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MDW - SJD

$218 Find cheap flights from Chicago Midway Airport to San José del Cabo

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 San José del Cabo departing on 5/25. 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
0 bags
Sat 5/25
Sat 6/1

Search hundreds of travel sites at once for deals on flights to San José del Cabo

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to San José del Cabo, 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 San José del Cabo, as well as popular online travel agencies
In the last 7 days travelers have searched 44,979,812 times on KAYAK, and here is why:

Save 22% or moreCompare multiple travel sites with one search.

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Filter your dealsChoose cabin class, free Wi-Fi and more.

Bundle and saveSave money when you bundle your flight + hotel.

Cheap flight deals from Midway to San José del Cabo (MDW-SJD)

Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Midway to San José del Cabo 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 and deals for you by selecting your travel dates.
Choose your dates
10:11 am - 9:51 pmMDW-SJD
13h 40m2 stops
12:12 pm - 9:44 pmSJD-MDW
7h 32m1 stop
$466Delta
Find Deal
Sat, Sep 21 - Fri, Sep 27
12:42 pm - 9:51 pmMDW-SJD
11h 09m2 stops
6:53 am - 10:01 pmSJD-MDW
13h 08m2 stops
$476Delta
Find Deal
Wed, May 29 - Sat, Jun 1
5:16 pm - 7:02 amMDW-SJD
15h 46m2 stops
4:54 pm - 9:06 amSJD-MDW
14h 12m1 stop
Tue, May 14 - Fri, May 17
6:00 am - 4:26 pmMDW-SJD
12h 26m2 stops
6:53 am - 10:01 pmSJD-MDW
13h 08m2 stops
$481Delta
Find Deal
Tue, May 21 - Wed, Jun 5
3:45 pm - 11:07 amMDW-SJD
21h 22m1 stop
6:51 pm - 5:59 pmSJD-MDW
21h 08m2 stops
$489Aeromexico
Find Deal
Thu, Sep 12 - Mon, Sep 16
10:39 am - 9:51 pmMDW-SJD
13h 12m2 stops
6:53 am - 9:46 pmSJD-MDW
12h 53m2 stops
$491Delta
Find Deal
Fri, Jun 7 - Wed, Jun 12
8:45 pm - 6:50 amMDW-SJD
12h 05m1 stop
5:00 pm - 9:47 amSJD-MDW
14h 47m1 stop
Mon, Jun 10 - Fri, Jun 14
8:45 pm - 7:02 amMDW-SJD
12h 17m1 stop
7:42 am - 9:47 amSJD-MDW
24h 05m1 stop
$500Volaris
Find Deal
Mon, May 13 - Sat, May 18
8:45 pm - 7:02 amMDW-SJD
12h 17m1 stop
4:54 pm - 9:06 amSJD-MDW
14h 12m1 stop
$505Volaris
Find Deal
Tue, May 14 - Fri, May 17
6:00 am - 11:07 amMDW-SJD
7h 07m1 stop
12:12 pm - 9:41 pmSJD-MDW
7h 29m1 stop
$521Aeromexico
Find Deal
Fri, Jul 19 - Fri, Jul 26

Flights from Midway to San José del Cabo - Travel Insights & Trends

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

What is the cheapest month to fly from Chicago Midway Airport to San José del Cabo?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for flights from Chicago Midway Airport to San José del Cabo, 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 San José del Cabo is January, where tickets cost $506 on average. On the other hand, the most expensive months are December and March, where the average cost of tickets is $721 and $629 respectively.

How far in advance should I book a flight from Chicago Midway Airport to San José del Cabo?

To calculate daily average prices, KAYAK takes all prices for each day before departure over the last year for flights from Chicago Midway Airport to San José del Cabo, removes the top 0.1% to account for outliers, and then takes the average of all the values for each month.
To get a below average price on the flight from Chicago Midway Airport to San José del Cabo, you should book around 4 days before departure. For the absolute cheapest price, our data suggests you should book 61 days before departure.

Which airlines provide the cheapest flights from Chicago Midway Airport to San José del Cabo?

The cheapest price for the route for each airline clicked by KAYAK users in the last 72 hours.
The cheapest return flight ticket from Chicago Midway Airport to San José del Cabo found by KAYAK users in the last 72 hours was for $466 on Delta, followed by Aeromexico ($489). One-way flight deals have also been found from as low as $218 on Frontier and from $240 on Delta.

Good to know

Low season

May

High season

March

Cheapest flight

$218
Best time to beat the crowds with an average 23% drop in price.
Most popular time to fly with an average 17% increase in price.
Flight from Chicago Midway Airport to San José del Cabo

When to book flights from Midway to San José del Cabo

Are your dates flexible? Find out the best times to travel from Midway to San José del Cabo 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 San José del Cabo flights

  • What is the cheapest flight from Chicago Midway Airport to San José del Cabo?

    In the last 3 days, the lowest price for a flight from Chicago Midway Airport to San José del Cabo was $218 for a one-way ticket and $466 for a round-trip.

  • Do I need a passport to fly between Chicago Midway Airport and San José del Cabo?

    A passport is required to fly from Chicago Midway Airport to San José del Cabo.

  • Which aircraft models fly most regularly from Chicago Midway Airport to San José del Cabo?

    We unfortunately don’t have that data for this specific route.

  • Which airline alliances offer flights from Chicago Midway Airport to San José del Cabo?

    SkyTeam is the only airline alliance operating flights between Chicago Midway Airport and San José del Cabo.

  • Which is the best airline for flights from Chicago to San José del Cabo, Delta or Aeromexico?

    The two airlines most popular with KAYAK users for flights from Chicago to San José del Cabo are Delta and Aeromexico. With an average price for the route of $666 and an overall rating of 8.0, Delta is the most popular choice. Aeromexico is also a great choice for the route, with an average price of $784 and an overall rating of 7.6.

  • How does KAYAK find such low prices on flights from Chicago Midway Airport to San José del Cabo?

    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 San José del Cabo.

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

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to San José del Cabo 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 San José del Cabo?

    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 San José del Cabo with an airline and back to Chicago Midway Airport with another airline. Booking your flights between Chicago Midway Airport and SJD 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 San José del Cabo?

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

See more FAQs

Top airlines flying from Midway to San José del Cabo

 
See real verified KAYAK customer reviews for airlines flying from Chicago to San José del Cabo. 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 San José del Cabo? 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.
8.0
DeltaOverall score based on 10975 reviews
8.2boarding
8.6crew
7.4food
7.9comfort
8.0entertainment
Airline reviews

Delta is one of the best airlines I have flown

10.0 ExcellentKellie, Apr 2024ANC - SEA
Read more about Delta reviews

Delta is one of the best airlines I have flown

Made the Atlanta to Pittsburgh trip many times, with Delta no issues

I always fly with Delta. My friends tell me their horror stories of flying with other airlines. I just smile and say, “You should fly Delta”

I'm a larger, athletic guy (6'2", 260lbs powerlifter) and I found the seats incredibly uncomfortable with minimal leg room, especially in a window seat. Now, I full understand that being smaller may change my view but even if I was 80lbs less, my legs would be the same size and I was sandwiched between my seat and the seat in front of me.

Horrible. This was not first class. This was a connecting flight whi h was late. My original flight never came. I hated the fact that delta gave me a connecting flight from New York to Orlando Florida. No meals and the television screens were not working. There wasn't even any power to charge your phones. This is NOT FIRST CLASS DELTA!!! Do better next time!

This flight was ridiculous. I had to have a connecting flight from New York to orlando Florida??? The flight left late and because it was a short flight there was no first class amenities. I had one alcohol drink. The flight crew was fine, but it sure did not feel like first class. Delta to me dropped the ball by giving me a connecting flight. By the time we got to Raleigh we would have missed the next flight. Lucky for me the flight never came so now I was stuck waiting for a later flight that came in late also.

Our flight was delayed in Atlanta. The staff could have gave us an explanation for the delay and how long it would be.

I liked the ease of checking in, luggage check in, wheel chair assistance, boarding and flight.

On my way home I had a layover. The flight from ATL to CLT was amended 5x while I was waiting. I could have driven home sooner. Overall from Dallas, Tx to Charlotte, NC I started my trip at 4:30pm, I didn’t get home until past midnight. I know things happen, but 5x to make me run back and forth in an airport from different terminals is excessive. I also upgraded to comfort + , I didn’t feel it was worth it. There was no benefit

On my way home I had a layover. The flight from ATL to CLT was amended 5x while I was waiting. I could have driven home sooner. Overall from Dallas, Tx to Charlotte, NC I started my trip at 4:30pm, I didn’t get home until past midnight. I know things happen, but 5x to make me run back and forth in an airport from different terminals is excessive.

Happy attentive flight crew. All in all good flight the night flight works well. Getting into Mexico City early so you don't get caught up it all the immigration and custom ques, additionally, this helps when exiting the airport and crossing the city to your final destination. All works very well and would do it again

Some entertainment and food/snack service would have been nice

All the pessengers should be wait in a line útil the creo and piloto are arrived.

Planes seat could be bigger very uncomfortable for tall humans.

Atraso de dos horas y media con vuelos sobre vendidos

Great airplane The confort was within the high standards. My only little problem was That all the movies ( only 3) was on Spanish, even though I was selecting the audio on English it didn't happen. After that I highly recommend aeromexico

1 hour waiting for suitcases to come out traveling in business class and food in business class is a sandwich? Avoid Aeromexico .

Aeromexico es siempre una buena opción, relación precio calidad adecuada!

No space reserved for anyone who didn’t have underseat in front of them. Made it inconvenient to get the backs secured. No inflight entertainment in the 190. Bring your own! Food was excellent and we were surprised to get a full breakfast.

Cons: "left Houston more than 2 hours later, arrive in Mexico over 2 am"

Book cheap flights from Chicago to San José del Cabo

Recent one-way flight deals

 
Only flying one-way? Below are some of the best one-way flight deals from Chicago to San José del Cabo found on KAYAK in the last 72 hours.
5/25Sat
1 stopFrontier
22h 47mMDW-SJD
$218
6/7Fri
2 stopsDelta
11h 06mMDW-SJD
$240
5/1Wed
2 stopsDelta
12h 51mMDW-SJD
$245
5/2Thu
1 stop
12h 05mMDW-SJD
$247
6/20Thu
1 stopVolaris
22h 09mMDW-SJD
$249
5/1Wed
1 stop
12h 00mMDW-SJD
$259
5/2Thu
2 stops
15h 34mMDW-SJD
$263
5/26Sun
2 stopsVolaris
20h 23mMDW-SJD
$291
5/25Sat
2 stopsAeromexico
28h 53mMDW-SJD
$380
5/25Sat
2 stopsAeromexico
32h 06mMDW-SJD
$385

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Last minute flights from Midway to San José del Cabo

Last minute flight, train and bus deals

 
These last-minute flight deals are the cheapest flights found on KAYAK in the last 72 hours for flights from Chicago to San José del Cabo that are departing in the next 10 days.
4/26Fri
multi-stopAeromexico
7h 10mMDW-SJD
5/2Thu
multi-stopAeromexico
13h 52mSJD-MDW
$906
4/26Fri
multi-stopDelta
11h 11mMDW-SJD
4/29Mon
multi-stopDelta
13h 21mSJD-MDW
$946
4/26Fri
multi-stopAeromexico
7h 10mMDW-SJD
4/29Mon
multi-stopAeromexico
7h 59mSJD-MDW
$1,336
4/26Fri
multi-stopAeromexico
19h 08mMDW-SJD
5/2Thu
multi-stopAeromexico
23h 25mSJD-MDW
$1,486

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Chicago Midway Airport - San José del Cabo Flights

Departure:

Chicago Midway Airport (MDW)United States

Destination:

San José del Cabo (SJD)Mexico

Return flight deals:

San José del Cabo - Chicago Midway Airport

Cabin classes: