$190 Find Cheap Flights from Mexico to Chicago Midway Airport - 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 to Midway departing on 8/20. 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, 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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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, Aug 13 - Tue, Aug 18
Delta Logo
12:15 pm - 9:17 am
MTY
-
MDW
20h 02m
2 stops
Delta Logo
6:05 am - 5:48 pm
MDW
-
MTY
12h 43m
2 stops
$357Delta
Mon, Aug 17 - Thu, Aug 20
Delta Logo
8:44 am - 10:36 pm
MTY
-
MDW
12h 52m
1 stop
Delta Logo
10:54 am - 11:54 pm
MDW
-
MTY
14h 00m
2 stops
$358Delta
Mon, Aug 17 - Wed, Aug 26
Delta Logo
8:44 am - 10:36 pm
MTY
-
MDW
12h 52m
1 stop
Delta Logo
6:05 am - 11:05 am
MDW
-
MTY
6h 00m
1 stop
$359Delta
Thu, Aug 27 - Mon, Aug 31
Southwest Logo
1:05 pm - 4:40 pm
CUN
-
MDW
3h 35mnonstop
Southwest Logo
8:25 am - 12:00 pm
MDW
-
CUN
3h 35mnonstop
$365Southwest
Fri, Sep 11 - Wed, Sep 16
Frontier Logo
3:55 pm - 10:58 am
CUN
-
MDW
19h 03m
1 stop
Frontier Logo
12:03 pm - 2:45 pm
MDW
-
CUN
26h 42m
1 stop
$383Frontier
Sat, Jul 25 - Tue, Jul 28
Frontier Logo
3:06 pm - 11:07 am
CUN
-
MDW
20h 01m
1 stop
Frontier Logo
12:11 pm - 1:46 pm
MDW
-
CUN
25h 35m
1 stop
$386Frontier
Tue, Jul 21 - Tue, Jul 28
Multiple Airlines Logo
3:06 pm - 11:07 am
CUN
-
MDW
20h 01m
1 stop
Multiple Airlines Logo
8:49 pm - 9:55 am
MDW
-
CUN
13h 06m
1 stop
$393Multiple Airlines
Wed, Aug 26 - Fri, Aug 28
Multiple Airlines Logo
3:34 pm - 8:31 pm
GDL
-
MDW
27h 57m
1 stop
Multiple Airlines Logo
8:23 pm - 11:30 pm
MDW
-
GDL
4h 07mnonstop
$396Multiple Airlines
Mon, Aug 24 - Mon, Aug 31
Volaris Logo
2:01 pm - 7:04 pm
GDL
-
MDW
4h 03mnonstop
Volaris Logo
8:23 pm - 11:30 pm
MDW
-
GDL
4h 07mnonstop
$404Volaris
Thu, Aug 13 - Mon, Aug 17
Volaris Logo
2:31 pm - 7:34 pm
GDL
-
MDW
4h 03mnonstop
Volaris Logo
8:23 pm - 11:30 pm
MDW
-
GDL
4h 07mnonstop
$416Volaris
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 5 days.

In the last 5 days, the cheapest flight deal to Chicago Midway Airport was found on the route from Cancún, at $357 return. The most popular connection is from Morelia to Chicago Midway Airport and KAYAK users have found round-trip deals for as low as $453 in the last 5 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.

A flight to Chicago Midway Airport costs $342 on average. The cheapest price found on KAYAK in the last 2 weeks cost $175 and departed from San Luis Potosí. The most popular routes on KAYAK are Guadalajara to Chicago Midway Airport which costs $462 on average, and Aguascalientes to Chicago Midway Airport, which costs $376 on average.

See prices from:

What is the cheapest day to fly to Chicago?

The average price of all round-trip flights to Chicago Midway Airport clicked on KAYAK for each day over the last 12 months.

Based on KAYAK data, the cheapest day to fly to Chicago is Thursday where round-trip tickets can be as cheap as $395. On the other hand, the most expensive day to fly is Tuesday, where round-trip prices are $497 on average.

What is the cheapest month to fly to Chicago Midway Airport?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights to Chicago Midway Airport, 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 to Chicago Midway Airport is April, where tickets cost $84 on average for return flights. On the other hand, the most expensive months are December and July, where the average cost of tickets from Mexico is $336 and $289 respectively. For one-way flights, the best month to travel is February with an average price of $111.

What is the cheapest time of day to fly to Chicago Midway Airport?

The average price for all round-trip flights to Chicago Midway Airport depending on the time of departure, clicked by users on KAYAK in the last 2 weeks.

The cheapest time of day to fly to Chicago Midway Airport is generally in the afternoon, when round-trip flights cost $363 on average. The most expensive time of day to fly to Chicago Midway Airport is generally in the morning, which is peak travel time and where the average cost of a ticket is $471.

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 San Luis Potosí $222 round-trip, from Guadalajara $354 round-trip, from Morelia $555 round-trip.

Good to know

Low seasonFebruary
Cheapest flight$190
Best time to beat the crowds with an average 18% drop in price.
Most popular time to fly and prices are also 1% 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 5 days, the cheapest flight deal to Chicago Midway Airport was found on the route from Cancún, at $357 return. The most popular connection is from Morelia to Chicago Midway Airport and KAYAK users have found round-trip deals for as low as $453 in the last 5 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 $342. The cheapest price found on KAYAK in the last 2 weeks cost $175 and departed from San Luis Potosi Airport.

  • 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.

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 León $263, from Cancun $291, from Guadalajara $305
  • 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 1156 reviews
4.9Entertainment
6.5Boarding
6.3Comfort
5.2Food
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

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

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

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

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.

I got to where I needed to go quickly. There were no amenities. And the seats were painful.

The flight was delayed an hour and a half, and they would not update the board on when the flight was supposed to take off. Once the plane arrived, they started the boarding process before the plane was even ready for the passengers so we had to wait another 45 minutes on the tarmac while we waited for the plane to be ready for us. In my opinion, there is no point in starting the boarding process when you are not ready to board the plane. This just causes a crowded gate with everyone from zone one and zone two standing up going nowhere.

My experience was good. But it seems that every time I go on Volaris the plane is always full, not sure if because the price is cheaper. And the flight attendants kept hitting my shoulder every time they walked by the aisle with their food cart. I’m 6’4” so I barely fit in the seat next to the aisle. Plus the seat was defective. I had a hard time raising the lever where I rest my left arm. I tried calling the flight attendant 3 times if she could assist me but she was too busy talking in the back with her fellow flight attendants. Finally after 20 mins she looked my way and she too struggled to fix the problem but she finally raised it so I could get out of my seat.

I never got an email for checking in for my flight back to Los Angeles so I got to airport extra early to sort it. they changed the gate, and so I had to run to the other end of the airport. Their app is wonky. They are not on WhatsApp and I didn’t have cell service to call for help. I think they need to up their game with communicating.

Inept company. Won't fly again with them if I can help it. Plane was the wrong size and they couldn't board 20 people.

Flight was scheduled at 9:40pm. Got delayed to 10 am, the next day. crazy

The bag check, flight check-in, and onboard experience convinced my wife and me that we will actively go out of our way to avoid flying Frontier Airlines in the future. At bag check, we were informed that check-in could only be completed via the Frontier mobile app. Unfortunately, the app was extremely frustrating—sending us through repetitive, confusing loops that repeatedly forced us to decline add-on services with nearly every click. While most airline apps upsell, this one felt intentionally exhausting. As the process dragged on, we became genuinely concerned that my phone battery would die before check-in could be completed. We approached the bag check staff—who were standing together talking—and explained both our frustration and our predicament. They laughed. Later, my wife described the interaction as “gaslighting,” which felt accurate. We were then informed it would cost $25 per person simply to have our boarding passes printed. From that point forward, the tone of the experience was consistently hostile. The bag check employees were condescending and combative, behaving more like bullies than customer service staff. Unfortunately, that same attitude continued onboard. One flight attendant argued with me when I attempted to stow my backpack in the overhead bin. I explained that we had each paid $75 to check our bags specifically so we would not need to use carry-on space and could have adequate legroom. She demanded to see my ticket, pointed out that it said “no carry-on”—which I acknowledged—and I reiterated that this was precisely why we paid to check our bags. Her response was, “I don’t make the rules.” She then walked away, but not before asking if I “truly wanted to fly back to Chicago today?”—an unnecessary and unmistakable threat. It is also worth noting that despite booking our tickets together in the same transaction, we were not seated together. Upon our return to Chicago—where we could once again sit together—we compared onboard experiences. We both remarked on how unhappy the flight attendants appeared and how each of us was separately asked whether we would like to purchase a beverage. We declined. At no point was water mentioned as an option, leaving us with the clear impression that even water came at a cost—or that complimentary water, if available at all, was deliberately left unmentioned. Overall, the experience was shocking and deeply disappointing, but it was also a profound learning experience—one we will not forget and will not repeat. -Steve

Good for a budget airline! It was easy to get on, staff was really nice. Can’t say anything about the food or entertainment because it wasn’t available, which is fine.

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

The flight itself was ok and the pilot was very communicative. However, our flight was delayed for almost 3 hours, the gate was changed 3 times and there was no communication as we were waiting. The flight staff was overall a little crabby...I understand as they probably had a long day but we all did.

After waiting several minutes to be acknowledged by 3 employees on their phones, was told we had missed our flight because the doors were closed at that literal moment. Had they given any actual service or help while we were standing there we would have been on with time to spare. More than 10 people were turned away in this fashion claiming there was no way they could let us on the plane, even though it was still sitting connected to the terminal. After the desk agents let us know they didn't care about the situation we were forced to pay more than twice the price of our original tickets as no credits were given for the price of the "missed" flight. And the icing on the cake was after being treated poorly, fleeced for another few hundred dollars for new tickets? We waited on the next plane for 25 minutes passed the "doors closed" time, letting almost an extra dozen passengers on board. You're company has lazy, disinterested employees and your lack of any real help will ensure this was the first and last time we fly Frontier. Awful.

terrible cascading delays and unhelpful customer service. uncomfortable plane. crew was great, however!

The trip was unremarkable which is good. Crew was very professional and courteous.

I was singled out for being a Latina flying solo and the attendants took me out of line to put my luggage in the personal item bin to see if it would fly. Keep In mind I had just flown with the same luggage with no problem not even 5 days ago. The tag was sticking out a bit and the attendant was belligerent about charging me $100. I could not refuse because I didn’t wanna cause a scene. But today I felt targeted and embarrassed. I went online and found out that this happens a lot with this airline and to many minority women.

Nothing I missed my first flight because my boarding pass said one thing and another passenger on the same flight said another. I didn’t get notified of a gate change until 8:39 pm which was one minute before the flight departed at 8:40pm when we explained this to gate agent Dorsey prior to the flight departing she was extremely short and had nasty attitude. Some of the passengers in my party including myself needed to catch that flight due work the next which included presentations and court litigation. We were deeply saddened and frustrated how Frontier handled this situation. We were told that the flight was over booked by 19 seats and they constantly change gates to make people miss their flight. If that is true I will ensure there will be a class action lawsuit against frontier airlines.

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
Schererville
Munster
Chesterton
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