$129 Cheap Delta flights Chicago (MDW) to San Diego (SAN)

Apply the “Price (lowest to highest)” filter on Expedia to look for cheap Delta Air Lines return flights from $234 from MDW to SAN. Affordable one-way tickets from $129 are also on offer.**These prices were available on Expedia within the past 7 days, for flights departing within the next year. Prices and availability are subject to change. Additional terms apply.

Browse for round-trip or one-way flights to San Diego in January or November. You could find lower fares with Delta Air Lines during these off-season months.

To find cheap Delta Air Lines fares from Midway Intl. Airport (MDW) to San Diego Intl. Airport (SAN), start searching one to three months before your planned departure. Reserving domestic flights 34 to 86 days in advance could save you 25% compared to booking just 6 to 12 days ahead. The day you book can also impact the overall cost. Sunday is typically the cheapest, while Monday is often the most expensive for domestic flights. You can save 6% on average by booking your flight on a Sunday.**Ideal booking window recommendation is based on average round-trip ticket prices for January through November for 2024. Best day of the week to book recommendation is based on average round-trip ticket prices for January through October 2024. All data sourced from ARC’s global airline sales database.

To see if there’s a direct journey from MDW to SAN with Delta Air Lines or another airline, use our “Nonstop” filter when browsing for flights.

To find the earliest departure from MDW to SAN with Delta Air Lines, sort your results by “Morning” and “Early Morning.” Booking an early flight usually means you’re less likely to experience cancellations.**Most reliable time of the day recommendation is based on January through August 2024 flight status data sourced from OAG’s global flight data platform.

Catch a Delta Air Lines flight from Midway Intl. Airport (MDW) to San Diego, and you’ll likely touch down at San Diego Intl. Airport (SAN). This is the airline’s primary hub in this city.

Delta Air Lines makes flying from MDW to SAN more comfortable with an excellent in-flight experience and a rewarding loyalty program. You could even start collecting points with Delta SkyMiles. Remember to sign up to our free One Key™ rewards program to earn OneKeyCash™*, which can be redeemed on future trips.*OneKeyCash™ disclaimer - OneKeyCash™ is not redeemable for cash and can only be used on Expedia, Hotels.com and Vrbo.

Depending on the ticket type you purchased, a fee may apply if you modify or cancel your booking more than 24 hours after confirmation. To find plane tickets with more flexibility, select our “Changes included” and “No cancel fee” boxes when you search for flights. To learn more about modifying or canceling your reservation, visit “Trips,” select your flight and click on “Manage Booking.”