$142 Find Cheap Flights from Chicago Midway Airport to Mexico - Compare and Save

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
Cancún1 stop$348
Mexico City
Mexico City1 stop$365
Guadalajara
Guadalajaranonstop$342
Puerto Vallarta
Puerto Vallarta1 stop$473
León
Leónnonstop$403
Tijuana
Tijuana1 stop$397
Monterrey
Monterrey1 stop$368
Oaxaca
Oaxaca2 stops$529
Morelia
Morelia1 stop$410
Mérida
Mérida1 stop$380
San Luis Potosí
San Luis Potosínonstop$282
Aguascalientes
Aguascalientesnonstop$408
Ixtapa
Ixtapa1 stop$528
Veracruz
Veracruz1 stop$404
Cancún
Cancún1 stop$348
Mexico City
Mexico City1 stop$365
Guadalajara
Guadalajaranonstop$342
Puerto Vallarta
Puerto Vallarta1 stop$473
León
Leónnonstop$403
Tijuana
Tijuana1 stop$397
Monterrey
Monterrey1 stop$368
Oaxaca
Oaxaca2 stops$529
Morelia
Morelia1 stop$410
Mérida
Mérida1 stop$380
San Luis Potosí
San Luis Potosínonstop$282
Aguascalientes
Aguascalientesnonstop$408
Ixtapa
Ixtapa1 stop$528
Veracruz
Veracruz1 stop$404

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, Sep 7 - Mon, Sep 14
Volaris Logo
8:23 pm - 11:30 pm
MDW
-
GDL
4h 07mnonstop
Volaris Logo
2:01 pm - 7:04 pm
GDL
-
MDW
4h 03mnonstop
$342Volaris
Mon, Aug 24 - Mon, Aug 31
Volaris Logo
8:23 pm - 9:55 am
MDW
-
CUN
13h 32m
1 stop
Volaris Logo
10:40 am - 7:04 pm
CUN
-
MDW
8h 24m
1 stop
$348Volaris
Fri, Aug 21 - Thu, Aug 27
Multiple Airlines Logo
8:23 pm - 11:30 pm
MDW
-
GDL
4h 07mnonstop
Multiple Airlines Logo
7:57 am - 10:47 pm
GDL
-
MDW
13h 50m
2 stops
$368Multiple Airlines
Fri, Aug 21 - Mon, Aug 24
Multiple Airlines Logo
8:23 pm - 11:30 pm
MDW
-
GDL
4h 07mnonstop
Multiple Airlines Logo
7:57 am - 10:47 pm
GDL
-
MDW
13h 50m
2 stops
$368Multiple Airlines
Sat, Sep 12 - Wed, Sep 16
Frontier Logo
1:06 pm - 10:45 pm
MDW
-
MEX
10h 39m
1 stop
Frontier Logo
7:00 am - 11:59 am
MEX
-
MDW
27h 59m
1 stop
$378Frontier
Sat, Sep 19 - Wed, Sep 30
Frontier Logo
1:02 pm - 10:45 pm
MDW
-
MEX
10h 43m
1 stop
Frontier Logo
7:00 am - 12:07 pm
MEX
-
MDW
28h 07m
1 stop
$378Frontier
Wed, Sep 9 - Wed, Sep 16
Aeromexico Logo
11:35 am - 7:50 pm
MDW
-
CUN
8h 15m
1 stop
Aeromexico Logo
3:20 pm - 10:44 pm
CUN
-
MDW
7h 24m
1 stop
$435Aeromexico
Wed, Sep 9 - Wed, Sep 16
Aeromexico Logo
11:35 am - 7:50 pm
MDW
-
CUN
8h 15m
1 stop
Aeromexico Logo
3:20 pm - 10:44 pm
CUN
-
MDW
7h 24m
1 stop
$436Aeromexico
Mon, Nov 9 - Thu, Nov 12
Southwest Logo
8:55 am - 1:40 pm
MDW
-
CUN
3h 45mnonstop
Southwest Logo
2:10 pm - 4:50 pm
CUN
-
MDW
3h 40mnonstop
$442Southwest
Mon, Aug 24 - Wed, Sep 2
Southwest Logo
8:25 am - 12:00 pm
MDW
-
CUN
3h 35mnonstop
Southwest Logo
12:40 pm - 4:15 pm
CUN
-
MDW
3h 35mnonstop
$442Southwest
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 5 days was to Guadalajara, at $317 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 5 days was $317.

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 morning, when round-trip flights cost $488 on average. Morning departures are around 6% cheaper 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.

Yes, flying with a layover may cost you more time, but you can also save money on the route, with a 1 stop layover the cheapest option at $512 on average.

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 February, when tickets cost $361 (return) on average. On the other hand, the most expensive months are December and July, when the average cost of round-trip tickets is $818 and $607 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 Thursdays 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 Mondays.

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 1 week before departure. For the absolute cheapest price, our data suggests you should book 4 weeks before departure.

Good to know

Low season

November

Cheapest flight

$142
Best time to beat the crowds but there is an average 1% increase in price.
Most popular time to fly with an average 50% increase in price.
Flight from Chicago Midway Airport to Guadalajara

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: Guadalajara $170 one-way - $411 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 4228 reviews
7.0Food
8.6Crew
7.5Entertainment
8.0Comfort
8.1Boarding
Airline reviews

Overall good, just screaming kids in the area the whole flight.

8.0 ExcellentAnonymous, Jul 2026
MDW - MHT
Read more Southwest reviews

Overall good, just screaming kids in the area the whole flight.

OKay. I sat in the back of the plane and it was really loud between babies and little kids, and adults who.like to talk a lot and loudly most of the flight.

The first time I flew in the extra legroom section. It was difficult to notice a difference. I had bad luck with my neighbors. The crew was okay. Southwest has reduced the live TV options.

I flew twice this week on Southwest, was delayed over 2 hours both ways. From Pittsburgh to Chicago it was due to weather but the gate agents, pilot etc were great at updating everyone. Today from Midway to Pittsburgh the plane had come from an international location, kept getting delayed, no information was given until we were delayed for the third time. It was ridiculous, whoever scheduled that plane to fly to Pittsburgh after didn’t consider a lot of things.

The staff was very friendly, professional, and courteous. The overall flight was a great experience.

All was good. I just had a hard time getting connected to the WiFi/internet during the flight

Better and more food and drinks. Put msnbc and free speech tv on the news channel selection list.

after landing, we stay 2 hours on the taxi way before reaching the gate The airline and the crew were good though

I'm not a fan of Southwest's model. I don't like the herding style of boarding.

My flight to Chicago left and landed early. My return flight left two minutes late and arrived 2 minutes late. My seat selections were ideal! There were no snacks going to Chicago and no snacks on the return trip. There are no charging outlets on board.

The crew was very inconsiderate and rude. My flight was scheduled to depart at 6:00am. I received a call from the crew at 5:40am, asking if I was going to make the flight because I was the only one that hasn't boarded yet and boarding ends at 5:50am. I let them know that I will be at the gate in a few minutes, before the 5:50am cutoff. When I arrived at the gate at 5:45am the gate was closed. Departing early on last minute notice without having all passengers on board is inconsiderate and unprofessional.

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

Okay considering we had weather delays which the Pilot notified us of immediately!

The boarding was organized and informative but the plane was tight meaning that you were sitting on one another and extremely uncomfortable. It’s disappointing that can’t have common seating comfort on the plane.

Everything could have benn better. Short fly, no food, no entertainment and no wifi.

Stop changing gates. Stop cancelling flights Stop moving my seat.

The staff was frielndly. The plane was terrible, it was too small and should be decommissioned. There were no back seat screens at all. The only beverages we had a choice from was coffee, tea or water. The only bathroom in the back was behind the flight attendant's jump seat and wasn't working. And I literally felt like I was sitting on top of the guy next to me. It was terribly hot in the plane and we had to sit on the tarmac in Chicago for 1/2 hour due to congestion in Mpls. Wouldn't they have know that before they even boarded us so that we could have sat in comfort in the terminal?

This was one of the worst flights I’ve been on in years. I upgraded to comfort and had such an uncomfortable experience. The person next to me was oversized - which I understand - however, they took up their space and mine. I could only use about 50% of my seat space to not be physically touching this person the entire flight and there was no spatial awareness. I also could not use the seat outlet because their body was obstructing it. It was very inconvenient. Their body kept touching me repeatedly during the flight and I felt very uncomfortable. To pay more for an upgraded space and then not even being able to use it was highly disappointing.

It was very cold because the air conditioner was on high power, and my son got sick.

Horrible. Flight ORD to CGH was okay, but Paris was a nightmare. Old planes, delays, involuntary downgrades, broken planes, terrible communication. CGH to CPT was my worst flight ever.

At my original departure Istanbul I was told my seat and flight was cancelled from the 3rd party. I had no seat to get to my other flights .. they charged me $481 USD to board the flight that I already paid for

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

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.

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

The plane was so outdated, that it made it uncomfortable. The temperature was hot during the whole flight

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.

1 hour waiting for suitcases to come out traveling in business class and food in business class is a sandwich? Avoid Aeromexico .

No space reserved for anyone who didn’t have underseat in front of them. Made it inconvenient to get the backs secured. No inflight entertainment in the 190. Bring your own! Food was excellent and we were surprised to get a full breakfast.

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

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

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.

The app doesn’t work. I am having a lot of trouble checking in for flight tomorrow. Very disconcerting. Then they es t to charge extra for checking in at the airport;(

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!

Our flight got overbooked and we missed one day of our trip.

Be prepared to pay extra for everything! I'm not sure I really saved any money?

The flight was 3 hrs delayed and no remorse from airline

During the flight I suddenly felt very sick, and no one from the crew even tried to help me or check on my condition. They seemed completely indifferent and showed no concern for my well-being. I was very disappointed by the lack of care and compassion. I hope the airline improves its customer service and trains its crew to respond better when passengers need assistance.

Flight was canceled. Most upsetting was message from Kayak, stating that the flight was canceled and click with Kayak for details regarding rebook, refund details. THERE'S NO INFORMATION PROVIDED BY KAYAK EXCEPT THAT FLIGHT IS CANCELED. AND NOW THIS SURVEY TO FIND OUT HOW WAS THE FLIGHT !!!!!!!

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

Just know that everything, and I mean everything is “ala cart”. 60$ just to put something in the overhead bin. I will never fly Frontier again nor do I recommend them to anyone else.

Great for the price. No wifi or entertainment, but gate agents and crew were fantastic and we boarded quickly and left on time.

Our flight was canceled for no known reason. We weren’t told until we were checking in at 5:00 am. This was after our last flight with Frontier where we sat on the plane for three hours (not an exaggeration) before we took off because of a mechanical issue. We won’t be flying Frontier again.

I didn’t have enough time to catch my connecting flight and had to use a different Airline. I will be requesting a refund.

I brought a ticket and car rental through Travelocity. There was no where to add a KTN. So I thought i’d add it by looking up ticket on frontier website. I tried 3 times with the frontier chat bot to add my KTN it never updated my boarding pass. So then I tried showing up early to do it in person at the airport. The first employee update my ktn in the system and gave me a new boarding pass. I was sent back by tsa to join regular line. Then I was told to add my Ktn. It would cost me $25 extra. Given the length of the cue I did pay. Congratulations! BUT I will NEVER fly frontier again. Plus the plane was very old. It had actual ashtrays and old looking tray backs. Worst travel experience ever. Im warning my friends and family not to use frontier ever.

Was just ok with over selling I guess. A lot of people in a short space and when we finally arrive i20 minutes, waiting to get out from the plain because we were waiting authorization for out boarding? Something like that.

They changed my flight and did not want to accommodate me or try to help me in any way. They do not care about their customers.

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

Information on your arrival and departure airports