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Flights from San Diego to Chicago – Direct & connecting routes

Non-stop airlines Connecting flights Show map Price search

SAN to MDW flights and routes map SAN to MDW – All flight route options from San Diego International Airport, California, USA to Chicago Midway International, Illinois, USA. These flights are operated by 3 airlines. Fly non-stop with Southwest Airlines or choose from 20 different transit flights. The shortest flight time is 4 hours. 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 SAN San Diego Airport San Diego, CA, USA
USA MDW Chicago Midway , IL, USA
SAN
San Diego Airport
USASan Diego, CA, USA
Chicago Midway
USAChicago, IL, USA
MDW
1 direct route found »
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22 routes with 1 stop found »
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Non-stop route options:

Duration

Southwest Airlines
Non-stop with Southwest Airlines. 3-6 flights per day.

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4h 00m

Southwest Airlines
Non-stop with Southwest Airlines.
4h 00m
3-6 flights per day.
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1 stop route options with the same airline:

Duration

Via Tucson TUS
1 stop with Southwest Airlines. 0-1 flights per day.
Begins in 30/11

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6h 10m

Begins in 30/11
Via Tucson TUS
1 stop with Southwest Airlines.
6h 10m
0-1 flights per day.
Begins in 30/11
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Via Saint Louis STL
1 stop with Southwest Airlines. 0-1 flights per day.

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6h 15m

Via Saint Louis STL
1 stop with Southwest Airlines.
6h 15m
0-1 flights per day.
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Via Omaha OMA
1 stop with Southwest Airlines. 0-1 flights per day.
Begins in 22/11

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6h 25m

Begins in 22/11
Via Omaha OMA
1 stop with Southwest Airlines.
6h 25m
0-1 flights per day.
Begins in 22/11
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Via Kansas City MCI
1 stop with Southwest Airlines. 0-3 flights per day.

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6h 33m

Via Kansas City MCI
1 stop with Southwest Airlines.
6h 33m
0-3 flights per day.
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Via Salt Lake City SLC
1 stop with Southwest Airlines. 0-1 flights per day.
Tue,Wed & Sun

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6h 38m

Tue,Wed & Sun
Via Salt Lake City SLC
1 stop with Southwest Airlines.
6h 38m
0-1 flights per day.
Tue,Wed & Sun
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Via Phoenix PHX
1 stop with Southwest Airlines. 4-7 flights per day.

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6h 48m

Via Phoenix PHX
1 stop with Southwest Airlines.
6h 48m
4-7 flights per day.
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Via Indianapolis IND
1 stop with Southwest Airlines.
Begins in 7/8

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6h 50m

Begins in 7/8
Via Indianapolis IND
1 stop with Southwest Airlines.
6h 50m
Begins in 7/8
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Via Dallas DFW
1 stop with Frontier Airlines. 0-1 flights per day.
Tue & Wed

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7h 05m

Tue & Wed
Via Dallas DFW
1 stop with Frontier Airlines.
7h 05m
0-1 flights per day.
Tue & Wed
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Via Las Vegas LAS
1 stop with Southwest Airlines. 6-10 flights per day.

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7h 05m

Via Las Vegas LAS
1 stop with Southwest Airlines.
7h 05m
6-10 flights per day.
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Via Phoenix PHX
1 stop with Frontier Airlines. 0-1 flights per day.
Begins in 21/8

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7h 12m

Begins in 21/8
Via Phoenix PHX
1 stop with Frontier Airlines.
7h 12m
0-1 flights per day.
Begins in 21/8
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Via Denver DEN
1 stop with Southwest Airlines. 3-7 flights per day.

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7h 15m

Via Denver DEN
1 stop with Southwest Airlines.
7h 15m
3-7 flights per day.
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Via Minneapolis MSP
1 stop with Delta Air Lines.

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7h 17m

Via Minneapolis MSP
1 stop with Delta Air Lines.
7h 17m
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Via Austin AUS
1 stop with Southwest Airlines. 1-4 flights per day.

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7h 25m

Via Austin AUS
1 stop with Southwest Airlines.
7h 25m
1-4 flights per day.
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Via Albuquerque ABQ
1 stop with Southwest Airlines. 0-1 flights per day.
Fri & Sun

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7h 30m

Fri & Sun
Via Albuquerque ABQ
1 stop with Southwest Airlines.
7h 30m
0-1 flights per day.
Fri & Sun
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Via Denver DEN
1 stop with Frontier Airlines. 0-1 flights per day.
Thu,Sat & Sun

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7h 32m

Thu,Sat & Sun
Via Denver DEN
1 stop with Frontier Airlines.
7h 32m
0-1 flights per day.
Thu,Sat & Sun
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Via Nashville BNA
1 stop with Southwest Airlines. 0-1 flights per day.

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7h 35m

Via Nashville BNA
1 stop with Southwest Airlines.
7h 35m
0-1 flights per day.
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Via El Paso ELP
1 stop with Southwest Airlines. 0-1 flights per day.
Mon,Thu & Fri

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7h 35m

Mon,Thu & Fri
Via El Paso ELP
1 stop with Southwest Airlines.
7h 35m
0-1 flights per day.
Mon,Thu & Fri
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Via Dallas DAL
1 stop with Southwest Airlines. 2-4 flights per day.

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7h 40m

Via Dallas DAL
1 stop with Southwest Airlines.
7h 40m
2-4 flights per day.
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Via Oklahoma City OKC
1 stop with Southwest Airlines. 0-1 flights per day.
Tue,Wed & Sun

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7h 40m

Tue,Wed & Sun
Via Oklahoma City OKC
1 stop with Southwest Airlines.
7h 40m
0-1 flights per day.
Tue,Wed & Sun
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Via San Antonio SAT
1 stop with Southwest Airlines. 0-2 flights per day.
Begins in 2/10

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7h 50m

Begins in 2/10
Via San Antonio SAT
1 stop with Southwest Airlines.
7h 50m
0-2 flights per day.
Begins in 2/10
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Via Detroit DTW
1 stop with Delta Air Lines. 0-1 flights per day.

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8h 15m

Via Detroit DTW
1 stop with Delta Air Lines.
8h 15m
0-1 flights per day.
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Via Boise BOI
1 stop with Southwest Airlines. 0-1 flights per day.
Only sundays

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11h 05m

Only sundays
Via Boise BOI
1 stop with Southwest Airlines.
11h 05m
0-1 flights per day.
Only sundays
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San Diego to Chicago flights

There are over 21 airlines and as many as 329 flights every week to this destination. You can fly non-stop to Chicago (MDW) from San Diego (SAN) with Southwest Airlines but if a stopover option suits you better you can choose to fly via Tucson, Saint Louis or any other of the 20 alternatives with connectiing airports.

San Diego to Chicago with Southwest Airlines

You can fly non-stop every weekday with flights departing from 6:00 am to 7:00 pm. You can also catch a transit flight via Tucson or Saint Louis.

With Frontier Airlines

If you fly to Chicago from San Diego with Frontier Airlines you will do a stopover in Dallas.

Distance & flight times: San Diego International Airport to Midway International Airport

The shortest flight time between SAN and MDW is 4 hours.

ViaTotal flight timeLayover timeDistance
Direct4h 0m-1734 miles (2790 km)
TUS Tucson6h 10m1h 30m1813 miles (2917 km)
STL Saint Louis6h 15m1h 50m1814 miles (2919 km)
OMA Omaha6h 25m1h 50m1741 miles (2801 km)
MCI Kansas City6h 33m2h 55m1743 miles (2804 km)
SLC Salt Lake City6h 38m1h 35m1892 miles (3044 km)
IND Indianapolis6h 50m35m1950 miles (3138 km)
LAS Las Vegas7h 5m2h 35m1785 miles (2872 km)
DFW Dallas7h 5m1h 15m1975 miles (3178 km)
PHX Phoenix7h 12m1h 57m1754 miles (2822 km)
MSP Minneapolis7h 17m2h 0m1888 miles (3038 km)
AUS Austin7h 25m45m2145 miles (3451 km)
ABQ Albuquerque7h 30m40m1755 miles (2824 km)
DEN Denver7h 32m1h 37m1754 miles (2822 km)
BNA Nashville7h 35m1h 55m2153 miles (3464 km)
ELP El Paso7h 35m2h 35m1879 miles (3023 km)
OKC Oklahoma City7h 40m1h 50m1834 miles (2951 km)
DAL Dallas7h 40m2h 10m1983 miles (3191 km)
SAT San Antonio7h 50m2h 30m2175 miles (3500 km)
DTW Detroit8h 15m2h 45m2192 miles (3527 km)
BOI Boise11h 5m2h 40m2206 miles (3549 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.SAN-MDW flight routesSan Diego to Chicago flight routes illustrated on a map.
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Departing from San Diego International Airport
Departing from San Diego International Airport. Copyright: San Diego International Airport
San Diego - Chicago route map and flight paths
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Show all destinations from SAN Show all destinations from MDW

You can fly non-stop from San Diego (SAN) to Chicago (MDW) with Southwest Airlines. The flight takes approximately 4 hours. If you travel with a connecting flight instead, for example via Tucson, the total flight time will be 6 hours and 10 minutes.

If you're interested in direct flights, Southwest Airlines is available. For flights with stopovers, Southwest Airlines, Frontier Airlines or Delta Air Lines is also an option.

The flight time between San Diego Airport (SAN) and Chicago Midway International (MDW) is approximately 4 hours. The distance between the two airports is 2192 miles (or 3527 kilometers).

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