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MDW - SJD

$173 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 6/5. 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 6/29
Sat 7/6

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 42,686,544 times on KAYAK, and here is why:

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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
6:00 am - 11:00 amMDW-SJD
7h 00m1 stop
12:05 pm - 9:46 pmSJD-MDW
7h 41m1 stop
$406Aeromexico
Find Deal
Sun, Aug 25 - Wed, Aug 28
6:00 am - 11:00 amMDW-SJD
7h 00m1 stop
12:05 pm - 9:46 pmSJD-MDW
7h 41m1 stop
$416Delta
Find Deal
Tue, Aug 13 - Tue, Aug 20
6:00 am - 11:00 amMDW-SJD
7h 00m1 stop
12:05 pm - 11:44 amSJD-MDW
21h 39m1 stop
$424Delta
Find Deal
Tue, Aug 13 - Fri, Aug 16
6:00 am - 11:00 amMDW-SJD
7h 00m1 stop
12:05 pm - 9:46 pmSJD-MDW
7h 41m1 stop
$431Delta
Find Deal
Sun, Aug 4 - Wed, Aug 14
6:00 am - 11:00 amMDW-SJD
7h 00m1 stop
12:05 pm - 11:44 amSJD-MDW
21h 39m1 stop
$439Delta
Find Deal
Mon, Aug 12 - Fri, Aug 16
3:47 pm - 11:00 amMDW-SJD
21h 13m1 stop
12:05 pm - 9:46 pmSJD-MDW
7h 41m1 stop
$454Aeromexico
Find Deal
Sat, Aug 3 - Tue, Aug 6
10:40 pm - 8:35 amMDW-SJD
11h 55m2 stops
9:40 am - 6:50 amSJD-MDW
19h 10m2 stops
$498Southwest
Find Deal
Sun, Jul 7 - Sun, Jul 14
5:35 am - 12:10 pmMDW-SJD
8h 35m1 stop
9:40 am - 12:30 amSJD-MDW
12h 50m1 stop
$526Southwest
Find Deal
Sun, Jul 7 - Sun, Jul 14
10:21 am - 4:14 pmMDW-SJD
7h 53m1 stop
3:31 pm - 9:47 amSJD-MDW
16h 16m1 stop
$590Volaris
Find Deal
Fri, Aug 30 - Mon, Sep 2
8:45 pm - 7:02 amMDW-SJD
11h 17m1 stop
3:31 pm - 8:47 amSJD-MDW
16h 16m1 stop
$593Volaris
Find Deal
Thu, Nov 7 - Mon, Nov 11

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 $504 on average. On the other hand, the most expensive months are December and March, where the average cost of tickets is $731 and $615 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 1 week before departure. For the absolute cheapest price, our data suggests you should book 22 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 $406 on Aeromexico, followed by Delta ($416). One-way flight deals have also been found from as low as $271 on Volaris and from $441 on Delta.

Good to know

Low season

June

High season

March

Cheapest flight

$173
Best time to beat the crowds but there is an average 17% increase in price.
Most popular time to fly with an average 14% 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 $173 for a one-way ticket and $406 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 10457 reviews
8.6Crew
8.2Boarding
8.0Entertainment
7.9Comfort
7.4Food
Airline reviews

I've flown many many times on Northwest and then Delta. The crew on this flight were absolutely the best I've had the pleasure of being looked after by.

10.0 ExcellentAnonymous, May 2024MSP - YVR
Read more about Delta reviews

I've flown many many times on Northwest and then Delta. The crew on this flight were absolutely the best I've had the pleasure of being looked after by.

Flew first class so everything was great. But maybe because the flights were red eye, no meals were served, just chips. I flew Alaska Air 1st class at 9PM (2 hour flight) and they served beef short rib sliders!

Had to change aircraft due to a faulty door. Surprisingly it only caused about an hour and a half of delay. Delta handled this situation as well as can be expected.

Awful. Flight was continuously getting delayed and gates kept changing without any reason. Flight was delayed for more then 3 hours

Paid premium for Delta only to be on safe but tired old 767 with ancient cabin in mediocre condition. Poor wifi and horrible inflight entertainment. Hardly a premium experience. Should have flown SW and had fun flight crew and no pretense

Our flight to Zurich was delayed by almost 3 hours, so we missed our next flight. There was no indication it would be delayed this much. We were told the gate had changed and then it apparently took over 2 hours to load the "catering" on the plane. We were not compensated in any way for the trouble.

Rated entertainment as Mediocre as there were major problems with the Infotainment system that took probably a half hour for them to fix.

Your crew could maybe answer the call bell at least one of the times I pressed it. I pressed it first time with 2.5 hours left in our flight bc my partner was hungry and wanted a sandwich. We finally got the sandwich with 40 mins left in the flight.

Half the bathrooms assigned to economy were out of action

Delta crushed it. Flight attendant in first was attentive and just never stopped. Honestly one of the best domestic flights I’ve been on.

The plane was so outdated, that it made it uncomfortable. The temperature was hot during the whole flight

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!

Business class was economy with a table in the middle seat. That is worse than economy. No food and no entertainment. Very poor representation.

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.
6/5Wed
2 stops
26h 50mMDW-SJD
$173
6/27Thu
2 stops
25h 10mMDW-SJD
$224
6/13Thu
2 stops
34h 50mMDW-SJD
$232
6/28Fri
1 stopVolaris
12h 17mMDW-SJD
$271
6/20Thu
1 stopVolaris
12h 17mMDW-SJD
$274
6/11Tue
1 stopVolaris
12h 17mMDW-SJD
$336
6/4Tue
2 stopsDelta
14h 58mMDW-SJD
$441
6/20Thu
2 stopsDelta
11h 08mMDW-SJD
$445
6/20Thu
2 stopsDelta
11h 08mMDW-SJD
$516
6/28Fri
2 stopsDelta
12h 20mMDW-SJD
$566

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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.
6/2Sun
multi-stop
12h 05mMDW-SJD
6/9Sun
multi-stop
24h 27mSJD-MDW
$499
6/2Sun
multi-stop
12h 05mMDW-SJD
6/9Sun
multi-stop
21h 16mSJD-MDW
$529
6/2Sun
multi-stopVolaris
18h 27mMDW-SJD
6/9Sun
multi-stopVolaris
14h 30mSJD-MDW
$665
6/2Sun
multi-stopVolaris
20h 23mMDW-SJD
6/9Sun
multi-stopVolaris
14h 30mSJD-MDW
$775
6/4Tue
multi-stopDelta
14h 58mMDW-SJD
6/9Sun
multi-stopDelta
11h 57mSJD-MDW
$912
5/31Fri
multi-stopDelta
15h 06mMDW-SJD
6/3Mon
multi-stopDelta
13h 12mSJD-MDW
$971
6/4Tue
multi-stopAeromexico
28h 55mMDW-SJD
6/9Sun
multi-stopAeromexico
22h 26mSJD-MDW
$1,036
6/4Tue
multi-stopVolaris
12h 17mMDW-SJD
6/9Sun
multi-stopVolaris
11h 40mSJD-MDW
$1,160
5/31Fri
multi-stopDelta
11h 09mMDW-SJD
6/3Mon
multi-stopDelta
7h 38mSJD-MDW
$1,166
5/31Fri
multi-stopAeromexico
7h 18mMDW-SJD
6/3Mon
multi-stopAeromexico
7h 38mSJD-MDW
$1,316

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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: