$149 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 2/28. 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
$250
Frontier
Thu 2/19Mon 2/23
CUN - MDW • 1 stop
Cheapest non-stop
$306
Typical prices: $250-$311
Frontier
Fri 2/13Mon 2/16
GDL - MDW • Non-stop
Top airlines
Volaris
Most flights • 28 per week
Volaris
Best reviews • 6.6 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
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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, Feb 19 - Mon, Feb 23
Frontier Logo
11:48 am - 9:12 pm
CUN
-
MDW
10h 24m1 stop
Frontier Logo
6:00 am - 1:37 pm
MDW
-
CUN
6h 37m1 stop
$250Frontier
Thu, Feb 19 - Tue, Feb 24
Delta Logo
11:38 am - 10:31 pm
QRO
-
MDW
10h 53m2 stops
Delta Logo
6:00 am - 8:37 pm
MDW
-
QRO
14h 37m2 stops
$257Delta
Wed, Feb 11 - Wed, Feb 18
Delta Logo
8:55 am - 5:29 pm
QRO
-
MDW
8h 34m1 stop
Delta Logo
6:00 am - 5:40 pm
MDW
-
QRO
11h 40m1 stop
$258Delta
Mon, Feb 23 - Mon, Mar 2
Frontier Logo
10:17 am - 7:47 pm
CUN
-
MDW
10h 30m1 stop
Frontier Logo
6:00 am - 1:37 pm
MDW
-
CUN
6h 37m1 stop
$258Frontier
Mon, Feb 2 - Mon, Feb 9
Aeromexico Logo
8:46 pm - 5:29 pm
AGU
-
MDW
20h 43m2 stops
Aeromexico Logo
6:00 am - 8:09 pm
MDW
-
AGU
14h 09m2 stops
$281Aeromexico
Mon, Feb 2 - Mon, Feb 9
Aeromexico Logo
8:46 pm - 10:22 pm
AGU
-
MDW
25h 36m2 stops
Aeromexico Logo
6:00 am - 8:09 pm
MDW
-
AGU
14h 09m2 stops
$282Aeromexico
Sat, Feb 21 - Sat, Feb 28
Multiple Airlines Logo
10:45 pm - 9:29 pm
QRO
-
MDW
22h 44m2 stops
Multiple Airlines Logo
9:15 am - 10:30 pm
MDW
-
QRO
13h 15m1 stop
$303Multiple Airlines
Fri, Feb 6 - Mon, Feb 9
Volaris Logo
9:15 am - 1:04 pm
MLM
-
MDW
3h 49mnonstop
Volaris Logo
2:32 pm - 6:48 pm
MDW
-
MLM
4h 16mnonstop
$317Volaris
Tue, Mar 10 - Tue, Mar 17
Volaris Logo
1:39 pm - 6:34 pm
GDL
-
MDW
3h 55mnonstop
Volaris Logo
7:54 pm - 11:24 pm
MDW
-
GDL
4h 30mnonstop
$319Volaris
Sat, Mar 7 - Mon, Mar 9
Multiple Airlines Logo
11:30 am - 8:21 pm
MTY
-
MDW
8h 51m1 stop
Multiple Airlines Logo
7:54 pm - 7:34 am
MDW
-
MTY
12h 40m1 stop
$333Multiple Airlines
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 $149 one-way and $250 return. The most popular connection is from Guadalajara to Chicago Midway Airport and KAYAK users have found round-trip deals for as low as $319 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 $351. The cheapest price found on KAYAK in the last 2 weeks cost $173 and departed from Morelia. The most popular routes on KAYAK are Morelia to Chicago Midway Airport which costs $514 on average, and Guadalajara to Chicago Midway Airport, which costs $267 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 Morelia $174 one-way - $345 round-trip, from Guadalajara $216 one-way - $265 round-trip, from Cancún $328 one-way - $358 round-trip.

Good to know

Low seasonNovember
Cheapest flight$149
Best time to beat the crowds but there is an average 4% increase in price.
Most popular time to fly and prices are also 6% lower on average.
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 $149 one-way and $250 return. The most popular connection is from Guadalajara to Chicago Midway Airport and KAYAK users have found round-trip deals for as low as $319 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 $351. The cheapest price found on KAYAK in the last 2 weeks cost $173 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 $331. On the other hand, the most expensive day to fly is Monday, where prices are $388 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 afternoon, when flights cost $358 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 $241, from Cancun $343, from León $375
  • 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.
6.6
VolarisOverall score based on 1170 reviews
6.6Boarding
4.9Entertainment
5.3Food
6.3Comfort
7.3Crew
Airline reviews

The money you save flying volaris is not worth it

4.0 OkayAnonymous, Jan 2026
MEX - EWR
Read more Volaris reviews

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.

Unfortunately it was not a good flight got canceled had to be at the airport all night long to get a different flight to another airport my first flight with Volaris was very bad. Poor services

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

Confusion over extra fees. Held up on ramp during boarding. Thin seat cushion. Minimal leg room.

Better communication about delayed flight. I am thankful for a small credit for late flight.

It was ok. It was expensive to check 2 bags ($75.00 per bag), and then it took a long time to wait for shuttle to take us from one terminal to the terminal where the plane was taking off at LAX. And all of this for a flight where we had to pay for any food or drink that was not water.

It didn’t happen. I booked it and then was told it wasn’t available and then forced to pay far higher prices for a worse option

A 630departure flight Delayed 6hours! They changed my gate, I moved to the new gate. Had our flight on the screen for 12noon departure. I go get above to eat, check screen again and the flight was gone, no notice no announcement, nothing!! They sent my bag on the flight I wasn’t on, got it back to me 3days later. Thank goodness they did refund my money but I will NEVER fly them again.

Due to weather, my flight was delayed, further delayed, then canceled. I eventually got through to a support person who helped me find a different route out of MSP, but to get to DIA, they didn't want to, but eventually did help with the connection ticket purchase. But even this replacement flight was delayed time and time again, and I would have missed my connecting flights and I didn't want to get stuck in a layover city, so after 12 hours at the airport with two young boys who were very tired, we just cancelled our plans and spent the week at home, instead of Nana's.

Plane and crew on board were fine. Everything else was terrible.

The third party booking with cheapflightsfares was awful. Kayak should NOT partner with them. They sold me a bundle including seat selection and carry-on, but did not book the carry-ons with Frontier, so I’m out of pocket for $414 more while I await resolution.

This company socks. It's fraud. They canceled our flight yesterday, and today we were late because of a really long line at the check in bag. At the rebook station, there was ton of people. The workers were all rude. I am gonna make a report to FTC.

One of the worst travel experiences I've had. Had a flight scheduled with CVG to RSW on VLSWQX this morning departing at 5:30. Two individuals at the gate and one was in training. Not her fault but she didn't have the ability to check people in resulting in at least 15 families that didn't make it on the plane because they weren't checked into the system in time. When arriving at the airport to drop off our prepaid checked bags, the bag drop off agent asked if we could check our bags at the gate because of the long line. We said no problem so arrived at the gate by 5:00. They told those people that had previously paid for checked bags to stand off to the side while they let others that either didn't have a checked bag or their bag was already on the plan through. Realizing the gate workers had an issue, they either called for help or this lady showed up late for work as she didn't arrive until 5:15. The worker who had been there training the other individual and working diligently to make sure all passengers got on board. He even said that at one point all people that are currently in line are fine but asked the person in training to stand outside the ticketing area around 5:15 to notify any late travels that the flight was in boarding process and they arrrived too late. At that point, we're sill standing off to the side with our pre-paid checked bags patiently waiting. When the new lady arrived she couldn't have been more rude. It was an awful seen. Essentially they had asked for those without an assigned seat to board last, those with pre-paid checked bag stand off to the site and any traveling with a larger items that needed to be checked at the gate (such as a stroller), wait on the side. They realized that the flight needed to leave on time so the gate attendant shut the gate. So anyone without a seat assignment, those that had pre-checked bags, and the worst one I saw was a mother with two infant children was in line with use because she was asked to stand to the side because her stroller. When they shut the door to the plan they told her she could no longer get on. Her checked bags were already on the plane with her car keys in them, and the lady told her we couldn't accept anyone else on because the door was shut. She didn't even have a way to get home from the airport. Truely evil behavior. I've flown Frontier enough to know customer service is not a top priority in the company's mission, but this was an all-time low. I'm sending this after an 18 hour drive that our family just completed to Bonita Springs . I felt really bad for the lady being trained and the other individual trying to help, but when the new lady came to the gate she was truly one of the rudest individuals I've ever met. One lady had been there since 4am but because she didn't have an assigned seat they wouldn't let her on the plan.

I loved the staff on the plane. So friendly and helpful! However, there was an argument and misunderstanding by the staff and a customer at the gate, and the staff member was being unprofessional. When we arrived in Atlanta, we waited 1.5 hrs for our luggage to arrive. When I asked the airport attendant, they said Frontier had the longest wait for luggage out of any airlines, and that they could not be held responsible for the delay.

Not clean and was told I would get a great seat and it was not great at all

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