$101 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 1/26. 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
1 adult, Economy, 0 bags

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Flight Deals

Cheap Flights from Midway to Mexico

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Cancún
Cancún1 stop$224
Mexico City
Mexico City1 stop$345
Guadalajara
Guadalajaranonstop$283
Puerto Vallarta
Puerto Vallarta1 stop$428
León
Leónnonstop$312
Tijuana
Tijuana1 stop$411
Oaxaca
Oaxaca2 stops$473
Monterrey
Monterrey1 stop$371
Morelia
Morelianonstop$319
Mérida
Mérida1 stop$296
Ixtapa
Ixtapa2 stops$569
Aguascalientes
Aguascalientesnonstop$307
Veracruz
Veracruz2 stops$418
Cancún
Cancún1 stop$224
Mexico City
Mexico City1 stop$345
Guadalajara
Guadalajaranonstop$283
Puerto Vallarta
Puerto Vallarta1 stop$428
León
Leónnonstop$312
Tijuana
Tijuana1 stop$411
Oaxaca
Oaxaca2 stops$473
Monterrey
Monterrey1 stop$371
Morelia
Morelianonstop$319
Mérida
Mérida1 stop$296
Ixtapa
Ixtapa2 stops$569
Aguascalientes
Aguascalientesnonstop$307
Veracruz
Veracruz2 stops$418

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, Jan 26 - Mon, Feb 2
Frontier Logo
6:20 am - 1:47 pm
MDW
-
CUN
6h 27m1 stop
Frontier Logo
2:57 pm - 10:19 pm
CUN
-
MDW
8h 22m1 stop
$224Frontier
Thu, Jan 8 - Mon, Jan 12
Frontier Logo
6:10 am - 2:04 pm
MDW
-
CUN
6h 54m1 stop
Frontier Logo
3:24 pm - 10:17 pm
CUN
-
MDW
7h 53m1 stop
$231Frontier
Wed, Feb 11 - Mon, Feb 23
Volaris Logo
6:54 pm - 11:24 pm
MDW
-
GDL
4h 30mnonstop
Volaris Logo
1:39 pm - 5:34 pm
GDL
-
MDW
3h 55mnonstop
$283Volaris
Fri, Jan 16 - Wed, Feb 18
Volaris Logo
6:54 pm - 11:24 pm
MDW
-
GDL
4h 30mnonstop
Volaris Logo
1:39 pm - 5:34 pm
GDL
-
MDW
3h 55mnonstop
$291Volaris
Tue, Feb 17 - Wed, Feb 18
Aeromexico Logo
6:00 am - 9:25 pm
MDW
-
MEX
15h 25m2 stops
Aeromexico Logo
8:40 am - 5:45 pm
MEX
-
MDW
9h 05m1 stop
$350Aeromexico
Tue, May 26 - Tue, Jun 2
Delta Logo
6:00 am - 4:33 pm
MDW
-
QRO
11h 33m1 stop
Delta Logo
9:50 am - 9:45 pm
QRO
-
MDW
10h 55m1 stop
$377Delta
Sun, Feb 1 - Thu, Feb 12
Delta Logo
6:00 am - 9:21 pm
MDW
-
QRO
15h 21m2 stops
Delta Logo
8:55 am - 10:42 pm
QRO
-
MDW
13h 47m1 stop
$397Delta
Mon, Jan 26 - Mon, Feb 2
Aeromexico Logo
6:00 am - 5:27 pm
MDW
-
QRO
11h 27m1 stop
Aeromexico Logo
8:55 am - 5:29 pm
QRO
-
MDW
8h 34m1 stop
$403Aeromexico
Sun, Mar 1 - Fri, Mar 6
Southwest Logo
6:15 am - 1:55 pm
MDW
-
SJD
8h 40m1 stop
Southwest Logo
1:35 pm - 6:30 pm
SJD
-
MDW
3h 55mnonstop
$490Southwest
Sun, Mar 8 - Sun, Mar 15
Southwest Logo
9:30 am - 12:25 pm
MDW
-
SJD
4h 55mnonstop
Southwest Logo
1:20 pm - 7:15 pm
SJD
-
MDW
3h 55mnonstop
$530Southwest
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?

Data is based on round-trip flight searches on KAYAK over the past month.

The cheapest ticket to Mexico from Chicago Midway Airport found in the last 72 hours was to Guadalajara, at $231 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 $231.

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 $578, 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 $371 (return) on average. On the other hand, the most expensive months are December and January, when the average cost of round-trip tickets is $710 and $695 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 Tuesdays.

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 33% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 6 weeks before departure.

Good to know

Low seasonNovember
Cheapest flight$101
Best time to beat the crowds but there is an average 2% increase in price.
Most popular time to fly and prices are also 4% 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 15% 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 $653.

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: Morelia $297 one-way - $389 round-trip

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.
7.9
SouthwestOverall score based on 4249 reviews
8.1Boarding
8.0Comfort
8.6Crew
7.5Entertainment
7.0Food
Airline reviews

The boarding and seat assignment system no longer works for me, but I know it is being replaced. Otherwise, I am good with the overall experience.

8.0 ExcellentRussell, Dec 2025
SAN - OAK
Read more Southwest reviews

The boarding and seat assignment system no longer works for me, but I know it is being replaced. Otherwise, I am good with the overall experience.

The lead steward kept singing about "San Francisco" and hotel California---more annoying than humorous....needs work. Flight was smooth and on time.

Still a fan of open seating. Flight was on schedule and arrived on time. The 737 MAX is very comfortable.

Airline travel is always too cramped to really be pleasant, but the cabin crew on this flight did a pretty good job of making up for it by putting on some music during boarding and sprinkling a few funny remarks into the safety briefing and announcements, and just generally being friendly and helpful. It definitely reminded me of why I prefer the in-flight experience on Southwest!

No delays and arrived to destination 30 min early. Staff was super friendly.

San Diego airport is brand new, spacious, airy and very smooth checkin at SW baggage drop.

It was rough. The staff was unprofessional, the choice of on board drinks terrible, it was cramped in space at every airport, they always ran out of overhead bin space so they pressured people to check bags for free or we couldn’t leave on the plane— so I did check my bag to help, and they nearly lost my bag. My bag did not arrive on the luggage belt, another man on my flight and I had to waste our time going to the baggage office to search for our bags. I would only fly southwest again if it was my last choice. Also, my flights were consistently delayed over and over again— at one point they straight up told us we were waiting for the pilot to arrive.

Crew could have been friendlier, maybe I'm spoiled by SW crews. In flight wifi was good. Would be nice to have more food offerings on a 4 plus hour flight

Had to get off plane from prior flight even though I had to reboard same plane to continue to my final destination.

Everything a cheap airline should be at normal airline rates.

None of the airplane features were available during the flight.

Original flight was cancelled and when i was rebooked by the airline, they couldn't seat me in the same type of seat as I had originally booked (went from window/aisle to middle/middle and one was a bulkhead seat, and other wasn't in the same class)

Lady Pilot was perfect in every way wheels up to wheels down communication, professionalism, excellent on time departure and on time arrival, excellent communication! Fantastic job with Superb attitude!!

The food is terrible. The staff is wonderful. Comfort is good.

Left on time, a bit delayed due to headwinds most of the trip.

I fly Delta all the time, have Platinum Medallion status. But this route seems to have major problems with delays and seems to never leave on time! Have only taken it twice in the last two weeks, and each time it had delays of more than 1 hour... very disappointed!!!!

Getting to the flight was arduous and lengthy. The flight itself was good but the food option wasn’t a good selection. I need to do a Kosher option on my return. Flight crew were nice

Good seats in Main cabin, excellent service and excellent landing

My flight was cancelled with no explanation after I had already cleared security. I was given 4 options to rebook, only one being non-stop like I had paid for. I grabbed it. It was 4 plus hours later and then took off even later. Biggest complaint is that I booked early and had an aisle seat. They gave me a "window" seat in front of the exit row, so the seat did not decline. I weigh all of 103 #s and it was tight for me! For what I paid, I feel I was kind of ripped off. I think they should have given me the empty comfort seat for the inconvenience. There was no apology nor any explanation as to why the flight was cancelled. My guess is it benefitted Delta in some way.

Very smooth, on-time, and pleasantly uneventful flight. The team at the gate and on board were professional and genuinely courteous. The pilot kept us well updated throughout, and both takeoff and landing were steady and enjoyable without any drama. Just a good, solid flight. Thank you! 💗

Unfortunately I had an awful boarding experience. Our first flight with Aeromexico was fine and landed on time however it couldn’t find a gate and we were late which made us lose our connecting flight with Aeromexico. The staff handled it horribly when we explained our situation and would not led us board when we missed the boarding time by a couple minutes. The staff were extremely rude and did not attempt to even help us. Because of this incident, my husband and I missed a full day of work which negatively impacted our salary which we need. Please compensate us for the work that we missed.

It was OK. The flight is pretty long for the airlines to only offer a simple sandwich on business class. The entertainment is similar to that on other Skyteam members. Ultimately the airline lost my bag and didn’t deliver it to me until the next day after a lengthy lost baggage report.

Aeroméxico cancelled my ticket without advice AND It make a last minute mess in my intinerary, no solving my situation, bad advice and bad customer service

Flight was on time, good service, but there was no free WiFi, even for first class passengers

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.

The fly was 2 hours delayed and the plane was old and dirty. A very umcorfotable flight, which I won't recomend to anyone

The flight was delayed by two hours. I had paid for extended leg room. Due to the delay, the plane was different and I didn't end up having extended leg room. I finally was able to reach Volaris on Whats App and they gave me an airline credit. I wanted a refund to the credit card since I hardly ever fly Volaris. Other than that, it was a very comfortable flight.

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.

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 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.

Not clean and was told I would get a great seat and it was not great at all

Flight got delayed for 5 hours no good explanation was offered ;(

Horrible. I would never fly Frontier again. The booking process is tricky at best, but fraudulent in my opinion. Frontier customer service did nothing to rectify my purchase -- I ended up paying more than double what I could have gotten from other airlines and nearly triple what I thought I was buying from Frontier. Their booking practices are unfair to the consumer.

Delayed. Text notifications were slow. Not much information o what was happening. Boarding was slow and confusing. Wasn’t even offered water other flight. Had to ask. No entertainment at all. Felt like.a Greyhound bus.

When I wanted to check in 3 hours prior to boarding time, the employees mentioned “a little over an hour delay” so I waited for an hour then I went to go look for food in the terminal and most people from that flight were in the same area looking for food. Finally I decided after food to check to see if it’s anytime closer and now it’s 2 mins until boarding closes?! What are you kidding me? I didn’t receive anything via sms about boarding now nor via email or on the intercom. I luckily made it through, barely, and then there’s no room for my carry on mind you I’m in the very first row so I had to place my purse in one further row back and my carry on sections down. Not sure who pays for better seats to get your stuff placed all over the plane but that was the worst experience I’ve ever had flying with anyone.

Better than expected. Staff were friendly and nice on both flights.

There was no one at the counter to assist with our check in. The app didn’t work, so I arrived at the airport with time to check in and I couldn’t because no employees were there. When I finally got someone on the phone, it was inside the 60min rule and they said I could no longer check in and they could sell me another ticket. We had to scramble and pay an additional $800 for tickets and THEN AFTER (about 60 min from my original convo with customer service and 10min after original departure time) I had boarded my new flight, there was email saying my original flight from Frontier was delayed and leaving 2hr 50min later, but I STILL wouldn’t have been able to check in. Which means customer service should have been able to see it and let me check in because I was well within my check in time. When I call Frontier, they hang up on me. So their app didn’t work and they employees left and they take zero responsibility or assistance with their “customer service”

Terrible. Flight cancelled with no reasoning and no flights to rebook. Employees were useless and did nothing to help. Did not even know where to retrieve luggage from the cancelled flight. Flyers beware.

No fault of Frontier staff: plane was very late, reached Orlando at 1 am, took a while to get luggage. Weather, gov financial shutdown impact on TSA, air controllers seemed to have multiple flights backed up. Frontier staff seemed to cope as gracefully as possible. It did reassure me that I and my new hip could adapt to travel challenges. Food/entertainment were irrelevant to my trip.

Terrible. The canceled my entire flight when I requested a refund for a trip frontier canceled trip one way.

Everything you need to know for your flight from Midway to Mexico

Information on your arrival and departure airports