￥29,417 Cheap Flights from Chicago (MDW) to San Diego (SAN)

Bundle Your Flight + Hotel & Save!

Featured airlines

    Plan, book, fly with confidence
    trending down icon
    Be in the know
    Get alerts if flight prices drop or rise*
    bex rewards loyalty icon
    Book smarter
    Save up to 40% on select hotels after you book a flight*
    payments icon
    Earn twice
    Earn your airline miles on top of our rewards
    Sign in

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

Prices were available within the past 7 days and start at ￥29,417 for one-way flights and ￥72,880 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Delta
Wed, Jun 19 - Sun, Jun 23
MDW
Chicago
SAN
San Diego
￥72,880 Roundtrip, found 1 day ago
￥72,880
Roundtrip
found 1 day ago
Select Delta flight, departing Wed, Jun 19 from Chicago to San Diego, returning Sun, Jun 23, priced at ￥72,880 found 1 day ago
Delta
Mon, May 6 - Wed, May 15
MDW
Chicago
SAN
San Diego
￥97,722 Roundtrip, found 6 days ago
￥97,722
Roundtrip
found 6 days ago
Select Delta flight, departing Mon, May 6 from Chicago to San Diego, returning Wed, May 15, priced at ￥97,722 found 6 days ago
Delta
Wed, Jun 19 - Sun, Jun 23
MDW
Chicago
SAN
San Diego
￥99,136 Roundtrip, found 1 day ago
￥99,136
Roundtrip
found 1 day ago
Select Delta flight, departing Wed, Jun 19 from Chicago to San Diego, returning Sun, Jun 23, priced at ￥99,136 found 1 day ago
Delta
Mon, May 6 - Wed, May 15
MDW
Chicago
SAN
San Diego
￥103,042 Roundtrip, found 6 days ago
￥103,042
Roundtrip
found 6 days ago
Select Delta flight, departing Mon, May 6 from Chicago to San Diego, returning Wed, May 15, priced at ￥103,042 found 6 days ago
Delta
Wed, Jun 19 - Sun, Jun 23
MDW
Chicago
SAN
San Diego
￥103,316 Roundtrip, found 1 day ago
￥103,316
Roundtrip
found 1 day ago
Select Delta flight, departing Wed, Jun 19 from Chicago to San Diego, returning Sun, Jun 23, priced at ￥103,316 found 1 day ago
Delta
Wed, Jun 19 - Sun, Jun 23
MDW
Chicago
SAN
San Diego
￥117,030 Roundtrip, found 1 day ago
￥117,030
Roundtrip
found 1 day ago
Select Delta flight, departing Wed, Jun 19 from Chicago to San Diego, returning Sun, Jun 23, priced at ￥117,030 found 1 day ago
Flights from Chicago (MDW) to San Diego (SAN)
Origin airport
Midway Intl.
Destination airport
San Diego Intl.
Roundtrip price
￥72,880
Distance
2761 km
Average flight time
3 hours 4 mins

Chicago to San Diego Flights

Sometimes you just need to get out of town or maybe you’re looking for a change of scenery. Regardless of the reason, a flight from Chicago to will do just the trick! Go on, plan to see all the famous landmarks and eat your weight in the local cuisine. Your trip is beckoning, so answer the call by packing your suitcase and filling your travel itinerary with exploring San Diego.

Whether you’re flying for business or jet-setting on your personal time, you’ve come to the right place. Here at Expedia.com, we’ll pair you up with MDW to SAN flights that won’t make your bank account wince. Ready to temporarily leave behind Chicago for new horizons? Browse through our cheap airfare, and filter by flight times and dates until you find just what you had in mind. From flights without layovers to ones that arrive early in the morning, you’ll come across plane tickets that suit your travel preferences. You can even bundle your flight to SAN with hotels and car rentals to score even bigger savings.

All set to hit the clouds? Book your travel arrangements with us today and have left-over money to put toward your travel outings and adventures.

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 ￥72,880. 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.
Chicago nearby Airports

Chicago

O'Hare Intl. to San Diego
￥57,259
*Available to Expedia members.