$163 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 5/16. 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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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, Jul 16 - Mon, Jul 20
Delta Logo
3:36 pm - 10:15 pm
CUN
-
MDW
6h 39m
1 stop
Delta Logo
6:00 am - 11:20 am
MDW
-
CUN
5h 20m
1 stop
$278Delta
Thu, Jul 16 - Mon, Jul 20
Delta Logo
8:00 am - 10:15 pm
CUN
-
MDW
14h 15m
1 stop
Delta Logo
6:00 am - 11:20 am
MDW
-
CUN
5h 20m
1 stop
$279Delta
Thu, Jul 9 - Wed, Jul 15
Delta Logo
3:36 pm - 10:15 pm
CUN
-
MDW
6h 39m
1 stop
Delta Logo
9:19 am - 8:15 pm
MDW
-
CUN
10h 56m
2 stops
$280Delta
Thu, Jul 9 - Mon, Jul 13
Aeromexico Logo
10:55 am - 10:15 pm
CUN
-
MDW
11h 20m
1 stop
Aeromexico Logo
6:00 am - 8:15 pm
MDW
-
CUN
14h 15m
1 stop
$282Aeromexico
Sat, Jul 11 - Tue, Jul 14
Frontier Logo
3:01 pm - 10:08 pm
CUN
-
MDW
7h 07m
1 stop
Frontier Logo
6:00 am - 1:44 pm
MDW
-
CUN
7h 44m
1 stop
$326Frontier
Tue, Aug 4 - Tue, Aug 18
Frontier Logo
3:01 pm - 10:08 pm
CUN
-
MDW
7h 07m
1 stop
Frontier Logo
6:00 am - 2:13 pm
MDW
-
CUN
8h 13m
1 stop
$331Frontier
Mon, May 18 - Tue, May 26
Volaris Logo
8:22 am - 1:15 pm
MLM
-
MDW
3h 53mnonstop
Volaris Logo
2:32 pm - 5:41 pm
MDW
-
MLM
4h 09mnonstop
$373Volaris
Mon, Jun 15 - Sun, Jun 21
Volaris Logo
2:01 pm - 7:04 pm
GDL
-
MDW
4h 03mnonstop
Volaris Logo
8:23 pm - 11:30 pm
MDW
-
GDL
4h 07mnonstop
$387Volaris
Thu, Aug 27 - Sun, Aug 30
Aeromexico Logo
9:05 am - 9:46 pm
QRO
-
MDW
11h 41m
1 stop
Aeromexico Logo
10:35 am - 5:40 pm
MDW
-
QRO
8h 05m
1 stop
$443Aeromexico
Sat, Jun 20 - Sat, Jul 4
Multiple Airlines Logo
11:30 am - 7:34 pm
MTY
-
MDW
7h 04m
1 stop
Multiple Airlines Logo
6:00 am - 4:25 pm
MDW
-
MTY
11h 25m
2 stops
$479Multiple 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 $278 return. The most popular connection is from New York to Chicago Midway Airport and KAYAK users have found round-trip deals for as low as $162 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.

A flight to Chicago Midway Airport costs $362 on average. The cheapest price found on KAYAK in the last 2 weeks cost $172 and departed from Guadalajara. The most popular routes on KAYAK are León to Chicago Midway Airport which costs $474 on average, and Morelia to Chicago Midway Airport, which costs $361 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 Saturday where round-trip tickets can be as cheap as $393. On the other hand, the most expensive day to fly is Sunday, where round-trip prices are $490 on average.

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 $358 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 Morelia $341 round-trip, from León $374 round-trip, from Durango $423 round-trip.

Good to know

Low seasonFebruary
Cheapest flight$163
Best time to beat the crowds with an average 18% drop in price.
Most popular time to fly with an average 3% 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 $278 return. The most popular connection is from New York to Chicago Midway Airport and KAYAK users have found round-trip deals for as low as $162 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 $362. The cheapest price found on KAYAK in the last 2 weeks cost $172 and departed from Guadalajara Miguel Hidal 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 Guadalajara $227, from Cancun $249, from León $323
  • 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.
6.5
VolarisOverall score based on 1165 reviews
6.3Comfort
6.5Boarding
7.3Crew
5.2Food
4.9Entertainment
Airline reviews

The flights were on time, the ground crew and on board crews were kind and efficient. The free snacks for Premium+ were good, similar to US First Class snacks. The plane were clean and bright! Complaints? The seats were worn and the seat-back pockets were missing. Overall, I'll book again with Volaris. Ignore the negative social media posts, understand what your fare includes, buy the add ons you need. We had no problems with our personal items and carryons.

10.0 ExcellentDarcy, Mar 2026
LAP - TIJ
Read more Volaris reviews

The flights were on time, the ground crew and on board crews were kind and efficient. The free snacks for Premium+ were good, similar to US First Class snacks. The plane were clean and bright! Complaints? The seats were worn and the seat-back pockets were missing. Overall, I'll book again with Volaris. Ignore the negative social media posts, understand what your fare includes, buy the add ons you need. We had no problems with our personal items and carryons.

It’s a 2 1/2 hour flight so good and comfort was not my real concern. Safety, easy, fast was what I was looking for. The crews were great, plane was clean, boarding from CBX was fantastic! Definitely traveling this way again.

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 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.

Frontier scheduled a 40 minute connection in DEN. What they failed to mention was that they “close the doors” 20 mins prior to departure, which means you only have 20 mins. Not enough time. Possibly against DOT regulations. Filing complaint.

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

Plane was hot and miserable and the crew was rude!

12 hour delay required getting on and off plane 3 times - would have at least liked to have been offered a snack or drink

They didn’t offer a water, even after I asked

Zero issues with this flight. Crew was outstanding and flight was super. Plane was clean and fine. The seats need more padding and water should be provided without cost. I recognize it's Frontier but there are some things that should still be part of the flight. But still very satisfied with the experience and quality.

They switched our terminal 3 times and we were delayed for four plus hours!!!

It was an early flight and most people napped/slept and the crew let us which was nice.

The crew acted like they had never done this and kept barking passive aggressive orders at people. + the security line + the delay + sitting on the tarmac for 2 hours + none of the apps or signage updating with correct times

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