Cheap Flights from Chicago (MDW) to San Diego (SAN) from HK$1,402~

View HK$1,402 flight on Wed, 9 Jul 2025Opens in a new window

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

Prices were available within the past 7 days and start at HK$1,402 for one-way flights and HK$2,976 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Delta
Thu, 31 Jul - Tue, 5 Aug
MDW
Chicago
SAN
San Diego
HK$2,976 Return, found 6 days ago
HK$2,976
Return
found 6 days ago
Select Delta flight, departing Thu, 31 Jul from Chicago to San Diego, returning Tue, 5 Aug, priced at HK$2,976 found 6 days ago
Delta
Thu, 31 Jul - Tue, 5 Aug
MDW
Chicago
SAN
San Diego
HK$3,525 Return, found 6 days ago
HK$3,525
Return
found 6 days ago
Select Delta flight, departing Thu, 31 Jul from Chicago to San Diego, returning Tue, 5 Aug, priced at HK$3,525 found 6 days ago

Find the cheapest month to fly from Chicago (MDW) to San Diego (SAN)

January is typically the cheapest month to fly

From HK$926 - HK$3,582 per traveller.

Graph displaying average flight prices per month

Chicago to San Diego route information
Origin airport
Midway Intl.
Destination airport
San Diego Intl.
Return price
HK$2,976
Distance
2761 km
Average flight time
3 hours 6 mins

Flights from Chicago to San Diego

Book cheap flights from Chicago (MDW) to San Diego (SAN) on Expedia.com.hk. Find the best flight deals to destinations around the world for your next leisure or business travel on Expedia.com.hk.

Search for flights from Chicago (MDW) to San Diego (SAN) to find great flight deals suitable to your travel date and time. Expedia.com.hk flight booking search engine is simple to use and looking for cheap flights is as easy as a click of a mouse or on your mobile devices.

Be assured that you’re seeing the best price guaranteed! Our friendly customer service representatives are here to serve you 24 hours day to provide assistance and answer any questions that you may have about booking your Chicago (MDW) to San Diego (SAN) trip. Call us at 3077-4857 (direct number - 24 hours day for English).

Save more when combine your San Diego flight with a hotel for a package deal! Discover additional savings by booking in advance. Now you can find activities in San Diego and things to do in San Diego for your perfect vacation with Expedia Thing to Do.

If you would like to book flights to San Diego more flexibly, many prefer to purchase one-way tickets with options to take different airlines. A one way ticket to San Diego is HK$1,402 now!

 

Frequently asked questions

How much is a flight from Midway Airport to San Diego Airport?
If you're traveling between Chicago Airport and San Diego Intl. Airport (SAN), round-trip flights start from HK$2,976. This price is based on fares available within the last 7 days on Expedia for flights departing within the next year, so don't delay. Book now and save yourself money and time. 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 Diego Airport?
This differs between air carriers, as each one has its own terms and conditions. Visit the Customer Service Portal, where you'll find instructions on how to cancel online.
How do I find cheap flights from Midway Intl. Airport (MDW) to San Diego Intl. Airport (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 MDW to San Diego Airport flights, you'll see a "no change fees" filter for you to select.
How far is the flight from Midway Airport to San Diego Airport?
The flight distance from Chicago to San Diego is 2,800 kilometers. Pack yourself a snack, a drink and a laptop filled with movies. Keep yourself entertained and the hours will zip by.
Which airlines fly direct from Midway Airport to San Diego Airport?
Southwest Airlines (WN) will take you from Chicago Airport to SAN safely and comfortably. You can choose from 86 flights each month along this route.
Are Midway Intl. Airport (MDW) to SAN flight tickets cheaper when they're purchased at the last minute?
It is possible to score an amazing last-minute deal from MDW to San Diego Airport, but it's also possible to miss out entirely! As many airlines advertise prices up to 12 months in advance, it's worth keeping an eye on fares early and being ready to book when you see a good bargain. Expedia compares carrier prices and updates flight deals often, so you can rest assured you're always seeing the latest offers.

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