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Flights from Chicago to San Jose Cabo – Direct & connecting routes

Non-stop airlines Connecting flights Show map Price search

MDW to SJD flights and routes map MDW to SJD – All flight route options from Chicago Midway International, Illinois, USA to Los Cabos International, Mexico. These flights are operated by 3 airlines. Fly non-stop with Southwest Airlines or choose from 8 different transit flights. The shortest flight time is 4 hours and 50 minutes. See the full flight schedule and time table, including departure times, airlines and stopover details to find the best option for you.

From
To
USA MDW Chicago Midway Chicago, IL, USA
Mexico SJD Los Cabos , Mexico
MDW
Chicago Midway
USAChicago, IL, USA
Los Cabos
MexicoSan Jose Cabo, Mexico
SJD
1 direct route found »
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9 routes with 1 stop found »
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Non-stop route options:

Duration

Southwest Airlines
Non-stop with Southwest Airlines. 0-1 flights per day.
Begins in 22/11

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4h 50m

Begins in 22/11
Southwest Airlines
Non-stop with Southwest Airlines.
4h 50m
0-1 flights per day.
Begins in 22/11
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1 stop route options with the same airline:

Duration

Via Austin AUS
1 stop with Southwest Airlines. 0-1 flights per day.

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5h 50m

Via Austin AUS
1 stop with Southwest Airlines.
5h 50m
0-1 flights per day.
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Via Kansas City MCI
1 stop with Southwest Airlines. 0-1 flights per day.
Only sundays

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6h 40m

Only sundays
Via Kansas City MCI
1 stop with Southwest Airlines.
6h 40m
0-1 flights per day.
Only sundays
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Via Saint Louis STL
1 stop with Southwest Airlines. 0-1 flights per day.
Begins in 8/11

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6h 40m

Begins in 8/11
Via Saint Louis STL
1 stop with Southwest Airlines.
6h 40m
0-1 flights per day.
Begins in 8/11
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Via Houston HOU
1 stop with Southwest Airlines. 2 flights per day.

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7h 05m

Via Houston HOU
1 stop with Southwest Airlines.
7h 05m
2 flights per day.
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Via Atlanta ATL
1 stop with Delta Air Lines. 1-2 flights per day.

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7h 30m

Via Atlanta ATL
1 stop with Delta Air Lines.
7h 30m
1-2 flights per day.
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Via Denver DEN
1 stop with Southwest Airlines. 1-3 flights per day.

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7h 45m

Via Denver DEN
1 stop with Southwest Airlines.
7h 45m
1-3 flights per day.
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Via Phoenix PHX
1 stop with Southwest Airlines. 2-4 flights per day.

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7h 55m

Via Phoenix PHX
1 stop with Southwest Airlines.
7h 55m
2-4 flights per day.
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Via Nashville BNA
1 stop with Southwest Airlines. 0-1 flights per day.
Only saturdays

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9h 30m

Only saturdays
Via Nashville BNA
1 stop with Southwest Airlines.
9h 30m
0-1 flights per day.
Only saturdays
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1 stop route options with codeshare or different airlines:

Duration

Via Atlanta ATL 1 stop with Aeromexico. 1-2 flights per day.
CODESHARE

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7h 30m

Via Atlanta ATL
7h 30m
1 stop with Aeromexico. 1-2 flights per day.
CODESHARE
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Chicago to San Jose Cabo flights

With over 90 flights every week and 9 different airlines you have a wide range of options. You can fly non-stop to San Jose Cabo (SJD) from Chicago (MDW) with Southwest Airlines but if a stopover option suits you better you can choose to fly via Austin, Saint Louis or any other of the 8 alternatives with connectiing airports.

Chicago to San Jose Cabo with Southwest Airlines

You can fly non-stop with Southwest Airlines every Saturday at 08:10. You can also catch a transit flight via Austin or Kansas City.

Note Non-stop flights with Southwest Airlines will begin in Nov 2025.

With Delta Air Lines

If you fly from Chicago with Delta Air Lines you will do a stopover in Atlanta, ATL before reaching San Jose Cabo. This flight trip will take 7 hours and 30 minutes and you can fly every weekday with departures at 06:00 or 06:04. Delta Air Lines is a member of SkyTeam.

Distance & flight times: Midway International Airport to Los Cabos International

The shortest flight time between MDW and SJD is 4 hours and 50 minutes.

ViaTotal flight timeLayover timeDistance
Direct4h 50m-1815 miles (2920 km)
AUS Austin5h 50m1h 5m1870 miles (3009 km)
STL Saint Louis6h 40m1h 5m1827 miles (2940 km)
MCI Kansas City6h 40m1h 45m1834 miles (2951 km)
HOU Houston7h 5m50m1947 miles (3133 km)
ATL Atlanta7h 30m1h 3m2296 miles (3694 km)
DEN Denver7h 45m3h 10m2096 miles (3372 km)
PHX Phoenix7h 55m1h 5m2177 miles (3503 km)
BNA Nashville9h 30m4h 5m2047 miles (3294 km)
The flight times and layover times in the table above are approximate and may vary depending on flight number, aircraft, airline, weather, and time of day.MDW-SJD flight routesChicago to San Jose Cabo flight routes illustrated on a map.
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Chicago - San Jose Cabo route map and flight paths
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From Chicago to Mexico

Below is a list of other destinations to Mexico from Chicago Midway International with either direct flights or 1 stop connections.

From USA to San Jose Cabo

Below is a list of other cities in USA with flights to San Jose Cabo with either non-stop or connecting flights.

You can fly non-stop from Chicago (MDW) to San Jose Cabo (SJD) with Southwest Airlines. The flight takes approximately 4 hours and 50 minutes. If you travel with a connecting flight instead, for example via Austin, the total flight time will be 5 hours and 50 minutes.

If you're interested in direct flights, Southwest Airlines is available. For flights with stopovers, Southwest Airlines and Aeromexico is also an option.

The flight time between Chicago Midway (MDW) and Los Cabos International (SJD) is approximately 4 hours and 50 minutes. The distance between the two airports is 2296 miles (or 3694 kilometers).

Yes, you can fly non-stop to SJD from MDW with Southwest Airlines.

A codeshare agreement means that cooperating airlines are able to sell seats on each other’s flights. This means that you are able to travel to more destinations than your airline of choice normally offers. Codeshare flights are also beneficial because of the seamless transits you can get with connecting flights from the same airline. The downside of choosing a codeshare flight can be that you in some cases can’t upgrade codeshare flights or use elite benefits.

A connecting or transit flight means that you reach your final destination through two or more flights – in other words a non-direct flight. You will change to a new aircraft after your first flight, this may include moving to another terminal at the airport aswell. The time required to transfer passengers and luggage between flights is called Minimum Connecting Time (MCT) and are always taken into account here on Flightroutes.com.

If you bought your whole flight on a single ticket, the airline will book you on the next available connecting flight.

With connecting flights, checked in luggage is most commonly forwarded to your final destination when buying a single ticket for both flights.

If you miss your connecting flight due to circumstances outside your control such as your first flight being delayed, you should turn to your airline who will provide you with a seat on the next available flight. This is usually done free of charge, and only applies if you purchased your trip as one ticket. If the next connecting flight is the following day, the airline usually provides accommodation and meals.
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