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We found 42 matches for direct flights, non-stop flights, and last-minute flights between SAN and MDW. Use the table below to sort by number of connections or the time of day to find flights that leave SAN for MDW in the morning, afternoon, or evening.
Be sure to check our list of deals to see which airlines are offering special prices on airfare to Chicago, IL (MDW) or airfare from San Diego, CA (SAN).
| Airline | Flt. | Departs | Time | Arrives | Time |
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| Southwest Airlines | 2726 | SAN | 6:55am | MDW | 12:55pm | nonstop | |
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| Southwest Airlines | 668 | SAN | 9:05am | MDW | 3:55pm | direct | |
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| Southwest Airlines | 1247 | SAN | 10:25am | MDW | 4:25pm | nonstop | |
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| Southwest Airlines | 861 | SAN | 12:35pm | MDW | 7:30pm | direct | |
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| Southwest Airlines | 1413 | SAN | 3:00pm | MDW | 9:00pm | nonstop | |
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| Southwest Airlines | 92 | SAN | 4:40pm | MDW | 10:40pm | nonstop | |
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| Southwest Airlines | 2356 | SAN | 1:30pm | MDW | 9:30pm | Nashville (BNA) | |
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| United Airlines | 484 | SAN | 6:20am | MDW | 2:11pm | Denver (DEN) | Search prices |
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| Frontier Airlines | 550 | SAN | 6:25am | MDW | 2:11pm | Denver (DEN) | Search prices |
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| Frontier Airlines | 566 | SAN | 9:10am | MDW | 6:17pm | Denver (DEN) | Search prices |
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| Southwest Airlines | 5300 | SAN | 10:05am | MDW | 7:30pm | Denver (DEN) | |
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| Southwest Airlines | 5300 | SAN | 10:05am | MDW | 5:30pm | Denver (DEN) | |
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| Frontier Airlines | 558 | SAN | 11:00am | MDW | 6:17pm | Denver (DEN) | Search prices |
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| Southwest Airlines | 861 | SAN | 12:35pm | MDW | 9:30pm | Denver (DEN) | |
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| United Airlines | 354 | SAN | 2:55pm | MDW | 10:27pm | Denver (DEN) | Search prices |
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| Frontier Airlines | 564 | SAN | 3:10pm | MDW | 10:27pm | Denver (DEN) | Search prices |
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| Southwest Airlines | 89 | SAN | 4:00pm | MDW | 11:15pm | Denver (DEN) | |
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| Northwest Airlines | 670 | SAN | 8:30am | MDW | 7:13pm | Detroit (DTW) | Search prices |
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| Delta Air Lines | 2754 | SAN | 8:30am | MDW | 5:29pm | Detroit (DTW) | Search prices |
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| Northwest Airlines | 670 | SAN | 8:30am | MDW | 5:29pm | Detroit (DTW) | Search prices |
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| Delta Air Lines | 2754 | SAN | 8:30am | MDW | 7:13pm | Detroit (DTW) | Search prices |
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| Southwest Airlines | 3336 | SAN | 11:15am | MDW | 8:40pm | Kansas City (MCI) | |
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| Southwest Airlines | 3336 | SAN | 11:15am | MDW | 7:30pm | Kansas City (MCI) | |
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| Northwest Airlines | 186 | SAN | 6:35am | MDW | 4:29pm | Minneapolis (MSP) | Search prices |
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| Northwest Airlines | 186 | SAN | 6:35am | MDW | 4:29pm | Minneapolis (MSP) | Search prices |
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| Delta Air Lines | 2724 | SAN | 6:35am | MDW | 4:29pm | Minneapolis (MSP) | Search prices |
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| Delta Air Lines | 2724 | SAN | 6:35am | MDW | 4:29pm | Minneapolis (MSP) | Search prices |
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| Northwest Airlines | 186 | SAN | 6:35am | MDW | 2:51pm | Minneapolis (MSP) | Search prices |
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| Northwest Airlines | 186 | SAN | 6:35am | MDW | 2:51pm | Minneapolis (MSP) | Search prices |
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| Delta Air Lines | 2724 | SAN | 6:35am | MDW | 2:51pm | Minneapolis (MSP) | Search prices |
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| Delta Air Lines | 2724 | SAN | 6:35am | MDW | 2:51pm | Minneapolis (MSP) | Search prices |
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| Delta Air Lines | 2723 | SAN | 11:51am | MDW | 8:12pm | Minneapolis (MSP) | Search prices |
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| Northwest Airlines | 184 | SAN | 11:51am | MDW | 8:12pm | Minneapolis (MSP) | Search prices |
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| Northwest Airlines | 184 | SAN | 11:51am | MDW | 8:12pm | Minneapolis (MSP) | Search prices |
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| Delta Air Lines | 2723 | SAN | 11:51am | MDW | 8:12pm | Minneapolis (MSP) | Search prices |
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| Southwest Airlines | 1585 | SAN | 7:00am | MDW | 3:30pm | Phoenix (PHX) | |
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| Southwest Airlines | 591 | SAN | 9:55am | MDW | 6:25pm | Phoenix (PHX) | |
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| Southwest Airlines | 1362 | SAN | 1:20pm | MDW | 9:50pm | Phoenix (PHX) | |
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| Southwest Airlines | 1362 | SAN | 1:20pm | MDW | 10:40pm | Phoenix (PHX) | |
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| Southwest Airlines | 1274 | SAN | 3:35pm | MDW | 11:20pm | Phoenix (PHX) | |
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| Southwest Airlines | 3781 | SAN | 9:05am | MDW | 7:05pm | San Antonio (SAT) | |
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| Southwest Airlines | 3781 | SAN | 9:05am | MDW | 7:05pm | San Antonio (SAT) | |
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BNA: Nashville Metropolitan Airport |
Note: Southwest Airlines tickets can be purchsed at Southwest.com.
Delta Air Lines |
Disclaimer
Smarter Travel Media LLC and Innovata, LLC have used their best efforts to collect and prepare material for inclusion in this travel directory, and cannot warrant that the information is totally complete or accurate.
Data shown in this directory are for information only. Neither Innovata nor Smarter Travel Media LLC will be responsible for the failure of flights to operate at the times listed in this publication, nor for errors herein, nor for failure to make connections with planes, nor for any omissions of data.
Schedules are subject to change without notice. Schedules shown are based on expected flight times as presented to Smarter Travel Media LLC. Weather and other factors may affect operating conditions, and departures and arrivals cannot be guaranteed. The mileage shown is approximate, based on industry standards, and will vary from actual airline mileage received for each flight segment.
Smarter Travel Media LLC and Innovata disclaim any liability to any person for loss or damage caused by errors or omissions in the data contained on this page, whether such errors or omissions result from negligence, accident or other cause.
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