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Find cheap flights from Chicago Midway Airport to Mexico from $104

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 6/5. 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
sáb 6/29
sáb 7/6

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Best Mexico Flight Deals

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours

Cancún
Cancún1 stop$289
Mexico City
Mexico City1 stop$330
Guadalajara
Guadalajara1 stop$292
Puerto Vallarta
Puerto Vallarta1 stop$359
Tijuana
Tijuana1 stop$443
León
Leónnonstop$365
Oaxaca
Oaxaca2 stops$549
Monterrey
Monterrey1 stop$376
Mazatlán
Mazatlán2 stops$521
Morelia
Morelianonstop$322
Mérida
Mérida2 stops$550
Ixtapa
Ixtapa2 stops$704
Aguascalientes
Aguascalientesnonstop$405
Veracruz
Veracruz1 stop$603
Acapulco
Acapulco1 stop$463
San Luis Potosí
San Luis Potosí2 stops$653

Good to know

Low season

August

High season

December

Cheapest flight

$104
Best time to beat the crowds with an average 13% drop in price.
Most popular time to fly with an average 59% increase in price.
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 to Mexico from Chicago Midway Airport 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 to Mexico with an airline and back to Chicago Midway Airport 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 to Mexico from Chicago Midway Airport 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 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 $233 one-way - $350 round-trip; Guadalajara $140 one-way - $328 round-trip; Morelia $160 one-way - $375 round-trip
  • Morning departure is around 10% cheaper than an evening flight, on average*.
*Average of the lowest prices shown in KAYAK’s search results for departures within the next 30 days

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
DeltaOverall score based on 10457 reviews
7.4Food
7.9Comfort
8.6Crew
8.2Boarding
8.0Entertainment
Airline reviews

I've flown many many times on Northwest and then Delta. The crew on this flight were absolutely the best I've had the pleasure of being looked after by.

10.0 ExcellentAnonymous, May 2024MSP - YVR
Read more about Delta reviews

I've flown many many times on Northwest and then Delta. The crew on this flight were absolutely the best I've had the pleasure of being looked after by.

Flew first class so everything was great. But maybe because the flights were red eye, no meals were served, just chips. I flew Alaska Air 1st class at 9PM (2 hour flight) and they served beef short rib sliders!

Had to change aircraft due to a faulty door. Surprisingly it only caused about an hour and a half of delay. Delta handled this situation as well as can be expected.

Awful. Flight was continuously getting delayed and gates kept changing without any reason. Flight was delayed for more then 3 hours

Paid premium for Delta only to be on safe but tired old 767 with ancient cabin in mediocre condition. Poor wifi and horrible inflight entertainment. Hardly a premium experience. Should have flown SW and had fun flight crew and no pretense

Our flight to Zurich was delayed by almost 3 hours, so we missed our next flight. There was no indication it would be delayed this much. We were told the gate had changed and then it apparently took over 2 hours to load the "catering" on the plane. We were not compensated in any way for the trouble.

Rated entertainment as Mediocre as there were major problems with the Infotainment system that took probably a half hour for them to fix.

Your crew could maybe answer the call bell at least one of the times I pressed it. I pressed it first time with 2.5 hours left in our flight bc my partner was hungry and wanted a sandwich. We finally got the sandwich with 40 mins left in the flight.

Half the bathrooms assigned to economy were out of action

Delta crushed it. Flight attendant in first was attentive and just never stopped. Honestly one of the best domestic flights I’ve been on.

The plane was so outdated, that it made it uncomfortable. The temperature was hot during the whole flight

Happy attentive flight crew. All in all good flight the night flight works well. Getting into Mexico City early so you don't get caught up it all the immigration and custom ques, additionally, this helps when exiting the airport and crossing the city to your final destination. All works very well and would do it again

Some entertainment and food/snack service would have been nice

All the pessengers should be wait in a line útil the creo and piloto are arrived.

Planes seat could be bigger very uncomfortable for tall humans.

Atraso de dos horas y media con vuelos sobre vendidos

Great airplane The confort was within the high standards. My only little problem was That all the movies ( only 3) was on Spanish, even though I was selecting the audio on English it didn't happen. After that I highly recommend aeromexico

1 hour waiting for suitcases to come out traveling in business class and food in business class is a sandwich? Avoid Aeromexico .

Aeromexico es siempre una buena opción, relación precio calidad adecuada!

Business class was economy with a table in the middle seat. That is worse than economy. No food and no entertainment. Very poor representation.

Overall good flight. The flight attendants were annoying and unfriendly. They would ask me to grab someone else’s trash can just waiting until the person woke up or after the flight is done. It’s not my job to pick up someone else’s trash. Especially when it’s not easily reachable.

The WiFi tv wasn’t working. The flight was over sold and moved several times. The gate assignment appeared on the screens right as we were supposed to board. Because of the flight being over sold we were almost stuck in Cancun for a couple of a days. The flight attendants were unfriendly and would wake you up to pick up other people’s trash.

The reason we chose Volaris to fly from LAX to Mazatlan, Mexico was because of the DATES and TIMES for the NON-STOP flights. When those flights got Totally Changed that was UNACCEPTABLE ! ! ! Also, when my husband Died unexpectedly, the Only statement that Customer Service kept repeating was "they would only offer Credit on a future flight". REALLY?! Volaris was only going to offer CREDIT on another flight to a DEAD PERSON ! ! !

Service of the person who gave us the boarding pass

Overall good but we had a minor scare when a wind shear caused the plane to re take off on the first landing attempt. The crew handled it well and we landed safely on the second attempt

It was unfortunate that I paid more than $120 one way to carry on my luggage to only have to have them checked baggage. We board the flight and there’s a lot of overhead space. They checked our bags in Group 2 but Group 3 was able to board with their luggage. I would not fly Volaris again. The flight attendance on the plane was very nice but the employees at the gate prior to boarding was very rude.

For the price, you pretty much can't beat this airlines. As far as comfort, you could do a lot better, but it'll cost you. Over all cheapest way to get from point A to point B.

To many extra fees, poor customer service and very uncomfortable flight. No leg room and seat wont recline.

I am disabled and was unable to get any assistance from Volaris. I had to wait in line at front desk for 45 minutes, I am by myself, and unable to stand. When I got to front desk check in, they had no assistance for me. I did however, have wheelchair assistance when I arrived in Mexico City. Thank God for that!

It was horrible, our flight back was overbooked and had to take a flight 12hours later in the day but to LAX. Volaris is horrible.

This was the smoothest flight I have had in awhile. I was also offered an exit row seat for a great upgrade cost and was able to sleep almost thr whole flight due to comfort and a smooth flight. We left on time and arrived on time.

No food not even water offered unless you buy it and no usb in the seat but other than that everything was good

Because our flight from marsh Harbor to Fort Lauderdale was over three hours delayed it caused us to miss our flight in Fort Lauderdale. Because we missed that flight, it cost us nearly $100 apiece for four different travelers which totaled nearly $400. We are seeking a reimbursement for the flight that we missed in Fort Lauderdale Florida.

Flight expected to leave at 6:40 pm ended leaving at 8:00 am the following day. I slept in a cold airport. Never again Spirit for me…

Flight was cancelled just 6 days before. No more flights that day, and the following date was sold out. Had to obtain a refund and buy more expensive flights on another airline.

The flight was on time and nice as always for me with spirit but the cabin crew were not good. They left the lights on on a red eye for the entire flight.

This was the return leg of my journey with Spirit Airlines. Despite its reputation, I found no issues as it got me from point A to B safely and without delay, especially with no mechanical delays, which is fantastic in my book! The staff, from ground crew to cabin crew, were all pleasant and hassle-free. The flight was smooth from takeoff to landing. I have absolutely no complaints about this no-frills airline!

It was the worst ever, i will be filing a lawsuit to get a refund. Our flight was delayed 4 hours so we would miss our connecting flight, we were not rebooked to our destination the same day, we were not offered any options to get home on the same day despite being clear that we absolutely cannot get stranded at night due to family, we were forced to book our own flights on a different airline to get home, and spririt is refusing a refund because our flight wasn't cancelled, only delayed. oh yeah, and they lost our luggage on the first part of the trip and you cannot get a hold of customer service when anything goes wrong, on hold for 30+ minutes. and their app breaks so you can't use that either.

My flight was cancelled!!! I had to spend 200.00 on another flight!!

The flight attendants were very personable, extremely friendly, and had a very good feeling of the energy around them not to mention they’re very funny and engaging. What made up for the discomfort of the seats and the fact that the plane sat for a long time on the Turmac. Not sure if the pilot was new, but the landing was very rough sort of like I was at a magic mountain theme park ride that was built in 1959

9hrs delay and didn’t provided anything until after flight landed $75 voucher for fiuture travel no meals or anything.

It was ridiculously hard to check in for the flight, and Frontier charged us a LOT of money to have a carry on suitcase, and then told everyone we could not carry on bags and had to check them through at the gate, and didn't refund the extra money we paid to have the suitcase as carry on.

I had a terrible experience with Frontier. I arrived before the 60 minute cut off and was told that Frontier has a two hour window for bags. I was then told the next available flight wasn’t until the end of the day (I had booked a 6am flight). I took a look around and saw other people being told that they could not board their flights or that they had to pay additional fees. I opted to rebook on American Airlines. There’s absolutely no straightforward way to contact Frontier, so this ticket was a complete waste of money. Oh - and the kicker is that the lady lied about the two hour cut off.

Frontier won’t help you at the airport without paying $25. Carry on was $75. Then you get on the plain and every beverage or snack is also a charge. Seats are hard and real packed in. I would never fly them again.

Worst experience I have seen. The flight was cancelled without any reason.

My experience with frontier staff at the Denver airport was absolutely horrible. The manager on duty was even worst if was the worst experience I have ever had, I have never been treated so poorly as a customer in my life! The staff was extremely rude, eye rolls and attitude and then refusal to help me at all. I wish I could never fly frontier again that’s how horrible it was!

The Frontier app wasn’t working. So I could not pay for a carry on the week prior to flying. They charged me 99$ at the gate to carry on a duffle bag.

Good for the price. My only complaint is that the pilot should keep the air flowing while passengers are waiting to getting out of airplane.

Plane could have been more on time. More leg room .

I arrived 1 hour prior to boarding, and they said I was too late for a domestic flight. First time I heard that :-(

Book cheap flights from Chicago to Mexico

Recent round-trip flight deals

6/5qua
1 stop
22h 28mMDW-CUN
6/12qua
1 stop
6h 40mCUN-MDW
$289
6/5qua
1 stop
15h 04mMDW-GDL
6/12qua
nonstop
4h 02mGDL-MDW
$292
6/5qua
1 stopFrontier
7h 15mMDW-CUN
6/12qua
1 stopFrontier
22h 06mCUN-MDW
$300
6/6qui
1 stopFrontier
13h 29mMDW-CUN
6/11ter
1 stopFrontier
25h 33mCUN-MDW
$303
6/10seg
nonstopVolaris
4h 05mMDW-GDL
6/18ter
nonstopVolaris
4h 02mGDL-MDW
$307
6/8sáb
nonstopVolaris
4h 05mMDW-GDL
6/11ter
nonstopVolaris
4h 02mGDL-MDW
$315
8/24sáb
1 stopDelta
9h 27mMDW-CUN
8/29qui
1 stopDelta
13h 46mCUN-MDW
$390
8/26seg
1 stopDelta
8h 07mMDW-CUN
8/31sáb
2 stopsDelta
9h 04mCUN-MDW
$394
8/25dom
1 stopAeromexico
7h 00mMDW-SJD
8/28qua
1 stopAeromexico
7h 41mSJD-MDW
$406
8/3sáb
1 stopAeromexico
21h 13mMDW-SJD
8/6ter
1 stopAeromexico
7h 41mSJD-MDW
$454

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Recent one-way flight deals

6/5qua
2 stops
19h 50mMDW-MEX
$104
6/6qui
2 stops
35h 55mMDW-MEX
$108
10/28seg
1 stopFrontier
19h 37mMDW-CUN
$122
7/16ter
1 stopFrontier
12h 09mMDW-CUN
$126
6/10seg
nonstopVolaris
4h 05mMDW-GDL
$136
6/10seg
nonstopVolaris
4h 05mMDW-GDL
$137
6/5qua
2 stopsDelta
10h 19mMDW-CUN
$180
7/5sex
1 stopAeromexico
13h 55mMDW-CUN
$191
6/5qua
2 stopsDelta
10h 19mMDW-CUN
$192
8/15qui
2 stopsAeromexico
19h 15mMDW-CUN
$224

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Last minute flights from Midway to Mexico

Last minute flight, train and bus deals

6/4ter
nonstopVolaris
4h 00mMDW-MLM
6/12qua
nonstopVolaris
3h 57mMLM-MDW
$323
6/2dom
nonstopVolaris
4h 05mMDW-GDL
6/4ter
nonstopVolaris
4h 02mGDL-MDW
$324
6/4ter
multi-stopFrontier
9h 06mMDW-CUN
6/11ter
multi-stopFrontier
9h 21mCUN-MDW
$324
6/4ter
multi-stopFrontier
19h 57mMDW-CUN
6/11ter
multi-stopFrontier
9h 21mCUN-MDW
$335
6/4ter
multi-stop
7h 39mMDW-GDL
6/8sáb
nonstop
4h 02mGDL-MDW
$341
6/4ter
multi-stop
7h 39mMDW-GDL
6/8sáb
multi-stop
15h 18mGDL-MDW
$347
6/1sáb
multi-stopDelta
10h 19mMDW-CUN
6/3seg
multi-stopDelta
13h 51mCUN-MDW
$439
6/1sáb
multi-stopAeromexico
19h 10mMDW-MEX
6/2dom
multi-stopAeromexico
15h 30mMEX-MDW
$595
6/2dom
multi-stopAeromexico
16h 58mMDW-CUN
6/4ter
multi-stopAeromexico
10h 52mCUN-MDW
$595
6/1sáb
multi-stopDelta
10h 19mMDW-CUN
6/8sáb
multi-stopDelta
11h 48mCUN-MDW
$739

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