$220 Cheap Flights from San José del Cabo (SJD) to Chicago (MDW)

View $220 flight on Wed, Feb 4, 2026Opens in a new window

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

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

Prices were available within the past 7 days and start at $220 for one-way flights and $384 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Aeromexico
Fri, Jan 16 - Wed, Jan 21
SJD
San José del Cabo
MDW
Chicago
$384 Roundtrip, found 3 days ago
$384
Roundtrip
found 3 days ago
Select Aeromexico flight, departing Fri, Jan 16 from San José del Cabo to Chicago, returning Wed, Jan 21, priced at $384 found 3 days ago
Southwest Airlines
Thu, Dec 11 - Sun, Dec 14
SJD
San José del Cabo
MDW
Chicago
$385 Roundtrip, found 3 days ago
$385
Roundtrip
found 3 days ago
Select Southwest Airlines flight, departing Thu, Dec 11 from San José del Cabo to Chicago, returning Sun, Dec 14, priced at $385 found 3 days ago
Aeromexico
Tue, Feb 3 - Tue, Feb 17
SJD
San José del Cabo
MDW
Chicago
$388 Roundtrip, found 3 days ago
$388
Roundtrip
found 3 days ago
Select Aeromexico flight, departing Tue, Feb 3 from San José del Cabo to Chicago, returning Tue, Feb 17, priced at $388 found 3 days ago
Southwest Airlines
Wed, Jan 14 - Sun, Jan 18
SJD
San José del Cabo
MDW
Chicago
$396 Roundtrip, found 3 days ago
$396
Roundtrip
found 3 days ago
Select Southwest Airlines flight, departing Wed, Jan 14 from San José del Cabo to Chicago, returning Sun, Jan 18, priced at $396 found 3 days ago
Southwest Airlines
Thu, Nov 13 - Wed, Nov 19
SJD
San José del Cabo
MDW
Chicago
$406 Roundtrip, found 3 days ago
$406
Roundtrip
found 3 days ago
Select Southwest Airlines flight, departing Thu, Nov 13 from San José del Cabo to Chicago, returning Wed, Nov 19, priced at $406 found 3 days ago
Southwest Airlines
Fri, Jan 16 - Wed, Jan 21
SJD
San José del Cabo
MDW
Chicago
$407 Roundtrip, found 3 days ago
$407
Roundtrip
found 3 days ago
Select Southwest Airlines flight, departing Fri, Jan 16 from San José del Cabo to Chicago, returning Wed, Jan 21, priced at $407 found 3 days ago
Southwest Airlines
Wed, Jan 14 - Sun, Jan 18
SJD
San José del Cabo
MDW
Chicago
$415 Roundtrip, found 3 days ago
$415
Roundtrip
found 3 days ago
Select Southwest Airlines flight, departing Wed, Jan 14 from San José del Cabo to Chicago, returning Sun, Jan 18, priced at $415 found 3 days ago
Delta
Sat, Nov 15 - Tue, Nov 18
SJD
San José del Cabo
MDW
Chicago
$432 Roundtrip, found 5 days ago
$432
Roundtrip
found 5 days ago
Select Delta flight, departing Sat, Nov 15 from San José del Cabo to Chicago, returning Tue, Nov 18, priced at $432 found 5 days ago
Frontier Airlines
Sat, Feb 28 - Sat, Mar 14
SJD
San José del Cabo
MDW
Chicago
$863 Roundtrip, found 3 days ago
$863
Roundtrip
found 3 days ago
Select Frontier Airlines flight, departing Sat, Feb 28 from San José del Cabo to Chicago, returning Sat, Mar 14, priced at $863 found 3 days ago
Volaris
Sat, Dec 13 - Sat, Dec 20
SJD
San José del Cabo
MDW
Chicago
$1,154 Roundtrip, found 3 days ago
$1,154
Roundtrip
found 3 days ago
Select Volaris flight, departing Sat, Dec 13 from San José del Cabo to Chicago, returning Sat, Dec 20, priced at $1,154 found 3 days ago

Alternative airports near Chicago

Prices were available within the past 7 days. Prices and availability are subject to change.

Select flight to O'Hare Intl. ORD. Cheapest option available. Average driving time to city center is 23 minutes. Flights from $416
ORD
O'Hare Intl.
Cheapest
Average driving time to city center23 min
Flights from $416

Frequently asked questions

How much does a flight from Los Cabos Intl. Airport (SJD) to Midway Intl. Airport (MDW) cost?
Secure a cheap one-way flight from $220 or cheap return flight from $384 from Los Cabos Intl. Airport (SJD) to Midway Intl. Airport (MDW) with Expedia. Enter your travel dates and sort by "Price (lowest to highest)" to find our cheapest flight offers on this route.
What is the cheapest month to fly from Los Cabos Intl. Airport (SJD) to Midway Intl. Airport (MDW)?
January is the cheapest month to fly from SJD to MDW. Traveling outside of peak seasons is often the key to finding better fares.
What is the cheapest airline that flies from Los Cabos Intl. Airport (SJD) to Midway Intl. Airport (MDW)?
To find the cheapest airline flying from SJD to MDW, use Expedia's filter tool. Customize your search based on what's important to you, such as preferred carriers and number of stops. You can then sort your results by "Price (lowest to highest)" to see the cheapest fares upfront.
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.

Travel information

Origin airport
Los Cabos Intl.
Destination airport
Midway Intl.
Airlines serving
Aeromexico, Delta, Southwest Airlines
Roundtrip price
$384
Distance
1805 mi

Book with confidence

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 January. 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 $220 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.

 

San José del Cabo to Chicago Flights

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*Available to One Key members.