$111 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 10/3. 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.
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1 adult, Economy

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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$271
Mexico City
Mexico City1 stop$304
Guadalajara
Guadalajara1 stop$305
Puerto Vallarta
Puerto Vallarta2 stops$368
León
Leónnonstop$364
Tijuana
Tijuana1 stop$408
Oaxaca
Oaxaca1 stop$539
Monterrey
Monterrey1 stop$282
Morelia
Morelia1 stop$297
Mérida
Mérida2 stops$616
Ixtapa
Ixtapa2 stops$651
Aguascalientes
Aguascalientesnonstop$310
Veracruz
Veracruz1 stop$588
Cancún
Cancúnnonstop$271
Mexico City
Mexico City1 stop$304
Guadalajara
Guadalajara1 stop$305
Puerto Vallarta
Puerto Vallarta2 stops$368
León
Leónnonstop$364
Tijuana
Tijuana1 stop$408
Oaxaca
Oaxaca1 stop$539
Monterrey
Monterrey1 stop$282
Morelia
Morelia1 stop$297
Mérida
Mérida2 stops$616
Ixtapa
Ixtapa2 stops$651
Aguascalientes
Aguascalientesnonstop$310
Veracruz
Veracruz1 stop$588

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, Dec 6 - Sat, Dec 13
Southwest Logo
3:40 pm - 8:25 pmMDW-CUN
3h 45mnonstop
Southwest Logo
3:10 pm - 5:55 pmCUN-MDW
3h 45mnonstop
$271Southwest
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Sun, Nov 16 - Fri, Nov 21
Southwest Logo
10:40 am - 3:25 pmMDW-CUN
3h 45mnonstop
Southwest Logo
2:15 pm - 5:00 pmCUN-MDW
3h 45mnonstop
$281Southwest
Find Deal
Sat, Nov 8 - Sat, Nov 15
Aeromexico Logo
6:00 am - 12:10 pmMDW-MTY
6h 10m1 stop
Aeromexico Logo
1:35 pm - 11:32 pmMTY-MDW
9h 57m1 stop
$282Aeromexico
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Thu, Sep 25 - Mon, Sep 29
Delta Logo
6:00 am - 11:02 amMDW-MTY
6h 02m1 stop
Delta Logo
12:12 pm - 9:36 pmMTY-MDW
8h 24m1 stop
$296Delta
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Thu, Sep 25 - Mon, Sep 29
Aeromexico Logo
6:00 am - 5:05 pmMDW-MTY
12h 05m1 stop
Aeromexico Logo
9:05 pm - 5:35 pmMTY-MDW
19h 30m2 stops
$300Aeromexico
Find Deal
Sun, Feb 8 - Wed, Feb 11
Delta Logo
6:00 am - 6:37 pmMDW-MTY
12h 37m2 stops
Delta Logo
5:35 pm - 4:25 pmMTY-MDW
22h 50m2 stops
$301Delta
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Wed, Nov 5 - Wed, Nov 19
Volaris Logo
5:33 pm - 9:40 pmMDW-AGU
4h 07mnonstop
Volaris Logo
12:38 pm - 4:18 pmAGU-MDW
3h 40mnonstop
$310Volaris
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Tue, Oct 7 - Tue, Oct 14
Volaris Logo
5:01 pm - 8:03 pmMDW-MLM
4h 02mnonstop
Volaris Logo
10:30 am - 3:23 pmMLM-MDW
3h 53mnonstop
$310Volaris
Find Deal
Thu, Oct 23 - Mon, Oct 27
Frontier Logo
5:20 pm - 10:06 amMDW-CUN
16h 46m1 stop
Frontier Logo
11:16 am - 11:20 pmCUN-MDW
12h 04m1 stop
$333Frontier
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Sat, Oct 18 - Sat, Oct 25
Frontier Logo
6:15 am - 12:31 pmMDW-CUN
6h 16m1 stop
Frontier Logo
11:26 am - 11:20 pmCUN-MDW
11h 54m2 stops
$338Frontier
Find Deal
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 $187 round-trip. The most popular route is from Chicago Midway Airport (MDW) to León (BJX), and the cheapest round-trip airline ticket found on this route in the last 72 hours was $216.

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 $429, 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 September, when tickets cost $431 (return) on average. On the other hand, the most expensive months are December and January, when the average cost of round-trip tickets is $710 and $694 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 Fridays if you are looking for the best rates. For your return to Chicago Midway Airport, you’ll find the best rates on Tuesdays and the most expensive ones on Mondays.

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 5 weeks before departure, which saves you about 25% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 6 weeks before departure.

Good to know

Low seasonJuly
Cheapest flight$111
Best time to beat the crowds with an average 9% drop in price.
Most popular time to fly and prices are also 9% lower on average.
Flight from Chicago Midway Airport to Mexico City

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.

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

    The cheapest time of day to fly to Mexico is generally at night, when round-trip flights cost $385 on average. Morning departures are around 23% 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 $713.

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: León $190 one-way - $354 round-trip; Morelia $178 one-way - $345 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 4248 reviews
8.6Crew
8.0Comfort
8.1Boarding
7.0Food
7.5Entertainment
Airline reviews

I wish they had movie screens in the headrests. The seats are much improved, more legroom and recently renovated. Bathroom was clean. Staff was outstanding!!

10.0 ExcellentG, Sep 2025LAS - ATL
Read more Southwest reviews

I wish they had movie screens in the headrests. The seats are much improved, more legroom and recently renovated. Bathroom was clean. Staff was outstanding!!

As always, the entire Southwest experience was wonderful, from online booking to flight to baggage retrieval. Very grateful.

The weather could have been better. There was a 40 minute ATC delay in SFO because of marine fog and a micro cell storm delayed landing and take-off at Nashville. The gate was changed 5 minutes from boarding from gate B3 to gate C23 at Nashville airport.

After being assaulted by a flight attendant I was then brushed off as oh well because he long braids didn’t mean to whip me in the eye. I have filed complaints and will see. But like any other issue I’ve had with kayak involved it’s been trash. Last time I’ll be using your app

AC sub par. WiFi not working correctly. Ac sucked. Seats very narrow.

Near 4 hour flight with only 1 service. Had to use call button to request water. Internet and power not working until into flight. Internet would stop working during flight.

Southwest's seats are the least comfortable I have ever sat in.

The cabin was quiet for the redeye flight. The area was clean. The staff was great. The 787 Max was in good condition. Drawbacks were that the seat widths were tight for some passengers. The seat padding was at best average and for a long flight uncomfortable.

Southwest like most American domestic airlines, is a mediocre airline. But it is among the cheapest. Oh well.

My flight was delayed 50 minutes and we were rushed to board to then sit for 15 minutes until the pilot arrived. Unacceptable since we could have waited to board. Also the delayed flight was updated AFTER we boarded to more than the 10 minutes as originally stated.

Perfect flight both ways. On time, courteous staff, plane comfortable and cool. Best domestic flights I’ve had in awhile.

The food was terrible especially for a 15 hour international flight. The crew was unpleasant as well.

Really low quality food especially for an international flight. The crew also was surprisingly unpleasant except couple of ladies. I know we were not in first class but that’s no reason to treat customers as less.

Flight delayed for two and half hours and then canceled altogether due to mechanical issues. No mechanic onsite to fix so had to send one from LAX.

Quick check in. Everything went smooth. I don't know what can be done about airline food.

Crew was good. The reservation got mixed up and they didn't have my TSA number. I am also a Silver Medallion and wasn't able to use Sky Priority.

Delta made it easy, comfortable and timely. The crew was fantastic.

This route with Delta always has delays or is cancelled. Aircrafts seem smaller and older. I fly Delta quite a bit - haven’t had issues with the international flights. But this route has always been the troublesome one

Nothing special. The crew never went out of their way for anything.

Three seats in first class were broken and while they were able to still acommodate us it was looking very touch and go and they had others they could not acommodate

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

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.

My flight was delayed, then I got transferred to a new flight that was also delayed- which wasn’t Aeromexico’s fault, it was because of weather conditions. Most of the crew was very nice and patient, except for one or two flight attendants who were rude. The entertainment wasn’t on, so all the screens were off.

My wife's entertainment system did not work. Payed for flight upgrade but did not receive advertised "free WiFi".

Annoying that we had to go to departures and get boarding passes. Should allow us to be booked all the way through, this is the only airline i have this problem with in MEX. Late boarding and take off

Lousy No wheelchair. As normal at Atlanta Cheap airline Cheap aero plane. - Neither entertainment nor food on a 5 hour saga

The airplane was an old airplane, seats were very uncomfortable and very little space, they changed my seat and that was no option to get back into my seat even when I was traveling a senior who required assistance.

This is not a low cost airline. Stop acting like o e.

Aeromexico crew made me check my hand luggage in the door of the plane. As soon as I reach Mexico City, I notice that my luggage was opened and 8 games of Nintendo Switch were stolen (700 dllrs value aprox) (the console was there) but the games were stolen. I am very dissapointed of Aeromexico and all the crew. Instead of being a good trip, It was a sad trip

Ok. But we arrived to a remote terminal which meant that a bus had to take us to the terminal building

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.

Better communication about delayed flight. I am thankful for a small credit for late flight.

Liked on time, rear entry and exit from plane Dislike the use of duct tape to repair seat rests

Terrible. And they charged over $400 just for luggage. And threatened that I would loose my flight if I didn’t pay. So I didn’t have another choice but to pay.

They don’t give anything for free you have to pay for everything which it’s expected but at least give out water and a snack as a courtesy for flying with them.

I got to where I needed to go quickly. There were no amenities. And the seats were painful.

The worst. Kayak sent notification at 2am and 10am regarding the delay. Then sends a notification an hour before original depart time that it will depart on time. I had to wait 8 hours at the airport. My family had to pay for lodging in Guadalajara where I was landing for pick up.

Seats were new and comfortable. Staff was fine. Missed my connection due to weather -which wasn’t their fault- but got no help at all. Gate staff sent me to customer service, which was and stayed unstaffed. Sign with QR code directed me to call or chat. Chat was useless. Call was returned after an hour. No itinerary offered by Frontier could get me home in less than 30 hours. Rebooked with another airline and got a partial refund that came to about 10 percent of what I paid to get home.

Finally a Frontier on time and efficient. I've had problems before with your airline, but this time everything went fine.

The experience was good. No frills but I got there safe and sound and on time.

Great for the price. No wifi or entertainment, but gate agents and crew were fantastic and we boarded quickly and left on time.

sluggish boarding and arrival procedures, fake nice flight attendants, and lots of delays.

Disaster. They lied every step of the way. We ended up being delayed due to crew and then allegedly abandoned the flight because of a curfew at LGA. No rebooking to LGA at any reasonable time. No hotel. No meal vouchers. Had to sleep in the airport and fly to Newark instead. Will never fly Frontier again.

What I expected, nickeled and dined and a frontier flight attendant loudly complained about her job and lack of communication as she headed to the gate on her cell phone. Not professional.

As every law enforcement agency I could imagine surrounded the plane and we didn’t disembark for 2 hours and then had to stick around for another hour to go get our personal belongings after leaving them behind and being bused away from the plane, it was scary and inconvenient. We were given no information as to why this was happening. Lack of communication with passengers was disappointing.

After boarding and un-boarding twice over 6+hours, the flight was canceled.

Severe turbulence. Captain never came on to reassure passengers after things settled down.

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

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