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$110+ 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 9/20. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — MEX
Jul 6 — Jul 131
Sun 7/6
Sun 7/13
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 July 1, 2025.

Round-trip from

$269
(Southwest)

One-way from

$110
(Priceline)

Popular in

December

Cheapest in

February

Average price

$430

Good round-trip deal

$280 or less

Good one-way deal

$121 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 ($51 potential increase over avg. RT price).
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Cheapest flight prices on average. 6% potential price decrease ($21 potential savings vs. average RT price).
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Average for round-trip flights in July 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 July 1, 2025.

This Southwest deal was found by Cheapflights users on 6/30. 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 7/135:25 pmMDW - CUN
Nonstop3h 35mSouthwest
Thu 7/178:15 amCUN - MDW
Nonstop3h 35mSouthwest
Deal found 6/30$269
This Booking.com deal was found by Cheapflights users on 6/30. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/126:02 pmMDW - CUN
1 stop15h 35mFrontier
Fri 8/1510:37 amCUN - MDW
1 stop27h 13mFrontier
Deal found 6/30$295
This Jettzy deal was found by Cheapflights users on 7/1. 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 Jettzy is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/208:39 pmMDW - GDL
Nonstop4h 10mVolaris
Thu 8/282:12 pmGDL - MDW
Nonstop4h 04mVolaris
Deal found 7/1$299
This SmartFares deal was found by Cheapflights users on 7/1. 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 SmartFares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/3010:31 amMDW - CUN
1 stop9h 49mAeromexico
Sat 9/68:00 amCUN - MDW
1 stop13h 12mAeromexico
Deal found 7/1$304
This Gotogate deal was found by Cheapflights users on 6/30. 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/55:33 pmMDW - AGU
Nonstop4h 07mVolaris
Wed 11/1912:38 pmAGU - MDW
Nonstop3h 40mVolaris
Deal found 6/30$306
This Aeromexico deal was found by Cheapflights users on 6/30. 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 Aeromexico is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/56:00 amMDW - MEX
1 stop14h 40mAeromexico
Sat 9/67:10 amMEX - MDW
2 stops13h 02mAeromexico
Deal found 6/30$310
This Delta deal was found by Cheapflights users on 6/30. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/2711:00 amMDW - CUN
1 stop9h 15mDelta
Sat 10/48:00 amCUN - MDW
1 stop7h 26mDelta
Deal found 6/30$323
This Aeromexico deal was found by Cheapflights users on 7/1. 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 9/56:00 amMDW - AGU
2 stops15h 01mAeromexico
Tue 9/308:59 pmAGU - MDW
2 stops19h 36mAeromexico
Deal found 7/1$327
This Expedia deal was found by Cheapflights users on 7/1. 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.
Mon 8/1112:43 pmMDW - BJX
1 stop7h 12mAeromexico
Mon 8/259:24 amBJX - MDW
1 stop11h 20mAeromexico
Deal found 7/1$328
This Kiwi.com deal was found by Cheapflights users on 7/1. 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 8/158:39 pmMDW - GDL
Nonstop4h 10mMultiple Airlines
Fri 8/226:20 amGDL - MDW
1 stop6h 50mMultiple Airlines
Deal found 7/1$328
This Delta deal was found by Cheapflights users on 6/30. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/216:04 amMDW - DGO
2 stops17h 33mDelta
Thu 8/286:02 amDGO - MDW
2 stops14h 42mDelta
Deal found 6/30$337
This Kiwi.com deal was found by Cheapflights users on 7/1. 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.
Thu 8/213:52 pmMDW - MEX
1 stop8h 03mMultiple Airlines
Sun 8/246:20 amMEX - MDW
1 stop6h 36mMultiple Airlines
Deal found 7/1$343

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 July 1, 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 7/13

5:25 pm-9:00 pm

Nonstop3h 35m

Cancun

Thu 7/17

8:15 am-11:50 am

Nonstop3h 35m

$269

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Tue 8/12

6:02 pm-9:37 am

1 stop15h 35m

Cancun

Fri 8/15

10:37 am-1:50 pm

1 stop27h 13m

$295

ChicagoGuadalajara

MDW - GDL

MDWGDL

Chicago Midway

Wed 8/20

8:39 pm-11:49 pm

Nonstop4h 10m

Guadalajara Miguel Hidal

Thu 8/28

2:12 pm-7:16 pm

Nonstop4h 04m

$299

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Sat 8/30

10:31 am-8:20 pm

1 stop9h 49m

Cancun

Sat 9/6

8:00 am-9:12 pm

1 stop13h 12m

$304

ChicagoAguascalientes

MDW - AGU

MDWAGU

Chicago Midway

Wed 11/5

5:33 pm-9:40 pm

Nonstop4h 07m

Aguascalients

Wed 11/19

12:38 pm-4:18 pm

Nonstop3h 40m

$306

ChicagoMexico City

MDW - MEX

MDWMEX

Chicago Midway

Fri 9/5

6:00 am-7:40 pm

1 stop14h 40m

Mexico City Benito Juarez

Sat 9/6

7:10 am-9:12 pm

2 stops13h 02m

$310

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Sat 9/27

11:00 am-8:15 pm

1 stop9h 15m

Cancun

Sat 10/4

8:00 am-3:26 pm

1 stop7h 26m

$323

ChicagoAguascalientes

MDW - AGU

MDWAGU

Chicago Midway

Fri 9/5

6:00 am-8:01 pm

2 stops15h 01m

Aguascalients

Tue 9/30

8:59 pm-5:35 pm

2 stops19h 36m

$327

ChicagoGuadalajara

MDW - GDL

MDWGDL

Chicago Midway

Fri 8/15

8:39 pm-11:49 pm

Nonstop4h 10m

Guadalajara Miguel Hidal

Fri 8/22

6:20 am-2:10 pm

1 stop6h 50m

$328

ChicagoLeón

MDW - BJX

MDWBJX

Chicago Midway

Mon 8/11

12:43 pm-6:55 pm

1 stop7h 12m

León Del Bajio

Mon 8/25

9:24 am-9:44 pm

1 stop11h 20m

$328

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/30

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 $388). 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 July 1, 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 July 1, 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
4,275 reviews

Comfort

8.0

Entertainment

7.6

Overall

8.0

Food

7.0

Boarding

8.2

Crew

8.6

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
Southwest
8.0
Very good
4,275 reviews
Southwest
8.0
Very good
4,275 reviews

Comfort

8.0

Entertainment

7.6

Overall

8.0

Food

7.0

Boarding

8.2

Crew

8.6

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
Delta
8.0
Very good
7,974 reviews
Southwest
8.0
Very good
4,275 reviews

Comfort

8.0

Entertainment

7.6

Overall

8.0

Food

7.0

Boarding

8.2

Crew

8.6

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
Aeromexico
7.5
Good
1,718 reviews
Southwest
8.0
Very good
4,275 reviews

Comfort

8.0

Entertainment

7.6

Overall

8.0

Food

7.0

Boarding

8.2

Crew

8.6

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
WestJet
7.2
Good
2,909 reviews
Southwest
8.0
Very good
4,275 reviews

Comfort

8.0

Entertainment

7.6

Overall

8.0

Food

7.0

Boarding

8.2

Crew

8.6

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
Volaris
6.7
Okay
1,172 reviews
Southwest
8.0
Very good
4,275 reviews

Comfort

8.0

Entertainment

7.6

Overall

8.0

Food

7.0

Boarding

8.2

Crew

8.6

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.

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 $110 on Frontier. Other airlines that offer cheap prices include Southwest from $123 and Volaris from $132 one-way.

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

    Most travelers choose Chicago Midway - Mexico City Benito Juarez, Chicago Midway - Cancun 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 $388). 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 July 1, 2025.
AirlineCheapestAverageFlexibilityOn-time
VivaCheapest$125Average$358FlexibilityNo cancel feeOn-timeN/A
FrontierCheapest$160Average$430FlexibilityNo cancel feeOn-time62%
United AirlinesCheapest$161Average$419FlexibilityNo cancel feeOn-time69%
VolarisCheapest$191Average$543FlexibilityNo cancel feeOn-time79%
Spirit AirlinesCheapest$241Average$341FlexibilityNo cancel feeOn-time65%
DeltaCheapest$273Average$651FlexibilityNo cancel feeOn-timeN/A
AeromexicoCheapest$319Average$575FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$345Average$685FlexibilityNo cancel feeOn-time63%
LATAM AirlinesCheapest$3,369Average$3,369FlexibilityNo cancel feeOn-time81%

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