$226 Cheap Flights from San José del Cabo (SJD) to Chicago (MDW)

View $226 flight on Thu, Aug 21, 2025Opens in a new window

Popular airlines from Los Cabos Intl. Airport (SJD) to Chicago Midway Airport (MDW)

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Cheap Flights from San José del Cabo to Chicago (SJD-MDW)

Prices were available within the past 7 days and start at $226 for one-way flights and $408 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Southwest Airlines
Fri, Jul 25 - Mon, Jul 28
SJD
San José del Cabo
MDW
Chicago
$408 Roundtrip, found 4 days ago
$408
Roundtrip
found 4 days ago
Select Southwest Airlines flight, departing Fri, Jul 25 from San José del Cabo to Chicago, returning Mon, Jul 28, priced at $408 found 4 days ago
Southwest Airlines
Fri, Oct 3 - Wed, Oct 8
SJD
San José del Cabo
MDW
Chicago
$409 Roundtrip, found 4 days ago
$409
Roundtrip
found 4 days ago
Select Southwest Airlines flight, departing Fri, Oct 3 from San José del Cabo to Chicago, returning Wed, Oct 8, priced at $409 found 4 days ago
Southwest Airlines
Wed, Aug 20 - Sun, Aug 24
SJD
San José del Cabo
MDW
Chicago
$417 Roundtrip, found 2 days ago
$417
Roundtrip
found 2 days ago
Select Southwest Airlines flight, departing Wed, Aug 20 from San José del Cabo to Chicago, returning Sun, Aug 24, priced at $417 found 2 days ago
Southwest Airlines
Wed, Aug 20 - Sun, Aug 24
SJD
San José del Cabo
MDW
Chicago
$419 Roundtrip, found 2 days ago
$419
Roundtrip
found 2 days ago
Select Southwest Airlines flight, departing Wed, Aug 20 from San José del Cabo to Chicago, returning Sun, Aug 24, priced at $419 found 2 days ago
Southwest Airlines
Fri, Aug 1 - Tue, Aug 5
SJD
San José del Cabo
MDW
Chicago
$439 Roundtrip, found 4 days ago
$439
Roundtrip
found 4 days ago
Select Southwest Airlines flight, departing Fri, Aug 1 from San José del Cabo to Chicago, returning Tue, Aug 5, priced at $439 found 4 days ago
Southwest Airlines
Thu, Jul 24 - Mon, Jul 28
SJD
San José del Cabo
MDW
Chicago
$440 Roundtrip, found 1 day ago
$440
Roundtrip
found 1 day ago
Select Southwest Airlines flight, departing Thu, Jul 24 from San José del Cabo to Chicago, returning Mon, Jul 28, priced at $440 found 1 day ago
Southwest Airlines
Fri, Aug 29 - Sat, Sep 6
SJD
San José del Cabo
MDW
Chicago
$445 Roundtrip, found 2 days ago
$445
Roundtrip
found 2 days ago
Select Southwest Airlines flight, departing Fri, Aug 29 from San José del Cabo to Chicago, returning Sat, Sep 6, priced at $445 found 2 days ago
Southwest Airlines
Mon, Jul 28 - Wed, Jul 30
SJD
San José del Cabo
MDW
Chicago
$447 Roundtrip, found 2 days ago
$447
Roundtrip
found 2 days ago
Select Southwest Airlines flight, departing Mon, Jul 28 from San José del Cabo to Chicago, returning Wed, Jul 30, priced at $447 found 2 days ago
Delta
Fri, Oct 3 - Wed, Oct 8
SJD
San José del Cabo
MDW
Chicago
$517 Roundtrip, found 4 days ago
$517
Roundtrip
found 4 days ago
Select Delta flight, departing Fri, Oct 3 from San José del Cabo to Chicago, returning Wed, Oct 8, priced at $517 found 4 days ago
Aeromexico
Fri, Aug 29 - Sat, Sep 6
SJD
San José del Cabo
MDW
Chicago
$565 Roundtrip, found 2 days ago
$565
Roundtrip
found 2 days ago
Select Aeromexico flight, departing Fri, Aug 29 from San José del Cabo to Chicago, returning Sat, Sep 6, priced at $565 found 2 days ago
Flights from San José del Cabo (SJD) to Chicago (MDW)
Origin airport
Los Cabos Intl.
Destination airport
Midway Intl.
Airlines serving
Delta, Southwest Airlines
Roundtrip price
$407
Distance
1805 mi

San José del Cabo to Chicago Flights

The cheapest times to fly from San José del Cabo to Chicago

On average, Thursday can be the cheapest time to fly, according to data from the Airlines Reporting Corporation (ARC), one of the world's biggest databases for global airline sales. The data reveals that you could save up to 16% by flying on a Thursday—the cheapest day to travel on average—instead of a Sunday—the most expensive. Some of the most affordable flights from San José del Cabo to Chicago are during the month of July. You can find some of the cheapest flights from San José del Cabo to Chicago with Expedia's search tool and vast selection of airlines.

 

The best time to book a flight from San José del Cabo to Chicago

Sunday is one of the best days to book for cheap flights from San José del Cabo to Chicago: Tickets reserved on a Sunday cost between 6% and 13% less than those reserved on a Friday, according to ARC data. The data also suggests booking early can also lead to cheaper airfares. You could save 24% by buying your tickets for domestic flights at least a month in advance and 10% by booking international flights 2 months in advance.

 

How to find cheap round-trip tickets from San José del Cabo to Chicago

Being flexible with your dates and using Expedia's Price Drop Protection and Price Tracking features are some of the best ways of finding a cheap ticket from San José del Cabo to Chicago in 2025. You can also book with separate airlines for your outbound and return journeys, from $226 one-way. Expedia also offers Price Drop Protection, so if the cost of your airfare goes down after booking, you'll receive a credit for the difference*. This is available for a small fee, and is free to One Key Gold and Platinum tier members.

 

Expedia's Price Tracking feature means you can stay on top of airfares without manually checking every day. It sends you automated price alerts for cheap San José del Cabo to Chicago flights and uses historical data to indicate when the best time to book is. Download Expedia's free app to activate this handy tool in a few easy taps.

 

You could also save big by booking one of Expedia's vacation packages. Bundling together your San José del Cabo to Chicago airfare with your accommodations and car rental is often cheaper than booking everything separately. There’s also One Key, Expedia's generous rewards program. Join for free and you could earn One Key cash on most bookings to save on future adventures.

 

*Terms apply.

 

Disclaimer: ARC The statistics are based on average round-trip ticket prices between January and August 2023. The percentages you see are averages.

 

Frequently asked questions

How much does a flight from Los Cabos Intl. Airport (SJD) to Midway Intl. Airport (MDW) cost?
Discover the latest flight deals from SJD to MDW by entering your preferred travel dates and searching on Expedia. Easily compare prices by departure date if you have flexibility with your schedule and use handy filters to explore prices for your preferred journey. As a member of One Key™, our free loyalty program, you can use Price Tracking to watch fares and receive notifications if prices go up or down.
What is the cheapest month to fly from SJD to MDW?
The cheapest flights from SJD to MDW are usually during off-peak season, when demand is lower. To save money, avoid flying during public holidays, school breaks and major local events.
What is the cheapest airline that flies from SJD to MDW?
Use the filter tool on Expedia to compare airlines and find the cheapest carrier that'll take you from SJD to MDW. Sort your results by "Price (lowest to highest)" to snap up a great deal.
How many flights per day from Los Cabos Intl. Airport (SJD) to Midway Intl. Airport (MDW)?
Nonstop flights from Los Cabos Intl. Airport (SJD) to Midway Intl. Airport (MDW) aren't available daily, so you'll need to take a flight with a layover. Explore your options with Expedia's filters. Enter your travel details and pick either "1 Stop" or "2+ Stops."
What day of the week has the most flights from SJD to MDW?
You'll generally find Tuesday the quietest day for flights, while Fridays tend to be the busiest.* However this can change from season to season and during public holidays or peak travel times.*Busiest/quietest day to travel is based on Expedia flight demand through January to December 2024.
What is the best time to fly from Los Cabos Intl. Airport (SJD) to Midway Intl. Airport (MDW)?
To avoid potential delays on the Los Cabos Intl. Airport (SJD) to Midway Intl. Airport (MDW) route, aim to travel before 3 PM. Flights after this time have a 22% higher chance of being canceled.**Most reliable time of the day and month to travel recommendation is based on January through August 2024 flight status data sourced from OAG's global flight data platform.
What airports do you fly into for Chicago from Los Cabos Intl. Airport (SJD)?
O'Hare Intl. Airport (ORD) is the only airport in Chicago with direct flights from Los Cabos Intl. Airport (SJD). Browse the available options and find affordable fares on Expedia.
Is it cheaper to buy a plane ticket from Los Cabos Intl. Airport (SJD) to Midway Intl. Airport (MDW) last-minute?
Last-minute bookings from SJD to MDW are usually more expensive. For the best prices, start searching for flights as early as possible. That being said, if your travel plans are flexible, you may land a cheap fare right before you leave.
Is it cheaper to book a SJD to MDW flight and hotel package?
You can save money by securing a SJD to MDW flight and hotel package compared to booking separately. In fact, you could save hundreds of dollars by bundling with Expedia. And it's easy to manage everything in one place. After choosing your ideal accommodations and flights, you can add extras such as car rentals, activities and tours.
Can I cancel or change the date of my flight from Los Cabos Intl. Airport (SJD) to Midway Intl. Airport (MDW)?
Typically, you're able to cancel or reschedule your SJD to MDW flight. However, there may be additional charges, especially if you booked more than 24 hours ago. Double-check your itinerary for the airline's fees and policies on flight changes, or if you want further details, head to our Customer Service portal.

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*Available to One Key members.