CUN - MDW

$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 12/6. 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
1 adult, Economy

KAYAK searches 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
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Flight Deals

Cheap Flights 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 for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Cancún to Midway

Sat, Dec 27 - Mon, Jan 5
Southwest Logo
11:20 am - 2:00 pmCUN-MDW
3h 40mnonstop
Southwest Logo
10:40 am - 3:25 pmMDW-CUN
3h 45mnonstop
$275Southwest
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Wed, Nov 12 - Sun, Nov 16
Delta Logo
8:00 am - 6:08 pmCUN-MDW
11h 08m2 stops
Delta Logo
6:48 pm - 12:37 pmMDW-CUN
16h 49m1 stop
$276Delta
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Thu, Nov 13 - Tue, Nov 18
Aeromexico Logo
8:00 am - 11:32 pmCUN-MDW
16h 32m1 stop
Aeromexico Logo
6:00 am - 3:34 pmMDW-CUN
8h 34m1 stop
$277Aeromexico
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Sat, Oct 4 - Tue, Oct 7
Southwest Logo
12:00 pm - 3:35 pmCUN-MDW
3h 35mnonstop
Southwest Logo
9:40 am - 1:15 pmMDW-CUN
3h 35mnonstop
$290Southwest
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Wed, Oct 15 - Mon, Oct 20
Southwest Logo
3:15 pm - 6:50 pmCUN-MDW
3h 35mnonstop
Southwest Logo
9:40 am - 1:15 pmMDW-CUN
3h 35mnonstop
$295Southwest
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Tue, Oct 21 - Thu, Oct 23
Logo
9:52 am - 11:20 pmCUN-MDW
13h 28m1 stop
Logo
5:20 pm - 10:06 amMDW-CUN
16h 46m1 stop
$311
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Wed, Nov 12 - Tue, Nov 18
Aeromexico Logo
8:00 am - 11:32 pmCUN-MDW
16h 32m1 stop
Aeromexico Logo
10:47 am - 9:20 pmMDW-CUN
9h 33m1 stop
$324Aeromexico
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Sat, Nov 15 - Thu, Nov 20
Frontier Logo
2:30 pm - 9:35 pmCUN-MDW
8h 05m1 stop
Frontier Logo
6:00 am - 4:00 pmMDW-CUN
9h 00m1 stop
$337Frontier
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Sat, Oct 25 - Sat, Nov 1
Frontier Logo
3:36 pm - 4:42 pmCUN-MDW
25h 06m1 stop
Frontier Logo
1:37 pm - 1:20 pmMDW-CUN
23h 43m1 stop
$340Frontier
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Fri, Oct 24 - Fri, Oct 31
Logo
9:09 am - 4:20 pmCUN-MDW
7h 11m1 stop
Logo
6:30 am - 6:58 pmMDW-CUN
12h 28m2 stops
$360
Find Deal

Everything you should know

Cheapest round-trip
$275
Southwest
Sat 12/27Mon 1/5
CUN - MDW • Non-stop
Cheapest non-stop
$290
Southwest
Sat 10/4Tue 10/7
CUN - MDW • Non-stop
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KAYAK searches 100s of sites at once to find you the best travel deals.
We hope you love your trip to Midway!
Booking Insights

KAYAK's insights & trends for Cancún to Midway flights

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.

What’s the cheapest day of the week to fly from Cancun to Chicago Midway Airport?

The average price of all round-trip flights from Cancún to Chicago Midway Airport clicked on KAYAK for each day over the last 12 months.

If you are looking for a flight deal from Cancun to Chicago Midway Airport, look for departures on Tuesdays and avoid leaving on a Monday, as it's usually the priciest day. When flying back from Chicago Midway Airport, Monday is the cheapest day to fly and Friday is the most expensive.

Can I save money by flying with a layover from Cancún to Chicago Midway Airport?

The average round-trip price for all non-stop flights, flights with one layover, and flights with two layovers for the route found by users searching on KAYAK in the last 2 weeks.

Yes, flying with a layover may cost you more time, but you can also save money on the route, with a 1 stop layover the cheapest option at $569 on average.

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Good to know

Low seasonJune
Cheapest flight$149
Best time to beat the crowds with an average 33% drop in price.
Most popular time to fly and prices are also 33% lower on average.
Flight from Cancun 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 $275 for a round-trip.

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

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

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

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

  • Which airlines offer Wi-Fi service onboard planes from Cancun to Chicago Midway Airport?

    American Airlines, Delta, and Aeromexico offer inflight Wi-Fi service on the Cancun to Chicago Midway Airport flight route.

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

    The Boeing 737-900 is the aircraft model that flies most regularly on the Cancun to Chicago Midway Airport flight route.

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

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

  • How does KAYAK find such low prices on flights from Cancun 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 Cancun to Chicago Midway Airport.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Cancun 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 Cancun 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 Cancun 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 Cancun with another airline. Booking your flights between Cancun 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 Cancun 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 Cancun up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

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 $329 or less one-way and $445 or less round-trip.

Prefer to fly direct from Cancun to Chicago Midway Airport?

 
Direct data is based off flight results for the next 60 days. Find direct flights from all airlines flying direct from Cancun to Chicago Midway.
Find which airlines fly direct from Cancun Airport to Chicago Midway Airport, which days they fly and book direct flights.

Direct 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

Direct 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

Everything you need to know for your flight from Cancún to Midway

Information on your arrival and departure airports

Cancun (CUN)
Midway (MDW)

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