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$111+ Cheap flights from Midway (MDW) to Mexico

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 7/7. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — MEX
avr. 27 — mai 41
dim. 4/27
dim. 5/4
1 adult, Economy
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Cheap flight deals from Midway to Mexico

Keep the following information in mind while searching for Midway to Mexico flight deals. Data was last updated avril 22, 2025.

Most accurate provider

AranGrant
3 stars

Most trusted provider

AranGrant
3 stars

Round-trip from

$246
(Southwest)

One-way from

$111
(Southwest)

Popular in

December

Cheapest in

February

Average price

$309

Good round-trip deal

$244 or less

Good one-way deal

$127 or less
Provider with most accurate pricing for Chicago (CHI)-Mexico City Benito Juarez flight deals.
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Provider most trusted by Cheapflights users for Chicago (CHI)-Mexico City Benito Juarez flights.
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From Chicago Midway to Mexico
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One-way flight from Chicago Midway to Mexico
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Highest demand for flights based on searches. 10% potential increase in price ($43 potential increase over avg. RT price).
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Cheapest flight prices on average. 5% potential price decrease ($19 potential savings vs. average RT price).
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Average for round-trip flights in April 2025
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Price to beat on a round-trip flight from Chicago Midway to Mexico.
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Price to beat on a one-way flight from Chicago Midway to Mexico.
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Find flight deals from Midway to Mexico

Cheapest flights from Midway to Mexico
Explore the most affordable flight options available from Midway to Mexico. Find the lowest fares from popular airlines and budget airlines, with prices last updated on avril 22, 2025.

This Southwest deal was found by Cheapflights users on 4/22. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
dim. 6/225:25 pmMDW - CUN
Nonstop3h 35mSouthwest
mer. 7/23:20 pmCUN - MDW
Nonstop3h 35mSouthwest
Deal found 4/22$246
This Trip.com deal was found by Cheapflights users on 4/21. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 5/136:00 amMDW - CUN
1 stop8h 25mAeromexico
mar. 5/208:00 amCUN - MDW
1 stop7h 20mAeromexico
Deal found 4/21$302
This Trip.com deal was found by Cheapflights users on 4/21. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jeu. 6/512:48 pmMDW - BJX
1 stop6h 44mAeromexico
jeu. 6/128:08 amBJX - MDW
1 stop8h 54mAeromexico
Deal found 4/21$311
This Delta deal was found by Cheapflights users on 4/21. 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.
mar. 5/69:52 amMDW - AGU
2 stops14h 38mDelta
mer. 5/218:46 amAGU - MDW
2 stops11h 41mDelta
Deal found 4/21$319
This Delta deal was found by Cheapflights users on 4/22. 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.
sam. 5/39:20 amMDW - CUN
1 stop5h 51mDelta
sam. 5/109:17 amCUN - MDW
2 stops11h 57mDelta
Deal found 4/22$321
This Trip.com deal was found by Cheapflights users on 4/21. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jeu. 6/510:25 amMDW - BJX
1 stop9h 07mMultiple Airlines
jeu. 6/123:50 pmBJX - MDW
Nonstop3h 54mMultiple Airlines
Deal found 4/21$323
This Delta deal was found by Cheapflights users on 4/22. 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.
jeu. 6/56:00 amMDW - BJX
2 stops11h 29mDelta
jeu. 6/125:55 amBJX - MDW
2 stops11h 07mDelta
Deal found 4/22$328
This Trip.com deal was found by Cheapflights users on 4/22. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
ven. 6/612:48 pmMDW - AGU
2 stops11h 29mAeromexico
ven. 6/138:46 amAGU - MDW
2 stops11h 59mAeromexico
Deal found 4/22$330
This Kiwi.com deal was found by Cheapflights users on 4/22. 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.
lun. 5/1212:48 pmMDW - CUN
1 stop7h 32mMultiple Airlines
ven. 5/1612:39 pmCUN - MDW
1 stop9h 34mMultiple Airlines
Deal found 4/22$339
This CheapOair deal was found by Cheapflights users on 4/21. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jeu. 5/1510:41 pmMDW - MLM
Nonstop4h 13mVolaris
jeu. 5/224:29 pmMLM - MDW
Nonstop3h 54mVolaris
Deal found 4/21$342
This Kiwi.com deal was found by Cheapflights users on 4/22. 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.
ven. 6/612:48 pmMDW - AGU
2 stops11h 29mMultiple Airlines
ven. 6/1312:07 pmAGU - MDW
Nonstop3h 47mMultiple Airlines
Deal found 4/22$346
This Kiwi.com deal was found by Cheapflights users on 4/21. 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.
jeu. 5/152:45 pmMDW - MLM
2 stops25h 15mMultiple Airlines
jeu. 5/224:29 pmMLM - MDW
Nonstop3h 54mMultiple Airlines
Deal found 4/21$355

Cheapflights Fare Finder

Customize your flight search to find flights from Midway to Mexico 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 avril 22, 2025.
Use the filters below to find and compare flights from Chicago Midway Airport to Mexico that are best for you.

Fly from

Midway

Fly to

Mexico

Route

Depart

Return

Price

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

dim. 4/27

10:45 am-2:25 pm

Nonstop3h 40m

Cancun

jeu. 5/1

9:00 am-12:40 pm

Nonstop3h 40m

$246

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

dim. 5/4

9:52 am-8:02 pm

1 stop10h 10m

Cancun

jeu. 5/8

11:00 am-5:43 pm

1 stop6h 43m

$302

ChicagoLeón

MDW - BJX

MDWBJX

Chicago Midway

jeu. 6/5

12:48 pm-6:32 pm

1 stop6h 44m

León Del Bajio

jeu. 6/12

8:08 am-6:02 pm

1 stop8h 54m

$311

ChicagoAguascalientes

MDW - AGU

MDWAGU

Chicago Midway

mar. 5/6

9:52 am-11:30 pm

2 stops14h 38m

Aguascalients

mer. 5/21

8:46 am-9:27 pm

2 stops11h 41m

$319

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

sam. 5/3

9:20 am-3:11 pm

1 stop5h 51m

Cancun

sam. 5/10

8:31 am-9:14 pm

2 stops12h 43m

$321

ChicagoLeón

MDW - BJX

MDWBJX

Chicago Midway

jeu. 6/5

10:25 am-6:32 pm

1 stop9h 07m

León Del Bajio

jeu. 6/12

3:50 pm-8:44 pm

Nonstop3h 54m

$323

ChicagoAguascalientes

MDW - AGU

MDWAGU

Chicago Midway

ven. 6/6

12:48 pm-11:17 pm

2 stops11h 29m

Aguascalients

ven. 6/13

8:46 am-9:45 pm

2 stops11h 59m

$330

ChicagoLeón

MDW - BJX

MDWBJX

Chicago Midway

mer. 9/3

6:00 am-3:15 pm

1 stop10h 15m

León Del Bajio

mer. 9/17

9:20 am-5:58 pm

1 stop7h 38m

$332

ChicagoMorelia

MDW - MLM

MDWMLM

Chicago Midway

jeu. 5/15

10:41 pm-1:54 am

Nonstop4h 13m

Morelia

jeu. 5/22

4:29 pm-9:23 pm

Nonstop3h 54m

$342

ChicagoAguascalientes

MDW - AGU

MDWAGU

Chicago Midway

ven. 6/6

12:48 pm-11:17 pm

2 stops11h 29m

Aguascalients

ven. 6/13

12:07 pm-4:54 pm

Nonstop3h 47m

$346

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/22

Showing 1-10 of 60 results
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Best time to book a flight from Midway to Mexico

Have a flexible travel schedule? Discover the best time to fly to Mexico 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 Mexico

What is the cheapest month to book a flight from Chicago Midway Airport to Mexico?

Currently, May is the cheapest month in which you can book a flight from Chicago Midway Airport to Mexico (average of $400). Flying from Chicago Midway Airport to Mexico in December is currently the most expensive (average of $615). 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.

What is the cheapest time of day to fly from MDW to MX?

Find hourly flight availability from Midway to Mexico. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated avril 22, 2025.

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Chicago Midway Airport to Mexico as you normally would.

Rainfall in Mexico by month

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

In terms of precipitation, rainfall in Mexico ranges from 0.0 - 4.7 inches per month. July is typically the wettest month, when rainfall can reach 4.7 in. January is typically the driest time to visit Mexico when rainfall is around 0.0 in.

Temperature in Mexico by month

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

If weather is an important factor for your trip to Mexico, 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 66.2 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 55.4 F).

Reviews of airlines servicing Mexico

Get insights into the airlines that provide service to Mexico. 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 Mexico. Reviews last updated avril 22, 2025.
Read reviews from past customers who have flown Southwest, Delta and LATAM Airlines from Chicago to Mexico. In addition to providing an overall rating, users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,287 reviews

Entertainment

7.6

Crew

8.6

Food

7.1

Comfort

8.0

Boarding

8.2

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

Entertainment

7.6

Crew

8.6

Food

7.1

Comfort

8.0

Boarding

8.2

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
7,920 reviews
Southwest
8.0
Very good
4,287 reviews

Entertainment

7.6

Crew

8.6

Food

7.1

Comfort

8.0

Boarding

8.2

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!
LATAM Airlines
7.5
Good
1,764 reviews
Southwest
8.0
Very good
4,287 reviews

Entertainment

7.6

Crew

8.6

Food

7.1

Comfort

8.0

Boarding

8.2

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
1,700 reviews
Southwest
8.0
Very good
4,287 reviews

Entertainment

7.6

Crew

8.6

Food

7.1

Comfort

8.0

Boarding

8.2

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
2,813 reviews
Southwest
8.0
Very good
4,287 reviews

Entertainment

7.6

Crew

8.6

Food

7.1

Comfort

8.0

Boarding

8.2

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 Mexico. 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 Mexico 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 $136 and Delta from $146 one-way.

  • What are the most popular routes from Chicago Midway Airport to Mexico?

    Most travelers choose Chicago Midway - Cancun, Chicago Midway - Mexico City Benito Juarez or Chicago Midway - Guadalajara Miguel Hidal when deciding on the best route from Chicago Midway Airport to Mexico.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Midway to Mexico 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 Mexico?

    Currently, May is the cheapest month in which you can book a flight from Chicago Midway Airport to Mexico (average of $400). Flying from Chicago Midway Airport to Mexico in December is currently the most expensive (average of $615). 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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Alternative routes for Midway to Mexico

See prices for flight routes from nearby airports that may be better suited for you.
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Top 9 airlines flying from Midway to Mexico

Discover the top 9 airlines that operate flights from Midway to Mexico. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated avril 22, 2025.
AirlineCheapestAverageFlexibilityOn-time
VivaCheapest$125Average$339FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$161Average$408FlexibilityNo cancel feeOn-time69%
FrontierCheapest$175Average$380FlexibilityNo cancel feeOn-time62%
VolarisCheapest$226Average$517FlexibilityNo cancel feeOn-time79%
Spirit AirlinesCheapest$241Average$333FlexibilityNo cancel feeOn-time65%
AeromexicoCheapest$320Average$603FlexibilityNo cancel feeOn-timeN/A
DeltaCheapest$380Average$645FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$430Average$722FlexibilityNo cancel feeOn-time63%
LATAM AirlinesCheapest$3,369Average$3,369FlexibilityNo cancel feeOn-time81%

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