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$115+ 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 11/30. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — MEX
Nov 29 — Dec 61
Sat 11/29
Sat 12/6
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 October 30, 2025.

Most accurate provider

Justfly.com
3 stars

Most trusted provider

Justfly.com
3 stars

Round-trip from

$252
(Southwest)

One-way from

$115
(Southwest)

Popular in

December

Cheapest in

February

Average price

$379

Good round-trip deal

$270 or less

Good one-way deal

$180 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. 14% potential increase in price ($57 potential increase over avg. RT price).
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Cheapest flight prices on average. 6% potential price decrease ($23 potential savings vs. average RT price).
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Average for round-trip flights in October 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 October 30, 2025.

This Southwest deal was found by Cheapflights users on 10/29. 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.
Sat 11/153:40 pmMDW - CUN
Nonstop3h 45mSouthwest
Fri 11/212:15 pmCUN - MDW
Nonstop3h 45mSouthwest
Deal found 10/29$262
This Southwest deal was found by Cheapflights users on 10/29. 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.
Sat 11/153:40 pmMDW - CUN
Nonstop3h 45mSouthwest
Sat 11/224:25 pmCUN - MDW
Nonstop3h 45mSouthwest
Deal found 10/29$272
This Southwest deal was found by Cheapflights users on 10/30. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/1610:40 amMDW - CUN
Nonstop3h 45mSouthwest
Sat 11/224:25 pmCUN - MDW
Nonstop3h 45mSouthwest
Deal found 10/30$282
This Southwest deal was found by Cheapflights users on 10/28. 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.
Sat 11/83:40 pmMDW - CUN
Nonstop3h 45mSouthwest
Sat 11/151:00 pmCUN - MDW
1 stop6h 55mSouthwest
Deal found 10/28$287
This Southwest deal was found by Cheapflights users on 10/28. 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.
Mon 11/38:40 amMDW - CUN
Nonstop3h 45mSouthwest
Fri 11/72:15 pmCUN - MDW
Nonstop3h 45mSouthwest
Deal found 10/28$292
This Southwest deal was found by Cheapflights users on 10/27. 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.
Sat 11/18:20 amMDW - CUN
1 stop11h 30mSouthwest
Sat 11/81:50 pmCUN - MDW
1 stop6h 15mSouthwest
Deal found 10/27$296
This Southwest deal was found by Cheapflights users on 10/27. 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.
Tue 11/47:00 amMDW - CUN
1 stop9h 00mSouthwest
Thu 11/62:15 pmCUN - MDW
Nonstop3h 45mSouthwest
Deal found 10/27$301
This Southwest deal was found by Cheapflights users on 10/28. 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.
Sun 11/210:40 amMDW - CUN
Nonstop3h 45mSouthwest
Thu 11/612:55 pmCUN - MDW
2 stops8h 35mSouthwest
Deal found 10/28$302
This Southwest deal was found by Cheapflights users on 10/30. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/159:20 amMDW - CUN
1 stop10h 05mSouthwest
Thu 12/182:15 pmCUN - MDW
Nonstop3h 45mSouthwest
Deal found 10/30$304
This Kiwi.com deal was found by Cheapflights users on 10/29. 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 11/42:32 pmMDW - MLM
Nonstop4h 16mVolaris
Thu 11/139:15 amMLM - MDW
Nonstop3h 49mVolaris
Deal found 10/29$318
This Aeromexico deal was found by Cheapflights users on 10/28. 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.
Mon 11/1712:47 pmMDW - AGU
2 stops20h 55mAeromexico
Mon 11/248:06 pmAGU - MDW
2 stops20h 32mAeromexico
Deal found 10/28$329
This Kiwi.com deal was found by Cheapflights users on 10/29. 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 12/72:01 pmMDW - MEX
1 stop7h 59mMultiple Airlines
Thu 12/117:00 amMEX - MDW
1 stop7h 04mMultiple Airlines
Deal found 10/29$340

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 October 30, 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

Tue 11/11

5:25 am-3:25 pm

1 stop9h 00m

Cancun

Sat 11/15

8:10 am-4:40 pm

1 stop9h 30m

$306

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Tue 1/20

10:05 am-7:45 pm

2 stops8h 40m

Cancun

Thu 1/29

1:45 pm-4:30 pm

Nonstop3h 45m

$311

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Sat 11/15

6:40 am-2:20 pm

1 stop6h 40m

Cancun

Fri 11/21

2:15 pm-5:00 pm

Nonstop3h 45m

$319

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Sat 2/7

6:00 am-3:30 pm

1 stop8h 30m

Cancun

Tue 2/10

8:00 am-5:32 pm

1 stop10h 32m

$326

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Sun 1/11

6:45 am-9:11 pm

1 stop13h 26m

Cancun

Fri 1/16

4:40 pm-10:09 pm

1 stop6h 29m

$326

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Fri 2/6

6:00 am-4:45 pm

1 stop9h 45m

Cancun

Tue 2/10

12:05 pm-10:26 pm

2 stops11h 21m

$331

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Thu 1/8

9:34 am-9:11 pm

2 stops10h 37m

Cancun

Thu 1/15

12:15 pm-10:09 pm

1 stop10h 54m

$331

ChicagoAguascalientes

MDW - AGU

MDWAGU

Chicago Midway

Wed 1/21

6:00 am-7:48 pm

2 stops13h 48m

Aguascalients

Wed 1/28

9:43 am-10:26 pm

2 stops12h 43m

$332

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Wed 12/10

12:50 pm-9:20 pm

1 stop7h 30m

Cancun

Fri 12/12

12:00 pm-11:47 pm

1 stop12h 47m

$344

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Wed 11/12

9:20 am-8:25 pm

1 stop10h 05m

Cancun

Sat 11/15

11:20 am-7:05 pm

2 stops8h 45m

$346

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/29

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 $106). Flying from Chicago Midway Airport to Mexico in November is currently the most expensive (average of $281). 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 October 30, 2025.

One of the essential ways to save on airfare from Chicago Midway Airport to Mexico is to remain as flexible as possible. Flights that are in the morning tend to be the most expensive. A flight in the evening could potentially save you up to 28% on airfare.

What is the cheapest day to fly from Chicago Midway Airport to Mexico?

Use this chart to determine the cheapest time to fly round-trip from Midway to Mexico. Price data was last updated on October 26, 2025.

Travelers seeking maximum savings on their Chicago Midway Airport to Mexico flight should consider departing on Friday at noon when fares are most often at their lowest. Thursday at noon flights should be avoided if possible as fares are typically the most expensive at this time.

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 October 30, 2025.
See what other customers who have flown with Southwest, Delta, and Aeromexico from Chicago Midway Airport to Mexico have to say. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,243 reviews

Overall

8.0

Entertainment

7.5

Boarding

8.1

Food

7.0

Crew

8.6

Comfort

8.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Southwest
8.0
Very good
4,243 reviews
Southwest
8.0
Very good
4,243 reviews

Overall

8.0

Entertainment

7.5

Boarding

8.1

Food

7.0

Crew

8.6

Comfort

8.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Delta
7.9
Good
7,998 reviews
Southwest
8.0
Very good
4,243 reviews

Overall

8.0

Entertainment

7.5

Boarding

8.1

Food

7.0

Crew

8.6

Comfort

8.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Aeromexico
7.4
Good
1,674 reviews
Southwest
8.0
Very good
4,243 reviews

Overall

8.0

Entertainment

7.5

Boarding

8.1

Food

7.0

Crew

8.6

Comfort

8.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Volaris
6.7
Okay
1,151 reviews
Southwest
8.0
Very good
4,243 reviews

Overall

8.0

Entertainment

7.5

Boarding

8.1

Food

7.0

Crew

8.6

Comfort

8.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Frontier
5.8
Fair
3,123 reviews
Southwest
8.0
Very good
4,243 reviews

Overall

8.0

Entertainment

7.5

Boarding

8.1

Food

7.0

Crew

8.6

Comfort

8.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines

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.

  • How long is the flight from Chicago Midway Airport to Mexico?

    For as low as $395, Southwest can have you in Mexico from Chicago Midway Airport in 4h 16m. The distance between Chicago Midway Airport and Mexico is about 1702 mi. Both multi-stop and nonstop flights can be found to your destination and back.

  • 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 $115 on Southwest. Other airlines that offer cheap prices include Volaris from $157 and Delta from $165 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 $106). Flying from Chicago Midway Airport to Mexico in November is currently the most expensive (average of $281). 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.

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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 8 airlines flying from Midway to Mexico

Discover the top 8 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 October 30, 2025.
AirlineCheapestAverageFlexibilityOn-time
VivaCheapest$125Average$337FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$161Average$490FlexibilityNo cancel feeOn-time69%
VolarisCheapest$187Average$555FlexibilityNo cancel feeOn-time79%
FrontierCheapest$200Average$451FlexibilityNo cancel feeOn-time62%
DeltaCheapest$292Average$608FlexibilityNo cancel feeOn-timeN/A
AeromexicoCheapest$296Average$454FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$345Average$691FlexibilityNo cancel feeOn-time63%
LATAM AirlinesCheapest$3,369Average$3,369FlexibilityNo cancel feeOn-time81%

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