MDW - SJD

$163 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 10/28. 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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Flight Deals

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

Sun, Jan 18 - Thu, Jan 22
Delta Logo
6:00 am - 2:00 pmMDW-SJD
9h 00m1 stop
Delta Logo
6:00 am - 9:46 pmSJD-MDW
14h 46m2 stops
$432Delta
Find Deal
Mon, Dec 29 - Wed, Jan 7
Southwest Logo
5:25 am - 1:45 pmMDW-SJD
9h 20m2 stops
Southwest Logo
2:35 pm - 10:55 pmSJD-MDW
7h 20m1 stop
$437Southwest
Find Deal
Tue, Nov 18 - Mon, Nov 24
Southwest Logo
8:15 am - 2:50 pmMDW-SJD
7h 35m1 stop
Southwest Logo
2:40 pm - 12:10 amSJD-MDW
8h 30m1 stop
$450Southwest
Find Deal
Tue, Nov 18 - Mon, Nov 24
Southwest Logo
5:00 am - 1:10 pmMDW-SJD
9h 10m2 stops
Southwest Logo
11:50 am - 11:30 pmSJD-MDW
10h 40m2 stops
$455Southwest
Find Deal
Sat, Nov 22 - Thu, Nov 27
Southwest Logo
5:25 am - 2:55 pmMDW-SJD
10h 30m1 stop
Southwest Logo
12:15 pm - 8:05 pmSJD-MDW
6h 50m1 stop
$461Southwest
Find Deal
Sun, Jan 4 - Thu, Jan 8
Aeromexico Logo
6:00 am - 12:42 pmMDW-SJD
7h 42m1 stop
Aeromexico Logo
1:40 pm - 9:46 pmSJD-MDW
7h 06m1 stop
$462Aeromexico
Find Deal
Sat, Oct 18 - Sat, Oct 25
Delta Logo
6:00 am - 2:30 pmMDW-SJD
10h 30m2 stops
Delta Logo
12:47 pm - 10:14 pmSJD-MDW
7h 27m1 stop
$463Delta
Find Deal
Sat, Nov 22 - Thu, Nov 27
Southwest Logo
5:25 am - 2:55 pmMDW-SJD
10h 30m1 stop
Southwest Logo
12:15 pm - 5:05 amSJD-MDW
15h 50m2 stops
$466Southwest
Find Deal
Sun, Jan 4 - Fri, Jan 9
Delta Logo
6:00 am - 12:42 pmMDW-SJD
7h 42m1 stop
Delta Logo
9:40 am - 9:46 pmSJD-MDW
11h 06m2 stops
$467Delta
Find Deal
Thu, Feb 26 - Tue, Mar 3
Aeromexico Logo
6:00 am - 9:40 pmMDW-SJD
16h 40m2 stops
Aeromexico Logo
1:40 pm - 9:46 pmSJD-MDW
7h 06m1 stop
$507Aeromexico
Find Deal

Everything you should know

Top airlines
Delta
Cheapest • from $432 (round-trip)
Southwest
Best reviews • 8.0 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
Nonstop flights
1 day a week
There are direct flights from Midway to San José del Cabo 1 day a week: Sat.
Direct flights
Direct flights
Direct flights
Direct flights
Cheapest round-trip
$432
Delta
Sun 1/18Thu 1/22
MDW - SJD • 1 stop
Cheapest non-stop
$898
Southwest
Sat 3/14Tue 3/17
MDW - SJD • Non-stop
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 San José del Cabo!
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.

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

The cheapest round-trip price for the route for each airline clicked by KAYAK users in the last 72 hours.

In the past 3 days, the cheapest round-trip tickets from Chicago Midway Airport to San José del Cabo were found on Delta ($432) and Southwest ($437).

Good to know

Low seasonOctober
Cheapest flight$163
Best time to beat the crowds with an average 37% drop in price.
Most popular time to fly and prices are also 5% 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 $163 for a one-way ticket and $432 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.

Prefer to fly direct from Chicago Midway Airport to San José del Cabo?

 
Direct data is based off flight results for the next 60 days. Find direct flights from all airlines flying direct from Chicago Midway to San José del Cabo Los Cabos.
Find which airlines fly direct from Chicago Midway Airport to San José del Cabo Los Cabos Airport, which days they fly and book direct flights.

Direct departures

Chicago Midway to San José del Cabo Los Cabos

Saturday

Southwest

Southwest

See more direct flights

Direct returns

San José del Cabo Los Cabos to Chicago Midway

Saturday

Southwest

Southwest

See more direct flights

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 4242 reviews
7.0Food
8.0Comfort
8.1Boarding
7.5Entertainment
8.6Crew
Airline reviews

I wish they had movie screens in the headrests. The seats are much improved, more legroom and recently renovated. Bathroom was clean. Staff was outstanding!!

10.0 ExcellentG, Sep 2025LAS - ATL
Read more Southwest reviews

I wish they had movie screens in the headrests. The seats are much improved, more legroom and recently renovated. Bathroom was clean. Staff was outstanding!!

As always, the entire Southwest experience was wonderful, from online booking to flight to baggage retrieval. Very grateful.

The weather could have been better. There was a 40 minute ATC delay in SFO because of marine fog and a micro cell storm delayed landing and take-off at Nashville. The gate was changed 5 minutes from boarding from gate B3 to gate C23 at Nashville airport.

After being assaulted by a flight attendant I was then brushed off as oh well because he long braids didn’t mean to whip me in the eye. I have filed complaints and will see. But like any other issue I’ve had with kayak involved it’s been trash. Last time I’ll be using your app

AC sub par. WiFi not working correctly. Ac sucked. Seats very narrow.

Near 4 hour flight with only 1 service. Had to use call button to request water. Internet and power not working until into flight. Internet would stop working during flight.

Southwest's seats are the least comfortable I have ever sat in.

The cabin was quiet for the redeye flight. The area was clean. The staff was great. The 787 Max was in good condition. Drawbacks were that the seat widths were tight for some passengers. The seat padding was at best average and for a long flight uncomfortable.

Southwest like most American domestic airlines, is a mediocre airline. But it is among the cheapest. Oh well.

My flight was delayed 50 minutes and we were rushed to board to then sit for 15 minutes until the pilot arrived. Unacceptable since we could have waited to board. Also the delayed flight was updated AFTER we boarded to more than the 10 minutes as originally stated.

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

Information on your arrival and departure airports

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