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$140+ 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 6/27. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — MEX
Jun 18 — Jun 251
Thu 6/18
Thu 6/25
1 adult, Economy
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Cheap 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 May 19, 2026.

This FlightHub deal was found by Cheapflights users on 5/19. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/38:23 pm
MDW
-
CUN
1 stop13h 32m
Volaris
Wed 7/810:40 am
CUN
-
MDW
1 stop8h 24m
Volaris
Deal found 5/19$338
This FlightHub deal was found by Cheapflights users on 5/19. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/228:23 pm
MDW
-
CUN
1 stop13h 32m
Volaris
Thu 6/2510:40 am
CUN
-
MDW
1 stop8h 54m
Volaris
Deal found 5/19$343
This FlightHub deal was found by Cheapflights users on 5/16. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/118:49 pm
MDW
-
CUN
1 stop13h 06m
Volaris
Wed 6/1710:40 am
CUN
-
MDW
1 stop8h 24m
Volaris
Deal found 5/16$348
This FlightHub deal was found by Cheapflights users on 5/16. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 6/148:23 pm
MDW
-
CUN
1 stop13h 32m
Volaris
Thu 6/1810:40 am
CUN
-
MDW
1 stop8h 54m
Volaris
Deal found 5/16$349
This Justfly.com deal was found by Cheapflights users on 5/18. 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 Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/228:23 pm
MDW
-
CUN
1 stop13h 32m
Volaris
Fri 6/2610:40 am
CUN
-
MDW
1 stop8h 24m
Volaris
Deal found 5/18$359
This FlightHub deal was found by Cheapflights users on 5/19. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 7/68:23 pm
MDW
-
CUN
1 stop13h 32m
Volaris
Fri 7/1010:40 am
CUN
-
MDW
1 stop8h 24m
Volaris
Deal found 5/19$360
This FlightHub deal was found by Cheapflights users on 5/18. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 6/218:23 pm
MDW
-
CUN
1 stop13h 32m
Volaris
Thu 6/2510:40 am
CUN
-
MDW
1 stop8h 54m
Volaris
Deal found 5/18$363
This FlightHub deal was found by Cheapflights users on 5/18. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/198:23 pm
MDW
-
CUN
1 stop13h 32m
Volaris
Fri 6/2610:40 am
CUN
-
MDW
1 stop8h 24m
Volaris
Deal found 5/18$367
This Justfly.com deal was found by Cheapflights users on 5/18. 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 Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/68:49 pm
MDW
-
CUN
1 stop13h 06m
Volaris
Wed 6/1710:40 am
CUN
-
MDW
1 stop8h 24m
Volaris
Deal found 5/18$369
This Super.com deal was found by Cheapflights users on 5/15. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/282:32 pm
MDW
-
MLM
Nonstop3h 59m
Volaris
Fri 9/118:14 am
MLM
-
MDW
Nonstop4h 01m
Volaris
Deal found 5/15$380
This Super.com deal was found by Cheapflights users on 5/16. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/202:32 pm
MDW
-
MLM
Nonstop3h 59m
Volaris
Thu 9/108:14 am
MLM
-
MDW
Nonstop4h 01m
Volaris
Deal found 5/16$391
This Super.com deal was found by Cheapflights users on 5/17. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/112:32 pm
MDW
-
MLM
Nonstop3h 59m
Volaris
Wed 9/168:14 am
MLM
-
MDW
Nonstop4h 01m
Volaris
Deal found 5/17$392

Find flight deals from Midway to Mexico

Keep the following information in mind while searching for Midway to Mexico flight deals. Data was last updated May 19, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$338
(FlightHub)

One-way from

$140
(FlightHub)

Popular in

December

Cheapest in

January

Average price

$374

Good round-trip deal

$382 or less

Good one-way deal

$178 or less
Provider with most accurate pricing for Chicago (CHI)-Mexico City Benito Juarez flight deals.
Search Deals
Provider most trusted by Cheapflights users for Chicago (CHI)-Mexico City Benito Juarez flights.
Search Deals
From Chicago Midway to Mexico
Search Deals
One-way flight from Chicago Midway to Mexico
Search Deals
Highest demand for flights based on searches. 7% potential increase in price ($27 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 4% potential price decrease ($17 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in May 2026
Search Deals
Price to beat on a round-trip flight from Chicago Midway to Mexico.
Search Deals
Price to beat on a one-way flight from Chicago Midway to Mexico.
Search Deals

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 May 19, 2026.
Use the filters below to find and compare flights from Chicago Midway Airport to Mexico that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Tue 7/7

6:00 am-1:00 pm

1 stop7h 00m

Cancun

Mon 7/13

8:00 am-10:15 pm

1 stop14h 15m

$408

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Sat 7/11

10:55 am-8:15 pm

1 stop9h 20m

Cancun

Sat 7/18

8:00 am-10:15 pm

1 stop14h 15m

$408
Quickest round-trip

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Tue 7/7

10:05 am-1:40 pm

Nonstop3h 35m

Cancun

Sat 7/11

10:05 am-1:40 pm

Nonstop3h 35m

$424

ChicagoMexico City

MDW - MEX

MDWMEX

Chicago Midway

Fri 5/29

10:59 am-9:50 pm

1 stop11h 51m

Mexico City Benito Juarez

Mon 6/1

1:20 pm-9:09 pm

1 stop6h 49m

$455

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Sat 5/30

10:45 am-8:16 pm

1 stop9h 31m

Cancun

Wed 6/3

11:10 am-9:09 pm

1 stop9h 59m

$468

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Wed 8/12

12:46 pm-8:15 pm

1 stop7h 29m

Cancun

Tue 8/18

8:05 am-4:15 pm

1 stop8h 10m

$473

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Thu 5/28

10:59 am-8:16 pm

1 stop9h 17m

Cancun

Wed 6/3

8:00 am-6:33 pm

2 stops10h 33m

$473

ChicagoMexico City

MDW - MEX

MDWMEX

Chicago Midway

Wed 6/3

12:53 pm-9:50 pm

1 stop9h 57m

Mexico City Benito Juarez

Wed 6/10

1:20 pm-10:17 pm

1 stop7h 57m

$475

ChicagoMexico City

MDW - MEX

MDWMEX

Chicago Midway

Tue 5/26

10:59 am-9:50 pm

1 stop11h 51m

Mexico City Benito Juarez

Thu 6/4

8:40 am-9:09 pm

1 stop11h 29m

$475

ChicagoMexico City

MDW - MEX

MDWMEX

Chicago Midway

Thu 6/18

11:05 am-7:00 pm

1 stop8h 55m

Mexico City Benito Juarez

Wed 6/24

1:20 pm-10:17 pm

1 stop7h 57m

$475

Flights are sorted by cheapest round-trip flights first.

Deals found on 5/19

Showing 1-10 of 60 resultsSorted by cheapest first
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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, January is the cheapest month in which you can book a flight from Chicago Midway Airport to Mexico (average of $101). Flying from Chicago Midway Airport to Mexico in June is currently the most expensive (average of $610). 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 May 19, 2026.

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 23% on airfare.

How often are flights from Chicago to Mexico delayed?

About 19% of weekly flights between Chicago and Mexico have experienced delays in the past year, with the average delay time being 154 minutes.

What is the most punctual flight time for Chicago to Mexico flights?

Historically, flights departing in the evening are less likely to be delayed, whereas flights leaving in the early afternoon tend to experience delays more often.

What day of the week experiences the fewest flight delays on this route?

Wednesday tends to have the lowest number of delays on this route, whereas Saturday has historically faced a higher average of delays compared to other days of the week.

Which airline has the best punctuality record on Chicago to Mexico flights?

Over the last year, Volaris have had the lowest number of delays on this route, with just 17% of flights being delayed.

How far ahead should I book a flight from Chicago Midway Airport to Mexico?

The best time to book flights from Chicago Midway Airport to Mexico is 57 days before your desired departure date. The cost of your flight will likely increase significantly if you book two weeks in advance of your flight.

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 May 19, 2026.
See what other customers who have flown with Southwest,Delta, andAeromexico 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
7.9
Good
4,283 reviews

Overall

7.9

Boarding

8.1

Crew

8.6

Entertainment

7.5

Food

7.0

Comfort

8.0

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.
Southwest
7.9
Good
4,283 reviews
Southwest
7.9
Good
4,283 reviews

Overall

7.9

Boarding

8.1

Crew

8.6

Entertainment

7.5

Food

7.0

Comfort

8.0

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.
Delta
7.9
Good
8,454 reviews
Southwest
7.9
Good
4,283 reviews

Overall

7.9

Boarding

8.1

Crew

8.6

Entertainment

7.5

Food

7.0

Comfort

8.0

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.
Aeromexico
7.4
Good
1,504 reviews
Southwest
7.9
Good
4,283 reviews

Overall

7.9

Boarding

8.1

Crew

8.6

Entertainment

7.5

Food

7.0

Comfort

8.0

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.
Volaris
6.6
Okay
1,161 reviews
Southwest
7.9
Good
4,283 reviews

Overall

7.9

Boarding

8.1

Crew

8.6

Entertainment

7.5

Food

7.0

Comfort

8.0

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.
Frontier
5.7
Fair
2,944 reviews
Southwest
7.9
Good
4,283 reviews

Overall

7.9

Boarding

8.1

Crew

8.6

Entertainment

7.5

Food

7.0

Comfort

8.0

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.

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 $424, Volaris can have you in Mexico from Chicago Midway Airport in 3h 35m. 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 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 $91 on Volaris. Other airlines that offer cheap prices include Frontier from $107 and Southwest from $121 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, January is the cheapest month in which you can book a flight from Chicago Midway Airport to Mexico (average of $101). Flying from Chicago Midway Airport to Mexico in June is currently the most expensive (average of $610). 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 5 airlines flying from Midway to Mexico

Discover the top 5 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 May 19, 2026.
AirlineCheapestAverageFlexibilityOn-time
AeromexicoCheapest$152Average$402FlexibilityNo cancel feeOn-timeN/A
VolarisCheapest$170Average$409FlexibilityNo cancel feeOn-time79%
DeltaCheapest$193Average$2,056FlexibilityNo cancel feeOn-timeN/A
FrontierCheapest$198Average$480FlexibilityNo cancel feeOn-time62%
SouthwestCheapest$293Average$621FlexibilityNo cancel feeOn-time63%

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