HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Midway

$149+ 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 10/16. Fares are subject to change and may not be available on all flights or dates of travel.
CUN — MDW
Aug 3 — Aug 101
Sun 8/3
Sun 8/10
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 July 29, 2025.

Round-trip from

$273
(Southwest)

One-way from

$149
(Southwest)

Popular in

August

Cheapest in

June

Average price

$339

Good round-trip deal

$321 or less

Good one-way deal

$148 or less
From Cancun to Chicago Midway
Search Deals
One-way flight from Cancun to Chicago Midway
Search Deals
Highest demand for flights based on searches. 6% potential increase in price ($25 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 July 2025
Search Deals
Price to beat on a round-trip flight from Cancun to Chicago Midway.
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 July 29, 2025.

This Southwest deal was found by Cheapflights users on 7/28. 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 10/163:20 pmCUN - MDW
Nonstop3h 35mSouthwest
Mon 10/209:40 amMDW - CUN
Nonstop3h 35mSouthwest
Deal found 7/28$273
This Delta deal was found by Cheapflights users on 7/29. 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 9/2512:25 pmCUN - MDW
1 stop9h 11mDelta
Tue 9/306:00 amMDW - CUN
1 stop6h 50mDelta
Deal found 7/29$276
This Frontier deal was found by Cheapflights users on 7/29. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/211:55 pmCUN - MDW
1 stop9h 25mFrontier
Sat 9/276:15 amMDW - CUN
1 stop6h 25mFrontier
Deal found 7/29$305
This Aeromexico deal was found by Cheapflights users on 7/28. 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.
Thu 9/1112:25 pmCUN - MDW
1 stop9h 11mAeromexico
Thu 9/186:00 amMDW - CUN
2 stops16h 37mAeromexico
Deal found 7/28$353
This CheapOair deal was found by Cheapflights users on 7/27. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/1012:40 pmCUN - MDW
1 stop8h 46mMultiple Airlines
Wed 9/179:00 amMDW - CUN
1 stop27h 40mMultiple Airlines
Deal found 7/27$354

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 July 29, 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 10/16

3:20 pm-6:55 pm

Nonstop3h 35m

Chicago Midway

Mon 10/20

9:40 am-1:15 pm

Nonstop3h 35m

$273

CancúnChicago

CUN - MDW

CUNMDW

Cancun

Fri 10/24

8:00 am-6:25 pm

2 stops10h 25m

Chicago Midway

Fri 10/31

10:35 am-8:20 pm

1 stop9h 45m

$276

CancúnChicago

CUN - MDW

CUNMDW

Cancun

Sun 9/21

1:55 pm-11:20 pm

1 stop9h 25m

Chicago Midway

Sat 9/27

6:15 am-12:40 pm

1 stop6h 25m

$305

CancúnChicago

CUN - MDW

CUNMDW

Cancun

Thu 9/11

12:25 pm-9:36 pm

1 stop9h 11m

Chicago Midway

Thu 9/18

6:00 am-10:37 pm

2 stops16h 37m

$353

CancúnChicago

CUN - MDW

CUNMDW

Cancun

Wed 9/10

12:40 pm-9:26 pm

1 stop8h 46m

Chicago Midway

Wed 9/17

9:00 am-12:40 pm

1 stop27h 40m

$354

CancúnChicago

CUN - MDW

CUNMDW

Cancun

Thu 10/16

3:20 pm-6:55 pm

Nonstop3h 35m

$149

CancúnChicago

CUN - MDW

CUNMDW

Cancun

Tue 10/7

9:54 am-12:11 am

1 stop14h 17m

$168

CancúnChicago

CUN - MDW

CUNMDW

Cancun

Thu 9/4

8:10 am-9:26 pm

2 stops13h 16m

$175

CancúnChicago

CUN - MDW

CUNMDW

Cancun

Fri 10/24

8:00 am-4:09 pm

1 stop8h 09m

$179

CancúnChicago

CUN - MDW

CUNMDW

Cancun

Sat 8/16

9:04 am-8:22 pm

1 stop11h 18m

$186

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/28

Showing 1-10 of 11 results
1
2

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 July 29, 2025.

A simple way to save on the total cost of your ticket is to fly from Cancún to Chicago Midway Airport at noon. If you’re flexible enough to do this you can expect to save up to 29% on your trip compared to booking a flight in the morning.

Weekly flight availability from Cancún to Chicago Midway Airport

Explore weekly flight availability from Cancún to Midway. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated July 29, 2025.

The most flights from CUN to MDW are scheduled on a Monday (2 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (1 on average).

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 July 29, 2025.
Read reviews from past customers who have flown Southwest, Delta, and Aeromexico from Cancún to Chicago Midway Airport. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,238 reviews

Comfort

8.0

Entertainment

7.5

Boarding

8.1

Food

7.0

Crew

8.6

Overall

8.0

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
Southwest
8.0
Very good
4,238 reviews
Southwest
8.0
Very good
4,238 reviews

Comfort

8.0

Entertainment

7.5

Boarding

8.1

Food

7.0

Crew

8.6

Overall

8.0

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
Delta
8.0
Very good
7,977 reviews
Southwest
8.0
Very good
4,238 reviews

Comfort

8.0

Entertainment

7.5

Boarding

8.1

Food

7.0

Crew

8.6

Overall

8.0

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
Aeromexico
7.5
Good
1,720 reviews
Southwest
8.0
Very good
4,238 reviews

Comfort

8.0

Entertainment

7.5

Boarding

8.1

Food

7.0

Crew

8.6

Overall

8.0

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
Volaris
6.6
Okay
1,163 reviews
Southwest
8.0
Very good
4,238 reviews

Comfort

8.0

Entertainment

7.5

Boarding

8.1

Food

7.0

Crew

8.6

Overall

8.0

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
Frontier
5.9
Fair
3,238 reviews
Southwest
8.0
Very good
4,238 reviews

Comfort

8.0

Entertainment

7.5

Boarding

8.1

Food

7.0

Crew

8.6

Overall

8.0

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.

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 1 outbound flight 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 ($273), Delta ($276), and Frontier ($305) offers the cheapest pricing from Cancún to Chicago Midway Airport. You may be able to fly from Cancún to Chicago Midway Airport for 26% less than the average price by searching for these airlines.

  • 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 $149 on Southwest. Other airlines that offer cheap prices include Delta from $175 and Aeromexico from $179 one-way.

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

    Looking at all options, your cheapest flight can be booked for $148. While the most popular route (Cancun - Chicago Midway) can be booked for $273 on average our data indicates $238 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 Chicago Midway Airport?

Book flights to Chicago Midway Airport if you plan to visit one of these locations
Merrillville
Lansing
Hammond
Benton Harbor
Porter
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.