$124 Find Cheap Flights from Chicago Midway Airport to Mexico

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 9/1. 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.
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Cheap Flights from Midway to Mexico

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Cancún
Cancúnnonstop$270
Mexico City
Mexico City1 stop$398
Guadalajara
Guadalajaranonstop$318
Puerto Vallarta
Puerto Vallarta2 stops$406
León
León1 stop$319
Tijuana
Tijuana2 stops$484
Oaxaca
Oaxaca2 stops$504
Monterrey
Monterrey1 stop$274
Mérida
Mérida2 stops$524
Morelia
Morelianonstop$340
Ixtapa
Ixtapa2 stops$670
Aguascalientes
Aguascalientesnonstop$297
Veracruz
Veracruz1 stop$452
Cancún
Cancúnnonstop$270
Mexico City
Mexico City1 stop$398
Guadalajara
Guadalajaranonstop$318
Puerto Vallarta
Puerto Vallarta2 stops$406
León
León1 stop$319
Tijuana
Tijuana2 stops$484
Oaxaca
Oaxaca2 stops$504
Monterrey
Monterrey1 stop$274
Mérida
Mérida2 stops$524
Morelia
Morelianonstop$340
Ixtapa
Ixtapa2 stops$670
Aguascalientes
Aguascalientesnonstop$297
Veracruz
Veracruz1 stop$452

Book Cheap Midway to Mexico Plane Tickets

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Midway to Mexico that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Midway to Mexico

Mon, Oct 27 - Sun, Nov 2
Southwest Logo
9:40 am - 1:15 pmMDW-CUN
3h 35mnonstop
Southwest Logo
2:15 pm - 5:00 pmCUN-MDW
3h 45mnonstop
$270Southwest
Find Deal
Sun, Sep 14 - Thu, Sep 18
Southwest Logo
10:35 am - 2:10 pmMDW-CUN
3h 35mnonstop
Southwest Logo
3:10 pm - 6:50 pmCUN-MDW
3h 40mnonstop
$280Southwest
Find Deal
Mon, Sep 15 - Fri, Sep 19
Volaris Logo
6:19 pm - 9:13 pmMDW-AGU
3h 54mnonstop
Volaris Logo
12:07 pm - 4:50 pmAGU-MDW
3h 43mnonstop
$297Volaris
Find Deal
Sat, Sep 6 - Thu, Sep 11
Aeromexico Logo
6:00 am - 11:30 amMDW-CUN
5h 30m1 stop
Aeromexico Logo
12:25 pm - 9:36 pmCUN-MDW
9h 11m1 stop
$303Aeromexico
Find Deal
Wed, Sep 17 - Wed, Sep 24
Volaris Logo
8:39 pm - 11:53 pmMDW-GDL
4h 14mnonstop
Volaris Logo
2:12 pm - 7:16 pmGDL-MDW
4h 04mnonstop
$318Volaris
Find Deal
Fri, Oct 31 - Wed, Nov 12
Aeromexico Logo
6:00 am - 3:10 pmMDW-BJX
10h 10m1 stop
Aeromexico Logo
9:46 am - 9:44 pmBJX-MDW
11h 58m1 stop
$319Aeromexico
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Sun, Oct 26 - Sat, Nov 1
Delta Logo
10:35 am - 8:20 pmMDW-CUN
9h 45m1 stop
Delta Logo
1:58 pm - 10:14 pmCUN-MDW
8h 16m1 stop
$324Delta
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Mon, Oct 27 - Fri, Nov 7
Delta Logo
6:23 pm - 8:20 pmMDW-CUN
25h 57m2 stops
Delta Logo
12:05 pm - 8:40 amCUN-MDW
21h 35m2 stops
$329Delta
Find Deal
Sat, Aug 30 - Sat, Sep 6
Frontier Logo
6:10 am - 12:39 pmMDW-CUN
6h 29m1 stop
Frontier Logo
1:55 pm - 11:17 pmCUN-MDW
9h 22m1 stop
$342Frontier
Find Deal
Sat, Nov 8 - Sat, Nov 15
Frontier Logo
6:10 am - 1:26 pmMDW-CUN
6h 16m1 stop
Frontier Logo
2:41 pm - 11:09 pmCUN-MDW
9h 28m1 stop
$343Frontier
Find Deal
Booking Insights

KAYAK's insights & trends for Midway to Mexico flights

Get data-powered insights and trends into flights from Midway to Mexico to help you find the cheapest flights, the best time to fly and much more.

What is the cheapest Chicago Midway Airport to Mexico flight route?

The cheapest price for flight routes found by users searching on KAYAK in the last 2 weeks for round-trip flights from Chicago Midway Airport to Mexico.

The cheapest ticket to Mexico from Chicago Midway Airport found in the last 72 hours was to León, at $208 round-trip. The most popular route is from Chicago Midway Airport (MDW) to Guadalajara (GDL), and the cheapest round-trip airline ticket found on this route in the last 72 hours was $226.

Can I save money by flying with a layover from Chicago Midway Airport to Mexico?

The average round-trip price for all non-stop flights, flights with one layover, and flights with two layovers for the route found by users searching on KAYAK in the last 2 weeks.

No, with an average price for the route of $524, prices are generally cheapest when you fly direct.

What is the cheapest month to fly from Chicago Midway Airport to Mexico?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Chicago Midway Airport to Mexico, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.

The cheapest month for flights from Chicago Midway Airport to Mexico is September, when tickets cost $450 (return) on average. On the other hand, the most expensive months are December and January, when the average cost of round-trip tickets is $711 and $694 respectively.

What’s the cheapest day of the week to fly from Chicago Midway Airport to Mexico?

The average price of all round-trip flights from Chicago Midway Airport to Mexico clicked on KAYAK for each day over the last 12 months.

When flying from Chicago Midway Airport to Mexico, you should consider leaving on a Monday and avoid Fridays if you are looking for the best rates. For your return to Chicago Midway Airport, you’ll find the best rates on Thursdays and the most expensive ones on Wednesdays.

How far in advance should I book a flight from Chicago Midway Airport to Mexico?

To calculate weekly average prices, KAYAK takes all prices for each week before departure over the last year for round-trip flights from Chicago Midway Airport to Mexico, removes the top 0.1% to account for outliers, and then takes the average of all the values for each week.

To get a below average price on the flight from Chicago Midway Airport to Mexico, you should book around 5 weeks before departure, which saves you about 22% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 6 weeks before departure.


Good to know

Low seasonApril
Cheapest flight$124
Best time to beat the crowds with an average 3% drop in price.
Most popular time to fly and prices are also 9% lower on average.
Flight from Chicago Midway Airport to Cancun

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 from Chicago Midway Airport to Mexico 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 from Chicago Midway Airport to Mexico with an airline and back 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 from Chicago Midway Airport to Mexico up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

  • What is the cheapest time of day to fly to Mexico?

    The cheapest time of day to fly to Mexico is generally at night, when round-trip flights cost $385 on average. Morning departures are around 23% more expensive than evening flights, on average. The most expensive time of day to fly to Mexico is generally in the afternoon, which is peak travel time and where the average cost of a ticket is $713.

Reviews of the 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
SouthwestOverall score based on 4241 reviews
7.0Food
8.1Boarding
8.0Comfort
8.6Crew
7.5Entertainment
Airline reviews

southwest just starting charging for luggage. hadnt realized it until it was too late. now out $70 when i couldve bought a carry on if i wouldve known. free bags was one of the only reasons i chose southwest over another airline (the other being no assigned seats, which is apparently also being changed). stupid business decision. wont be flying southwest anymore.

2.0 MediocreAnonymous, Jul 2025AUS - RDU
Read more Southwest reviews

southwest just starting charging for luggage. hadnt realized it until it was too late. now out $70 when i couldve bought a carry on if i wouldve known. free bags was one of the only reasons i chose southwest over another airline (the other being no assigned seats, which is apparently also being changed). stupid business decision. wont be flying southwest anymore.

The quality of Southwest Airlines continues to degrade each time I fly with them. If it were not for the free luggage, I would probably choose another airline. Their prices are a little bit competitive, but way too high for the quality of the service. Southwest is not unique in this way. Domestic flight in the United States of America has continued to be a lower and lower quality product. Very sad when you compare the quality of domestic airlines to that of many international airlines around the world.

Very smooth checking in our luggage with a super pleasant SW agent. I enjoyed a fun entertaining movie.

WiFi did not work. For as outrageous as these flights cost, when they’re advertised with certain services/ features they should be in working order

Worst experience I had on Southwest. Still better than most, but the seating was barely tolerable.

The Southwest employees (all two of them) were very nice and cheerful despite the fact the line to self-check a bag (simply drop it off) was hundreds of people long. Thank God I arrived early to the airport because I stood in this line for at least an hour. Once on the flight that had been delayed by an hour, we had no Wi-Fi and thus no entertainment. Finally, I hope the investor strong arm tactics against Southwest pay off in a short-term windfall to your C-Suite because the rest of you are screwed. I have been a faithful Southwest customer for 15 years due to everything you just got rid of. I'm flying to Idaho and Washington in October, both places I used to simply book with Southwest without a second thought now with Frontier (Washington) and United (Idaho) because they offer everything the "new" Southwest does but cheaper and at better times, destinations, etc. This really makes me sad...

It was okay. The plane was delayed from earlier in the day, but they kept updating the departure time, sometimes later, sometimes earlier. That was stressful. Once we finally got on and took off, it was fine. I was supposed to have a connection in Chicago to Los Angeles, and the time for so late I was rebooked to arrive in LA 3 hours late. The departure time to Chicago later became early enough to have taken my original connection and arrive earlier but that wasn't an option.

It was one and half hour late... Not sure if any other experience matters.

Delayed flight. Nicest crew member was a SW pilot flying seated next to me who kindly move to seat the final passenger. Flight extra delayed. My cup of refreshment of ginger ale was so packed with ice it was literally 2 sips.

For my birthday trip this was my second time ever flying, this trip was the best.

Delayed and took off even later than the scheduled delay time

For a 69 year old with health problems I had the worse experience, no wheelchair when I entered a lady told me to sit and wait while a gentleman told me I had to walk to the Delta station, which I did. I had a carry on and a bag, and I was traveling with my service dog, which was on his carrier and the lady charged me for my carry on luggage, beside all the waiting cause of the delay, I had to walk to get my luggage cause no wheelchair showed up, I am so disappointed. I will get in touch with the company. I got home at 3:00 am, not good for my health situation.

Only issue was with seating. The economy fare we purchased did say there was no guarantee the three people in our party would be seated together, and we were not. At the gate, the agent told us more specifically, the fare we purchased meant we would be seated in middle seats only. This should just be made more obvious.

Great experience on Delta. Staff from baggage check to flight attendants were very courteous and professional. My only issue was a personal preference for pretzels instead of the chips and cookies that were offered.

There was no problems, just a little uncomfortable with seats that do not lay back a little

Always good but we must do something about people in rows ahead of you that don't put their seats back up when they are suppose to. And It's rough to not be able to even lean over to get something out of my purse.

Flight was delayed, 30+ bags had to be gate checked. Crew were very friendly!

Everything was good until we were boarding our connection flight in Atlanta, we were told to gate check our carry-on, but when we got inside the plane, there was plenty of room in the overhead.

Did not know my son and I had different seating arrangements. He was fine, but it was disappointing.

Flight was canceled, and no effort was made to help with rebooking, no hotel vouchers, no car transportation and minimal food voucher and most places for food were closed by the time the voucher was given. Waited for 3 hours for bags. Simply the worst travel experience I have ever had

The ground staff were not as friendly and nice to the passengers as the air crew. Flight attendants, cockpit crew were great and very nice to everyone on board.

My flight was delayed, then I got transferred to a new flight that was also delayed- which wasn’t Aeromexico’s fault, it was because of weather conditions. Most of the crew was very nice and patient, except for one or two flight attendants who were rude. The entertainment wasn’t on, so all the screens were off.

My wife's entertainment system did not work. Payed for flight upgrade but did not receive advertised "free WiFi".

Annoying that we had to go to departures and get boarding passes. Should allow us to be booked all the way through, this is the only airline i have this problem with in MEX. Late boarding and take off

Lousy No wheelchair. As normal at Atlanta Cheap airline Cheap aero plane. - Neither entertainment nor food on a 5 hour saga

The airplane was an old airplane, seats were very uncomfortable and very little space, they changed my seat and that was no option to get back into my seat even when I was traveling a senior who required assistance.

This is not a low cost airline. Stop acting like o e.

Aeromexico crew made me check my hand luggage in the door of the plane. As soon as I reach Mexico City, I notice that my luggage was opened and 8 games of Nintendo Switch were stolen (700 dllrs value aprox) (the console was there) but the games were stolen. I am very dissapointed of Aeromexico and all the crew. Instead of being a good trip, It was a sad trip

Ok. But we arrived to a remote terminal which meant that a bus had to take us to the terminal building

Old aircraft the audio of the entertainment dosent work Dirty seats

In Mexico charges too much for my luggage and I ask for help and nothing one lady she just disappeared 😡😡😡😡😡never going to fly there

Confusion over extra fees. Held up on ramp during boarding. Thin seat cushion. Minimal leg room.

The check-in is either at a kiosk that didn’t allow me to check-in because my middle name was not on the reservation or at an agent that cost $15.

Better communication about delayed flight. I am thankful for a small credit for late flight.

Liked on time, rear entry and exit from plane Dislike the use of duct tape to repair seat rests

Terrible. And they charged over $400 just for luggage. And threatened that I would loose my flight if I didn’t pay. So I didn’t have another choice but to pay.

They check you everything before entering to waiting room, if you have any liquid they take it away even if you buy it inside the airport, no recommend volaris, for mi know Alaska airline is better

They don’t give anything for free you have to pay for everything which it’s expected but at least give out water and a snack as a courtesy for flying with them.

I got to where I needed to go quickly. There were no amenities. And the seats were painful.

The worst. Kayak sent notification at 2am and 10am regarding the delay. Then sends a notification an hour before original depart time that it will depart on time. I had to wait 8 hours at the airport. My family had to pay for lodging in Guadalajara where I was landing for pick up.

Boarding in Orlando was not good. Giant mob at the gate, should have been lines.

The worst. They don’t follow procedure for boarding per group. Flight got delayed for no understandably reasons, they changed our destination from PR to Miami, left us inside a plane for more than 8 hours, then cancelled flight in Miami leaving us stranded. Poorly managed re-accommodation for a new flight and overnight stay so I have to spend in a new ticket and my own hotel room to been able to get to my office next day. Lost 2 days of work and as a doctor, patients loosing their appointments. to other flights and besides

Decent clean onboard experience. Okay discount airline experience. Unfortunately, any customer service interactions are difficult and unhelpful. There is no service. Also, a premium seat only gets you premium boarding if you line up first. Once they start general boarding you must go to the back of the line. Not very premium

baggage clamed had to wait over a hour and half for all people on my flight it was terrible

The ticketing agents were rude but then we had a great gate agent very nice we had to ride a buss out to where the plane was parked but it was in some back corner of the airport when we got to the plane the captain who was great btw was cleaning the plane because the same rude ticketing agent told them they we not contracted to vacuum the plane. The ride to las Vegas was fine We had a connecting flight to Dallas. The flight was fine but when we arrived in Dallas everyone who flew on any frontier airlines the picked up bags from baggage claim D15 had to wait over a hour for their bags to start we arrived at 11:30pm ish to the gate we didn't leave the baggage clamed till 12:50 am very not happy and i used to fly frontier 4 times a week for work in Denver i will not be using them again

I was 2 hr arrive in the airport and 45 min in the line . After take to my turn . The agent tell me I’m later . I can not board . So my vacation was going to the floor . Just for their bad customer service agent in the airline

Frontier Airlines was AWFUL. I was an hour early for my flight and the lady refused to check me in. I had to purchase a whole new ticket with a different airline.

My flight was canceled I was promised a reginf still not received.

Late, terrible communication, horrible planning of passenger seating until the literal last minute. One of the worst flying experiences of my life. Y'all suck

Both legs of the flight were changed. The day of the flight and length of the trip.

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