Cheap Flights from San Diego International Airport to Chicago (MDW) Find and Compare the Best Airline Deals | Skyticket

Departure Date

2025/5
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Total Fares（Round-Trip/Economy）: USD /Per Person

* Displayed fare(s) may differ from the actual search result

San Diego－Chicago Midway Airport
May Lowest Airfares
USD276

The airfare displayed above is for Delta Air Lines

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San Diego－Chicago Midway Airport
June Lowest Airfares
USD256

The airfare displayed above is for Delta Air Lines

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San Diego－Chicago Midway Airport
July Lowest Airfares
USD271

The airfare displayed above is for Delta Air Lines

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San Diego－Chicago Midway Airport
August Lowest Airfares
USD256

The airfare displayed above is for Delta Air Lines

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San Diego－Chicago Midway Airport
September Lowest Airfares
USD326

The airfare displayed above is for Delta Air Lines

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San Diego－Chicago
Estimated Flight Time
5 Hours 29 Minutes
San Diego－Chicago
Number of Operating Airlines
1

Operating Airlines for San Diego－Chicago Midway Airport Route
Delta Air Lines

Other Destinations from:San Diego

San Diego－Chicago(O'Hare)
USD253〜
San Diego－Dallas(/Fort Worth)
USD240〜
San Diego－Dallas(Love Field)
USD430〜
San Diego－Atlanta(Hartsfield-Jackson)
USD240〜
San Diego－Houston(George Bush Intercontinental)
USD237〜
San Diego－Salt Lake City(SLC)
USD196〜
San Diego－Miami(MIA)
USD252〜
* Fares vary in accordance to seat availability
Other Departures to: Chicago

Portland Airport－Chicago(Midway)
USD178〜
Hartsfield-Jackson Atlanta Airport－Chicago(Midway)
USD134〜
Denver Airport－Chicago(Midway)
USD213〜
William P. Hobby Airport－Chicago(Midway)
USD213〜
George Bush Intercontinental Airport－Chicago(Midway)
USD222〜
Miami Airport－Chicago(Midway)
USD215〜
* Fares vary in accordance to seat availability