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

Non-stop airlines Connecting flights Show map Price search

SJD to MDW flights and routes map SJD to MDW – All flight route options from Los Cabos International, Mexico to Chicago Midway International, Illinois, USA. These flights are operated by 2 airlines. Fly non-stop with Southwest Airlines or choose from 8 different transit flights. The shortest flight time is 4 hours and 5 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
Mexico SJD Los Cabos San Jose Cabo, Mexico
USA MDW Chicago Midway , IL, USA
SJD
Los Cabos
MexicoSan Jose Cabo, Mexico
Chicago Midway
USAChicago, IL, USA
MDW
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 05m

Begins in 22/11
Southwest Airlines
Non-stop with Southwest Airlines.
4h 05m
0-1 flights per day.
Begins in 22/11
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1 stop route options with the same airline:

Duration

Via Saint Louis STL
1 stop with Southwest Airlines. 0-1 flights per day.
Only saturdays

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6h 40m

Only saturdays
Via Saint Louis STL
1 stop with Southwest Airlines.
6h 40m
0-1 flights per day.
Only saturdays
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Via Nashville BNA
1 stop with Southwest Airlines. 0-1 flights per day.
Only saturdays

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7h 00m

Only saturdays
Via Nashville BNA
1 stop with Southwest Airlines.
7h 00m
0-1 flights per day.
Only saturdays
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Via Austin AUS
1 stop with Southwest Airlines. 0-1 flights per day.

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7h 23m

Via Austin AUS
1 stop with Southwest Airlines.
7h 23m
0-1 flights per day.
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Via Kansas City MCI
1 stop with Southwest Airlines. 0-1 flights per day.
Sat & Sun

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7h 23m

Sat & Sun
Via Kansas City MCI
1 stop with Southwest Airlines.
7h 23m
0-1 flights per day.
Sat & Sun
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Via Phoenix PHX
1 stop with Southwest Airlines. 1-2 flights per day.

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8h 18m

Via Phoenix PHX
1 stop with Southwest Airlines.
8h 18m
1-2 flights per day.
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Via Houston HOU
1 stop with Southwest Airlines. 2-3 flights per day.

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8h 25m

Via Houston HOU
1 stop with Southwest Airlines.
8h 25m
2-3 flights per day.
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Via Denver DEN
1 stop with Southwest Airlines. 1-2 flights per day.

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8h 35m

Via Denver DEN
1 stop with Southwest Airlines.
8h 35m
1-2 flights per day.
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Via Guadalajara GDL
1 stop with Volaris. 0-1 flights per day.

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8h 47m

Via Guadalajara GDL
1 stop with Volaris.
8h 47m
0-1 flights per day.
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1 stop route options with codeshare or different airlines:

Duration

Via Guadalajara GDL With Volaris & Frontier Airlines 0-1 flights per day.
CODESHARE

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8h 47m

Via Guadalajara GDL
8h 47m
With Volaris & Frontier Airlines 0-1 flights per day.
CODESHARE
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San Jose Cabo to Chicago flights

With over 78 flights every week and 9 different airlines you have a wide range of options. You can fly non-stop to Chicago (MDW) from San Jose Cabo (SJD) with Southwest Airlines but if a stopover option suits you better you can choose to fly via Saint Louis, Nashville or any other of the 8 alternatives with connectiing airports.

San Jose Cabo to Chicago with Southwest Airlines

You can fly non-stop with Southwest Airlines every Saturday at 14:00. You can also catch a transit flight via Saint Louis or Nashville.

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

With Volaris

If you fly from San Jose Cabo with Volaris you will do a stopover in Guadalajara, GDL before reaching Chicago. This flight trip will take 8 hours and 47 minutes and you can fly every day of the week except Mondays and Tuesday with departures at 08:29 or 08:41.

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

The shortest flight time between SJD and MDW is 4 hours and 5 minutes.

ViaTotal flight timeLayover timeDistance
Direct4h 5m-1815 miles (2920 km)
STL Saint Louis6h 40m4h 5m1827 miles (2940 km)
BNA Nashville7h 0m4h 30m2047 miles (3294 km)
AUS Austin7h 23m1h 45m1870 miles (3009 km)
MCI Kansas City7h 23m4h 30m1834 miles (2951 km)
PHX Phoenix8h 18m2h 55m2177 miles (3503 km)
HOU Houston8h 25m1h 30m1947 miles (3133 km)
DEN Denver8h 35m2h 20m2096 miles (3372 km)
GDL Guadalajara8h 47m3h 12m2187 miles (3519 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.SJD-MDW flight routesSan Jose Cabo to Chicago flight routes illustrated on a map.
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San Jose Cabo - Chicago route map and flight paths
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From San Jose Cabo to USA

Below is a list of other destinations to USA from Los Cabos International with either direct flights or 1 stop connections.

From Mexico to Chicago

Below is a list of other cities in Mexico with flights to Chicago with either non-stop or connecting flights.

You can fly non-stop from San Jose Cabo (SJD) to Chicago (MDW) with Southwest Airlines. The flight takes approximately 4 hours and 5 minutes. If you travel with a connecting flight instead, for example via Saint Louis, the total flight time will be 6 hours and 40 minutes.

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

The flight time between Los Cabos (SJD) and Chicago Midway International (MDW) is approximately 4 hours and 5 minutes. The distance between the two airports is 2177 miles (or 3503 kilometers).

Yes, you can fly non-stop to MDW from SJD 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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