Direct (non-stop) flights from Chicago to San Jose Cabo

All flight schedules from Chicago Midway International , Illinois , USA to Los Cabos International, Mexico. This route is operated by Southwest Airlines and the flight time is 4 hours and 45 minutes. The distance is 1815 miles.

Monthly schedule
Week schedules
Airlines
Aircrafts
Price search
MDW Chicago Midway International
USA
Chicago , IL , USA
SJD Los Cabos International
Mexico
San Jose Cabo, Mexico
CHANGE DIRECTION
Flight time
4h 45m
Flight distance
1815mi, 2920km
Flights from Chicago to San Jose Cabo route map
VIEW LARGER MAP
USA
USA
MDW
Chicago , IL
aircraft image
Mexico
Mexico
SJD
San Jose Cabo
Distance
1815 miles · (2920 km)
CHANGE DIRECTION
Flight time
4 hours and 45 minutes

Airlines with direct flights from Chicago (MDW) to San Jose Cabo (SJD)

  • Southwest Airlines
    S
    M
    T
    W
    T
    F
    S
    Begins in 2027-03-11
    Low-cost airline
    1 daily flight
FLIGHTS WITH STOPS
SELECT DATES & SHOW PRICES
MDW SJD
Select dates
Check prices
MONTHLY
WN
WEEKLY

Chicago (MDW) to San Jose Cabo (SJD) flight schedule

The monthly calendar shows every direct flight departure from Chicago Midway International (MDW) with all airlines. Click on a date to see a list of flights or search for the best prices.

Southwest

View return flights from SJD to MDW

Southwest Airlines flight schedule from Chicago to San Jose Cabo

All weekly departures with Southwest Airlines. The week calendar shows every flight departure from Chicago (MDW) to San Jose Cabo (SJD). Click on a blue date to see a list of flights.

Week 10 (Mar 8 - Mar 14)
  • Week 10 (Mar 8 - Mar 14)
  • Week 11 (Mar 15 - Mar 21)
  • Week 12 (Mar 22 - Mar 28)
  • Week 13 (Mar 29 - Apr 4)
  • Week 14 (Apr 5 - Apr 11)
Flight
Mon
Mar 8
Tue
Mar 9
Wed
Mar 10
Thu
Mar 11
Fri
Mar 12
Sat
Mar 13
Sun
Mar 14
WN3636
----
----
----
10:10
10:10
08:50
08:55
Flight time
4h 40m - 4h 45m
Route added
June 2018

MX
Arriving at Los Cabos (SJD)

Los Cabos International (SJD) is a mid-sized airport based in San Jose Cabo, Mexico. You can fly to 56 destinations with 18 airlines in scheduled passenger traffic.

Show all flights from SJD

Best prices on rental cars in San Jose Cabo
Compare prices and book now with free cancellation.
SEARCH FOR RENTAL CARS
Hotel deals in San Jose Cabo with free cancellation
HOTEL PRICES
Top 10 things to do in San Jose Cabo
Find out what other travelers are looking for in San Jose Cabo.
SHOW ACTIVITIES

US
Departing from Chicago Midway (MDW) , Illinois

Chicago Midway International (MDW) is a large airport in USA. You can fly to 97 destinations with 6 airlines in scheduled passenger traffic.

Show all flights from MDW

Airlines with alternative airports from Chicago to San Jose Cabo

The airlines below are departing from or arriving to other airports in the same city or very close.

American Airlines
Oneworld
Chicago O Hare International Los Cabos International
Duration
5 hours and 03 minutes
Frontier Airlines
Chicago O Hare International Los Cabos International
Duration
4 hours and 43 minutes
United
Star Alliance
Chicago O Hare International Los Cabos International
Duration
5 hours and 00 minutes
Show detailed flight schedule from ORD to SJD

Chicago - San Jose Cabo flight price statistics

$1130
Approximate

The numbers are avarage prices found based on user searches for direct flights between Chicago Midway International and Los Cabos International. Its calculated from the cheapest prices found per month for a round-trip with 1 adult and can vary depending on the amount of data we have for this particular route.

N/A
Jan
N/A
Feb
$582
Mar
$622
Apr
$604
May
$751
Jun
$938
Jul
N/A
Aug
N/A
Sep
N/A
Oct
$1048
Nov
$780
Dec

Approximate prices for one round-trip flight from Chicago (MDW) to San Jose Cabo (SJD). Graph is not to scale.

CLICK HERE FOR EXACT PRICES

Type of aircraft(s) on this route

Below is a list of aircraft types we have within our database with flights on this route. You can also see the aircrafts seat capacity together with classes.

Boeing 737-700 Passenger (Scimitar Winglets)
Southwest Airlines
137 seats
 (All economy)
Boeing 737MAX 8 Passenger
Southwest Airlines
Boeing 737MAX 8 Passenger illustration
Boeing 737MAX 8 Passenger illustration
175 seats
 (All economy)
ROUTE EXPLORING

Chicago Midway International - all destinations

With FlightsFrom.com’s brilliant search features you can explore all non-stop flights from a specific airport. Simply select your preferred airport to get an overview of every single non-stop flight offered. Click on one of the routes to get information about which airline’s operate the route, when the next scheduled flight is or to filter your search even more.

EXPLORE ALL DESTINATIONS

 

Chicago flight map

Select your flight details

Round trip
1 adult
Economy

You may have missed to select a date. Please check the calendar. If you dont know your date, use on the button "I dont know my dates"

I HAVE NO DATES
CHECK PRICES

Frequently asked questions FAQ

  • The flight between Chicago (MDW) and San Jose Cabo (SJD) typically takes about 4 hour and 43 minute.
  • The flight number is WN3636 and it's operated by Southwest Airlines.
  • From Chicago you will fly out from Chicago Midway International (MDW) and you will be landing at Los Cabos International (SJD).
  • Boeing 737 flies this route operated by Southwest.
  • Southwest have non-stop flights to San Jose Cabo.
  • They arrive at terminal 2.
VIEW IN
MAP EXPLORER Flights from Chicago to San Jose Cabo route map
Non-stop flights from MDW to SJD
1815 miles (2920 km) · 4 hours and 45 minutes
CHECK PRICES

Popular routes from Chicago

Southwest Airlines Southwest Airlines routes

Chicago (MDW) - Phoenix (PHX)

US

Chicago (MDW) - New York (LGA)

US

Chicago (MDW) - Orlando (MCO)

US

Chicago (MDW) - Washington (DCA)

US

Chicago (MDW) - Dallas (DAL)

US

For more destinations from Chicago with Southwest Airlines (WN), check out the Southwest Airlines route map .

What is FlightsFrom?

FlightsFrom.com is a useful website for finding airline routes and flight schedules globally. The idea is being able to explore destination opportunities through non-stop flights from a specific airport. It's a tool to set up your business meeting or weekend holiday based on your timeschedule and your closest airport.

Part of its appeal is that it just makes trips easier to plan; you see the departure times of every non-stop flight in a list.

- MSN.com

I always wondered where you could fly direct from a particular airport (Burbank, I’m looking at you) and those answers can be tough to find. Not anymore!

- Rich on tech

Many mainstream sites don’t list low-cost carriers or link transoceanic flights to regionally based carriers that can provide less expensive options. For that, you need a bigger tool kit… (Hint: search by destination airport at FlightsFrom.com)

- The New York Times

Many low-cost carriers airlines prevent their flights from showing up on some of these (read Vayama or Google Flights) third-party travel websites. If you want a chance to view all local departures, try using FlightsFrom.com

- Lifehacker

Social Media

Don't want to miss anything new?
Follow us!

Select airport
Airport map
Fun facts
Privacy policy
About FlightsFrom.com
Copyright 2017-2026 FLIGHTSFROM.COM