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Find cheap flights from Chicago Midway Airport to Mexico from $94

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 5/18. 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
Mon 6/10
Mon 6/17

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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$271
Mexico City
Mexico City1 stop$355
Guadalajara
Guadalajaranonstop$315
Puerto Vallarta
Puerto Vallarta1 stop$364
Tijuana
Tijuana2 stops$674
León
Leónnonstop$354
Oaxaca
Oaxaca1 stop$540
Monterrey
Monterrey1 stop$343
Mazatlán
Mazatlán2 stops$503
Morelia
Morelianonstop$298
Mérida
Mérida1 stop$571
Ixtapa
Ixtapa2 stops$753
Aguascalientes
Aguascalientesnonstop$284
Veracruz
Veracruz2 stops$457
Acapulco
Acapulco2 stops$487
San Luis Potosí
San Luis Potosí2 stops$688

Good to know

Low season

August

High season

December

Cheapest flight

$94
Best time to beat the crowds with an average 14% drop in price.
Most popular time to fly with an average 59% increase in price.
Flight from Chicago Midway Airport to Cancún

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 $166 one-way - $350 round-trip; Guadalajara $167 one-way - $347 round-trip; Morelia $163 one-way - $355 round-trip
  • On average*, there is no price difference when choosing to fly in the morning or the evening on this flight route.
*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 10751 reviews
7.4Food
8.6Crew
7.9Comfort
8.2Boarding
8.0Entertainment
Airline reviews

Boarding was chaotic. I didn’t finish dinner because I went to bed early. Breakfast omelet was overcooked and tasteless but croissant was better than usual. Plane was dirty—crumbs in every seam and lavatory was poorly maintained (paint peeling, etc.) and toilet paper had not been refreshed before takeoff. No cubby for storage in first and seat was narrow.

4.0 OkayPatricia, May 2024DTW - CDG
Read more about Delta reviews

Boarding was chaotic. I didn’t finish dinner because I went to bed early. Breakfast omelet was overcooked and tasteless but croissant was better than usual. Plane was dirty—crumbs in every seam and lavatory was poorly maintained (paint peeling, etc.) and toilet paper had not been refreshed before takeoff. No cubby for storage in first and seat was narrow.

Boarding was somewhat chaotic. Unable to evaluate crew or food/drink because captain kept them seated due to turbulence. Have no idea if entertainment was offered.

West Jet has a horrible boarding process and the seats have no cushion.

Everything went smoothly. I didn’t like that when I booked in the main cabin my wife and I weren’t seated together. One would think when booking on an option that allows picking your seat. They would put you and your travel partner together. Had to call to get it sorted. They did fix.

The gate area was incredibly short staffed, with one representative manning 4-5 flights, which caused a 3 hr delay in boarding even though the plane was all ready to leave. Other flights also were delayed because of this. The flight crew was awesome and I feel bad for the only gate worker on call, but Delta needs to hire more employees.

Very frustrated with boarding gate crew. She announced the plane was small and they would be limiting us to one item to carry on. Not a problem for me as I understand the tiny planes have limited space!! Not the case here! It was a rather large plane and had plenty of room for bags! So because I don’t want to be one of “those people” who ignores the request to check a carry on I did so asking if I would be able to pick it up at the bottom of the ramp on arrival in Knoxville to which she responded “yes”! Then I watched as every other passenger held onto their 2 items and boarded!! Then when we arrived in Knoxville our 2 carry ons had been put with all the other luggage and we had to go to baggage pick up and wait for all the big checked bags to come off the carousel! So she lied!! Frustrating. Next time I won’t be so nice!

It was a good experience except when boarding a female flight attendant did not go out of her way to assist my teenage daughters in finding space for their carry-ons after their compartments were full.

Big plane, long flight, absolutely no leg room and basically non existent air! I am 5”4’ and always travel Main Cabin, I was miserable on this plane and could barely move when we arrived in Cabo due to the cramped leg area!

I had a great travel experience as there weren't any delays and I was able to get to Mexico City on time for conference.

I like using the Delta app to keep informed, boarding was smooth, and flight attendants were awesome and on top of everything, good communication from pilots.

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!

No space reserved for anyone who didn’t have underseat in front of them. Made it inconvenient to get the backs secured. No inflight entertainment in the 190. Bring your own! Food was excellent and we were surprised to get a full breakfast.

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.

Flight delayed then canceled! I will NEVER fly Spirit Airlines again and will tell all my friends!

Absolutely terrible. The boarding process had zero organization. Mobs of people trying to board. People were climbing over my child's stroller with her in it. No families were boarded first. Boarding was delayed with no reasoning or notification that it would be late. We were then stuck on the plane for 45 minutes after landing. Then waited over two hours for our luggage. There was zero communication with the travelers. Never have I experienced such I professionalism and disgrace of others. Extremely disappointed.

For it to have left on time! Instead of two hours early with zero notice

Flight kept delayed from morning to late afternoon so I had to make other arrangements

Crew was nice, explained emergency protocol very well. Flight took off and arrived on time. Pilot explained the small delay that occurred with docking and providing updates. I would definitely fly spirit again.

Terrible… missed our flight due to ridiculously long time to go thru baggage check-in!

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

Flight was delayed 2+ hours missed a concert because of it…

Very bad. Plane delayed. Crew not nice. Luggage weight limit is 40lbs and they overcharge for over weight

Seats could use more padding. Kind of hard on the tush.

Over an hour delay in departure but I was notified beforehand. Another delay on tarmac upon arrival at LGA. We ended up departing the plane almost 2 hours later than expected

I fly Frontier because it’s affordable. I understand that the seats are tight and not the most comfortable…but that’s part of it. The problem with this flight was that there was a group of travelers directly behind me at the back of the plane who were ridiculously loud and obnoxious the entire flight. I’m pretty sure they were drunk and I could periodically smell an odd odor that I believe was one of them using a smokeless vape pen. The stewards had to remind them to keep quiet during the pre-flight instruction, but that was it. They never said another thing to them for the rest of the flight. It was a miserable.

I checked a bag because it was $5 less than carry on. They managed to lose my bag on a 2.5 hr direct flight! Frontier has no airport staff at baggage claim to help. As soon as I got home around 11 pm I tried to use their online system to file the claim for lost bag - system wouldn't take the # on my baggage claim ticket - said it was not the correct number. Also said that I had not checked a bag, which wasn't true - even my online boarding pass showed that I had checked a bag. Wasted about an hour on that process with no luck. Tried again in the morning - same thing. So tried online chat with Frontier bot - waited 35-40" twice to be connected to a baggage agent and it never happened. Eventually drove to PDX after work and waited 2 hrs for the Frontier ticket agents to arrive prior to the next Frontier flight out of PDX and FINALLY got some help from one of them, to take me to lost luggage area where I was able to retrive my bag. Probably took 4-5 hrs. of my time and endless frustration to get my bag. This was my first -- and LAST -- experience flying Frontier Airlines. Check-in was also extremely difficult and time consuming. The flight itself (and staff) were fine but everything else about the experience was a total disaster! The fact that Frontier literally has NO WAY to connect to a human voice for customer service (in this case for lost luggage) is the WORST!!!!!

Frontier is a crappy airline nothing about it is honest

I didn't get to do this flight l, hard to review

Not good 😐 Over priced baggage fees Small hard seats No wifi or entertainment options 😕

Didn't like anything!! Horrible flight. Small seating area and hard seats. Butt was sore after 2 hour flight to Seattle No entertainment or free refreshments No wifi or USB charging receptacles to charge phone entoute like other airliners Luggage rates were 3 times as much as competitors. Difficult to navigate online luggue process to pre pay before flight Overall bad experience WILL NEVER RIDE OR RECOMMEND FRONTIER TO FRIENDS OR FAMILY MEMBERS!!! THIS IS A SHAME!! MOST MESERIBLE FLIGHT OF MY LIFE!! AND I THOUGHT SPIRIT WAS 👎 YOU GOT THEM BEAD HANDS DOWN!!

Flight was a little late taking off. Seats are too upright, no ports to charge devices, no wifi, no entertainment

Six hour delay. Poor customer service. No voucher. Bad communication. Missed important appointments.

Our flight was delayed an hour, then when we got to board our flight finally, we were waiting in our seats for take off for 45 minutes before it was communicated that there was a maintenance issue therefore we waited on the plane for over an hour while that was resolved. We did not get to Phoenix until almost 3 hours after we were originally supposed to. This was the first and last time I will be flying Frontier.

Book cheap flights from Chicago to Mexico

Recent round-trip flight deals

9/1Sun
1 stopFrontier
9h 23mMDW-CUN
9/6Fri
1 stopFrontier
12h 32mCUN-MDW
$271
5/21Tue
1 stopFrontier
9h 11mMDW-CUN
5/23Thu
1 stopFrontier
8h 01mCUN-MDW
$274
10/11Fri
nonstopVolaris
3h 51mMDW-AGU
10/25Fri
nonstopVolaris
3h 47mAGU-MDW
$284
9/21Sat
nonstopVolaris
4h 00mMDW-MLM
9/28Sat
nonstopVolaris
3h 57mMLM-MDW
$298
5/29Wed
1 stop
8h 12mMDW-CUN
6/8Sat
1 stop
7h 22mCUN-MDW
$317
6/1Sat
1 stop
19h 49mMDW-CUN
6/8Sat
1 stop
7h 22mCUN-MDW
$319
6/21Fri
1 stopDelta
7h 55mMDW-MTY
6/25Tue
1 stopDelta
8h 22mMTY-MDW
$343
9/13Fri
1 stopDelta
9h 42mMDW-CUN
9/16Mon
2 stopsDelta
12h 44mCUN-MDW
$390
6/6Thu
1 stopAeromexico
12h 36mMDW-MTY
6/10Mon
1 stopAeromexico
7h 53mMTY-MDW
$446
5/28Tue
1 stopAeromexico
13h 51mMDW-CUN
6/1Sat
1 stopAeromexico
13h 51mCUN-MDW
$446

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Recent one-way flight deals

5/18Sat
1 stopFrontier
11h 39mMDW-CUN
$94
5/18Sat
1 stopFrontier
11h 39mMDW-CUN
$98
5/21Tue
nonstopVolaris
4h 00mMDW-MLM
$137
5/19Sun
nonstopVolaris
4h 00mMDW-MLM
$139
6/4Tue
1 stop
15h 25mMDW-MEX
$141
6/18Tue
1 stop
15h 15mMDW-MEX
$142
6/3Mon
1 stopDelta
6h 29mMDW-MTY
$148
5/18Sat
2 stopsDelta
10h 19mMDW-CUN
$180
5/19Sun
2 stopsAeromexico
14h 14mMDW-MTY
$256
7/31Wed
1 stopAeromexico
7h 07mMDW-SJD
$274

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Last minute flights from Midway to Mexico

Last minute flight, train and bus deals

5/16Thu
multi-stopFrontier
8h 31mMDW-CUN
5/21Tue
multi-stopFrontier
12h 25mCUN-MDW
$230
5/16Thu
nonstopVolaris
4h 00mMDW-MLM
5/22Wed
nonstopVolaris
3h 57mMLM-MDW
$289
5/13Mon
multi-stopFrontier
26h 36mMDW-CUN
5/22Wed
multi-stopFrontier
8h 44mCUN-MDW
$301
5/16Thu
nonstopVolaris
4h 00mMDW-MLM
5/23Thu
nonstopVolaris
3h 57mMLM-MDW
$328
5/13Mon
multi-stopAeromexico
13h 51mMDW-CUN
5/22Wed
multi-stopAeromexico
10h 52mCUN-MDW
$400
5/13Mon
multi-stopDelta
6h 55mMDW-CUN
5/22Wed
multi-stopDelta
8h 56mCUN-MDW
$439
5/16Thu
multi-stopDelta
11h 41mMDW-CUN
5/22Wed
multi-stopDelta
8h 56mCUN-MDW
$503
5/14Tue
multi-stopAeromexico
16h 45mMDW-MEX
5/15Wed
multi-stopAeromexico
7h 46mMEX-MDW
$599
5/15Wed
multi-stopWestJet
12h 43mMDW-CUN
5/18Sat
multi-stopWestJet
22h 20mCUN-MDW
$3,293
5/14Tue
multi-stopWestJet
12h 43mMDW-CUN
5/16Thu
multi-stopWestJet
32h 41mCUN-MDW
$3,328

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