$115 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 5/18. 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$296
Mexico City
Mexico City1 stop$374
Guadalajara
Guadalajaranonstop$370
Puerto Vallarta
Puerto Vallarta2 stops$488
León
Leónnonstop$474
Monterrey
Monterrey1 stop$430
Tijuana
Tijuana2 stops$497
Oaxaca
Oaxaca2 stops$575
Morelia
Morelianonstop$371
Mérida
Mérida1 stop$492
San Luis Potosí
San Luis Potosínonstop$291
Ixtapa
Ixtapa1 stop$765
Aguascalientes
Aguascalientesnonstop$380
Veracruz
Veracruz1 stop$465
Cancún
Cancún1 stop$296
Mexico City
Mexico City1 stop$374
Guadalajara
Guadalajaranonstop$370
Puerto Vallarta
Puerto Vallarta2 stops$488
León
Leónnonstop$474
Monterrey
Monterrey1 stop$430
Tijuana
Tijuana2 stops$497
Oaxaca
Oaxaca2 stops$575
Morelia
Morelianonstop$371
Mérida
Mérida1 stop$492
San Luis Potosí
San Luis Potosínonstop$291
Ixtapa
Ixtapa1 stop$765
Aguascalientes
Aguascalientesnonstop$380
Veracruz
Veracruz1 stop$465

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, May 11 - Fri, May 15
Frontier Logo
6:00 am - 2:07 pm
MDW
-
CUN
8h 07m
1 stop
Frontier Logo
3:22 pm - 11:04 am
CUN
-
MDW
19h 42m
1 stop
$296Frontier
Mon, May 18 - Fri, May 22
Southwest Logo
9:35 am - 1:10 pm
MDW
-
CUN
3h 35mnonstop
Southwest Logo
4:10 pm - 7:50 pm
CUN
-
MDW
3h 40mnonstop
$333Southwest
Fri, May 15 - Mon, May 18
Frontier Logo
12:04 pm - 2:07 pm
MDW
-
CUN
26h 03m
1 stop
Frontier Logo
3:22 pm - 11:09 am
CUN
-
MDW
19h 47m
1 stop
$338Frontier
Mon, May 11 - Wed, May 20
Delta Logo
10:59 am - 8:16 pm
MDW
-
CUN
9h 17m
1 stop
Delta Logo
12:45 pm - 9:09 pm
CUN
-
MDW
8h 24m
1 stop
$340Delta
Sun, May 10 - Thu, May 14
Delta Logo
6:23 am - 7:43 pm
MDW
-
CUN
13h 20m
2 stops
Delta Logo
12:45 pm - 9:09 pm
CUN
-
MDW
8h 24m
1 stop
$348Delta
Mon, May 11 - Mon, May 18
Frontier Logo
6:00 am - 2:07 pm
MDW
-
CUN
8h 07m
1 stop
Frontier Logo
3:22 pm - 11:09 am
CUN
-
MDW
19h 47m
1 stop
$351Frontier
Tue, May 19 - Sat, May 23
Southwest Logo
10:30 am - 2:00 pm
MDW
-
CUN
3h 30mnonstop
Southwest Logo
10:35 am - 2:15 pm
CUN
-
MDW
3h 40mnonstop
$358Southwest
Mon, Jun 1 - Sat, Jun 6
Volaris Logo
8:23 pm - 11:30 pm
MDW
-
GDL
4h 07mnonstop
Volaris Logo
2:31 pm - 7:34 pm
GDL
-
MDW
4h 03mnonstop
$370Volaris
Sat, May 23 - Thu, May 28
Volaris Logo
8:48 pm - 12:12 am
MDW
-
GDL
4h 24mnonstop
Volaris Logo
2:25 pm - 7:20 pm
GDL
-
MDW
3h 55mnonstop
$371Volaris
Sat, Oct 3 - Wed, Oct 7
Aeromexico Logo
6:00 am - 7:13 am
MDW
-
BJX
26h 13m
2 stops
Aeromexico Logo
5:55 am - 9:45 pm
BJX
-
MDW
14h 50m
2 stops
$520Aeromexico
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 Cancun, at $322 round-trip. The most popular route is from Chicago Midway Airport (MDW) to Cancun (CUN), and the cheapest round-trip airline ticket found on this route in the last 72 hours was $322.

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

The average price for all round-trip flights from Chicago Midway Airport to Mexico depending on the time of departure, clicked by users on KAYAK in the last 2 weeks.

The cheapest time of day to fly to Mexico is generally in the evening, when round-trip flights cost $430 on average. Morning departures are around 7% 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 $664.

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 $512, 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 January, when tickets cost $101 (return) on average. On the other hand, the most expensive months are June and February, when the average cost of round-trip tickets is $631 and $198 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 Tuesday and avoid Saturdays 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 2 weeks before departure, which saves you about 64% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 2 weeks before departure.

Good to know

Low seasonNovember
Cheapest flight$115
Best time to beat the crowds but there is an average 2% increase in price.
Most popular time to fly with an average 5% increase in price.
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.

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: Cancun $150 one-way - $382 round-trip; Morelia $167 one-way - $370 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.
8.0
SouthwestOverall score based on 4314 reviews
8.1Boarding
7.0Food
8.6Crew
7.5Entertainment
8.0Comfort
Airline reviews

The entire experience from boarding to landing was amazing! The crew were very friendly. Will definitely be back.

10.0 Excellentlarry, Apr 2026
LGB - PHX
Read more Southwest reviews

The entire experience from boarding to landing was amazing! The crew were very friendly. Will definitely be back.

no service at all due to turbulence. they should've at least given us snacks, there were only 10 people on the entire flight.

First time I've had to use the disabled accommodations. And I could not have had a better experience with Southwest, i was having trouble getting from one terminal to another due to my heart failure. And the next thing I know a Southwest agent had made sure. I had a wheelchair at all my flights. Can't thank them enough.

Delayed flight, lack of information, boarding process is a mess as is the carryon luggage causing issues when leaving the plane….just a poor experience.

Comfortable. Easy. No problems. Just wish they had gf options for snacks.

The crew was very kind and made going to Hawaii relaxing and fun to look forward to! Thank you Southwest for a pleasant flight!

This leg was much better, but we did have to have a 3 hour lay o er after coming from a very exhausting hiccup with our flight from BNA to Den

We waited in the airplane for over 45 min for a southwest employee to make the flight. This cause over half the plane to miss their connecting flight in Denver. When we confronted the desk upon arrival, they told us the only flight they had was the next day leaving at 8:50 pm!!! Or they offered to get us to Burbank or LA, but after that we were on our own to get back to Santa Barbara. I paid for a flight from sba to bna bna to sba. My re entry into mom mode has been 💯 rough because of southwest mistake with my flight. And now I’m leaving to Reno tomorrow for a vballl tournament and just discovered that my leg in Vegas has me and my 3 kids on a stand by flight even though I had booked these ticket last year November!! Do better southwest!

Southwest is kind of a slum airline. It’s gotten more expensive over the years for less and less service. I am a Southwest Chase Visa card holder and was forced to choose a seat in the 26th row in the middle seat. However my wife who is a rewards member but doesn’t hold a card or anything else, gets randomly assigned a normally paid seat in row 6! How does that work?

For the first time in a long time, the Wi-Fi actually worked the entire flight! The flight crew was amazing as usual.

The flight was operated by Latam. The aircraft had a technical issue and the flight was delayed for the next day. They grounded other passengers to get their airplane assigned to my flight. Most of he ground staff don't speak English (Orlando Airport), but were very polite.The crew on the other hand could speak English and Portuguese. On board service was good.

The agent at check in and at the gate were less than thrilled to be at work. I'm not a fan of Kayak's placement on the plane. I got put in the middle seat and none of my preferences were used.

In ATL they have two sets of departure screens. Follow what is on your airline's departure board - the ATL Airport Authority departure board had completely incorrect details about the gate assignment for my flight, which would have made me miss boarding.

Flight was delayed it was hot while sitting on the plane, one engine was working on the plane until they had to do some jimmy rigging down the runway in order for the other engine to charge up. It was ridiculous

The flight was very good and the staff was very friendly and helpful!

The only thing I would say is we tried to get on a standby earlier flight, but with our fair we couldn’t. That seems senseless to leave with open seats..

Very easy to use and convenient, you can perform any action within the same portal

In a world of delays, Delta was on time both ways! Boarding was fast and efficient. Staff was friendly. AND wifi worked.

WiFi didn’t work. Flight delayed 3 hours Crew members were illiterate Seat lean back did not work.

Flight was delayed, we could have been notified earlier and in a consistent manner. App was not refreshing for another passenger to get the latest flight status. We could have stayed and waited at the hotel instead of waiting at the airport had we known the flight was going to delayed for more than 5 hours. The toilet is too tight, and needs to be cleaned more frequently (every hour). The entertainment screen froze, the touch screen not responding to touch. We were upgraded to comfort, it is more comfortable than regular economy seats.

All went very well. We used the AIFI Airport, such a lovely facility. Definitely needs better transportation options to get there.

Both ground crew and flight crew were rude, and did not provide any level of service. They made it very difficult as we were traveling with a passenger the required assistance.

From the check-in, to the flight, and arriving, everything went very smoothly. Unfortunately, when I received my baggage it was severely damaged. I have a hard shelled suitcase and it was completely smashed it. I’m not sure how this could happened but I am extremely disappointed that my belongings were damaged beyond repair and continued use.

Really nice, all good, nice crew and all on time

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.

Good, the flight from Miami to Mexico City was better than Mexico City to Miami

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

It was good in general. The Crew during the flight were very nice at all times.

The flights were on time, the ground crew and on board crews were kind and efficient. The free snacks for Premium+ were good, similar to US First Class snacks. The plane were clean and bright! Complaints? The seats were worn and the seat-back pockets were missing. Overall, I'll book again with Volaris. Ignore the negative social media posts, understand what your fare includes, buy the add ons you need. We had no problems with our personal items and carryons.

Overall a good red eye. Crew chatted very loudly the whole time making it difficult to sleep.

It’s a 2 1/2 hour flight so good and comfort was not my real concern. Safety, easy, fast was what I was looking for. The crews were great, plane was clean, boarding from CBX was fantastic! Definitely traveling this way again.

The money you save flying volaris is not worth it

Is was a good short flight with some turbulence! I would fly Volaris again.

We had boarding passes for the next flight but we could not catch the flight in the small airport just because volaris closed the boarding at the counters an hour before for which we had to sepnd almost 3+ hours to catch next flight. There are hardly anyone who can speak english, but thank God, we have found an young man who could not only speak English but helped us book for the next flight. The air crafts are noisy and scary sometimes to hear that squeeking noises during the take off and during the flight. They do not even offer a cup of coffee for free in flight. The prices are super high and the services are zero. That’s pretty much for this airlines in summary.

The boarding , and it would be nice if they would let us know head of time about flight changes

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

Plane was hot and miserable and the crew was rude!

12 hour delay required getting on and off plane 3 times - would have at least liked to have been offered a snack or drink

They didn’t offer a water, even after I asked

They switched our terminal 3 times and we were delayed for four plus hours!!!

It was an early flight and most people napped/slept and the crew let us which was nice.

The crew acted like they had never done this and kept barking passive aggressive orders at people. + the security line + the delay + sitting on the tarmac for 2 hours + none of the apps or signage updating with correct times

More inflight connection. And leg space is horrible. And the paying for baggage I'd ridiculous!!!

My flight was originally from SAT to MCO connecting from MCO to ORD. We got diverted to ATL and than Frontier staff there was sooo un helpful first they said they couldn’t give us any accommodation since our flight first got delayed that cancelled and now it’s 221am and I am still in ATL since they said they need to create a new flight my final destination is ORD and I have been delayed twice and cancelled. With no real help the frontier app didn’t work no email updates over all such a horrible experience

There's no seats that lean back with little leg space i wad uncomfortable the entire flight. Your charges for extra baggage is despicable and costly!!

Remind customers of the need to have passport or new ID for boarding.

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

Information on your arrival and departure airports