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$117+ 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 10/25. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — MEX
Oct 17 — Oct 241
Fri 10/17
Fri 10/24
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 September 17, 2025.

Round-trip from

$261
(Southwest)

One-way from

$117
(Kiwi.com)

Popular in

December

Cheapest in

February

Average price

$337

Good round-trip deal

$237 or less

Good one-way deal

$124 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. 12% potential increase in price ($50 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 September 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 September 17, 2025.

This Southwest deal was found by Cheapflights users on 9/15. 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 11/1610:40 amMDW - CUN
Nonstop3h 45mSouthwest
Wed 11/191:45 pmCUN - MDW
Nonstop3h 45mSouthwest
Deal found 9/15$261
This Southwest deal was found by Cheapflights users on 9/15. 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 11/153:40 pmMDW - CUN
Nonstop3h 45mSouthwest
Wed 11/191:45 pmCUN - MDW
Nonstop3h 45mSouthwest
Deal found 9/15$266
This Southwest deal was found by Cheapflights users on 9/16. 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
Thu 11/201:45 pmCUN - MDW
Nonstop3h 45mSouthwest
Deal found 9/16$271
This Southwest deal was found by Cheapflights users on 9/16. 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 9/2810:35 amMDW - CUN
Nonstop3h 35mSouthwest
Thu 10/23:20 pmCUN - MDW
Nonstop3h 35mSouthwest
Deal found 9/16$281
This Southwest deal was found by Cheapflights users on 9/16. 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 9/309:55 amMDW - CUN
Nonstop3h 35mSouthwest
Sat 10/41:00 pmCUN - MDW
1 stop9h 35mSouthwest
Deal found 9/16$286
This Southwest deal was found by Cheapflights users on 9/17. 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 11/158:40 amCUN - MDW
1 stop9h 05mSouthwest
Deal found 9/17$291
This Southwest deal was found by Cheapflights users on 9/15. 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 10/1910:40 amMDW - CUN
Nonstop3h 35mSouthwest
Thu 10/231:45 pmCUN - MDW
1 stop10h 40mSouthwest
Deal found 9/15$294
This Delta deal was found by Cheapflights users on 9/16. 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.
Sun 11/166:00 amMDW - QRO
2 stops14h 05mDelta
Sun 11/239:52 amQRO - MDW
2 stops13h 40mDelta
Deal found 9/16$317
This Kiwi.com deal was found by Cheapflights users on 9/16. 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.
Fri 12/127:00 amMDW - GDL
1 stop16h 28mMultiple Airlines
Mon 12/156:20 amGDL - MDW
1 stop7h 16mMultiple Airlines
Deal found 9/16$323
This Kiwi.com deal was found by Cheapflights users on 9/15. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/62:26 pmMDW - GDL
1 stop23h 50mMultiple Airlines
Thu 10/232:12 pmGDL - MDW
Nonstop4h 04mMultiple Airlines
Deal found 9/15$334
This Kiwi.com deal was found by Cheapflights users on 9/15. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/57:00 amMDW - MEX
1 stop15h 00mMultiple Airlines
Mon 12/86:20 amMEX - MDW
1 stop7h 16mMultiple Airlines
Deal found 9/15$337
This Kiwi.com deal was found by Cheapflights users on 9/14. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/209:00 amMDW - MEX
1 stop14h 00mMultiple Airlines
Sat 10/256:20 amMEX - MDW
1 stop8h 49mMultiple Airlines
Deal found 9/14$339

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 September 17, 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

Sun 11/16

10:40 am-3:25 pm

Nonstop3h 45m

Cancun

Thu 11/20

1:45 pm-4:30 pm

Nonstop3h 45m

$266

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Sat 11/15

5:05 am-2:00 pm

1 stop7h 55m

Cancun

Thu 11/20

1:45 pm-4:30 pm

Nonstop3h 45m

$285

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Sat 10/18

6:30 am-1:40 pm

1 stop7h 10m

Cancun

Sat 11/1

11:55 am-8:20 pm

2 stops8h 25m

$310

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Tue 12/9

12:55 pm-8:25 pm

1 stop6h 30m

Cancun

Sat 12/13

11:55 am-2:45 pm

Nonstop3h 50m

$315

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Mon 11/17

8:40 am-1:25 pm

Nonstop3h 45m

Cancun

Fri 11/21

6:55 pm-12:10 am

1 stop6h 15m

$316

ChicagoSantiago de Querétaro

MDW - QRO

MDWQRO

Chicago Midway

Sun 11/16

6:00 am-8:05 pm

2 stops14h 05m

Santiago de Querétaro

Sun 11/23

9:52 am-11:32 pm

2 stops13h 40m

$317

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Tue 11/11

6:20 am-5:00 pm

2 stops9h 40m

Cancun

Sat 11/15

1:50 pm-7:05 pm

1 stop6h 15m

$318

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Sun 9/28

10:35 am-2:10 pm

Nonstop3h 35m

Cancun

Fri 10/3

2:40 pm-12:25 am

2 stops9h 45m

$321

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Sat 11/29

6:00 am-1:55 pm

1 stop6h 55m

Cancun

Wed 12/10

3:07 pm-11:32 pm

1 stop9h 25m

$326

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Sun 11/16

6:00 am-1:55 pm

1 stop6h 55m

Cancun

Wed 11/19

3:05 pm-11:32 pm

1 stop9h 27m

$326

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/15

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 September 17, 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 September 17, 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
4,242 reviews

Entertainment

7.5

Overall

8.0

Boarding

8.1

Comfort

8.0

Crew

8.6

Food

7.0

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
4,242 reviews
Southwest
8.0
Very good
4,242 reviews

Entertainment

7.5

Overall

8.0

Boarding

8.1

Comfort

8.0

Crew

8.6

Food

7.0

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
8.0
Very good
7,961 reviews
Southwest
8.0
Very good
4,242 reviews

Entertainment

7.5

Overall

8.0

Boarding

8.1

Comfort

8.0

Crew

8.6

Food

7.0

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
7.5
Good
1,696 reviews
Southwest
8.0
Very good
4,242 reviews

Entertainment

7.5

Overall

8.0

Boarding

8.1

Comfort

8.0

Crew

8.6

Food

7.0

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
6.6
Okay
1,154 reviews
Southwest
8.0
Very good
4,242 reviews

Entertainment

7.5

Overall

8.0

Boarding

8.1

Comfort

8.0

Crew

8.6

Food

7.0

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
3,173 reviews
Southwest
8.0
Very good
4,242 reviews

Entertainment

7.5

Overall

8.0

Boarding

8.1

Comfort

8.0

Crew

8.6

Food

7.0

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 $266, Southwest can have you in Mexico from Chicago Midway Airport in 3h 45m. The distance between Chicago Midway Airport and Mexico is about 1434 mi. Both multi-stop and nonstop flights can be found to your destination and back.

  • 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 $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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Midway to Seattle flights
O'Hare Intl to Salt Lake City flights

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 September 17, 2025.
AirlineCheapestAverageFlexibilityOn-time
VivaCheapest$125Average$339FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$161Average$419FlexibilityNo cancel feeOn-time69%
FrontierCheapest$200Average$444FlexibilityNo cancel feeOn-time62%
VolarisCheapest$216Average$554FlexibilityNo cancel feeOn-time79%
DeltaCheapest$292Average$612FlexibilityNo cancel feeOn-timeN/A
AeromexicoCheapest$296Average$452FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$345Average$692FlexibilityNo cancel feeOn-time63%
LATAM AirlinesCheapest$3,369Average$3,369FlexibilityNo cancel feeOn-time81%

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