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Find cheap flights from Chicago Midway Airport to Mexico from $103

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 6/21. 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
Wed 7/10
Wed 7/17

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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$246
Mexico City
Mexico City1 stop$339
Guadalajara
Guadalajaranonstop$306
Puerto Vallarta
Puerto Vallarta1 stop$264
Tijuana
Tijuana1 stop$466
León
Leónnonstop$343
Oaxaca
Oaxaca1 stop$523
Monterrey
Monterrey1 stop$392
Mazatlán
Mazatlán2 stops$581
Mérida
Mérida1 stop$482
Morelia
Morelianonstop$303
Ixtapa
Ixtapa2 stops$687
Aguascalientes
Aguascalientesnonstop$500
Veracruz
Veracruz2 stops$474
Acapulco
Acapulco1 stop$713
San Luis Potosí
San Luis Potosí2 stops$673

Good to know

Low season

April

High season

December

Cheapest flight

$103
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 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 $218 one-way - $349 round-trip; Guadalajara $143 one-way - $333 round-trip; Morelia $169 one-way - $368 round-trip
  • Morning departure is around 13% 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 10295 reviews
8.2Boarding
8.0Entertainment
8.6Crew
7.9Comfort
7.4Food
Airline reviews

3 hours late and all they have is was a $12 meal voucher. That’s not even enough to cover fast food.

2.0 MediocreCraig, Jun 2024CVG - LGA
Read more about Delta reviews

3 hours late and all they have is was a $12 meal voucher. That’s not even enough to cover fast food.

Among the poorest flights I’ve had with Delta in a while. Entertainment system failed completely on a 7.5 hr flight. Crew seemed distracted and not the normal friendly crew. Flight overbooked it seemed… very crowded.

If I can, I always fly Delta. I’ve found their service to always be reliable and pleasant.

You could have not cancelled the flight (AA, which I will be flying from now on) left for BOS despite the fictitious weather issues (that no one in my Boston family could see). You could have rebooked my direct flight to another direct flight instead of sending me though JFK, the worst US airport after O’Hara You could have rebooked me on a Main Cabin seat (like the one I paid for in my original ticket instead of putting me a the last row on JFK->BOS leg, pocketing the difference in ticket price But I do not really care whether you will ever do that in a future because in a future neither I nor anyone from my company (unless they pay out of pocket) nor an of my clients and partners (if they heed my advice) will ever be caught dead on any of Delta flights

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.

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.

Flight was canceled less than 6 hours before takeoff, rebooked on a flight that was twice as long and left earlier so we couldn’t make it, when using text support option took over 2 hours to speak with someone.

Not enough help at airport during boarding process. Flight was delayed. Overall WORST flying experience I’ve ever had. Will NEVER FLT SPIRIT AGAIN

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.

I strongly dislike Frontier. I find them barebones, the seats not particularly comfortable, the nickel and diming is maddening, the app is TERRIBLE - super confusing to navigate, and the last 4 frontier flights I have flown have been on AVERAGE 2 hours late, one ruining a fancy night out in Vegas with reservations made well in advance, which was nodded to with a measly 5000 miles, which translates to almost nothing. At least credit a free checked bag or something.

8 hr delay. had to buy another ticket with another airline

Four and a half hour delay in total. What frustrates me most is the poor communication and disorganization.

I appreciated the upgrade to free cary-on bag and seat selection at no charge

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.

Book cheap flights from Chicago to Mexico

Recent round-trip flight deals

6/21Fri
1 stopFrontier
15h 03mMDW-CUN
6/24Mon
1 stopFrontier
15h 08mCUN-MDW
$246
6/26Wed
1 stopFrontier
7h 15mMDW-CUN
7/8Mon
1 stopFrontier
14h 58mCUN-MDW
$249
8/28Wed
nonstopVolaris
4h 00mMDW-MLM
9/4Wed
nonstopVolaris
3h 57mMLM-MDW
$303
8/27Tue
nonstopVolaris
4h 05mMDW-GDL
9/3Tue
nonstopVolaris
4h 02mGDL-MDW
$306
9/13Fri
1 stop
10h 03mMDW-CUN
9/18Wed
1 stop
11h 31mCUN-MDW
$316
9/15Sun
nonstop
4h 05mMDW-GDL
9/20Fri
nonstop
4h 02mGDL-MDW
$327
11/18Mon
1 stopAeromexico
6h 48mMDW-CUN
11/26Tue
1 stopAeromexico
6h 56mCUN-MDW
$410
9/17Tue
2 stopsDelta
10h 36mMDW-CUN
9/23Mon
1 stopDelta
13h 23mCUN-MDW
$414
9/6Fri
2 stopsDelta
11h 57mMDW-CUN
9/11Wed
2 stopsDelta
13h 09mCUN-MDW
$432
10/22Tue
1 stopAeromexico
21h 22mMDW-SJD
10/23Wed
2 stopsAeromexico
23h 35mSJD-MDW
$444

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Recent one-way flight deals

6/21Fri
1 stopFrontier
15h 03mMDW-CUN
$103
9/11Wed
1 stopFrontier
10h 22mMDW-CUN
$113
7/9Tue
nonstopVolaris
4h 05mMDW-GDL
$128
7/9Tue
nonstopVolaris
4h 05mMDW-GDL
$129
8/20Tue
1 stop
15h 12mMDW-MEX
$135
9/5Thu
1 stop
15h 12mMDW-MEX
$139
11/28Thu
2 stopsDelta
10h 18mMDW-CUN
$190
8/28Wed
2 stopsDelta
12h 19mMDW-PVR
$228
9/11Wed
2 stopsAeromexico
27h 38mMDW-CZM
$245
7/3Wed
2 stopsAeromexico
10h 20mMDW-MEX
$323

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Last minute flights from Midway to Mexico

Last minute flight, train and bus deals

6/13Thu
multi-stopFrontier
25h 06mMDW-CUN
6/18Tue
multi-stopFrontier
9h 21mCUN-MDW
$332
6/15Sat
multi-stopFrontier
25h 51mMDW-CUN
6/19Wed
multi-stopFrontier
22h 06mCUN-MDW
$333
6/13Thu
multi-stop
17h 08mMDW-GDL
6/27Thu
nonstop
4h 02mGDL-MDW
$421
6/13Thu
multi-stop
17h 08mMDW-GDL
6/15Sat
multi-stop
15h 18mGDL-MDW
$425
6/11Tue
multi-stopDelta
10h 21mMDW-CUN
6/19Wed
multi-stopDelta
13h 46mCUN-MDW
$516
6/15Sat
nonstopVolaris
4h 00mMDW-MLM
6/21Fri
nonstopVolaris
3h 57mMLM-MDW
$540
6/11Tue
multi-stopAeromexico
13h 55mMDW-CUN
6/18Tue
multi-stopAeromexico
13h 46mCUN-MDW
$544
6/11Tue
multi-stopDelta
10h 21mMDW-CUN
6/18Tue
multi-stopDelta
13h 46mCUN-MDW
$548
6/15Sat
nonstopVolaris
4h 05mMDW-GDL
6/17Mon
nonstopVolaris
4h 02mGDL-MDW
$572
6/12Wed
multi-stopAeromexico
13h 02mMDW-SJD
6/19Wed
multi-stopAeromexico
7h 46mSJD-MDW
$691

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