MDW - SJD

$167 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 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

KAYAK searches 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
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Cheap Flights 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 for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Midway to San José del Cabo

Tue, Aug 12 - Fri, Aug 15
Southwest Logo
6:40 am - 12:50 pmMDW-SJD
8h 10m1 stop
Southwest Logo
10:40 am - 12:05 amSJD-MDW
11h 25m1 stop
$401Southwest
Find Deal
Sun, Aug 31 - Thu, Sep 4
Delta Logo
6:00 am - 4:40 pmMDW-SJD
12h 40m2 stops
Delta Logo
6:01 am - 9:26 pmSJD-MDW
13h 25m2 stops
$406Delta
Find Deal
Mon, Sep 29 - Wed, Oct 8
Delta Logo
6:30 pm - 1:13 pmMDW-SJD
20h 43m2 stops
Delta Logo
2:23 pm - 8:55 amSJD-MDW
16h 32m2 stops
$410Delta
Find Deal
Sun, Sep 21 - Wed, Sep 24
Southwest Logo
6:00 am - 1:10 pmMDW-SJD
9h 10m1 stop
Southwest Logo
12:40 pm - 11:20 pmSJD-MDW
8h 40m1 stop
$430Southwest
Find Deal
Sun, Sep 21 - Wed, Sep 24
Southwest Logo
5:30 am - 1:10 pmMDW-SJD
9h 40m2 stops
Southwest Logo
1:45 pm - 11:00 pmSJD-MDW
7h 15m1 stop
$434Southwest
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Tue, Oct 7 - Tue, Oct 14
Delta Logo
6:00 am - 3:00 pmMDW-SJD
11h 00m2 stops
Delta Logo
6:00 am - 10:14 pmSJD-MDW
14h 14m2 stops
$436Delta
Find Deal
Fri, Sep 12 - Fri, Sep 19
Delta Logo
6:00 am - 11:25 amMDW-SJD
7h 25m1 stop
Delta Logo
6:01 am - 9:36 pmSJD-MDW
13h 35m2 stops
$451Delta
Find Deal
Sun, Nov 2 - Fri, Nov 7
Southwest Logo
5:10 am - 1:45 pmMDW-SJD
9h 35m1 stop
Southwest Logo
1:05 pm - 12:05 amSJD-MDW
10h 00m1 stop
$454Southwest
Find Deal
Mon, Oct 6 - Thu, Oct 9
Aeromexico Logo
6:00 am - 11:41 amMDW-SJD
7h 41m1 stop
Aeromexico Logo
12:46 pm - 10:14 pmSJD-MDW
7h 28m1 stop
$476Aeromexico
Find Deal
Wed, Oct 1 - Tue, Oct 7
Aeromexico Logo
6:00 am - 9:56 pmMDW-SJD
17h 56m2 stops
Aeromexico Logo
6:00 am - 10:14 pmSJD-MDW
14h 14m2 stops
$540Aeromexico
Find Deal
Booking Insights

KAYAK's insights & trends for Midway to San José del Cabo flights

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 round-trip 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 August, where tickets cost $548 (return) on average. On the other hand, the most expensive months are November and September, where the average cost of round-trip tickets is $995 and $859 respectively.

Good to know

Low seasonJune
Cheapest flight$167
Best time to beat the crowds with an average 12% drop in price.
Most popular time to fly and prices are also 0% lower on average.
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 $167 for a one-way ticket and $401 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 airlines offer Wi-Fi service onboard planes from Chicago Midway Airport to San José del Cabo?

    American Airlines, Aeromexico, and Delta offer inflight Wi-Fi service on the Chicago Midway Airport to San José del Cabo flight route.

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

    The Boeing 737-800 is the aircraft model that flies most regularly on the Chicago Midway Airport to San José del Cabo flight 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.

  • 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.

Reviews of the top airline 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
SouthwestOverall score based on 4241 reviews
8.0Comfort
8.6Crew
8.1Boarding
7.0Food
7.5Entertainment
Airline reviews

southwest just starting charging for luggage. hadnt realized it until it was too late. now out $70 when i couldve bought a carry on if i wouldve known. free bags was one of the only reasons i chose southwest over another airline (the other being no assigned seats, which is apparently also being changed). stupid business decision. wont be flying southwest anymore.

2.0 MediocreAnonymous, Jul 2025AUS - RDU
Read more Southwest reviews

southwest just starting charging for luggage. hadnt realized it until it was too late. now out $70 when i couldve bought a carry on if i wouldve known. free bags was one of the only reasons i chose southwest over another airline (the other being no assigned seats, which is apparently also being changed). stupid business decision. wont be flying southwest anymore.

The quality of Southwest Airlines continues to degrade each time I fly with them. If it were not for the free luggage, I would probably choose another airline. Their prices are a little bit competitive, but way too high for the quality of the service. Southwest is not unique in this way. Domestic flight in the United States of America has continued to be a lower and lower quality product. Very sad when you compare the quality of domestic airlines to that of many international airlines around the world.

Very smooth checking in our luggage with a super pleasant SW agent. I enjoyed a fun entertaining movie.

WiFi did not work. For as outrageous as these flights cost, when they’re advertised with certain services/ features they should be in working order

Worst experience I had on Southwest. Still better than most, but the seating was barely tolerable.

The Southwest employees (all two of them) were very nice and cheerful despite the fact the line to self-check a bag (simply drop it off) was hundreds of people long. Thank God I arrived early to the airport because I stood in this line for at least an hour. Once on the flight that had been delayed by an hour, we had no Wi-Fi and thus no entertainment. Finally, I hope the investor strong arm tactics against Southwest pay off in a short-term windfall to your C-Suite because the rest of you are screwed. I have been a faithful Southwest customer for 15 years due to everything you just got rid of. I'm flying to Idaho and Washington in October, both places I used to simply book with Southwest without a second thought now with Frontier (Washington) and United (Idaho) because they offer everything the "new" Southwest does but cheaper and at better times, destinations, etc. This really makes me sad...

It was okay. The plane was delayed from earlier in the day, but they kept updating the departure time, sometimes later, sometimes earlier. That was stressful. Once we finally got on and took off, it was fine. I was supposed to have a connection in Chicago to Los Angeles, and the time for so late I was rebooked to arrive in LA 3 hours late. The departure time to Chicago later became early enough to have taken my original connection and arrive earlier but that wasn't an option.

It was one and half hour late... Not sure if any other experience matters.

Delayed flight. Nicest crew member was a SW pilot flying seated next to me who kindly move to seat the final passenger. Flight extra delayed. My cup of refreshment of ginger ale was so packed with ice it was literally 2 sips.

For my birthday trip this was my second time ever flying, this trip was the best.

Everything you need to know for your flight from Midway to San José del Cabo

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