￥21,230 Cheap Flights from Chicago (MDW) to San Diego (SAN)

View ￥21,230 flight on Thu, Jul 10, 2025Opens in a new window

Popular airlines from Chicago Midway Airport (MDW) to San Diego Intl. Airport (SAN)

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Cheap Flights from Chicago to San Diego (MDW-SAN)

Prices were available within the past 7 days and start at ￥21,230 for one-way flights and ￥50,100 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Delta
Sat, Jun 21 - Wed, Jun 25
MDW
Chicago
SAN
San Diego
￥50,100 Roundtrip, found 5 days ago
￥50,100
Roundtrip
found 5 days ago
Select Delta flight, departing Sat, Jun 21 from Chicago to San Diego, returning Wed, Jun 25, priced at ￥50,100 found 5 days ago
Delta
Sat, Jun 21 - Wed, Jun 25
MDW
Chicago
SAN
San Diego
￥52,680 Roundtrip, found 5 days ago
￥52,680
Roundtrip
found 5 days ago
Select Delta flight, departing Sat, Jun 21 from Chicago to San Diego, returning Wed, Jun 25, priced at ￥52,680 found 5 days ago

Frequently asked questions

How much is a flight from MDW to San Diego Intl. Airport (SAN)?
Based on airfares listed within the last 7 days on Expedia for flights departing within the next year, round-trip flights from Chicago Airport to San Diego Airport start from ￥50,100. Book now to get the best price for your big adventure. Prices and availability are subject to change. Additional terms apply.
Do I need to pay a cancellation fee if I cancel my flight from MDW to SAN?
Most flights can be canceled online, but every airline has a different set of terms and conditions. If you do decide to cancel your flight, go to our Customer Service Portal and follow the instructions.
How do I find cheap flights from Chicago Airport to SAN that have flexible change policies?
Many airlines offer the option to reschedule your flight without a change fee. All you pay is the difference between the original flight and the new flight. When you’re searching for Midway Intl. Airport (MDW) to San Diego Intl. Airport (SAN) flights, you’ll see a “no change fees” filter for you to select.
How many hours is the flight from Midway Intl. Airport (MDW) to San Diego Airport?
The average flight between Chicago Airport and San Diego Airport is 5 hours and 50 minutes. If you’re traveling with kids, it’s always a good idea to pack a few healthy snacks in your carry-on bag.
How far is the flight from Midway Intl. Airport (MDW) to San Diego Airport?
The flight distance from Chicago to San Diego is 2,800 kilometers. Bring a snack, a drink and a good book to read. Keep yourself entertained and the time will fly by.
Which airlines fly direct from Midway Airport to San Diego Intl. Airport (SAN)?
Unfortunately, there are no airlines that fly directly between Midway Intl. Airport (MDW) and San Diego Intl. Airport (SAN). You’ll need to book a flight with one or more stops.
Are Midway Airport to SAN flight tickets cheaper when they're purchased at the last minute?
Flight prices always go up and down, so there are no guarantees. While last-minute deals between Midway Intl. Airport (MDW) and SAN are possible, it also makes sense to keep track of prices well before you fly. In fact, some air carriers publicize their prices up to a year prior to the departure date. Expedia is constantly updating the best bargains around, so keep checking back and be ready to lock in your seat when the price is right.
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