CA $212 Cheap Flights from Chicago (MDW) to San José del Cabo (SJD)

View CA $212 flight on Tue, Sep. 9, 2025Opens in a new window

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

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

Prices were available within the past 7 days and start at CA $212 for one-way flights and for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Find the cheapest month to fly from Chicago (MDW) to San José del Cabo (SJD)

July is typically the cheapest month to fly

From CA $484 - CA $1,339 per traveller.

Graph displaying average flight prices per month

Flight from Chicago to San José del Cabo (MDW - SJD) route information
Origin airport
Midway Intl.
Destination airport
Los Cabos Intl.
Distance
2888 km

Chicago to San José del Cabo Flights

The easy way to book your flights from Chicago to San José del Cabo 

With Expedia, it’s simple to find and book flights to San José del Cabo from Chicago whether you’re traveling for business or pleasure. Enter your travel dates, hit search, and choose your flight from 20 airlines that cover this route. There are nonstop flights to Los Cabos Intl., too.  

Choose your preferred carrier and cabin class with the advanced search tool and select your ideal departure time. Then, if you want, you can see just nonstop or refundable flights. And if you’re traveling last minute, just enter the date to check out flights from Chicago to San José del Cabo today, tomorrow, or this week.  

 

Save dollars with cheap flights from Midway Intl., MDW to Los Cabos Intl., SJD 

Sort your search results by price to find great deals on your flight from Chicago to San José del Cabo—you get all your cheapest options first. Grab yourself a bargain now—the lowest price on flights to San José del Cabo from Chicago currently is just rising to .  

Here are more money-saving tips: 

  • Fly in when flight prices are normally at their lowest 
  • Book about a month to 6 weeks before you travel for the best prices to San José del Cabo  
  • Avoid peak season and weekends when flights can cost more
  • Early morning and late-night flights are sometimes cheaper, so try varying your travel times 
  • One surefire way to save money on your flight is to book your flight and hotel together with Expedia. Sometimes, the savings are so large that the flight is basically free! 

 

Reasons to choose Expedia for your flight to San José del Cabo from Chicago 

Whatever your destination, budget, or reason to travel, in just one quick search, you can choose from loads of flights, airlines, and cabin classes. The filters make it quick and easy to find your ideal flights, and if you choose one of the flexible options, you won’t be charged to change your flight. So book your flight to San José del Cabo with Expedia today.

Frequently asked questions

How much is a flight from MDW to SJD?
The lowest price advertised for a round-trip flight from Chicago Airport to Los Cabos Intl. Airport (SJD) is . But you better get moving. This figure is based on fares offered within the last 7 days on Expedia for flights departing within the next year. Prices and availability are subject to change. Additional terms apply.
Do I need to pay a cancellation fee if I cancel my flight from Midway Airport to SJD?
Each airline has its own set of terms and conditions. If you decide to cancel your trip, visit our Customer Service Portal.
How do I find cheap flights from Midway Airport to Los Cabos Intl. Airport (SJD) that have flexible change policies?
Select our "No change fees" filter to find flexible travel options for your flight from Midway Airport to SJD. This allows you to secure a great deal ahead of time and still have the freedom to make changes without any extra fees. If the new flight costs more, you'll just cover the difference.
How many hours is the flight from Midway Airport to Los Cabos Airport?
It takes approximately 6 hours and 16 minutes to jet from Midway Intl. Airport (MDW) to Los Cabos Intl. Airport (SJD). But with a solid playlist and a good book, the hours will pass by quicker.
How far is the flight from Midway Intl. Airport (MDW) to Los Cabos Airport?
It's around 2,900 kilometres between Midway Intl. Airport (MDW) and Los Cabos Intl. Airport (SJD), so you'll be flying for a while. Keep yourself occupied with things like playing cards (if you're travelling with friends) or a gripping book.
Which airlines fly direct from Midway Airport to SJD?
If you want to travel straight from MDW to Los Cabos Intl. Airport (SJD), you'll need to book a flight with at least one stop. Unfortunately, there aren't any airlines that fly directly between these airports.
Are Midway Intl. Airport (MDW) to Los Cabos Airport flight tickets cheaper when they're purchased at the last minute?
Flight prices go up and down like a yo-yo, so not always. While last-minute flight deals between Midway Intl. Airport (MDW) and Los Cabos Airport are possible, it also makes sense to keep track of prices well before you fly. In fact, some air carriers release their prices up to a year before the departure date. Expedia is constantly updating the biggest airfare bargains around, so check back often and be ready to grab your seat when the fares dip.

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Chicago nearby Airports

Chicago

O'Hare Intl. to San José del Cabo
CA $491.42
*Available to Expedia members.