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Flights from San Jose to Chicago – Direct & connecting routes

Non-stop airlines Connecting flights Show map Price search

SJC to MDW flights and routes map SJC to MDW – All flight route options from Norman Y Mineta San Jose International, 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 and 10 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 SJC Norman Y Mineta San Jose San Jose, CA, USA
USA MDW Chicago Midway , IL, USA
SJC
Norman Y Mineta San Jose
USASan Jose, CA, USA
Chicago Midway
USAChicago, IL, USA
MDW
1 direct route found »
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21 routes with 1 stop found »
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Non-stop route options:

Duration

Southwest Airlines
Non-stop with Southwest Airlines. 1-5 flights per day.

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4h 10m

Southwest Airlines
Non-stop with Southwest Airlines.
4h 10m
1-5 flights per day.
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1 stop route options with the same airline:

Duration

Via Denver DEN
1 stop with Frontier Airlines. 0-1 flights per day.
Thu & Sun

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6h 36m

Thu & Sun
Via Denver DEN
1 stop with Frontier Airlines.
6h 36m
0-1 flights per day.
Thu & Sun
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Via Portland PDX
1 stop with Southwest Airlines. 0-1 flights per day.

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6h 40m

Via Portland PDX
1 stop with Southwest Airlines.
6h 40m
0-1 flights per day.
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Via Reno RNO
1 stop with Southwest Airlines.
Begins in 7/8

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6h 40m

Begins in 7/8
Via Reno RNO
1 stop with Southwest Airlines.
6h 40m
Begins in 7/8
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Via Boise BOI
1 stop with Southwest Airlines. 0-1 flights per day.

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6h 50m

Via Boise BOI
1 stop with Southwest Airlines.
6h 50m
0-1 flights per day.
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Via Los Angeles LAX
1 stop with Southwest Airlines. 2-3 flights per day.

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7h 13m

Via Los Angeles LAX
1 stop with Southwest Airlines.
7h 13m
2-3 flights per day.
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Via Burbank BUR
1 stop with Southwest Airlines. 0-1 flights per day.
Only sundays

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7h 15m

Only sundays
Via Burbank BUR
1 stop with Southwest Airlines.
7h 15m
0-1 flights per day.
Only sundays
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Via Salt Lake City SLC
1 stop with Southwest Airlines. 0-2 flights per day.
Only sundays

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7h 15m

Only sundays
Via Salt Lake City SLC
1 stop with Southwest Airlines.
7h 15m
0-2 flights per day.
Only sundays
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Via Tulsa TUL
1 stop with Southwest Airlines.
Begins in 5/10

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7h 20m

Begins in 5/10
Via Tulsa TUL
1 stop with Southwest Airlines.
7h 20m
Begins in 5/10
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Via Denver DEN
1 stop with Southwest Airlines. 2-7 flights per day.

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7h 25m

Via Denver DEN
1 stop with Southwest Airlines.
7h 25m
2-7 flights per day.
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Via Las Vegas LAS
1 stop with Southwest Airlines. 5-12 flights per day.

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7h 25m

Via Las Vegas LAS
1 stop with Southwest Airlines.
7h 25m
5-12 flights per day.
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Via Ontario ONT
1 stop with Southwest Airlines. 0-1 flights per day.
Begins in 5/8

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7h 30m

Begins in 5/8
Via Ontario ONT
1 stop with Southwest Airlines.
7h 30m
0-1 flights per day.
Begins in 5/8
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Via San Diego SAN
1 stop with Southwest Airlines. 3-6 flights per day.

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7h 30m

Via San Diego SAN
1 stop with Southwest Airlines.
7h 30m
3-6 flights per day.
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Via Phoenix PHX
1 stop with Southwest Airlines. 4-9 flights per day.

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7h 33m

Via Phoenix PHX
1 stop with Southwest Airlines.
7h 33m
4-9 flights per day.
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Via Long Beach LGB
1 stop with Southwest Airlines. 0-1 flights per day.

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7h 35m

Via Long Beach LGB
1 stop with Southwest Airlines.
7h 35m
0-1 flights per day.
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Via Saint Louis STL
1 stop with Southwest Airlines. 0-3 flights per day.

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7h 58m

Via Saint Louis STL
1 stop with Southwest Airlines.
7h 58m
0-3 flights per day.
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Via Detroit DTW
1 stop with Delta Air Lines.

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8h 10m

Via Detroit DTW
1 stop with Delta Air Lines.
8h 10m
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Via Dallas DAL
1 stop with Southwest Airlines. 1-5 flights per day.

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8h 10m

Via Dallas DAL
1 stop with Southwest Airlines.
8h 10m
1-5 flights per day.
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Via Nashville BNA
1 stop with Southwest Airlines. 0-1 flights per day.

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8h 30m

Via Nashville BNA
1 stop with Southwest Airlines.
8h 30m
0-1 flights per day.
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Via Kansas City MCI
1 stop with Southwest Airlines. 0-1 flights per day.
Tue,Wed & Fri

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8h 35m

Tue,Wed & Fri
Via Kansas City MCI
1 stop with Southwest Airlines.
8h 35m
0-1 flights per day.
Tue,Wed & Fri
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Via El Paso ELP
1 stop with Southwest Airlines. 0-1 flights per day.
Tue & Wed

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8h 50m

Tue & Wed
Via El Paso ELP
1 stop with Southwest Airlines.
8h 50m
0-1 flights per day.
Tue & Wed
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Via Albuquerque ABQ
1 stop with Southwest Airlines.
Only fridays

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9h 20m

Only fridays
Via Albuquerque ABQ
1 stop with Southwest Airlines.
9h 20m
Only fridays
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San Jose to Chicago flights

There are over 21 airlines and as many as 334 flights every week to this destination. You can fly non-stop to Chicago (MDW) from San Jose (SJC) with Southwest Airlines but if a stopover option suits you better you can choose to fly via Portland, Reno or any other of the 20 alternatives with connectiing airports.

San Jose to Chicago with Southwest Airlines

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

With Frontier Airlines

If you fly from San Jose with Frontier Airlines you will do a stopover in Denver, DEN before reaching Chicago. This flight trip will take 6 hours and 36 minutes and you can fly every Thursday or Sunday with departures at 12:18.

Distance & flight times: Norman Y Mineta San Jose International to Midway International Airport

The shortest flight time between SJC and MDW is 4 hours and 10 minutes.

ViaTotal flight timeLayover timeDistance
Direct4h 10m-1843 miles (2965 km)
PDX Portland6h 40m55m2328 miles (3746 km)
RNO Reno6h 40m1h 50m1874 miles (3015 km)
BOI Boise6h 50m2h 55m1977 miles (3181 km)
LAX Los Angeles7h 13m1h 55m2065 miles (3323 km)
SLC Salt Lake City7h 15m2h 5m1848 miles (2973 km)
BUR Burbank7h 15m1h 35m2043 miles (3287 km)
TUL Tulsa7h 20m50m2031 miles (3268 km)
LAS Las Vegas7h 25m1h 30m1912 miles (3076 km)
DEN Denver7h 25m2h 25m1849 miles (2975 km)
SAN San Diego7h 30m2h 15m2153 miles (3464 km)
ONT Ontario7h 30m2h 30m2046 miles (3292 km)
PHX Phoenix7h 33m2h 10m2072 miles (3334 km)
LGB Long Beach7h 35m2h 25m2072 miles (3334 km)
STL Saint Louis7h 58m1h 15m1972 miles (3173 km)
DAL Dallas8h 10m1h 0m2252 miles (3623 km)
DTW Detroit8h 10m1h 55m2298 miles (3697 km)
BNA Nashville8h 30m50m2349 miles (3780 km)
MCI Kansas City8h 35m50m1888 miles (3038 km)
ELP El Paso8h 50m1h 0m2210 miles (3556 km)
ABQ Albuquerque9h 20m2h 40m1997 miles (3213 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.SJC-MDW flight routesSan Jose to Chicago flight routes illustrated on a map.
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Departing from Norman Y Mineta San Jose International
Departing from Norman Y Mineta San Jose International. Copyright: SJC Airport
San Jose - Chicago route map and flight paths
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You can fly non-stop from San Jose (SJC) to Chicago (MDW) with Southwest Airlines. The flight takes approximately 4 hours and 10 minutes. If you travel with a connecting flight instead, for example via Portland, 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 Delta Air Lines is also an option.

The flight time between Norman Y Mineta San Jose (SJC) and Chicago Midway International (MDW) is approximately 4 hours and 10 minutes. The distance between the two airports is 2298 miles (or 3697 kilometers).

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