Find flights
Deals
When to book
FAQs & Tips
Airlines

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 8/29. 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
Sat 6/15
Sat 6/22

Search hundreds of travel sites at once for deals on flights to Mexico

In the last 7 days travelers have searched 42,211,976 times on KAYAK, and here is why:

Save 21% or moreCompare multiple travel sites with one search.

Track pricesNot ready to book? Create a price alert for when prices drop.

Filter your dealsChoose cabin class, free Wi-Fi and more.

Bundle and saveSave money when you bundle your flight + hotel.

Best Mexico Flight Deals

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

Cancún
Cancún1 stop$262
Mexico City
Mexico City1 stop$349
Guadalajara
Guadalajaranonstop$268
Puerto Vallarta
Puerto Vallarta1 stop$358
Tijuana
Tijuana1 stop$491
León
Leónnonstop$328
Oaxaca
Oaxaca2 stops$449
Monterrey
Monterrey1 stop$343
Mazatlán
Mazatlán2 stops$583
Morelia
Morelianonstop$274
Mérida
Mérida1 stop$533
Ixtapa
Ixtapa2 stops$514
Aguascalientes
Aguascalientesnonstop$242
Veracruz
Veracruz2 stops$675
Acapulco
Acapulco1 stop$625
San Luis Potosí
San Luis Potosí2 stops$613

Good to know

Low season

August

High season

December

Cheapest flight

$104
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 Morelia

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 $187 one-way - $347 round-trip; Guadalajara $152 one-way - $339 round-trip; Morelia $173 one-way - $347 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 10673 reviews
8.0Entertainment
7.4Food
8.2Boarding
7.9Comfort
8.6Crew
Airline reviews

5-hour delay due to storms in Tanoa and airspace restricted by Miami traffic controllers.

6.0 GoodGary, May 2024MSP - TPA
Read more about Delta reviews

5-hour delay due to storms in Tanoa and airspace restricted by Miami traffic controllers.

A regional sized plane was used for a cross country flight with no overhead bin space. I had to "pink check" my laptop and my medications. I was NOT pleased!!!!

Absolutely nothing flight was cancelled and delayed for 2 days. Barely a heads up I want a full refund

The plane from SNA wouldn’t start after 5 tries. The team gave me an option of flying direct from LAX and giving me a Lyft ride there! Perfect!

Best airline! Always friendly and welcoming. Skyclub was great and loved the fast free wifi on board. I also love that you can pre-order your meal on the app!

Atlanta boarding crew at gate were filled with arrogance and were disrespectful. In flight crew showed indifference to the needs of passengers. This is about the flight from ATL to BDL.

The plane was FREEZING SEATS UNCOMFORTABLE Otherwise smooth Thank you

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.

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 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.

Never been on this flight as i had missed it due to delayed connecting flight

Horrible. Delays, no customer support and fake promises and everything. i am suffering to help as due to connecting flight getting missed no support on ground and customer support window is closed and we are sitting o ground without anything

Missed our departing flight due to poor baggage drop staff. At the airport with 2 & 1/2 hours to spare and waited in bag check in until 15 minutes prior to gates closing before baggage staff asked us to move to the front of the line. We weren’t the only passengers that missed the flight. Poor organizational operations by Spirit staff. Otherwise , the return trip was fine.

My experience with Spirit was perfect. Did not expect it to be this good

Worst airline experience ever. Lost my IPad going thru security. Charged for my dog carriage at the gate not at ticket counter. Gave away my seat 6D. Expressed I wanted my seat back after charging me 99 for dog carriage. Should have thrown it out. Had a 16 yr old Yorkie heading to Boston after being a snowbird. Seats small. Very bad experience. Still don’t have my IPad. Horrible

My mother was HARASSED AND ACCOSTED by the gate agent for her bag. I pre purchased the bag fee and the gate agent made my 78 year old mother board, deplane, re pay for her bag fee and board again. The gate agent made my mother pick up her own bag and REFUSED to help her, she is an older woman who wasn’t bothering anyone on a flight that had maybe 30’total passengers. I am going to sue this airlines for their HORRIBLE customer service and treatment of my mother, and all this occurred the day after Mother’s Day!!!

The boarding gate was moved so many times that I missed my flight. No attendants would help me. The wrong gate was even on my boarding pass. I had to repurchase everything. I’ll never fly again. Really a terrible day as I had planned to see a former student who is dying in Louisville Never ever will I forget that day. Your airline is totally uncaring.

Horrible, first flight delayed. They switched my connecting flight while I was en route and even though I was originally supposed to be on the flight going back home to boston, refused to let me board and told me I would have to wait for next flight that was 14 hours later. Ended up renting a car and driving 6.5 hours back home. Still getting messages about flight and it is now showing that the other flight they put me on is now canceled and I would have to wait 24 hours for the next one. I will never book with spirit again

Hated it I would not use Kayak or Spirit ever again.

They stuck us with multiple extra fees. I will never fly spirit again

Check in online was easy. Seats aren’t very comfortable

Fecal matter in seat back pocket. Presumably from a kids diaper.

Worst airline to travel with. They treat you like a prisoner in a jailhouse barking out orders and threats. Nickle and dime you to the same price or higher than a respectable airline like one of the big 3 . Might as well fly with standard airlines

Well I mean u get what u pay for so 🤷‍♂️

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 😕

Book cheap flights from Chicago to Mexico

Recent round-trip flight deals

9/14Sat
1 stopFrontier
10h 22mMDW-CUN
9/21Sat
1 stopFrontier
11h 57mCUN-MDW
$262
8/23Fri
nonstopVolaris
4h 05mMDW-GDL
8/27Tue
nonstopVolaris
4h 02mGDL-MDW
$268
9/6Fri
nonstopVolaris
4h 00mMDW-MLM
9/9Mon
nonstopVolaris
3h 57mMLM-MDW
$274
9/21Sat
nonstopVolaris
4h 05mMDW-GDL
9/25Wed
nonstopVolaris
4h 02mGDL-MDW
$276
10/24Thu
nonstopVolaris
4h 00mMDW-MLM
11/7Thu
nonstopVolaris
3h 57mMLM-MDW
$277
6/5Wed
1 stopFrontier
7h 15mMDW-CUN
6/12Wed
1 stopFrontier
6h 40mCUN-MDW
$279
9/21Sat
1 stopDelta
17h 51mMDW-MTY
9/25Wed
1 stopDelta
8h 18mMTY-MDW
$343
9/13Fri
1 stopDelta
6h 48mMDW-CUN
9/25Wed
1 stopDelta
9h 19mCUN-MDW
$390
5/31Fri
1 stopAeromexico
6h 29mMDW-MTY
6/3Mon
1 stopAeromexico
8h 17mMTY-MDW
$392
8/13Tue
1 stopAeromexico
7h 07mMDW-SJD
8/21Wed
1 stopAeromexico
7h 35mSJD-MDW
$416

Search by stops

Search by airline

Search by price

Recent one-way flight deals

8/29Thu
nonstopVolaris
4h 00mMDW-MLM
$104
8/23Fri
nonstopVolaris
4h 05mMDW-GDL
$110
6/1Sat
1 stopFrontier
19h 49mMDW-CUN
$119
7/16Tue
1 stopFrontier
9h 21mMDW-CUN
$120
6/24Mon
1 stopFrontier
7h 15mMDW-CUN
$122
5/30Thu
1 stopDelta
6h 29mMDW-MTY
$148
5/21Tue
2 stopsDelta
10h 19mMDW-CUN
$180
7/7Sun
1 stopAeromexico
13h 55mMDW-CUN
$190
5/29Wed
1 stopAeromexico
6h 29mMDW-MTY
$202
5/25Sat
3 stopsSpirit Airlines
25h 29mMDW-CUN
$348

Search by stops

Search by airline

Search by price

Last minute flights from Midway to Mexico

Last minute flight, train and bus deals

5/21Tue
multi-stopFrontier
9h 11mMDW-CUN
5/24Fri
multi-stopFrontier
19h 11mCUN-MDW
$311
5/20Mon
nonstopVolaris
4h 05mMDW-GDL
5/23Thu
nonstopVolaris
4h 02mGDL-MDW
$315
5/18Sat
multi-stopFrontier
7h 54mMDW-CUN
5/22Wed
multi-stopFrontier
19h 07mCUN-MDW
$316
5/20Mon
nonstopVolaris
4h 00mMDW-MLM
5/27Mon
nonstopVolaris
3h 57mMLM-MDW
$319
5/19Sun
multi-stopDelta
8h 11mMDW-CUN
5/22Wed
multi-stopDelta
18h 40mCUN-MDW
$396
5/20Mon
multi-stopAeromexico
13h 51mMDW-CUN
5/23Thu
multi-stopAeromexico
10h 52mCUN-MDW
$400
5/21Tue
multi-stopDelta
10h 19mMDW-CUN
5/23Thu
multi-stopDelta
10h 52mCUN-MDW
$437
5/20Mon
multi-stopAeromexico
13h 51mMDW-CUN
5/24Fri
multi-stopAeromexico
6h 45mCUN-MDW
$457
5/20Mon
multi-stopWestJet
12h 43mMDW-CUN
5/27Mon
multi-stopWestJet
22h 47mCUN-MDW
$3,372
5/20Mon
multi-stopWestJet
30h 06mMDW-CUN
5/24Fri
multi-stopWestJet
25h 50mCUN-MDW
$3,431

Search by stops

Search by airline

Search by price