Cheap Flight Tickets from Chicago (MDW) to San José del Cabo (SJD), Starting at $329

Good to Know: Cheapest and Fastest MDW - SJD Flights

Useful information for finding best airline tickets from Chicago Midway International to Los Cabos International on your next trip.

Cheapest Round Trip Flight

$329

AM Aeromexico • 1 stop • 11h 42m

Sep 23 – Sep 27

The cheapest round trip flight from Chicago to San José del Cabo (MDW-SJD-MDW) is currently $329

🔍 Search Flights

Fastest Flight

11h 42m

The fastest nonstop flight from Chicago to San José del Cabo (MDW-SJD) takes 11h 42m

Top Airlines Flying from Chicago to San José del Cabo

Southwest Airlines-WN

Southwest Airlines

Delta Airline, DL

Delta Airlines

Aeromexico Airline (AM)

Aeromexico

Latest Flight Deals from Chicago (MDW) to San José del Cabo (SJD)

Compare and book low fare round-trip air tickets from Chicago to San José del Cabo. Ideal for travelers with confirmed return itineraries.

Sep 23 - Sep 27, Economy
AM
Chicago → San José del Cabo
11h 42m
6:05 AM - 11:07 AM • 1 stop
AM
Chicago → San José del Cabo
15h 8m
12:51 PM - 11:59 PM • 1 stop
$329
Aeromexico
Sep 23 - Sep 27, Economy
DL
Chicago → San José del Cabo
18h 50m
1:00 PM - 10:30 PM • 2 stops
DL
Chicago → San José del Cabo
15h 8m
12:51 PM - 11:59 PM • 1 stop
$329
Delta Airlines
Sep 23 - Sep 27, Economy
DL
Chicago → San José del Cabo
11h 42m
6:05 AM - 11:07 AM • 1 stop
DL
Chicago → San José del Cabo
15h 8m
12:51 PM - 11:59 PM • 1 stop
$329
Delta Airlines
Sep 23 - Sep 27, Economy
WN
Chicago → San José del Cabo
25h 20m
8:25 PM - 9:45 AM • 1 stop
WN
Chicago → San José del Cabo
15h 5m
1:10 PM - 12:15 AM • 1 stop
$329
Southwest Airlines

Fly from Chicago to San José del Cabo with the Best Airfare Deals on FareLeaders

Looking for a cheap last-minute deal or the best round-trip flight from Chicago to San José del Cabo? Find the biggest savings on one-way and round-trip tickets right here.

FAQs on Chicago to San José del Cabo Flights

What are the airports in Chicago?
ORD,MDW
What’s the most popular airline flying from MDW to SJD?
The most popular airline flying from Chicago to San José del Cabo are
Can I fly from MDW to SJD non-stop?
NO
Which airlines fly nonstop between Chicago and San José del Cabo?
The non-stop flights between Chicago and San José del Cabo are .
What’s the earliest departure time from MDW to SJD Airport?
The earliest flight leaves MDW at 6:05 am and lands in SJD - Los Cabos International
What are the airports in San José del Cabo?
SJD
Can I make changes to my Chicago to San José del Cabo flight tickets or cancel them on FareLeaders.com?
No. We are an airfare comparison site. All the tickets are booked by the travel agent offering the flight deal and any changes or cancellations to be made are directly done directly by them or the airlines.
Can I cancel my flight tickets from MDW to SJD?
Read the fare rules of the Chicago to San José del Cabo air tickets booked. Some airlines allow you to cancel the tickets within a stipulated time period with a cancellation fee.
Which airline alliances offer flights from Chicago and San José del Cabo?
operate flights between Chicago and San José del Cabo
How long does a flight from Chicago to San José del Cabo take?
It takes approximately 4 hour to fly non-stop from MDW to SJD, which is 1804.82 miles by air.
Which airlines provide the cheapest flights from Chicago (MDW) to San José del Cabo (SJD) ?
In the past couple of days, the cheapest tickets to SJD from MDW were found on AM : USD 329
Do I need a passport to fly between MDW and SJD?
Yes
What’s the latest departure time from MDW to SJD ?
The last flight leaves MDW at 8:25 pm

Chicago (MDW) to San José del Cabo (SJD): Airport Information

Origin Airport Chicago Midway International , Chicago, US
Destination Airport Los Cabos International , San José del Cabo, MX
Distance 1805 miles

More Flight Options for Chicago (MDW) and San José del Cabo (SJD)

Why Fareleaders for MDW to SJD Plane Tickets

Lowest Prices
Lowest Prices
Uncover the best deals on Chicago to San José del Cabo flights by comparing fares from hundreds of airlines and agencies.
New Deals
New Deals Everyday
Get the best prices on MDW to SJD flights—we update our fares daily so you never miss a saving.
Best Travel Options
No Service Fees
Compare hundreds of Chicago to San José del Cabo flights and secure the best deals—we never add any service fees.
Get Fare Drop Alert
Be the first to know when fares drop for the Chicago (MDW) to San José del Cabo (SJD)
Terms and Conditions*