MDW - GDL

$166 Find Cheap Flights from Chicago Midway Airport to Guadalajara

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Midway to Guadalajara departing on 10/16. 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 Guadalajara

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to Guadalajara, as well as popular online travel agencies
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to Guadalajara, as well as popular online travel agencies
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Everything you should know

Cheapest round-trip
$392
Typical prices: $533-$288
Volaris
Wed 10/21Sun 10/25
MDW - GDL • Non-stop
Cheapest one-way
$166
Typical prices: $294-$400
Volaris
Fri 10/16
MDW - GDL • Non-stop
Nonstop flights
You can fly direct with Volaris. Average duration is 4h 07m
Direct flights
Direct flights
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Direct flights
Direct flights
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Avoid delays
Most punctual • 83% on-time
Best time • Fewest delays
Insights
Insights
Insights
Insights
Top layover airports
Cheapest • Avg $453 (round-trip)
Shortest trip • 7h 34m (one-way)
Insights
Insights
Insights
Insights
When to travel
Cheapest • 18% price drop
Most popular
Good to know
Good to know
+1
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Good to know
Good to know
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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 Guadalajara!
Flight Deals
Booking Insights
Flight Deals

Cheap Flights from Midway to Guadalajara (MDW-GDL)

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

Wed, Oct 21 - Sun, Oct 25
Volaris Logo
8:23 pm - 11:30 pm
MDW
-
GDL
4h 07mnonstop
Volaris Logo
2:01 pm - 7:04 pm
GDL
-
MDW
4h 03mnonstop
$392Volaris
Thu, Aug 13 - Mon, Aug 24
Volaris Logo
8:49 pm - 11:56 pm
MDW
-
GDL
4h 07mnonstop
Volaris Logo
2:01 pm - 7:04 pm
GDL
-
MDW
4h 03mnonstop
$394Volaris
Wed, Jun 3 - Mon, Jun 8
Volaris Logo
8:23 pm - 11:30 pm
MDW
-
GDL
4h 07mnonstop
Volaris Logo
2:01 pm - 7:04 pm
GDL
-
MDW
4h 03mnonstop
$395Volaris
Sat, Aug 15 - Mon, Aug 24
Volaris Logo
8:49 pm - 11:56 pm
MDW
-
GDL
4h 07mnonstop
Volaris Logo
2:01 pm - 7:04 pm
GDL
-
MDW
4h 03mnonstop
$397Volaris
Fri, Aug 28 - Fri, Sep 25
Volaris Logo
8:23 pm - 11:30 pm
MDW
-
GDL
4h 07mnonstop
Volaris Logo
2:01 pm - 7:04 pm
GDL
-
MDW
4h 03mnonstop
$399Volaris
Sun, Jul 5 - Tue, Jul 28
Volaris Logo
8:23 pm - 11:30 pm
MDW
-
GDL
4h 07mnonstop
Volaris Logo
2:31 pm - 7:34 pm
GDL
-
MDW
4h 03mnonstop
$401Volaris
Sat, Jun 27 - Fri, Jul 3
Volaris Logo
8:49 pm - 11:56 pm
MDW
-
GDL
4h 07mnonstop
Volaris Logo
2:01 pm - 7:04 pm
GDL
-
MDW
4h 03mnonstop
$402Volaris
Sat, Aug 8 - Wed, Aug 19
Volaris Logo
8:49 pm - 11:56 pm
MDW
-
GDL
4h 07mnonstop
Volaris Logo
2:01 pm - 7:04 pm
GDL
-
MDW
4h 03mnonstop
$405Volaris
Mon, Oct 12 - Fri, Oct 16
Volaris Logo
8:23 pm - 11:30 pm
MDW
-
GDL
4h 07mnonstop
Volaris Logo
2:01 pm - 7:04 pm
GDL
-
MDW
4h 03mnonstop
$406Volaris
Mon, Jul 20 - Sun, Sep 20
Volaris Logo
8:23 pm - 11:30 pm
MDW
-
GDL
4h 07mnonstop
Volaris Logo
2:01 pm - 7:04 pm
GDL
-
MDW
4h 03mnonstop
$408Volaris
Booking Insights

KAYAK's insights & trends for Midway to Guadalajara flights

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

How much is a round-trip flight from Chicago Midway Airport to Guadalajara?

This analysis is based on the cheapest round-trip price found on KAYAK in the last 12 months by searching for a flight from Chicago Midway Airport to Guadalajara departing in October.

What’s the cheapest day of the week to fly from Chicago Midway Airport to Guadalajara?

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

When flying from Chicago Midway Airport to Guadalajara, you should consider leaving on a Sunday and avoid Wednesdays if you are looking for the best rates. For your return to Chicago Midway Airport, you’ll find the best rates on Sundays and the most expensive ones on Mondays.

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

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Chicago Midway Airport to Guadalajara, 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 from Chicago Midway Airport to Guadalajara is February, where tickets cost $361 (return) on average. On the other hand, the most expensive months are December and June, where the average cost of round-trip tickets is $713 and $498 respectively.

Can I save money by flying with a layover from Chicago Midway Airport to Guadalajara?

The average round-trip price for all non-stop flights, flights with one layover, and flights with two layovers for the route found by users searching on KAYAK in the last 2 weeks.

Yes, flying with a layover may cost you more time, but you can also save money on the route, with a 1 stop layover the cheapest option at $425 on average.

How far in advance should I book a flight from Chicago Midway Airport to Guadalajara?

To calculate weekly average prices, KAYAK takes all prices for each week before departure over the last year for round-trip flights from Chicago Midway Airport to Guadalajara, removes the top 0.1% to account for outliers, and then takes the average of all the values for each week.

To get a below average price on the flight from Chicago Midway Airport to Guadalajara, you should book around 1 week before departure. For the absolute cheapest price, our data suggests you should book 26 weeks before departure.

Good to know

Low seasonApril
Cheapest flight$166
Best time to beat the crowds with an average 12% drop in price.
Most popular time to fly with an average 61% increase in price.
Flight from Chicago Midway Airport to Guadalajara

When to book flights from Midway to Guadalajara

Are your dates flexible? Find out the best times to travel from Midway to Guadalajara based on our flight data from the last year. Discover the cheapest month and even day to fly.
Estimated round-trip price
KAYAK looks at all historical flight data for each date to provide a predicted price for one-way trips or round-trips with a duration up to 40 days. While we try to provide actual minimum prices for each date, some prices are predictions and actual prices may differ.

FAQs for booking Chicago Midway Airport to Guadalajara flights

  • What is the cheapest flight from Chicago Midway Airport to Guadalajara?

    In the last 7 days, the lowest price for a flight from Chicago Midway Airport to Guadalajara was $166 for a one-way ticket and $392 for a round-trip.

  • Do I need a passport to fly between Chicago Midway Airport and Guadalajara?

    Yes

  • Which airports will I be using when flying from Chicago Midway Airport to Guadalajara?

    On your way to Guadalajara, you’ll fly out from Chicago Midway. You’ll be landing at Guadalajara Miguel Hidal.

  • Which airlines offer Wi-Fi service onboard planes from Chicago Midway Airport to Guadalajara?

    Only American Airlines offers inflight Wi-Fi service on the Chicago Midway Airport to Guadalajara flight route.

  • Which aircraft models fly most regularly from Chicago Midway Airport to Guadalajara?

    The Airbus A320-100/200 is the aircraft model that flies most regularly on the Chicago Midway Airport to Guadalajara flight route.

  • On which days can I fly direct from Chicago Midway Airport to Guadalajara?

    You can catch a nonstop flight from Chicago Midway Airport to Guadalajara on Monday, Wednesday, Thursday, Friday, Saturday, and Sunday.

  • Which is the best airline for flights from Chicago to Guadalajara, Volaris or Frontier?

    The two airlines most popular with KAYAK users for flights from Chicago to Guadalajara are Volaris and Frontier. With an average price for the route of $437 and an overall rating of 6.6, Volaris is the most popular choice. Frontier is also a great choice for the route, with an average price of $546 and an overall rating of 5.6.

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

    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 from Chicago Midway Airport to Guadalajara.

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

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Guadalajara from 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 from Chicago Midway Airport to Guadalajara?

    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 Guadalajara with an airline and back to Chicago Midway Airport with another airline. Booking your flights between Chicago Midway Airport and GDL can sometimes prove cheaper using this method.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Chicago Midway Airport to Guadalajara?

    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 Guadalajara from Chicago Midway Airport up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

KAYAK’s top tips for finding a cheap flight from Chicago Midway Airport to Guadalajara

  • Looking for a cheap flight? 25% of our users found flights on this route for $186 or less one-way and $386 or less round-trip.

Prefer to fly direct from Chicago Midway Airport to Guadalajara?

 
Direct data is based off flight results for the next 60 days. Find direct flights from all airlines flying direct from Chicago Midway to Guadalajara Miguel Hidal.
Find which airlines fly direct from Chicago Midway Airport to Guadalajara Miguel Hidal Airport, which days they fly and book direct flights.

Direct departures

Chicago Midway to Guadalajara Miguel Hidal

Monday

Volaris

Volaris

Tuesday

Volaris

Volaris

Wednesday

Volaris

Volaris

Thursday

Volaris

Volaris

Friday

Volaris

Volaris

Saturday

Volaris

Volaris

Sunday

Volaris

Volaris

See more direct flights

Direct returns

Guadalajara Miguel Hidal to Chicago Midway

Monday

Volaris

Volaris

Tuesday

Volaris

Volaris

Wednesday

Volaris

Volaris

Thursday

Volaris

Volaris

Friday

Volaris

Volaris

Saturday

Volaris

Volaris

Sunday

Volaris

Volaris

See more direct flights

Reviews of the top airlines flying from Midway to Guadalajara

 
See real verified KAYAK customer reviews for airlines flying from Chicago to Guadalajara. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
Need help choosing which airline to fly with from Midway to Guadalajara? 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 1162 reviews
6.3Comfort
6.5Boarding
7.3Crew
4.9Entertainment
5.2Food
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.

Overall a good red eye. Crew chatted very loudly the whole time making it difficult to sleep.

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 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.

There weren't enough employees at check in took awhile to get bags checked. There wasn't a wheel chair for me, I was sent to someone who turns out to work for a different airline, if My flight hadn't been delayed I probably would have missed my flight as it was, by the time I arrived at my gate, they started boarding in about 15 minutes. I don't know who took me to my gate, definitely was not the normal people who take passengers to the gate. I'm guessing she may have been in a management position. I wish I knew her name, she went beyond to help me. With that said everyone was kind, and were doing the best they could. So, I choose to say it was an Adventure, stressful start, but good. In the end went well. The situation was not only difficult for passengers but the employee's.

The staff at the check in counter was so rude. Made you feel Incompetent

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

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.

Everything you need to know for your flight from Midway to Guadalajara

Information on your arrival and departure airports