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CUN - MDW

$129 Find cheap flights from Cancun to Chicago Midway Airport

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Cancún to Midway departing on 5/14. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
0 bags
Tue 6/4
Tue 6/11

Search hundreds of travel sites at once for deals on flights to Chicago Midway Airport

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Cancún to Chicago, as well as popular online travel agencies
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Cancún to Chicago, as well as popular online travel agencies
In the last 7 days travelers have searched 43,369,418 times on KAYAK, and here is why:

Save 22% or moreCompare multiple travel sites with one search.

Track pricesNot ready to book? Create a price alert for when prices drop.

Filter your dealsChoose cabin class, free Wi-Fi and more.

Bundle and saveSave money when you bundle your flight + hotel.

Cheap flight deals from Cancún to Midway (CUN-MDW)

Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Cancún to Midway that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices and deals for you by selecting your travel dates.
Choose your dates
11:05 am - 8:30 pmCUN-MDW
9h 25m1 stop
9:53 pm - 8:26 amMDW-CUN
10h 33m1 stop
$295
Find Deal
Thu, May 30 - Sun, Jun 2
11:05 am - 8:30 pmCUN-MDW
9h 25m1 stop
7:05 am - 4:11 pmMDW-CUN
9h 06m1 stop
$312
Find Deal
Thu, May 30 - Tue, Jun 4
11:59 am - 7:56 pmCUN-MDW
7h 57m1 stop
7:00 am - 4:21 pmMDW-CUN
9h 21m1 stop
$317Frontier
Find Deal
Thu, Jun 6 - Tue, Jun 11
9:11 am - 10:55 amCUN-MDW
25h 44m1 stop
8:13 pm - 3:50 pmMDW-CUN
19h 37m1 stop
$325Frontier
Find Deal
Thu, Sep 26 - Mon, Sep 30
8:15 am - 5:59 pmCUN-MDW
9h 44m1 stop
2:05 pm - 8:53 pmMDW-CUN
5h 48m1 stop
$345Aeromexico
Find Deal
Tue, Oct 22 - Tue, Nov 5
9:00 am - 9:44 pmCUN-MDW
12h 44m2 stops
1:05 pm - 7:53 pmMDW-CUN
6h 48m1 stop
$346Delta
Find Deal
Thu, Sep 26 - Mon, Sep 30
8:10 am - 5:58 pmCUN-MDW
9h 48m1 stop
12:42 pm - 7:51 pmMDW-CUN
7h 09m1 stop
$403Delta
Find Deal
Fri, May 24 - Tue, May 28
8:15 am - 5:59 pmCUN-MDW
9h 44m1 stop
6:00 am - 11:19 amMDW-CUN
5h 19m1 stop
$443Aeromexico
Find Deal
Tue, Aug 20 - Tue, Aug 27
10:04 pm - 9:47 amCUN-MDW
11h 43m1 stop
8:45 pm - 11:23 amMDW-CUN
14h 38m1 stop
$597Volaris
Find Deal
Fri, Oct 11 - Tue, Oct 15
10:04 pm - 9:52 amCUN-MDW
11h 48m1 stop
8:45 pm - 11:23 amMDW-CUN
14h 38m1 stop
$600Volaris
Find Deal
Tue, Oct 15 - Fri, Oct 25

Flights from Cancún to Midway - Travel Insights & Trends

Get data-powered insights and trends into flights from Cancún to Midway to help you find the cheapest flights, the best time to fly and much more.

How far in advance should I book a flight from Cancún to Chicago Midway Airport?

To calculate daily average prices, KAYAK takes all prices for each day before departure over the last year for flights from Cancún to Chicago Midway Airport, removes the top 0.1% to account for outliers, and then takes the average of all the values for each month.
To get a below average price on the flight from Cancún to Chicago Midway Airport, you should book around 1 week before departure. For the absolute cheapest price, our data suggests you should book 29 days before departure.

Which airlines provide the cheapest flights from Cancún to Chicago Midway Airport?

The cheapest price for the route for each airline clicked by KAYAK users in the last 72 hours.
The best deals for a one-way ticket found by KAYAK users over the last 3 days were on Frontier ($129) and Aeromexico ($208). The cheapest round-trip tickets were found on Frontier ($317) and Aeromexico ($345).

How many flights are there between Cancún and Chicago Midway Airport per day?

Each day, there are between 1 and 2 nonstop flights that take off from Cancún and land in Chicago Midway Airport, with an average flight time of 3h 40m. The most common departure time is 12:00 pm and most flights take off in the morning. Each week, there are 9 flights. The most frequent day of departure is Saturday, when 22% of all weekly flights depart. The fewest flights depart on a Friday.

Which cabin class options are there for flights between Cancún and Chicago Midway Airport?

The average price of flights for each cabin class for the route found by users searching on KAYAK over the last 2 weeks.
There is only one cabin class option available for the route, which is Economy. Perform a search on KAYAK to find the latest prices and availability for all cabin fares, which differ across airlines.

What’s the earliest departure time from Cancún to Chicago Midway Airport?

Early birds can take the earliest flight from Cancún at 11:00 am and will be landing in Chicago Midway Airport at 2:45 pm.

What’s the latest departure time from Cancún to Chicago Midway Airport?

If you prefer to fly at night, the latest flight from Cancún to Chicago Midway Airport jets off at 4:40 pm and lands at 8:20 pm.

Good to know

High season

December

Cheapest flight

$129
Most popular time to fly and prices are also 51% lower on average.
Flight from Cancún to Chicago Midway Airport

When to book flights from Cancún to Midway

Are your dates flexible? Find out the best times to travel from Cancún to Midway based on our flight data from the last year. Discover the cheapest month and even day to fly.
Estimated round-trip price
KAYAK looks at all historical flight data for each date to provide a predicted price for one-way trips or round-trips with a duration up to 40 days. While we try to provide actual minimum prices for each date, some prices are predictions and actual prices may differ.

FAQs for booking Cancun to Chicago Midway Airport flights

  • What is the cheapest flight from Cancún to Chicago Midway Airport?

    In the last 3 days, the lowest price for a flight from Cancún to Chicago Midway Airport was $129 for a one-way ticket and $295 for a round-trip.

  • Do I need a passport to fly between Cancún and Chicago Midway Airport?

    Yes, you’ll need a passport to travel to Chicago Midway Airport from Cancún.

  • Which airports will I be using when flying from Cancún to Chicago Midway Airport?

    Cancún airport is called Cancun and the only airport in Chicago Midway Airport is Chicago Midway.

  • Which aircraft models fly most regularly from Cancún to Chicago Midway Airport?

    The Airbus A320neo is the aircraft model that flies most regularly on the Cancún to Chicago Midway Airport flight route.

  • On which days can I fly direct from Cancún to Chicago Midway Airport?

    There are nonstop flights from Cancún to Chicago Midway Airport on a daily basis.

  • How does KAYAK find such low prices on flights from Cancún to Chicago Midway Airport?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Cancún to Chicago Midway Airport.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Cancún to Chicago Midway Airport?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Chicago Midway Airport from Cancún is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Cancún to Chicago Midway Airport?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly to Chicago Midway Airport with an airline and back to Cancún with another airline. Booking your flights between Cancún and MDW can sometimes prove cheaper using this method.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Cancún to Chicago Midway Airport?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to Chicago Midway Airport from Cancún up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

See more FAQs

Top tips for finding a cheap flight from CUN to Chicago Midway Airport

  • Looking for a cheap flight? 25% of our users found flights on this route for $61 or less one-way.

Prefer to fly non-stop from Cancún to Chicago Midway Airport?

Find which airlines fly direct from Cancun to Midway, which days they fly and book direct flights.

Nonstop departures

Cancun to Chicago Midway

Monday

Southwest

Southwest

Tuesday

Southwest

Southwest

Wednesday

Southwest

Southwest

Thursday

Southwest

Southwest

Friday

Southwest

Southwest

Saturday

Southwest

Southwest

Sunday

Southwest

Southwest

See more direct flights

Nonstop returns

Chicago Midway to Cancun

Monday

Southwest

Southwest

Tuesday

Southwest

Southwest

Wednesday

Southwest

Southwest

Thursday

Southwest

Southwest

Friday

Southwest

Southwest

Saturday

Southwest

Southwest

Sunday

Southwest

Southwest

See more direct flights
See more direct flights

Book cheap flights from Cancun to Chicago

Recent one-way flight deals

 
Only flying one-way? Below are some of the best one-way flight deals from Cancún to Chicago found on KAYAK in the last 72 hours.
5/14Tue
1 stopFrontier
10h 27mCUN-MDW
$129
5/11Sat
1 stopFrontier
10h 49mCUN-MDW
$131
5/31Fri
2 stops
26h 55mCUN-MDW
$169
6/3Mon
1 stop
25h 53mCUN-MDW
$176
7/11Thu
1 stopAeromexico
6h 39mCUN-MDW
$208
8/24Sat
2 stopsDelta
13h 55mCUN-MDW
$223
7/3Wed
1 stopVolaris
11h 43mCUN-MDW
$241
5/20Mon
1 stopVolaris
12h 08mCUN-MDW
$250
6/4Tue
2 stopsAeromexico
24h 17mCUN-MDW
$334
5/18Sat
2 stopsDelta
8h 03mCUN-MDW
$335

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Last minute flights from Cancún to Midway

Last minute flight, train and bus deals

 
These last-minute flight deals are the cheapest flights found on KAYAK in the last 72 hours for flights from Cancún to Chicago that are departing in the next 10 days.
5/10Fri
multi-stopFrontier
12h 31mCUN-MDW
5/12Sun
multi-stopFrontier
9h 21mMDW-CUN
$259
5/10Fri
multi-stopFrontier
21h 28mCUN-MDW
5/13Mon
multi-stopFrontier
26h 36mMDW-CUN
$267
5/8Wed
multi-stopFrontier
12h 31mCUN-MDW
5/11Sat
multi-stopFrontier
11h 12mMDW-CUN
$270
5/7Tue
multi-stopFrontier
10h 27mCUN-MDW
5/14Tue
multi-stopFrontier
9h 06mMDW-CUN
$275
5/8Wed
multi-stopDelta
7h 40mCUN-MDW
5/15Wed
multi-stopDelta
7h 09mMDW-CUN
$444
5/8Wed
multi-stopAeromexico
7h 40mCUN-MDW
5/15Wed
multi-stopAeromexico
7h 09mMDW-CUN
$553
5/9Thu
multi-stopAeromexico
15h 59mCUN-MDW
5/13Mon
multi-stopAeromexico
12h 00mMDW-CUN
$558
5/8Wed
multi-stopDelta
7h 40mCUN-MDW
5/15Wed
multi-stopDelta
11h 46mMDW-CUN
$568
5/6Mon
multi-stopWestJet
16h 14mCUN-MDW
5/18Sat
multi-stopWestJet
12h 43mMDW-CUN
$1,924
5/10Fri
multi-stopWestJet
42h 07mCUN-MDW
5/12Sun
multi-stopWestJet
26h 58mMDW-CUN
$2,187

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Cancún - Chicago Midway Airport Flights

Departure:

Cancun (CUN)Mexico

Destination:

Chicago Midway Airport (MDW)United States

Return flight deals:

Chicago Midway Airport - Cancun

Cabin classes:

$166

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