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$114+ 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 10/31. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — MEX
Aug 21 — Aug 281
Thu 8/21
Thu 8/28
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 August 16, 2025.

Round-trip from

$251
(eDestinos)

One-way from

$114
(Cheapflightsfares)

Popular in

December

Cheapest in

February

Average price

$378

Good round-trip deal

$306 or less

Good one-way deal

$153 or less
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. 13% potential increase in price ($52 potential increase over avg. RT price).
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Cheapest flight prices on average. 5% potential price decrease ($20 potential savings vs. average RT price).
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Average for round-trip flights in August 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 August 16, 2025.

This eDestinos deal was found by Cheapflights users on 8/15. 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 9/88:39 pmMDW - GDL
Nonstop4h 14mVolaris
Fri 9/122:12 pmGDL - MDW
Nonstop4h 04mVolaris
Deal found 8/15$251
This Mytrip deal was found by Cheapflights users on 8/14. 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.
Sat 11/155:33 pmMDW - AGU
Nonstop4h 07mVolaris
Wed 11/2612:38 pmAGU - MDW
Nonstop3h 40mVolaris
Deal found 8/14$271
This Southwest deal was found by Cheapflights users on 8/14. 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
Wed 11/121:45 pmCUN - MDW
Nonstop3h 45mSouthwest
Deal found 8/14$271
This Southwest deal was found by Cheapflights users on 8/15. 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 9/67:00 amMDW - CUN
1 stop7h 40mSouthwest
Sat 9/132:25 pmCUN - MDW
Nonstop3h 40mSouthwest
Deal found 8/15$276
This Cheapflightsfares deal was found by Cheapflights users on 8/15. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/156:19 pmMDW - AGU
Nonstop3h 54mVolaris
Fri 9/1912:07 pmAGU - MDW
Nonstop3h 43mVolaris
Deal found 8/15$277
This Cheapflightsfares deal was found by Cheapflights users on 8/13. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/308:39 pmMDW - GDL
Nonstop4h 14mVolaris
Wed 11/121:36 pmGDL - MDW
Nonstop3h 58mVolaris
Deal found 8/13$278
This Mytrip deal was found by Cheapflights users on 8/13. 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.
Wed 8/208:39 pmMDW - GDL
Nonstop4h 10mVolaris
Fri 9/52:12 pmGDL - MDW
Nonstop4h 04mVolaris
Deal found 8/13$279
This Flightnetwork deal was found by Cheapflights users on 8/14. 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.
Mon 9/18:39 pmMDW - GDL
Nonstop4h 14mVolaris
Wed 9/102:12 pmGDL - MDW
Nonstop4h 04mVolaris
Deal found 8/14$281
This Southwest deal was found by Cheapflights users on 8/15. 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 9/1410:35 amMDW - CUN
Nonstop3h 35mSouthwest
Thu 9/183:10 pmCUN - MDW
Nonstop3h 40mSouthwest
Deal found 8/15$281
This Cheapflightsfares deal was found by Cheapflights users on 8/13. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/18:39 pmMDW - GDL
Nonstop4h 14mVolaris
Thu 9/112:12 pmGDL - MDW
Nonstop4h 04mVolaris
Deal found 8/13$287
This Mytrip deal was found by Cheapflights users on 8/14. 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.
Mon 9/155:01 pmMDW - MLM
Nonstop4h 02mVolaris
Mon 9/2210:30 amMLM - MDW
Nonstop3h 53mVolaris
Deal found 8/14$294
This Cheapflightsfares deal was found by Cheapflights users on 8/14. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/223:36 pmMDW - BJX
Nonstop3h 51mVolaris
Fri 8/299:27 amBJX - MDW
Nonstop3h 54mVolaris
Deal found 8/14$295

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 August 16, 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

ChicagoGuadalajara

MDW - GDL

MDWGDL

Chicago Midway

Mon 9/8

8:39 pm-11:53 pm

Nonstop4h 14m

Guadalajara Miguel Hidal

Fri 9/12

2:12 pm-7:16 pm

Nonstop4h 04m

$251

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Sat 11/8

3:40 pm-8:25 pm

Nonstop3h 45m

Cancun

Wed 11/12

1:45 pm-4:30 pm

Nonstop3h 45m

$271

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Sat 9/6

9:15 am-12:50 pm

Nonstop3h 35m

Cancun

Sat 9/13

2:25 pm-6:05 pm

Nonstop3h 40m

$271

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Tue 10/28

9:40 am-1:15 pm

Nonstop3h 35m

Cancun

Tue 11/4

1:45 pm-4:30 pm

Nonstop3h 45m

$271

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Sat 11/8

3:40 pm-8:25 pm

Nonstop3h 45m

Cancun

Sat 11/15

3:10 pm-5:55 pm

Nonstop3h 45m

$271

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Mon 10/27

9:40 am-1:15 pm

Nonstop3h 35m

Cancun

Tue 11/4

1:45 pm-4:30 pm

Nonstop3h 45m

$271

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Sat 10/25

9:40 am-1:15 pm

Nonstop3h 35m

Cancun

Sat 11/1

2:00 pm-5:45 pm

Nonstop3h 45m

$271

ChicagoAguascalientes

MDW - AGU

MDWAGU

Chicago Midway

Mon 9/15

6:19 pm-9:13 pm

Nonstop3h 54m

Aguascalients

Fri 9/19

12:07 pm-4:50 pm

Nonstop3h 43m

$277

ChicagoGuadalajara

MDW - GDL

MDWGDL

Chicago Midway

Thu 10/30

8:39 pm-11:53 pm

Nonstop4h 14m

Guadalajara Miguel Hidal

Wed 11/12

1:36 pm-5:34 pm

Nonstop3h 58m

$278

ChicagoGuadalajara

MDW - GDL

MDWGDL

Chicago Midway

Wed 8/20

8:39 pm-11:49 pm

Nonstop4h 10m

Guadalajara Miguel Hidal

Fri 9/5

2:12 pm-7:16 pm

Nonstop4h 04m

$279

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/13

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 $387). 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 August 16, 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.

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 August 16, 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
4,246 reviews

Overall

8.0

Entertainment

7.5

Crew

8.6

Comfort

8.0

Boarding

8.1

Food

7.0

Reviews

1 / 20
8.0
Excellent

Walter,Aug 2025

OAK - SAN

Dozens of flights and I've never seen a row's beverages forgotten. I even went back and asked the attendant to check on them and nothing. I really hope it didn't have something to do with the Black mother with her kid in the row. Otherwise it was a typical Southwest flight, rapid boarding, tolerable leg room.
Southwest
8.0
Very good
4,246 reviews
Southwest
8.0
Very good
4,246 reviews

Overall

8.0

Entertainment

7.5

Crew

8.6

Comfort

8.0

Boarding

8.1

Food

7.0

Reviews

1 / 20
8.0
Excellent

Walter,Aug 2025

OAK - SAN

Dozens of flights and I've never seen a row's beverages forgotten. I even went back and asked the attendant to check on them and nothing. I really hope it didn't have something to do with the Black mother with her kid in the row. Otherwise it was a typical Southwest flight, rapid boarding, tolerable leg room.
Delta
8.0
Very good
7,985 reviews
Southwest
8.0
Very good
4,246 reviews

Overall

8.0

Entertainment

7.5

Crew

8.6

Comfort

8.0

Boarding

8.1

Food

7.0

Reviews

1 / 20
8.0
Excellent

Walter,Aug 2025

OAK - SAN

Dozens of flights and I've never seen a row's beverages forgotten. I even went back and asked the attendant to check on them and nothing. I really hope it didn't have something to do with the Black mother with her kid in the row. Otherwise it was a typical Southwest flight, rapid boarding, tolerable leg room.
Aeromexico
7.5
Good
1,722 reviews
Southwest
8.0
Very good
4,246 reviews

Overall

8.0

Entertainment

7.5

Crew

8.6

Comfort

8.0

Boarding

8.1

Food

7.0

Reviews

1 / 20
8.0
Excellent

Walter,Aug 2025

OAK - SAN

Dozens of flights and I've never seen a row's beverages forgotten. I even went back and asked the attendant to check on them and nothing. I really hope it didn't have something to do with the Black mother with her kid in the row. Otherwise it was a typical Southwest flight, rapid boarding, tolerable leg room.
Volaris
6.6
Okay
1,162 reviews
Southwest
8.0
Very good
4,246 reviews

Overall

8.0

Entertainment

7.5

Crew

8.6

Comfort

8.0

Boarding

8.1

Food

7.0

Reviews

1 / 20
8.0
Excellent

Walter,Aug 2025

OAK - SAN

Dozens of flights and I've never seen a row's beverages forgotten. I even went back and asked the attendant to check on them and nothing. I really hope it didn't have something to do with the Black mother with her kid in the row. Otherwise it was a typical Southwest flight, rapid boarding, tolerable leg room.
Frontier
5.8
Fair
3,211 reviews
Southwest
8.0
Very good
4,246 reviews

Overall

8.0

Entertainment

7.5

Crew

8.6

Comfort

8.0

Boarding

8.1

Food

7.0

Reviews

1 / 20
8.0
Excellent

Walter,Aug 2025

OAK - SAN

Dozens of flights and I've never seen a row's beverages forgotten. I even went back and asked the attendant to check on them and nothing. I really hope it didn't have something to do with the Black mother with her kid in the row. Otherwise it was a typical Southwest flight, rapid boarding, tolerable leg room.

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 $114 on Volaris. Other airlines that offer cheap prices include Delta from $125 and Southwest from $125 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 - Puerto Vallarta Ordaz 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 $387). 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 August 16, 2025.
AirlineCheapestAverageFlexibilityOn-time
VivaCheapest$125Average$339FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$161Average$419FlexibilityNo cancel feeOn-time69%
FrontierCheapest$175Average$441FlexibilityNo cancel feeOn-time62%
VolarisCheapest$211Average$548FlexibilityNo cancel feeOn-time79%
Spirit AirlinesCheapest$241Average$333FlexibilityNo cancel feeOn-time65%
DeltaCheapest$292Average$651FlexibilityNo cancel feeOn-timeN/A
AeromexicoCheapest$312Average$569FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$345Average$651FlexibilityNo cancel feeOn-time63%
LATAM AirlinesCheapest$3,369Average$3,369FlexibilityNo cancel feeOn-time81%

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