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Find cheap flights from Chicago Midway Airport to Mexico from $59

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 10/2. 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. 7/6
sáb. 7/13

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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$257
Mexico City
Mexico City1 stop$294
Guadalajara
Guadalajaranonstop$201
Puerto Vallarta
Puerto Vallarta1 stop$332
Tijuana
Tijuana1 stop$503
León
Leónnonstop$168
Oaxaca
Oaxaca1 stop$521
Monterrey
Monterrey1 stop$365
Mazatlán
Mazatlán2 stops$581
Morelia
Morelianonstop$259
Mérida
Mérida2 stops$431
Ixtapa
Ixtapa2 stops$1,255
Aguascalientes
Aguascalientesnonstop$315
Veracruz
Veracruz2 stops$410
Acapulco
Acapulco2 stops$669
San Luis Potosí
San Luis Potosí2 stops$648

Good to know

Low season

April

High season

December

Cheapest flight

$59
Best time to beat the crowds with an average 21% drop in price.
Most popular time to fly with an average 54% increase in price.
Flight from Chicago Midway Airport to León

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 $218 one-way - $349 round-trip; Guadalajara $143 one-way - $333 round-trip; Morelia $169 one-way - $368 round-trip
  • Morning departure is around 9% 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 10371 reviews
7.9Comfort
7.4Food
8.0Entertainment
8.2Boarding
8.6Crew
Airline reviews

Really bad baggage handling. Had my Rimowa bag badly damaged at the latches.

4.0 OkayDavwinder Singh, Jun 2024SEA - ATL
Read more about Delta reviews

Really bad baggage handling. Had my Rimowa bag badly damaged at the latches.

It was pretty good I was worried with the short Layover that I might not catch my connection but the gate was there

It was good until there was a 3 hour delay because there was not any pilots to fly the plane.

There was plenty of overhead room but half of the passengers were told they had to check their carryon bags. My partner and I checked in as early as possible and our seats were split across the aisle.

Friendly flight attendants. Comfort plus seats were very comfortable and had lots of leg room. 10A and 10 B.

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

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.

Terrible legroom, seats do not recline, tray table the size of an iPhone, delayed flight, have to pay 5$ to get a cup of water onboard.

Could have TV/Movie and some water ou soda free

Flight was good and clean but delayed over an hour on the return flight.

The non stop flight and able to go into Atlantic City airport. They could lower the prices. It starts out low but then if you want to bring luggage and pick your seat the price goes up quite a bit.

Flight got diwngraded last minute and left us stranded. I was told I’ll be given credit for my luggage and seat upgrades but haven’t got anything yet

We can’t predict circumstances like this ahead of time, but I give your staff a hats off for immediately giving us updated informations.

It was nice! There was a very unhappy child in front of us and the flight attendant did a great job calming the child. I was impressed.

The plane was not on time for boarding or departure or arrivals.

EVERYTHING WAS WONDERFUL HOSPITALITY THE HELP.THE SEATING FRIENDLY ALWAYS HAVE A GOOD RIDE NOT ONE BAD EXPERIENCE WITH THEM

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.

FRONTIER SUCKS! The agent downstairs tricked me into booking, just to get to the gate. At the gate, they told me they couldn't help. I then called Customer Service. They and the gate attendants kept blaming each other. Neither side was willing to help the customer.

The agent at check-in was strident, unwelcoming, and condescending to customers ahead of me.

Flight was delay 9hrs and nothing was provided at airport, had to go and get a room to sleep in, paid for Uber back and fort with no offers until we landed back home a 1hr later for a $75 voucher for a future flight.

Didn't like anything..entire crew was very rude to everyone on the flight. Plane old and the trays fall down on you the while time you're flying. Charged more for a carry on bag than for the plane ticket itself. Did make it from point a to point b, but worth the extra money to fly with another airline

9 hours of delay!! Was not able to check my luggage that I paid for!!!

It was delayed 9 hours for operational reasons, despite the plane arriving to the airport on time.

I am very disappointed with Frontier Airlines. They cancelled our flight because they couldn't find a crew member, and then didn't get us to our connecting flight. We had to cancel our whole vacation. We were promised flight and hotel vouchers, but they never sent them.

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.

Book cheap flights from Chicago to Mexico

Recent round-trip flight deals

9/4mié.
nonstopVolaris
3h 56mMDW-BJX
10/24jue.
nonstopVolaris
3h 48mBJX-MDW
$168
9/12jue.
nonstopVolaris
3h 56mMDW-BJX
9/19jue.
nonstopVolaris
3h 48mBJX-MDW
$174
10/1mar.
1 stop
10h 41mMDW-GDL
11/1vie.
nonstop
4h 02mGDL-MDW
$220
10/10jue.
1 stop
10h 41mMDW-GDL
10/15mar.
nonstop
4h 02mGDL-MDW
$221
9/21sáb.
1 stopFrontier
22h 06mMDW-CUN
9/28sáb.
1 stopFrontier
23h 45mCUN-MDW
$257
9/22dom.
1 stopFrontier
9h 23mMDW-CUN
9/27vie.
1 stopFrontier
12h 32mCUN-MDW
$258
11/16sáb.
1 stopDelta
9h 42mMDW-CUN
11/22vie.
1 stopDelta
9h 25mCUN-MDW
$410
8/15jue.
1 stopDelta
17h 40mMDW-CUN
8/21mié.
1 stopDelta
10h 05mCUN-MDW
$416
9/26jue.
1 stopAeromexico
21h 19mMDW-SJD
10/1mar.
1 stopAeromexico
7h 26mSJD-MDW
$484
7/6sáb.
1 stopAeromexico
13h 55mMDW-CUN
7/10mié.
1 stopAeromexico
13h 46mCUN-MDW
$498

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Recent one-way flight deals

10/2mié.
nonstopVolaris
3h 56mMDW-BJX
$59
7/6sáb.
nonstopVolaris
4h 05mMDW-GDL
$117
7/16mar.
1 stopFrontier
9h 21mMDW-CUN
$123
7/16mar.
1 stopFrontier
9h 21mMDW-CUN
$124
7/23mar.
1 stop
6h 30mMDW-GDL
$147
7/17mié.
1 stop
15h 04mMDW-GDL
$148
7/6sáb.
1 stopAeromexico
13h 55mMDW-CUN
$182
8/5lun.
1 stopDelta
7h 00mMDW-SJD
$200
9/10mar.
2 stopsAeromexico
24h 09mMDW-MLM
$210
6/11mar.
2 stopsDelta
10h 21mMDW-CUN
$267

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Last minute flights from Midway to Mexico

Last minute flight, train and bus deals

6/9dom.
nonstopVolaris
4h 00mMDW-MLM
6/18mar.
nonstopVolaris
3h 57mMLM-MDW
$292
6/10lun.
nonstopVolaris
3h 56mMDW-BJX
6/15sáb.
nonstopVolaris
3h 48mBJX-MDW
$309
6/11mar.
multi-stopFrontier
6h 16mMDW-CUN
6/14vie.
multi-stopFrontier
15h 29mCUN-MDW
$366
6/9dom.
multi-stopFrontier
6h 31mMDW-CUN
6/11mar.
multi-stopFrontier
9h 21mCUN-MDW
$369
6/11mar.
multi-stop
17h 03mMDW-GDL
6/18mar.
multi-stop
7h 29mGDL-MDW
$395
6/11mar.
multi-stop
17h 03mMDW-GDL
6/18mar.
nonstop
4h 02mGDL-MDW
$397
6/7vie.
multi-stopDelta
7h 10mMDW-CUN
6/12mié.
multi-stopDelta
13h 46mCUN-MDW
$512
6/9dom.
multi-stopAeromexico
19h 50mMDW-CUN
6/17lun.
multi-stopAeromexico
24h 02mCUN-MDW
$675
6/8sáb.
multi-stopAeromexico
5h 24mMDW-CUN
6/12mié.
multi-stopAeromexico
15h 41mCUN-MDW
$692
6/7vie.
multi-stopDelta
7h 10mMDW-CUN
6/12mié.
multi-stopDelta
9h 04mCUN-MDW
$696

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