$139 Find Cheap Flights from Mexico to Chicago Midway Airport

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight to Midway departing on 11/20. 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

KAYAK searches hundreds of travel sites at once for deals on flights to Chicago Midway Airport

 
These are the airlines KAYAK users have selected most often from within our search results for flights to Chicago, as well as popular online travel agencies
These are the airlines KAYAK users have selected most often from within our search results for flights to Chicago, as well as popular online travel agencies
Travelers love KAYAK
41,299,237 searches in the past 7 days on KAYAK

Save 23% or moreCompare multiple travel sites with one search.

Track pricesNot ready to book? Create a price alert for when prices drop.

Bundle and saveSave money when you bundle your flight + hotel.

Filter your dealsChoose cabin class, free Wi-Fi and more.

Everything you should know

Cheapest round-trip
$255
Southwest
Thu 11/6Sat 11/15
CUN - MDW • Non-stop
Cheapest one-way
$139
Typical prices: $395-$452
Southwest
Thu 11/20
CUN - MDW • Non-stop
Top airlines
Volaris
Most flights • 31 per week
Volaris
Best reviews • 6.7 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
Top routes
CUN-MDW
Cheapest
GDL-MDW
Most popular
Insights
Insights
Insights
Insights
Start a new search
KAYAK searches 100s of sites at once to find you the best travel deals.
We hope you love your trip to Midway!
Flight Deals
Booking Insights
Flight Deals

Cheap Flights from Mexico to Midway

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Mexico to Midway 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 Mexico to Midway

Thu, Nov 6 - Sat, Nov 15
Southwest Logo
2:15 pm - 5:00 pmCUN-MDW
3h 45mnonstop
Southwest Logo
3:40 pm - 8:25 pmMDW-CUN
3h 45mnonstop
$255Southwest
Find Deal
Fri, Dec 5 - Tue, Dec 9
Delta Logo
8:00 am - 6:00 pmCUN-MDW
11h 00m2 stops
Delta Logo
9:34 am - 9:20 pmMDW-CUN
10h 46m2 stops
$274Delta
Find Deal
Thu, Mar 19 - Mon, Mar 23
Frontier Logo
8:15 am - 1:04 pmMLM-MDW
3h 49mnonstop
Frontier Logo
2:32 pm - 5:48 pmMDW-MLM
4h 16mnonstop
$301Frontier
Find Deal
Sun, Mar 1 - Wed, Mar 4
Frontier Logo
9:15 am - 1:04 pmMLM-MDW
3h 49mnonstop
Frontier Logo
2:32 pm - 6:48 pmMDW-MLM
4h 16mnonstop
$316Frontier
Find Deal
Sat, Nov 1 - Sun, Nov 2
Aeromexico Logo
8:00 am - 3:26 pmCUN-MDW
7h 26m1 stop
Aeromexico Logo
5:00 am - 8:20 pmMDW-CUN
14h 20m1 stop
$332Aeromexico
Find Deal
Thu, Nov 6 - Sat, Nov 8
Multiple Airlines Logo
6:20 am - 12:37 pmMEX-MDW
6h 17m1 stop
Multiple Airlines Logo
6:30 am - 10:00 pmMDW-MEX
15h 30m1 stop
$334Multiple Airlines
Find Deal
Thu, Dec 4 - Mon, Dec 8
Multiple Airlines Logo
8:10 am - 8:36 pmMEX-MDW
12h 26m1 stop
Multiple Airlines Logo
7:00 am - 10:00 pmMDW-MEX
15h 00m1 stop
$347Multiple Airlines
Find Deal
Thu, Nov 13 - Sun, Nov 16
Aeromexico Logo
2:10 pm - 11:40 pmMEX-MDW
9h 30m1 stop
Aeromexico Logo
6:00 am - 8:45 pmMDW-MEX
14h 45m1 stop
$351Aeromexico
Find Deal
Wed, Feb 11 - Sun, Feb 15
Volaris Logo
8:26 am - 5:34 pmTLC-MDW
9h 08m1 stop
Volaris Logo
6:54 pm - 7:37 amMDW-TLC
12h 43m1 stop
$388Volaris
Find Deal
Mon, Feb 9 - Mon, Feb 16
Volaris Logo
8:26 am - 5:34 pmTLC-MDW
9h 08m1 stop
Volaris Logo
6:54 pm - 7:37 amMDW-TLC
12h 43m1 stop
$401Volaris
Find Deal
Booking Insights

KAYAK's insights & trends for flights to Midway

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

What is the cheapest flight to Chicago Midway Airport?

These are the best round-trip prices found by users searching on KAYAK in the last 72 hours.

In the last 3 days, the cheapest flight deal to Chicago Midway Airport was found on the route from Cancún, at $139 one-way and $255 return. The most popular connection is from Guadalajara to Chicago Midway Airport and KAYAK users have found round-trip deals for as low as $331 in the last 3 days.

How much is a flight to Chicago Midway Airport?

The average and cheapest price for all round-trip flights to Chicago Midway Airport from each origin found by users searching on KAYAK in the last month.

On average, a flight to Chicago Midway Airport costs $322. The cheapest price found on KAYAK in the last 2 weeks cost $134 and departed from Morelia. The most popular routes on KAYAK are Zacatecas to Chicago Midway Airport which costs $323 on average, and Durango to Chicago Midway Airport, which costs $362 on average.

See prices from:

What is a good deal for flights to Chicago Midway Airport?

If you’re looking for cheap airfare to Chicago Midway Airport, 25% of our users found tickets to Chicago Midway Airport for the following prices or less: From León $195 one-way - $244 round-trip, from Guadalajara $204 one-way - $336 round-trip, from Zacatecas $209 one-way - $303 round-trip.

Good to know

Low seasonJanuary
Cheapest flight$139
Best time to beat the crowds but there is an average 10% increase in price.
Most popular time to fly with an average 15% increase in price.
Flight from Cancun to Chicago Midway Airport

FAQs - booking Chicago Midway Airport flights

  • What is the cheapest flight to Chicago Midway Airport?

    In the last 3 days, the cheapest flight deal to Chicago Midway Airport was found on the route from Cancún, at $139 one-way and $255 return. The most popular connection is from Guadalajara to Chicago Midway Airport and KAYAK users have found round-trip deals for as low as $331 in the last 3 days.

  • How far is Chicago Midway Airport from central Chicago?

    Central Chicago is 9 miles away from Chicago Midway Airport.

  • How much is a flight to Chicago?

    On average, a flight to Chicago costs $322. The cheapest price found on KAYAK in the last 2 weeks cost $134 and departed from Morelia Airport.

  • What is the cheapest day to fly to Chicago?

    Based on KAYAK data, the cheapest day to fly to Chicago is Thursday where tickets can be as cheap as $313. On the other hand, the most expensive day to fly is Sunday, where prices are $408 on average.

  • How does KAYAK find such low prices on flights to Chicago Midway Airport?

    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 to Chicago Midway Airport.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket to Chicago Midway Airport?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Chicago Midway Airport is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights to Chicago Midway Airport?

    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 to Chicago Midway Airport 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 to Chicago Midway Airport?

    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 to Chicago Midway Airport 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 Chicago Midway Airport?

    The cheapest time of day to fly to Chicago Midway Airport is generally in the morning, when flights cost $451 on average. The most expensive time of day to fly to Chicago Midway Airport is generally in the evening, which is peak travel time and where the average cost of a ticket is $538.

Top tips for finding cheap flights to Chicago Midway Airport

  • Looking for cheap airfare to Chicago Midway Airport? 25% of our users found round-trip tickets to Chicago Midway Airport for the following prices or less: From Cancun $148, from León $219, from Guadalajara $270
  • Enter your preferred departure airport and travel dates into the search form above to unlock the latest Chicago Midway Airport flight deals.

Reviews of the top airlines flying from Mexico to Midway

 
See real verified KAYAK customer reviews for airlines flying to Chicago. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline from Mexico to Chicago. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
Need help choosing which airline to fly with to Midway? 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.
6.7
VolarisOverall score based on 1150 reviews
6.6Boarding
6.4Comfort
7.3Crew
5.0Entertainment
5.3Food
Airline reviews

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.

8.0 ExcellentKaren, Sep 2025PVR - TIJ
Read more Volaris reviews

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

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.

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.

The single worst check in experience I could imagine. I’ll never do any business with Frontier or any affiliated company

Too many extra fees, uncomfortable, little leg room. Will not recommend this airline.

Everyone seemed to be in zone 1 for boarding. Maybe break it up a little. Otherwise, smooth flight.

Frontier is the Walmart of airlines. Frontier has removed adjustability and comfort from their seats to make the flight lighter and save gas. This makes it impossible to sleep on their flights. Their customer service is abysmal. Once, I bought a drink on the plane, and they swiped my credit card on the plane to pay for it. Then I got three weeks of daily notices from my bank telling me they tried to charge the wrong card number over and over again. I tried to call them, but they removed the ability to actually talk to someone that can resolve such a problem from their company to cut corners. The only way to talk to someone in person is to go to the check-in counter at the airport (40 minutes drive from my house). Eventually their system gave up on trying to charge the card, after 21 days of repeated tries. They don't pad their prices even a little to handle customer service issues like missed flights. They also have a blanket policy preventing helping you reschedule a missed flight if their system says you "cancelled" your own flight online. This is a major problem because their website is broken on mobile devices, the only web browser you have at the airport when their gate staff tell you that you have to reschedule your own missed flight online because they can't help you. I tried to reschedule my flight on my android device and instead, their website crashed and "cancelled" my missed flight. When I got to the counter, the agent argued with me for 5 minutes insisting that I intentionally cancelled my own flight (implying I had to buy another flight). She missed the point: the problem was that I could not buy another flight because their website is broken. I left to avoid more conflict with the "customer service" agent. I tried to redress my issue with their only other "customer service" chanel available: the contact form on their website. The response I got was more of the same: you cancelled your own flight, according to our website / computer records, therefore we won't help you. I was trying to explain the problem with their broken website that cost me hundreds of dollars by crashing / malfunctioning and resulting in a cancelled flight, but they only had deaf ears for this problem. Worst customer service I have ever experienced. I will never buy another Frontier flight again, because it is a risky, painful move that I will likely regret often.

I think Frontier was very good at communication. Their app worked very well. Loading was great and the flight was nice and easy.

This airline sucks. They offer low rates then charge you for everything, the app does not work well, the seats are the most uncomfortable. Maintenance issues on the flight, and you still have to sit through their credit card commercials. People are nice enough but does not make up for overall poor experience.

Seats were new and comfortable. Staff was fine. Missed my connection due to weather -which wasn’t their fault- but got no help at all. Gate staff sent me to customer service, which was and stayed unstaffed. Sign with QR code directed me to call or chat. Chat was useless. Call was returned after an hour. No itinerary offered by Frontier could get me home in less than 30 hours. Rebooked with another airline and got a partial refund that came to about 10 percent of what I paid to get home.

Finally a Frontier on time and efficient. I've had problems before with your airline, but this time everything went fine.

The experience was good. No frills but I got there safe and sound and on time.

Traveling to a place near Midway?

Book flights to Midway if you plan to visit one of these locations
Merrillville
Saint Joseph
Hammond
Portage
Lansing
Valparaiso
Munster
Chesterton
Schererville
Porter
Monticello
Saint John
Griffith

Everything you need to know for your flight to Midway

Information on the airport you'll fly into in Chicago

Not what you’re looking for? Find thousands of other hotels, flights, car rentals and package deals with KAYAK.