$144 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 1/22. 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

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
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Everything you should know

Cheapest round-trip
$265
Southwest
Thu 1/22Mon 1/26
CUN - MDW • Non-stop
Cheapest one-way
$144
Typical prices: $262-$461
Southwest
Thu 1/22
CUN - MDW • Non-stop
Top airlines
Volaris
Most flights • 30 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
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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, Jan 22 - Mon, Jan 26
Southwest Logo
1:45 pm - 4:30 pmCUN-MDW
3h 45mnonstop
Southwest Logo
9:15 am - 1:55 pmMDW-CUN
3h 40mnonstop
$265Southwest
Find Deal
Fri, Jan 30 - Mon, Feb 2
Delta Logo
12:05 pm - 10:26 pmCUN-MDW
11h 21m2 stops
Delta Logo
6:00 am - 4:45 pmMDW-CUN
9h 45m1 stop
$274Delta
Find Deal
Fri, Feb 13 - Mon, Feb 16
Frontier Logo
1:39 pm - 5:34 pmGDL-MDW
3h 55mnonstop
Frontier Logo
6:54 pm - 11:24 pmMDW-GDL
4h 30mnonstop
$280Frontier
Find Deal
Wed, Jan 28 - Sun, Feb 1
Frontier Logo
1:39 pm - 5:34 pmGDL-MDW
3h 55mnonstop
Frontier Logo
6:54 pm - 11:24 pmMDW-GDL
4h 30mnonstop
$283Frontier
Find Deal
Tue, Dec 23 - Wed, Dec 31
Multiple Airlines Logo
5:45 am - 9:40 amGDL-MDW
3h 55mnonstop
Multiple Airlines Logo
2:16 pm - 11:31 pmMDW-GDL
9h 15m1 stop
$316Multiple Airlines
Find Deal
Sat, Dec 13 - Fri, Jan 2
Multiple Airlines Logo
11:45 am - 3:34 pmMLM-MDW
3h 49mnonstop
Multiple Airlines Logo
8:00 am - 8:22 pmMDW-MLM
12h 22m1 stop
$331Multiple Airlines
Find Deal
Fri, Dec 19 - Mon, Dec 29
Volaris Logo
9:15 am - 1:04 pmMLM-MDW
3h 49mnonstop
Volaris Logo
2:32 pm - 6:48 pmMDW-MLM
4h 16mnonstop
$335Volaris
Find Deal
Wed, Feb 11 - Sun, Feb 15
Volaris Logo
1:39 pm - 5:34 pmGDL-MDW
3h 55mnonstop
Volaris Logo
6:54 pm - 11:24 pmMDW-GDL
4h 30mnonstop
$343Volaris
Find Deal
Wed, Dec 24 - Wed, Jan 7
Aeromexico Logo
9:50 am - 10:22 pmMEX-MDW
12h 32m2 stops
Aeromexico Logo
6:45 am - 9:25 pmMDW-MEX
14h 40m2 stops
$373Aeromexico
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Sat, Nov 22 - Tue, Nov 25
Aeromexico Logo
2:10 pm - 11:40 pmMEX-MDW
9h 30m1 stop
Aeromexico Logo
6:00 am - 9:25 pmMDW-MEX
15h 25m2 stops
$377Aeromexico
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 $144 one-way and $265 return. The most popular connection is from Guadalajara to Chicago Midway Airport and KAYAK users have found round-trip deals for as low as $280 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 $318. The cheapest price found on KAYAK in the last 2 weeks cost $128 and departed from Aguascalientes. The most popular routes on KAYAK are Durango to Chicago Midway Airport which costs $232 on average, and Guadalajara to Chicago Midway Airport, which costs $421 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 $199 one-way - $376 round-trip, from Durango $208 one-way - $230 round-trip, from Guadalajara $215 one-way - $249 round-trip.

Good to know

Low seasonJanuary
Cheapest flight$144
Best time to beat the crowds but there is an average 10% 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 $144 one-way and $265 return. The most popular connection is from Guadalajara to Chicago Midway Airport and KAYAK users have found round-trip deals for as low as $280 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 $318. The cheapest price found on KAYAK in the last 2 weeks cost $128 and departed from Aguascalients 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 $319. On the other hand, the most expensive day to fly is Sunday, where prices are $425 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 $461 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 Guadalajara $232, from León $287
  • 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 1151 reviews
5.0Entertainment
6.6Boarding
7.3Crew
5.3Food
6.4Comfort
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.

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.

Boarding was on time and plane departed as scheduled. There are obviously no amenities (food, drink, entertainment) on Frontier, but there also didn't seem to be any issues with luggage space either.

Inbound plane was on time and flight departed on time with no issues while boarding.

I knew going into this that Frontier, being a low cost carrier, would be pretty bare bones and charge for most extras but this was made up for by the fact that the airplane was a reasonably new Airbus, every employee was great and best of all, Everett Washington is an amazing airport - thanks Frontier for flying there!!!

i was unable to check in the flight. refund requested

It was well done. It was my first time flying with them and I was nervous b/c I have heard of many cancelled and/or delray flights. Everything went smoothly.

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.

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
Chesterton
Schererville
Munster
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