MDW - GDL

$148 Find Cheap Flights from Chicago Midway Airport to Guadalajara - 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 from Midway to Guadalajara departing on 9/26. 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

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Everything you should know

Cheapest round-trip
$378
Typical prices: $209-$459
Frontier
Tue 8/11Wed 8/26
MDW - GDL • 1 stop
Cheapest non-stop
$387
Typical prices: $211-$459
Volaris
Wed 8/12Mon 8/31
MDW - GDL • Non-stop
Top airlines
Cheapest • from $378 (round-trip)
Best reviews • 6.6 score
Airline reviews
Airline reviews
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Airline reviews
Airline reviews
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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
+1
Avoid delays
Most punctual • 84% on-time
Best time • Fewest delays
Insights
Insights
Insights
Insights
Top layover airports
Cheapest • Avg $453 (round-trip)
Shortest trip • 7h 57m (one-way)
Insights
Insights
Insights
Insights
When to travel
Cheapest • 19% price drop
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
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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

Tue, Aug 11 - Wed, Aug 26
Frontier Logo
5:46 pm - 2:09 pm
MDW
-
GDL
21h 23m
1 stop
Frontier Logo
3:34 pm - 8:31 pm
GDL
-
MDW
27h 57m
1 stop
$378Frontier
Wed, Aug 12 - Mon, Aug 31
Volaris Logo
8:23 pm - 11:30 pm
MDW
-
GDL
4h 07mnonstop
Volaris Logo
2:01 pm - 7:04 pm
GDL
-
MDW
4h 03mnonstop
$387Volaris
Fri, Aug 21 - Sun, Aug 30
Volaris Logo
8:23 pm - 11:30 pm
MDW
-
GDL
4h 07mnonstop
Volaris Logo
2:01 pm - 7:04 pm
GDL
-
MDW
4h 03mnonstop
$388Volaris
Fri, Aug 21 - Sun, Aug 30
Volaris Logo
8:23 pm - 11:30 pm
MDW
-
GDL
4h 07mnonstop
Volaris Logo
2:01 pm - 7:04 pm
GDL
-
MDW
4h 03mnonstop
$389Volaris
Fri, Aug 21 - Sun, Aug 30
Volaris Logo
8:23 pm - 11:30 pm
MDW
-
GDL
4h 07mnonstop
Volaris Logo
2:01 pm - 7:04 pm
GDL
-
MDW
4h 03mnonstop
$391Volaris
Fri, Aug 21 - Sun, Aug 30
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
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
$393Volaris
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
$394Volaris
Mon, Aug 17 - Mon, Aug 24
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
Mon, Aug 17 - Mon, Aug 31
Volaris Logo
8:23 pm - 11:30 pm
MDW
-
GDL
4h 07mnonstop
Volaris Logo
2:01 pm - 7:04 pm
GDL
-
MDW
4h 03mnonstop
$396Volaris
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 August.

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 Friday and avoid Sundays if you are looking for the best rates. For your return to Chicago Midway Airport, you’ll find the best rates on Thursdays and the most expensive ones on Wednesdays.

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 $364 (return) on average. On the other hand, the most expensive months are December and July, where the average cost of round-trip tickets is $780 and $494 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 16 weeks before departure.

Good to know

Low seasonApril
Cheapest flight$148
Best time to beat the crowds with an average 14% drop in price.
Most popular time to fly with an average 73% 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

  • How many flights are there between Chicago Midway Airport and Guadalajara per day?

    There is a maximum of 1 nonstop flight a day that takes off from Chicago Midway Airport and lands in Guadalajara, with an average flight time of 4h 07m. The most common departure time is 8:00 pm and most flights take off in the evening. Each week, there are 6 flights.

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

    In the last 5 days, the lowest price for a flight from Chicago Midway Airport to Guadalajara was $162 for a one-way ticket and $378 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?

    There are nonstop flights from Chicago Midway Airport to Guadalajara on a daily basis.

  • 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 $439 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 $197 or less one-way and $392 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 1154 reviews
6.3Comfort
6.5Boarding
4.9Entertainment
7.3Crew
5.2Food
Airline reviews

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

8.0 ExcellentAnonymous, Jan 2026
OAK - BJX
Read more Volaris reviews

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

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.

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.

Stood inside the plane for more than an hour before take off

For the price, you pretty much can't beat this airlines. As far as comfort, you could do a lot better, but it'll cost you. Over all cheapest way to get from point A to point B.

Our flight was delayed both ways going there and coming back an hour plus. I have taken Volaris many times and this problem seems to be more common each time.

Be prepared to pay extra for everything! I'm not sure I really saved any money?

Viva Aerobus Is honesto the worst airline and I don't think I'll fly with them ever again.

The flight was 3 hrs delayed and no remorse from airline

Flight was canceled. Most upsetting was message from Kayak, stating that the flight was canceled and click with Kayak for details regarding rebook, refund details. THERE'S NO INFORMATION PROVIDED BY KAYAK EXCEPT THAT FLIGHT IS CANCELED. AND NOW THIS SURVEY TO FIND OUT HOW WAS THE FLIGHT !!!!!!!

Better than expected. Staff were friendly and nice on both flights.

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.

Great for the price. No wifi or entertainment, but gate agents and crew were fantastic and we boarded quickly and left on time.

Our flight was canceled for no known reason. We weren’t told until we were checking in at 5:00 am. This was after our last flight with Frontier where we sat on the plane for three hours (not an exaggeration) before we took off because of a mechanical issue. We won’t be flying Frontier again.

I didn’t have enough time to catch my connecting flight and had to use a different Airline. I will be requesting a refund.

I brought a ticket and car rental through Travelocity. There was no where to add a KTN. So I thought i’d add it by looking up ticket on frontier website. I tried 3 times with the frontier chat bot to add my KTN it never updated my boarding pass. So then I tried showing up early to do it in person at the airport. The first employee update my ktn in the system and gave me a new boarding pass. I was sent back by tsa to join regular line. Then I was told to add my Ktn. It would cost me $25 extra. Given the length of the cue I did pay. Congratulations! BUT I will NEVER fly frontier again. Plus the plane was very old. It had actual ashtrays and old looking tray backs. Worst travel experience ever. Im warning my friends and family not to use frontier ever.

It was delayed 9 hours for operational reasons, despite the plane arriving to the airport on time.

Was just ok with over selling I guess. A lot of people in a short space and when we finally arrive i20 minutes, waiting to get out from the plain because we were waiting authorization for out boarding? Something like that.

They changed my flight and did not want to accommodate me or try to help me in any way. They do not care about their customers.

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

Information on your arrival and departure airports