$90 Find Cheap Flights from Chicago Midway Airport to Mexico

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Midway to Mexico departing on 5/22. 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, 0 bags

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Cheap Flights from Midway to Mexico

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Cancún
Cancúnnonstop$281
Mexico City
Mexico City1 stop$247
Guadalajara
Guadalajaranonstop$245
Puerto Vallarta
Puerto Vallarta1 stop$390
León
Leónnonstop$275
Monterrey
Monterrey1 stop$339
Tijuana
Tijuana1 stop$338
Oaxaca
Oaxaca2 stops$562
Morelia
Morelianonstop$242
Mérida
Mérida1 stop$355
Ixtapa
Ixtapa2 stops$434
San Luis Potosí
San Luis Potosínonstop$300
Aguascalientes
Aguascalientesnonstop$238
Veracruz
Veracruz1 stop$322
Cancún
Cancúnnonstop$281
Mexico City
Mexico City1 stop$247
Guadalajara
Guadalajaranonstop$245
Puerto Vallarta
Puerto Vallarta1 stop$390
León
Leónnonstop$275
Monterrey
Monterrey1 stop$339
Tijuana
Tijuana1 stop$338
Oaxaca
Oaxaca2 stops$562
Morelia
Morelianonstop$242
Mérida
Mérida1 stop$355
Ixtapa
Ixtapa2 stops$434
San Luis Potosí
San Luis Potosínonstop$300
Aguascalientes
Aguascalientesnonstop$238
Veracruz
Veracruz1 stop$322

Book Cheap Midway to Mexico Plane Tickets

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Midway to Mexico 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 Midway to Mexico

Sat, May 16 - Sat, May 23
Volaris Logo
5:53 pm - 9:03 pm
MDW
-
AGU
4h 10mnonstop
Volaris Logo
11:52 am - 4:30 pm
AGU
-
MDW
3h 38mnonstop
$238Volaris
Mon, Apr 27 - Wed, May 13
Volaris Logo
2:32 pm - 5:41 pm
MDW
-
MLM
4h 09mnonstop
Volaris Logo
8:22 am - 1:15 pm
MLM
-
MDW
3h 53mnonstop
$242Volaris
Sat, Apr 18 - Mon, Apr 27
Volaris Logo
2:32 pm - 5:41 pm
MDW
-
MLM
4h 09mnonstop
Volaris Logo
8:22 am - 1:15 pm
MLM
-
MDW
3h 53mnonstop
$244Volaris
Mon, Mar 23 - Mon, Mar 30
Southwest Logo
4:05 pm - 7:45 pm
MDW
-
CUN
3h 40mnonstop
Southwest Logo
8:30 am - 12:10 pm
CUN
-
MDW
3h 40mnonstop
$285Southwest
Sat, Apr 11 - Sat, Apr 18
Frontier Logo
8:30 am - 12:20 pm
MDW
-
CUN
3h 50mnonstop
Frontier Logo
1:25 pm - 10:14 pm
CUN
-
MDW
8h 49m
1 stop
$297Frontier
Sat, Apr 11 - Thu, Apr 16
Frontier Logo
8:30 am - 12:20 pm
MDW
-
CUN
3h 50mnonstop
Frontier Logo
12:04 pm - 10:22 pm
CUN
-
MDW
10h 18m
1 stop
$300Frontier
Wed, May 6 - Wed, May 13
Delta Logo
12:52 pm - 10:18 pm
MDW
-
SJD
11h 26m
2 stops
Delta Logo
6:07 am - 9:09 pm
SJD
-
MDW
13h 02m
2 stops
$454Delta
Wed, Apr 8 - Wed, Apr 15
Delta Logo
6:00 am - 1:14 pm
MDW
-
SJD
9h 14m
1 stop
Delta Logo
12:36 pm - 10:28 pm
SJD
-
MDW
7h 52m
1 stop
$456Delta
Mon, May 11 - Fri, May 15
Southwest Logo
8:35 am - 1:25 pm
MDW
-
SJD
6h 50m
1 stop
Southwest Logo
1:55 pm - 4:35 am
SJD
-
MDW
12h 40m
1 stop
$470Southwest
Sat, Apr 18 - Sat, Apr 25
Aeromexico Logo
6:00 am - 12:57 pm
MDW
-
CZM
7h 57m
1 stop
Aeromexico Logo
2:14 pm - 10:28 pm
CZM
-
MDW
7h 14m
1 stop
$701Aeromexico
Booking Insights

KAYAK's insights & trends for Midway to Mexico flights

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

What is the cheapest Chicago Midway Airport to Mexico flight route?

Data is based on round-trip flight searches on KAYAK over the past month.

The cheapest ticket to Mexico from Chicago Midway Airport found in the last 72 hours was to Guadalajara, at $160 round-trip. The most popular route is from Chicago Midway Airport (MDW) to Cancún (CUN), and the cheapest round-trip airline ticket found on this route in the last 72 hours was $258.

What is the cheapest time of day to fly to Mexico?

The average price for all round-trip flights from Chicago Midway Airport to Mexico depending on the time of departure, clicked by users on KAYAK in the last 2 weeks.

The cheapest time of day to fly to Mexico is generally in the evening, when round-trip flights cost $430 on average. Morning departures are around 12% more expensive than evening flights, on average. The most expensive time of day to fly to Mexico is generally in the afternoon, which is peak travel time and where the average cost of a ticket is $704.

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

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.

No, with an average price for the route of $434, prices are generally cheapest when you fly direct.

What is the cheapest month to fly from Chicago Midway Airport to Mexico?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Chicago Midway Airport to Mexico, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.

The cheapest month for flights from Chicago Midway Airport to Mexico is October, when tickets cost $313 (return) on average. On the other hand, the most expensive months are December and May, when the average cost of round-trip tickets is $686 and $683 respectively.

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

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

When flying from Chicago Midway Airport to Mexico, you should consider leaving on a Monday and avoid Saturdays if you are looking for the best rates. For your return to Chicago Midway Airport, you’ll find the best rates on Thursdays and the most expensive ones on Tuesdays.

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

To calculate weekly average prices, KAYAK takes all prices for each week before departure over the last year for round-trip flights from Chicago Midway Airport to Mexico, removes the top 0.1% to account for outliers, and then takes the average of all the values for each week.

To get a below average price on the flight from Chicago Midway Airport to Mexico, you should book around 2 weeks before departure, which saves you about 53% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 6 weeks before departure.

Good to know

Low seasonNovember
Cheapest flight$90
Best time to beat the crowds but there is an average 3% increase in price.
Most popular time to fly and prices are also 4% lower on average.
Flight from Chicago Midway Airport to Guadalajara

FAQs - booking Mexico flights

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

    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 Chicago Midway Airport to Mexico.

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

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight from Chicago Midway Airport to Mexico 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 Chicago Midway Airport to Mexico?

    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 from Chicago Midway Airport to Mexico with an airline and back with another airline.

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

    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 from Chicago Midway Airport to Mexico up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

Top tips for finding cheap flights to Mexico

  • Looking for a cheap flight? 25% of our users found tickets from Chicago Midway Airport to the following destinations at these prices or less: Cancun $258 one-way - $439 round-trip; Morelia $141 one-way - $337 round-trip

Reviews of the top 5 airlines serving from Midway to Mexico

 
Need help choosing which airline to fly with from Midway to Mexico? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
8.0
SouthwestOverall score based on 4317 reviews
7.5Entertainment
8.0Comfort
8.6Crew
7.0Food
8.1Boarding
Airline reviews

Long layover between flights to Long Island from BWI - need better coordination between flights

4.0 OkayKenny, Mar 2026
TPA - BWI
Read more Southwest reviews

Long layover between flights to Long Island from BWI - need better coordination between flights

I elected to pay for the upgrades and found very little difference

The new seating arrangement is so over priced for what you get.

The problem with the seat assignments is that there were a lot of rows in the front that were empty but my row at the back was full. Just not so pleasant.

No food or entertainment, just a quick 40 minute flight. A little bumpy due to Santa Ana winds but pilot has no control over that. Good flight and landing!

Good but I prefer choose your own seat. With the new assigned seats they should board from the back I see no advantage to this new boarding. Just like every other airline

I realize they are still working out kinks with the new boarding process, but by the time I boarded in group 5, most of the bins were full. All airlines should better enforce small bags and jackets going under the seats until everyone has boarded.

WiFi was not working and didn’t have a beverage service

Snacks are always pretzels. Why can't you also offer peanuts ?

Flight boarded late after announcing on time boarding. Flight arrived only a little late despite late departure. Had trouble connecting to WiFi

We landed and sat on the tarmac for 45 minutes because they only have one gate at the airport and there was another plane running late so we had to wait

The WiFi was not working. That made for a long flight.

With Aeromexico it ended up good but with Delta it was bad because we did everything through Delta... Showed up at the Delta terminal... It was the wrong place! Nothing ever told us to go to the Aeromexico terminal. It said "in partnership with Aeromexico" but I was never instructed to check in with them or go to their terminal. We had to haul @$$ running through the airport and almost didn't make it thanks to this poor communication. 👎🏽

Absolutely no communication on why there's a delay and multiple flight time reschedules. I would have canceled the flight and drove back home if I known it was going to be rescheduled 3 or 4 times.

Another late night flight and MORE men belligerently drinking and yelling. I had to move from first to economy because they were so obnoxious and disruptive. Crazy to go from a cozy chair to cardboard when you were supposed to be in first. Delta allows was too much drinking which leads to belligerent behavior.

I was in first class and literally the men behind me were so aggressively loud I moved myself to economy. This has become so common on Delta - people using audio without headphones, and men on 12am / late night flights drinking and yelling to talk to each other which prevents anyone around them from resting. Pretty crazy to have to move from first to economy (poorer service, less comfort...). Wild wild. Looking into other airlines.

Love delta smaller commuter plane so no entertainment and paid wifi on MKE-LGA leg was extremely unreliable and slow

Stop changing gates. Stop cancelling flights Stop moving my seat.

Extremely disappointed with Delta. They canceled flight last minute and then I rebooked the other flights and with which were delayed as well

Could not get my connecting flight boarding pass until four hrs before departure! Ver annoying especially since the staff could not explain why!

All went very well. We used the AIFI Airport, such a lovely facility. Definitely needs better transportation options to get there.

Both ground crew and flight crew were rude, and did not provide any level of service. They made it very difficult as we were traveling with a passenger the required assistance.

From the check-in, to the flight, and arriving, everything went very smoothly. Unfortunately, when I received my baggage it was severely damaged. I have a hard shelled suitcase and it was completely smashed it. I’m not sure how this could happened but I am extremely disappointed that my belongings were damaged beyond repair and continued use.

Really nice, all good, nice crew and all on time

Unfortunately I had an awful boarding experience. Our first flight with Aeromexico was fine and landed on time however it couldn’t find a gate and we were late which made us lose our connecting flight with Aeromexico. The staff handled it horribly when we explained our situation and would not led us board when we missed the boarding time by a couple minutes. The staff were extremely rude and did not attempt to even help us. Because of this incident, my husband and I missed a full day of work which negatively impacted our salary which we need. Please compensate us for the work that we missed.

It was OK. The flight is pretty long for the airlines to only offer a simple sandwich on business class. The entertainment is similar to that on other Skyteam members. Ultimately the airline lost my bag and didn’t deliver it to me until the next day after a lengthy lost baggage report.

Good, the flight from Miami to Mexico City was better than Mexico City to Miami

Aeroméxico cancelled my ticket without advice AND It make a last minute mess in my intinerary, no solving my situation, bad advice and bad customer service

Flight was on time, good service, but there was no free WiFi, even for first class passengers

The ground staff were not as friendly and nice to the passengers as the air crew. Flight attendants, cockpit crew were great and very nice to everyone on board.

Overall a good red eye. Crew chatted very loudly the whole time making it difficult to sleep.

It’s a 2 1/2 hour flight so good and comfort was not my real concern. Safety, easy, fast was what I was looking for. The crews were great, plane was clean, boarding from CBX was fantastic! Definitely traveling this way again.

Is was a good short flight with some turbulence! I would fly Volaris again.

We had boarding passes for the next flight but we could not catch the flight in the small airport just because volaris closed the boarding at the counters an hour before for which we had to sepnd almost 3+ hours to catch next flight. There are hardly anyone who can speak english, but thank God, we have found an young man who could not only speak English but helped us book for the next flight. The air crafts are noisy and scary sometimes to hear that squeeking noises during the take off and during the flight. They do not even offer a cup of coffee for free in flight. The prices are super high and the services are zero. That’s pretty much for this airlines in summary.

The boarding , and it would be nice if they would let us know head of time about flight changes

The fly was 2 hours delayed and the plane was old and dirty. A very umcorfotable flight, which I won't recomend to anyone

The flight was delayed by two hours. I had paid for extended leg room. Due to the delay, the plane was different and I didn't end up having extended leg room. I finally was able to reach Volaris on Whats App and they gave me an airline credit. I wanted a refund to the credit card since I hardly ever fly Volaris. Other than that, it was a very comfortable flight.

In Mexico charges too much for my luggage and I ask for help and nothing one lady she just disappeared 😡😡😡😡😡never going to fly there

Confusion over extra fees. Held up on ramp during boarding. Thin seat cushion. Minimal leg room.

The check-in is either at a kiosk that didn’t allow me to check-in because my middle name was not on the reservation or at an agent that cost $15.

Remind customers of the need to have passport or new ID for boarding.

Flight was canceled. Most upsetting was message from Kayak, stating that the flight was canceled and click with Kayak for details regarding rebook, refund details. THERE'S NO INFORMATION PROVIDED BY KAYAK EXCEPT THAT FLIGHT IS CANCELED. AND NOW THIS SURVEY TO FIND OUT HOW WAS THE FLIGHT !!!!!!!

The flight never took off and we spent 7 hours at the airport

Gate not determined until I got to the airport - hard to plan the trip to the airport.

Our flight was canceled. I will never use Kayak nor Frontier for travel again. The entire experience was a headache.

Frontier.. nickel and dime add-ons. Flight late, on time, late again, last minute gate change, arrival gate required a shuttle to the terminal. They sure keep you guessing.. if you like a little chaos and airport anxiety, this is the airline for you!

This is my second time flying with Frontier. My current experience was very favorable. The staff from the gate to the plane was friendly, warm and professional. The food options lacked in my opinion. This area needs some attention in my opinion.

First of all we hade waited 3 hours in the airplane waiting to leave. Second the return schedule was changed and it messed up my entire vaction. I won't buy never again another flight and recommend to nobody traveling with them.

There was no food and no entertainment, so I'm not sure why these are even in the survey, as my understanding is frontier does not ever offer food without a few, not even a snack, and there are no screens so unless the flight safety talk is our entertainment why ask how we liked it?. One of the flight attendants say in the back of the plane as people filed in to their seats, yelling orders about where to put baggage and telling people to hurry up. It was the least professional experience I've ever had on a flight.

Very well recently! Frontier is improving and less harrassing customer on luggages! Positive!

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

Information on your arrival and departure airports