$123 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 7/18. 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

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Best Mexico Flight Deals from Midway

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Cancún
Cancúnnonstop$269
Mexico City
Mexico City1 stop$414
Guadalajara
Guadalajaranonstop$354
Puerto Vallarta
Puerto Vallarta1 stop$400
Tijuana
Tijuana1 stop$508
León
León1 stop$330
Oaxaca
Oaxaca2 stops$503
Monterrey
Monterrey1 stop$275
Mérida
Mérida2 stops$573
Morelia
Morelianonstop$351
Ixtapa
Ixtapa2 stops$849
Aguascalientes
Aguascalientes2 stops$323
Veracruz
Veracruz1 stop$543
Acapulco
Acapulco1 stop$666
Cancún
Cancúnnonstop$269
Mexico City
Mexico City1 stop$414
Guadalajara
Guadalajaranonstop$354
Puerto Vallarta
Puerto Vallarta1 stop$400
Tijuana
Tijuana1 stop$508
León
León1 stop$330
Oaxaca
Oaxaca2 stops$503
Monterrey
Monterrey1 stop$275
Mérida
Mérida2 stops$573
Morelia
Morelianonstop$351
Ixtapa
Ixtapa2 stops$849
Aguascalientes
Aguascalientes2 stops$323
Veracruz
Veracruz1 stop$543
Acapulco
Acapulco1 stop$666

Cheap Flights from Midway to Mexico

 
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

Thu, Jul 10 - Tue, Jul 15
Southwest Logo
4:35 pm - 8:10 pmMDW-CUN
3h 35mnonstop
Southwest Logo
8:30 am - 12:05 pmCUN-MDW
3h 35mnonstop
$269Southwest
Find Deal
Sat, Aug 23 - Sat, Aug 30
Frontier Logo
6:10 am - 12:39 pmMDW-CUN
6h 29m1 stop
Frontier Logo
1:54 pm - 11:11 pmCUN-MDW
9h 17m1 stop
$292Frontier
Find Deal
Tue, Jun 24 - Sat, Sep 6
Aeromexico Logo
12:44 pm - 8:20 pmMDW-CUN
7h 36m1 stop
Aeromexico Logo
12:40 pm - 9:12 pmCUN-MDW
8h 32m1 stop
$305Aeromexico
Find Deal
Fri, Aug 22 - Sat, Aug 30
Aeromexico Logo
12:43 pm - 8:20 pmMDW-CUN
7h 37m1 stop
Aeromexico Logo
8:00 am - 3:28 pmCUN-MDW
7h 28m1 stop
$314Aeromexico
Find Deal
Tue, Jun 24 - Wed, Jun 25
 Logo
12:44 pm - 8:20 pmMDW-CUN
7h 36m1 stop
 Logo
3:25 pm - 8:53 pmCUN-MDW
29h 28m1 stop
Mon, Sep 8 - Sat, Sep 13
Delta Logo
6:00 am - 2:10 pmMDW-CUN
8h 10m1 stop
Delta Logo
8:15 am - 3:30 pmCUN-MDW
7h 15m1 stop
$323Delta
Find Deal
Thu, Sep 11 - Wed, Sep 17
Delta Logo
9:30 am - 8:02 pmMDW-CUN
10h 32m2 stops
Delta Logo
12:25 pm - 9:44 pmCUN-MDW
9h 19m1 stop
$328Delta
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
$342Volaris
Find Deal
Sun, Oct 12 - Sat, Oct 25
Volaris Logo
10:41 pm - 1:43 amMDW-MLM
4h 02mnonstop
Volaris Logo
4:29 pm - 9:22 pmMLM-MDW
3h 53mnonstop
$351Volaris
Find Deal
Fri, Oct 24 - Sat, Nov 1
 Logo
8:39 pm - 11:53 pmMDW-GDL
4h 14mnonstop
 Logo
2:12 pm - 7:16 pmGDL-MDW
4h 04mnonstop
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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 Guadalajara, at $135 round-trip. The most popular route is from Chicago Midway Airport (MDW) to Cancún (CUN), and the cheapest round-trip airline ticket found on this route in the last 72 hours was $268.

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 $487, 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 July, when tickets cost $441 (return) on average. On the other hand, the most expensive months are December and January, when the average cost of round-trip tickets is $717 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 Wednesdays and the most expensive ones on Thursdays.

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 3 weeks before departure. For the absolute cheapest price, our data suggests you should book 7 weeks before departure.


Good to know

Low seasonApril
High seasonJanuary
Cheapest flight$123
Best time to beat the crowds with an average 7% drop in price.
Most popular time to fly and prices are also 11% 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.

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 $121 one-way - $346 round-trip

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 4287 reviews
7.6Entertainment
8.2Boarding
8.0Comfort
7.1Food
8.6Crew
Airline reviews

Southwest is typically delayed, and it gets wearisome. It is no longer a discount airline and you get way less than you pay for when it comes to comfort and Ce.

6.0 GoodDavid, Jun 2025BWI - COS
Read more Southwest reviews

Southwest is typically delayed, and it gets wearisome. It is no longer a discount airline and you get way less than you pay for when it comes to comfort and Ce.

We sat on the plane on the tarmac for 4 hours.

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

Flight crew and cabin crew were great. I had to rearrange flights because my original flight was 3hrs delayed for weather, the rub is the flight I moved to boarded on time then we sat at the gate for 2 hours because scheduling stole our first officer for another flight, TWICE. Then our actual FO was an hour delayed. To make it worse my original flight went from a 3 hour delay to departing 15min EARLY. Just poor scheduling operations all around.

Bring back peanuts Take our drink orders when were all seated, especially after you switch to assigned seating.

Staff was far less than helpful at all times. Departure and arrival times mean nothing to Southwest. Extremely disappointed, will never fly with them again, and I’ll be sure to share my experience with all.

It is southwest seat was ok. Not the most comfortable seat

I’ve always loved Southwest. No issues at all. I was flying standby and the gate agent was extremely friendly and helpful. Boarding was smooth and I was able to get a window seat in the emergency exit row. Crew was fantastic! They were very professional and accommodating. We had to divert from our destination due to weather but the flight crew kept everyone at ease and informed us of all pertinent information. Excellent flight

The price of the tickets isn't matching the flight experience. No matter how long the flight is, you're only getting pretzels. The flight attendants looked unkept and over it.

Plz don't take away free bags and free seating

Great service. Flight was delayed while we sat on the runway for a couple of hours. Weather related. Staff made is very bearable. The steward servicing the first class cabin was exceptional. Thank you! 💗

5 hours of delay that could've been much shorter if Delta had taken the 1 hour delay they imposed on the flight before boarding to run any of the plane checks required for flight to find the hydraulic issue that required nearly 3 hours to fix. $24 of meal credit buys a sandwich and a soft drink. Poor communication within the terminal about what gate we'd be re-boarding from and when we'd be re-boarding.

Great flight! Only complaint I had was that I didn’t get breakfast that morning because I don’t eat eggs for breakfast.. I ate an energy bar I bought in the airport which I had never done before. Otherwise, another great Delta flight!

Amazing flight! I have never noticed the uniforms of the attendants before in twenty years of flying except today when one female had the most amazing dress on. It was beautifully designed and showed she was in charge. I never dreamed I would google who designed Delta uniforms . The ultimate compliment is when another woman admires your outfit. . I hope your designer puts it on the market

It would be nice if was given wires ear buds. Overall was a good experience was able to sleep on the plane

My flight was 6 pm 6/6. Every hour they delayed it again - air condition issues then no pilot then the crew had worked too many hours and cancelled the flight at 11 pm. Sent customers to NJ a 45 minutes uber ride to a hotel. Had to be back by 5 am for a 7 am flight and again no pilot etc with another three hours of delays.

The entertainment and wifi mostly didn't work on this flight.

Terrible entertainment system - kept freezing and audio kept cutting out. Snacks were mediocre at best for a 5 hour flight.

The check in and bag drop off for Sky Priority members is slow. The Clear security was also slow - a TSA issue.

I am still upset that my bag was lost on a recent trip to Rome ; we were inconvenienced and out €150 Euros ; delta has refused to reimburse us

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

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

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.

They were only able to give me a seat and not my travel companion, she had to fly on a different airline. unacceptable

Book with frontier airlines with the mentality that they'll cancel your flight, kick you off and lose your luggage. Anything besides that is a win. Compare prices with other airlines (to include luggage) and if frontier is still worth it, book it but know all of their policies.

You get what you pay for nothing essentially but a hard uncomfortable seat that doesn’t recline and kids screaming all around you and chaotic boarding and limited check bag weight allowance when compared to other airlines

I never got to experience the flight because they delayed my first flight and I missed this one. Then Frontier didn't want to help me rebook a flight to get me to my final destination.

The Boarding process in Denver was chaotic, and since the line was so long, we were lined up very far from the gate. If there were any announcements from the gate staff, we didn't hear them. The flight attendants were spectacular. The only negative part of the flight was sitting by a 2 1/2 year old who was unruly and unfortunately had parents that matched his behaviors. Also, the restaurants in Denver on the E concourse, they didn't have food (passengers could only order 1 item on the entire menu) or the restaurants had 12-14 people waiting for orders to be prepared and another 6 people waiting to order. If you have a layover in Denver and need to grab food, be prepared to visit the shops with pre-packaged sandwiches, or you can visit another concourse but it may take a while to transit throughout the airport.

I liked the turn-style feature at gate 209B at LAX. Very efficient process. The gate staff also made several, clearly directed announcements so I felt very informed.

Although an hour and a half early was told by staff at check in they had overbooked and could not check us in for the flight.

The crew was delayed because they came on another flight that was delayed due to weather 10pm flight left at 1.30 am The airline made no effort to align alternate crew

I liked the price of the flight and the chance to buy a seat with no person seated in the middle seat.. Also the flight was right on time.

Plane was down graded and I lost my uncharged exit row with more leg room. No mention or offer of refund from podium. Flight attendant was nice to explain this happens often and that I could request a refund via online form submission. I did this and have heard nothing back.

Worst airline experience. They were rude and kept changing our seats and/or giving our seats away so our family didn’t get to sit with each other. Almost everyone we dealt with at both airports with this airline was rude. The app kept giving us wrong information making things take longer. Dealing with them before TSA can take close to an hour…longer than I’ve ever had to deal with before. Never using this airline again.

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

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