

CUN - MDW

CUNMDW

Cancun

Fri 5/30

2:00 pm-10:00 pm

1 stop8h 00m

Chicago Midway

Fri 6/6

4:35 pm-8:10 pm

Nonstop3h 35m

$341

CancúnChicago

CUN - MDW

CUNMDW

Cancun

Wed 5/7

3:56 pm-7:08 pm

1 stop27h 12m

Chicago Midway

Mon 5/12

12:48 pm-8:20 pm

1 stop7h 32m

$367

CancúnChicago

CUN - MDW

CUNMDW

Cancun

Fri 4/11

10:50 am-10:32 pm

1 stop11h 42m

Chicago Midway

Sun 4/20

6:45 am-1:28 pm

1 stop30h 43m

$377

MéridaChicago

MID - MDW

MIDMDW

Mérida Rejon

Sat 5/10

5:47 am-9:14 pm

2 stops14h 27m

Chicago Midway

Wed 5/21

10:25 am-11:59 pm

2 stops14h 34m

$472

CancúnChicago

CUN - MDW

CUNMDW

Cancun

Mon 8/25

1:57 pm-9:26 pm

1 stop7h 29m

Chicago Midway

Sat 8/30

10:44 pm-1:02 pm

1 stop14h 18m

$543

CancúnChicago

CUN - MDW

CUNMDW

Cancun

Fri 7/25

1:10 pm-9:51 am

2 stops20h 41m

Chicago Midway

Tue 7/29

1:05 pm-9:23 am

2 stops20h 18m

$1,305

CancúnChicago

CUN - MDW

CUNMDW

Cancun

Thu 5/8

3:45 pm-9:40 am

2 stops17h 55m

Chicago Midway

Tue 5/13

4:15 pm-4:20 pm

2 stops24h 05m

$2,977

CancúnChicago

CUN - MDW

CUNMDW

Cancun

Thu 6/26

12:25 pm-9:38 pm

1 stop9h 13m

$161

Flights are sorted by cheapest round-trip flights first.

Deals found on 3/30

Showing 1-10 of 17 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 March 31, 2025.
Peruse reviews from past customers who have flown with Southwest, Delta and LATAM Airlines 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
4,275 reviews

Crew

8.7

Overall

8.0

Food

7.1

Comfort

8.1

Entertainment

7.6

Boarding

8.2

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
4,275 reviews
Southwest
8.0
Very good
4,275 reviews

Crew

8.7

Overall

8.0

Food

7.1

Comfort

8.1

Entertainment

7.6

Boarding

8.2

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
7,899 reviews
Southwest
8.0
Very good
4,275 reviews

Crew

8.7

Overall

8.0

Food

7.1

Comfort

8.1

Entertainment

7.6

Boarding

8.2

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.
LATAM Airlines
7.5
Good
1,754 reviews
Southwest
8.0
Very good
4,275 reviews

Crew

8.7

Overall

8.0

Food

7.1

Comfort

8.1

Entertainment

7.6

Boarding

8.2

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
4,275 reviews

Crew

8.7

Overall

8.0

Food

7.1

Comfort

8.1

Entertainment

7.6

Boarding

8.2

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
4,275 reviews

Crew

8.7

Overall

8.0

Food

7.1

Comfort

8.1

Entertainment

7.6

Boarding

8.2

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 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 Aeromexico. According to our data, you can fly for as low as $161. Users have also found prices from $174 and $178 on Delta and Frontier, 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
New Buffalo
Hammond
Benton Harbor
Porter
Lansing
Valparaiso
Chesterton

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