HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Midway

$137+ Cheap flights from Cancún (CUN) to Midway (MDW)

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 4/23. Fares are subject to change and may not be available on all flights or dates of travel.
CUN — MDW
Apr 20 — Apr 271
Sun 4/20
Sun 4/27
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Cancún to Midway with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

Cheap flight deals from Cancún to Midway

Discover tips and strategies to find the most affordable flight options for your journey from Cancún (CUN) to Midway (MDW). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated April 15, 2025.

Most accurate provider

AranGrant
3 stars

Most trusted provider

AranGrant
3 stars

Round-trip from

$249
(Southwest)

One-way from

$137
(Southwest)

Popular in

June

Cheapest in

January

Average price

$284

Good one-way deal

$267 or less
Provider with most accurate pricing for Cancun-Chicago Midway flight deals.
Search Deals
Provider most trusted by Cheapflights users for Cancun-Chicago Midway flights.
Search Deals
From Cancun to Chicago Midway
Search Deals
One-way flight from Cancun to Chicago Midway
Search Deals
Highest demand for flights based on searches. 7% potential increase in price ($20 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($8 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in April 2025
Search Deals
Price to beat on a one-way flight from Cancun to Chicago Midway.
Search Deals

Find flight deals from Cancún to Midway

Cheapest flights from Cancún to Midway
Explore the most affordable flight options available from Cancún to Midway. Find the lowest fares from popular airlines and budget airlines, with prices last updated on April 15, 2025.

This Southwest deal was found by Cheapflights users on 4/14. 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.
Thu 5/89:00 amCUN - MDW
Nonstop3h 40mSouthwest
Sun 5/1110:45 amMDW - CUN
Nonstop3h 40mSouthwest
Deal found 4/14$249
This Delta deal was found by Cheapflights users on 4/14. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/178:15 amCUN - MDW
2 stops10h 05mDelta
Sun 4/206:04 amMDW - CUN
1 stop7h 57mDelta
Deal found 4/14$274
This Aeromexico deal was found by Cheapflights users on 4/14. 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 Aeromexico is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/193:07 pmCUN - MDW
1 stop6h 37mAeromexico
Tue 9/231:05 pmMDW - CUN
1 stop6h 57mAeromexico
Deal found 4/14$360
This Booking.com deal was found by Cheapflights users on 4/14. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/152:43 pmCUN - MDW
1 stop8h 56mFrontier
Mon 5/1912:15 pmMDW - CUN
1 stop23h 01mFrontier
Deal found 4/14$385
This eDestinos deal was found by Cheapflights users on 4/14. 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/91:57 pmCUN - MDW
1 stop7h 25mVolaris
Sun 10/1210:41 pmMDW - CUN
1 stop14h 21mVolaris
Deal found 4/14$543
This Kiwi.com deal was found by Cheapflights users on 4/15. 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.
Sun 6/157:39 amCUN - MDW
1 stop9h 15mMultiple Airlines
Sun 6/159:12 pmMDW - CUN
1 stop11h 00mMultiple Airlines
Deal found 4/15$605
This WestJet deal was found by Cheapflights users on 4/14. 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 WestJet is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/176:00 pmCUN - MDW
2 stops20h 22mWestJet
Sun 4/207:00 pmMDW - CUN
2 stops24h 10mWestJet
Deal found 4/14$3,735

Cheapflights Fare Finder

Customize your flight search to find flights from Cancún to Midway 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 April 15, 2025.
Use the filters below to find and compare flights from Cancún to Chicago Midway Airport that are best for you.

Fly from

Cancún

Fly to

Midway

Route

Depart

Return

Price

CancúnChicago

CUN - MDW

CUNMDW

Cancun

Thu 5/8

9:00 am-12:40 pm

Nonstop3h 40m

Chicago Midway

Sun 5/11

10:45 am-2:25 pm

Nonstop3h 40m

$249

CancúnChicago

CUN - MDW

CUNMDW

Cancun

Thu 5/1

8:15 am-4:12 pm

1 stop7h 57m

Chicago Midway

Sun 5/4

9:52 am-8:02 pm

1 stop10h 10m

$274

CancúnChicago

CUN - MDW

CUNMDW

Cancun

Fri 9/19

3:07 pm-9:44 pm

1 stop6h 37m

Chicago Midway

Tue 9/23

1:05 pm-8:02 pm

1 stop6h 57m

$360

CancúnChicago

CUN - MDW

CUNMDW

Cancun

Thu 5/15

2:43 pm-11:39 pm

1 stop8h 56m

Chicago Midway

Mon 5/19

12:15 pm-11:16 am

1 stop23h 01m

$385

CancúnChicago

CUN - MDW

CUNMDW

Cancun

Thu 10/9

1:57 pm-9:22 pm

1 stop7h 25m

Chicago Midway

Sun 10/12

10:41 pm-1:02 pm

1 stop14h 21m

$543

CancúnChicago

CUN - MDW

CUNMDW

Cancun

Sun 6/15

7:39 am-4:54 pm

1 stop9h 15m

Chicago Midway

Sun 6/15

9:12 pm-8:12 am

1 stop11h 00m

$605

CancúnChicago

CUN - MDW

CUNMDW

Cancun

Wed 4/23

9:00 am-12:40 pm

Nonstop3h 40m

$137

CancúnChicago

CUN - MDW

CUNMDW

Cancun

Thu 5/1

8:15 am-4:12 pm

1 stop7h 57m

$171

CancúnChicago

CUN - MDW

CUNMDW

Cancun

Wed 5/14

11:00 am-9:28 pm

1 stop10h 28m

$174

CancúnChicago

CUN - MDW

CUNMDW

Cancun

Fri 6/6

2:03 pm-1:42 pm

1 stop23h 39m

$186

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/13

Showing 1-10 of 13 results
1
2

Compare providers for flights from Cancún to Midway

Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Cancún to Midway in April.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*2 stars
AranGrantPrice Accuracy3 starsTrust Score*3 stars
Kiwi.comPrice Accuracy3 starsTrust Score*3 stars

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

  • Most accurate provider: When it comes to deals on Cancún-Chicago Midway Airport flights, users find the pricing of AranGrant to be most consistent on Cheapflights vs. AranGrant Users can find the same prices on Cancún-Chicago Midway Airport flight deals on Cheapflights vs. AranGrant >95% of the time. Price accuracy is based on data collected from Cancún-Chicago Midway Airport flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Cancún-Chicago Midway Airport flights, Cheapflights users trust AranGrant the most. AranGrant has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Cancún-Chicago Midway Airport flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

Best time to book a flight from Cancún to Midway

Have a flexible travel schedule? Discover the best time to fly to Midway from Cancún 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 Cancún to Chicago Midway Airport

What is the cheapest time of day to fly from CUN to MDW?

Find hourly flight availability from Cancún to Midway. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated April 15, 2025.

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Cancún to Chicago Midway Airport as you normally would.

Rainfall in Midway by month

Plan your trip to Midway by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Chicago Midway Airport ranges from 1.7 - 4.9 inches per month. August is typically the wettest month, when rainfall can reach 4.9 in. January is typically the driest time to visit Chicago Midway Airport when rainfall is around 1.7 in.

Temperature in Midway by month

Plan your trip to Midway by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Chicago Midway Airport, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 73.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 23.0 F).

Reviews of airlines servicing Midway

Get insights into the airlines that provide service to Midway. 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 Midway. Reviews last updated April 15, 2025.
Southwest
8.0
Very good
4,279 reviews

Comfort

8.0

Crew

8.6

Entertainment

7.6

Food

7.1

Boarding

8.2

Overall

8.0

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
Southwest
8.0
Very good
4,279 reviews
Southwest
8.0
Very good
4,279 reviews

Comfort

8.0

Crew

8.6

Entertainment

7.6

Food

7.1

Boarding

8.2

Overall

8.0

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
Delta
8.0
Very good
7,918 reviews
Southwest
8.0
Very good
4,279 reviews

Comfort

8.0

Crew

8.6

Entertainment

7.6

Food

7.1

Boarding

8.2

Overall

8.0

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
Aeromexico
7.5
Good
1,698 reviews
Southwest
8.0
Very good
4,279 reviews

Comfort

8.0

Crew

8.6

Entertainment

7.6

Food

7.1

Boarding

8.2

Overall

8.0

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
WestJet
7.2
Good
2,805 reviews
Southwest
8.0
Very good
4,279 reviews

Comfort

8.0

Crew

8.6

Entertainment

7.6

Food

7.1

Boarding

8.2

Overall

8.0

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
Volaris
6.7
Okay
1,172 reviews
Southwest
8.0
Very good
4,279 reviews

Comfort

8.0

Crew

8.6

Entertainment

7.6

Food

7.1

Boarding

8.2

Overall

8.0

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.

Related info for your journey

Find useful and relevant information for your journey from Cancún to Midway. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What airport do you fly from for flights from Cancún to Chicago Midway?

    For a flight from Cancún to Chicago Midway, you will be flying from Cancun. Cancun (CUN) is just 8.9 mi from the center of the city. Cancun is the only Cancún airport and it handles 0 outbound flights to Chicago Midway per day. 0 airlines have flights to Chicago Midway from Cancun on a regular basis.

  • What are the cheapest airlines flying from Cancún to Chicago Midway Airport round-trip?

    According to our current data, Southwest ($249), Delta ($274), and Aeromexico ($360) offers the cheapest pricing from Cancún to Chicago Midway Airport.

  • What are the cheapest airlines to fly from Cancún to Chicago Midway Airport one-way?

    One-way options have recently been found by users for as low as $137 on Southwest. Other airlines that offer cheap prices include Aeromexico from $171 and Delta from $174 one-way.

  • What are the cheapest flights from Cancún to Chicago Midway Airport?

    Looking at all options, your cheapest flight can be booked for $137. While the most popular route (Cancun - Chicago Midway) can be booked for $264 on average our data indicates $338 when flying from Cancún to Chicago Midway Airport.

  • Can I find deals for flights from Cancún to Midway that include hotel bookings?

    Yes. In addition to deals on Cancún to Midway flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Cancún to Midway?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Cancún to Midway.

  • Can I find deals for business class flights from Cancún to Midway?

    Yes. Cheapflights offers flight deals from Cancún to Midway 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 Cancún to Chicago Midway Airport?

    Currently, April is the cheapest month in which you can book a flight from Cancún to Chicago Midway Airport (average of $160). Flying from Cancún to Chicago Midway Airport in November is currently the most expensive (average of $249). 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

Traveling to a place near Cancún?

Book flights to Cancún if you plan to visit one of these locations
Merrillville
Hammond
Benton Harbor
Porter
Lansing
Valparaiso
Chesterton

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Cancún to Midway

See prices for flight routes from nearby airports that may be better suited for you.
Cancún to O'Hare Intl flights
Cozumel to O'Hare Intl flights

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.