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$149 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 8/28. 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 7/2
Tue 7/9

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 41,909,192 times on KAYAK, and here is why:

Save 21% or moreCompare multiple travel sites with one search.

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

 
These are the cheapest deals for flights from Cancún to Midway currently on KAYAK along with options from the most popular airlines KAYAK users selected for this route. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.

Recent round-trip flight deals from Cancún to Midway

Recommended round-trip deals departing in the coming months from the most popular airlines that fly from Cancún to Midway.

Recent one-way flight deals from Cancún to Midway

Only flying one-way? Below are some of the best one-way flight deals from Cancún to Midway found on KAYAK recently.

Recent last minute flight deals from Cancún to Midway

Leaving soon but still want a bargain? Check out these latest deals for last minute flights from Cancún to Midway.

Recent direct flight deals from Cancún to Midway

The latest deals for direct flights from Cancún to Midway so you can sit back and relax without the need for a layover.

Cheap bus & train deals from Cancún to Midway

Find recent round-trip train or bus tickets from Cancún to Midway.

All round-trip flight deals to Midway

The cheapest plane tickets to Midway found on KAYAK recently.
Discover the best prices and deals for you by selecting your travel dates.
Choose your dates
11:59 am - 7:56 pmCUN-MDW
7h 57m1 stop
5:54 am - 4:26 pmMDW-CUN
10h 32m1 stop
$310Frontier
Find Deal
Thu, Jun 13 - Sun, Jun 16
5:05 pm - 7:18 pmCUN-MDW
26h 13m1 stop
7:48 am - 12:55 pmMDW-CUN
29h 07m1 stop
$344Frontier
Find Deal
Tue, Oct 1 - Sun, Oct 6
8:15 am - 2:58 pmCUN-MDW
6h 43m1 stop
12:47 pm - 7:53 pmMDW-CUN
7h 06m1 stop
$346Delta
Find Deal
Thu, Sep 26 - Mon, Sep 30
8:00 am - 9:46 pmCUN-MDW
13h 46m1 stop
10:28 am - 7:55 pmMDW-CUN
9h 27m1 stop
$356Aeromexico
Find Deal
Wed, Aug 28 - Thu, Sep 5
8:29 am - 9:46 pmCUN-MDW
13h 17m2 stops
10:28 am - 7:55 pmMDW-CUN
9h 27m1 stop
$358Delta
Find Deal
Wed, Aug 28 - Thu, Sep 5
8:00 am - 6:05 pmCUN-MDW
10h 05m1 stop
6:00 am - 2:07 pmMDW-CUN
8h 07m1 stop
$390Aeromexico
Find Deal
Thu, Aug 22 - Tue, Aug 27
9:39 pm - 9:47 amCUN-MDW
12h 08m1 stop
8:45 pm - 12:40 pmMDW-CUN
15h 55m2 stops
$798Volaris
Find Deal
Thu, Jun 13 - Sun, Jun 16
10:04 pm - 9:52 amCUN-MDW
11h 48m1 stop
8:45 pm - 9:19 amMDW-CUN
11h 34m1 stop
$963Volaris
Find Deal
Tue, Oct 22 - Sun, Nov 10
1:16 pm - 2:55 pmCUN-MDW
25h 39m2 stops
6:00 am - 12:11 pmMDW-CUN
30h 11m2 stops
$1,126WestJet
Find Deal
Thu, Jun 13 - Sun, Jun 16
1:16 pm - 2:55 pmCUN-MDW
25h 39m2 stops
2:24 pm - 12:11 pmMDW-CUN
21h 47m2 stops
$1,127WestJet
Find Deal
Thu, Jun 13 - Sun, Jun 16
11:10 am - 10:41 pmCUN-MDW
11h 31m1 stop
$149
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Wed, Aug 28
5:12 pm - 2:37 pmCUN-MDW
21h 25m1 stop
$156Frontier
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Tue, Aug 6
9:11 am - 8:49 pmCUN-MDW
11h 38m1 stop
$160Frontier
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Thu, Oct 24
2:05 pm - 1:38 pmCUN-MDW
23h 33m1 stop
$176
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Sun, Jun 9
8:00 am - 9:46 pmCUN-MDW
13h 46m1 stop
$209Aeromexico
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Sat, Aug 10
8:00 am - 9:46 pmCUN-MDW
13h 46m1 stop
$221Delta
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Wed, Jun 26
10:04 pm - 9:47 amCUN-MDW
11h 43m1 stop
$274Volaris
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Wed, Sep 4
10:04 pm - 9:47 amCUN-MDW
11h 43m1 stop
$279Volaris
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Sat, Aug 31
6:57 am - 9:44 pmCUN-MDW
14h 47m2 stops
$287Delta
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Sun, Oct 27
8:59 am - 9:44 pmCUN-MDW
13h 45m2 stops
$333Aeromexico
Find Deal
Fri, Nov 22
11:59 am - 7:56 pmCUN-MDW
7h 57m1 stop
5:54 am - 4:26 pmMDW-CUN
10h 32m1 stop
$337Frontier
Find Deal
Thu, Jun 6 - Sun, Jun 9
11:59 am - 7:56 pmCUN-MDW
7h 57m1 stop
8:27 am - 3:42 pmMDW-CUN
7h 15m1 stop
$381Frontier
Find Deal
Thu, Jun 6 - Wed, Jun 12
12:33 pm - 10:01 pmCUN-MDW
9h 28m1 stop
10:41 am - 1:50 amMDW-CUN
15h 09m2 stops
$474Aeromexico
Find Deal
Tue, Jun 4 - Sun, Jun 9
11:59 am - 7:56 pmCUN-MDW
7h 57m1 stop
10:41 pm - 1:02 pmMDW-CUN
14h 21m1 stop
$476Frontier
Find Deal
Thu, Jun 6 - Thu, Jun 13
8:00 am - 9:46 pmCUN-MDW
13h 46m1 stop
6:00 am - 12:29 amMDW-CUN
18h 29m2 stops
$624Aeromexico
Find Deal
Fri, Jun 7 - Fri, Jun 14
8:00 am - 9:46 pmCUN-MDW
13h 46m1 stop
6:00 am - 2:15 pmMDW-CUN
8h 15m1 stop
$729Delta
Find Deal
Fri, Jun 7 - Fri, Jun 14
8:29 am - 9:46 pmCUN-MDW
13h 17m2 stops
12:45 pm - 12:29 amMDW-CUN
11h 44m2 stops
$935Delta
Find Deal
Fri, Jun 7 - Fri, Jun 14
9:39 pm - 9:47 amCUN-MDW
12h 08m1 stop
8:45 pm - 9:04 amMDW-CUN
12h 19m1 stop
$1,378Volaris
Find Deal
Fri, Jun 7 - Sun, Jun 9
4:55 pm - 1:44 pmCUN-MDW
20h 49m2 stops
3:45 pm - 12:21 pmMDW-CUN
20h 36m2 stops
$1,639WestJet
Find Deal
Thu, Jun 6 - Thu, Jun 13
1:16 pm - 11:55 amCUN-MDW
22h 39m2 stops
6:00 am - 2:35 pmMDW-CUN
32h 35m2 stops
$1,664WestJet
Find Deal
Fri, Jun 7 - Fri, Jun 14

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 ($156) and Aeromexico ($209). The cheapest round-trip tickets were found on Frontier ($310) and Delta ($346).

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 42m. The most common departure time is 11:00 am and most flights take off in the afternoon. 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 4:30 pm and lands at 8:10 pm.

Good to know

High season

December

Cheapest flight

$149
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 $149 for a one-way ticket and $310 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 A321-100/200 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

KAYAK’s top tips for finding a cheap flight from Cancún 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.
8/28Wed
1 stop
11h 31mCUN-MDW
$149
8/6Tue
1 stopFrontier
21h 25mCUN-MDW
$156
10/24Thu
1 stopFrontier
11h 38mCUN-MDW
$160
6/9Sun
1 stop
23h 33mCUN-MDW
$176
8/10Sat
1 stopAeromexico
13h 46mCUN-MDW
$209
6/26Wed
1 stopDelta
13h 46mCUN-MDW
$221
9/4Wed
1 stopVolaris
11h 43mCUN-MDW
$274
8/31Sat
1 stopVolaris
11h 43mCUN-MDW
$279
10/27Sun
2 stopsDelta
14h 47mCUN-MDW
$287
11/22Fri
2 stopsAeromexico
13h 45mCUN-MDW
$333

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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.
6/6Thu
multi-stopFrontier
7h 57mCUN-MDW
6/9Sun
multi-stopFrontier
10h 32mMDW-CUN
$337
6/6Thu
multi-stopFrontier
7h 57mCUN-MDW
6/12Wed
multi-stopFrontier
7h 15mMDW-CUN
$381
6/4Tue
multi-stopAeromexico
9h 28mCUN-MDW
6/9Sun
multi-stopAeromexico
15h 09mMDW-CUN
$474
6/6Thu
multi-stopFrontier
7h 57mCUN-MDW
6/13Thu
multi-stopFrontier
14h 21mMDW-CUN
$476
6/7Fri
multi-stopAeromexico
13h 46mCUN-MDW
6/14Fri
multi-stopAeromexico
18h 29mMDW-CUN
$624
6/7Fri
multi-stopDelta
13h 46mCUN-MDW
6/14Fri
multi-stopDelta
8h 15mMDW-CUN
$729
6/7Fri
multi-stopDelta
13h 17mCUN-MDW
6/14Fri
multi-stopDelta
11h 44mMDW-CUN
$935
6/7Fri
multi-stopVolaris
12h 08mCUN-MDW
6/9Sun
multi-stopVolaris
12h 19mMDW-CUN
$1,378
6/6Thu
multi-stopWestJet
20h 49mCUN-MDW
6/13Thu
multi-stopWestJet
20h 36mMDW-CUN
$1,639
6/7Fri
multi-stopWestJet
22h 39mCUN-MDW
6/14Fri
multi-stopWestJet
32h 35mMDW-CUN
$1,664

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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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