￥29,190 Cheap Flights from San Diego (SAN) to Chicago (MDW)

View ￥29,190 flight on Fri, Jul 17, 2026Opens in a new window

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

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

Prices were available within the past 7 days and start at ￥29,190 for one-way flights and ￥58,270 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Delta
Fri, Jul 17 - Mon, Jul 20
SAN
San Diego
MDW
Chicago
￥58,270 Roundtrip, found 1 day ago
￥58,270
Roundtrip
found 1 day ago
Select Delta flight, departing Fri, Jul 17 from San Diego to Chicago, returning Mon, Jul 20, priced at ￥58,270 found 1 day ago
Delta
Wed, May 6 - Sat, May 9
SAN
San Diego
MDW
Chicago
￥63,980 Roundtrip, found 5 days ago
￥63,980
Roundtrip
found 5 days ago
Select Delta flight, departing Wed, May 6 from San Diego to Chicago, returning Sat, May 9, priced at ￥63,980 found 5 days ago
Delta
Tue, May 5 - Tue, May 12
SAN
San Diego
MDW
Chicago
￥66,560 Roundtrip, found 2 hours ago
￥66,560
Roundtrip
found 2 hours ago
Select Delta flight, departing Tue, May 5 from San Diego to Chicago, returning Tue, May 12, priced at ￥66,560 found 2 hours ago
Delta
Thu, Apr 30 - Mon, May 11
SAN
San Diego
MDW
Chicago
￥67,850 Roundtrip, found 2 hours ago
￥67,850
Roundtrip
found 2 hours ago
Select Delta flight, departing Thu, Apr 30 from San Diego to Chicago, returning Mon, May 11, priced at ￥67,850 found 2 hours ago
Delta
Fri, May 1 - Tue, May 12
SAN
San Diego
MDW
Chicago
￥68,180 Roundtrip, found 2 hours ago
￥68,180
Roundtrip
found 2 hours ago
Select Delta flight, departing Fri, May 1 from San Diego to Chicago, returning Tue, May 12, priced at ￥68,180 found 2 hours ago
Delta
Thu, Apr 30 - Mon, May 11
SAN
San Diego
MDW
Chicago
￥69,470 Roundtrip, found 2 hours ago
￥69,470
Roundtrip
found 2 hours ago
Select Delta flight, departing Thu, Apr 30 from San Diego to Chicago, returning Mon, May 11, priced at ￥69,470 found 2 hours ago
Delta
Wed, May 6 - Sun, May 10
SAN
San Diego
MDW
Chicago
￥72,050 Roundtrip, found 5 days ago
￥72,050
Roundtrip
found 5 days ago
Select Delta flight, departing Wed, May 6 from San Diego to Chicago, returning Sun, May 10, priced at ￥72,050 found 5 days ago
Delta
Sat, Jul 18 - Mon, Jul 20
SAN
San Diego
MDW
Chicago
￥72,560 Roundtrip, found 1 day ago
￥72,560
Roundtrip
found 1 day ago
Select Delta flight, departing Sat, Jul 18 from San Diego to Chicago, returning Mon, Jul 20, priced at ￥72,560 found 1 day ago
Delta
Fri, Jul 17 - Mon, Jul 20
SAN
San Diego
MDW
Chicago
￥76,760 Roundtrip, found 1 day ago
￥76,760
Roundtrip
found 1 day ago
Select Delta flight, departing Fri, Jul 17 from San Diego to Chicago, returning Mon, Jul 20, priced at ￥76,760 found 1 day ago
Delta
Fri, May 8 - Sun, May 10
SAN
San Diego
MDW
Chicago
￥80,000 Roundtrip, found 5 days ago
￥80,000
Roundtrip
found 5 days ago
Select Delta flight, departing Fri, May 8 from San Diego to Chicago, returning Sun, May 10, priced at ￥80,000 found 5 days ago

Alternative airports near Chicago

Prices were available within the past 7 days. Prices and availability are subject to change.

Select flight to O'Hare Intl. ORD. Cheapest option available. Average driving time to city center is 23 minutes. Flights from ￥51,410
ORD
O'Hare Intl.
Cheapest
Average driving time to city center23 min
Flights from ￥51,410

Frequently asked questions

How much is a flight from SAN to MDW?
Pack your bags, because round-trip journeys between San Diego Airport and Midway Intl. Airport (MDW) start from ￥58,270. That's based on fares listed within the last 7 days on Expedia for flights departing within the next year. Prices can change quickly, so book today to secure the best deal. Prices and availability are subject to change. Additional terms apply.
Do I need to pay a cancellation fee if I cancel my flight from SAN to Midway Airport?
Most flights can be canceled online, but each air carrier has its own terms and conditions. If you do decide to cancel your flight, check out our Customer Service Portal and follow the instructions.
How do I find cheap flights from San Diego Airport to Midway Airport 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 San Diego Airport to Midway Airport flights, you'll see a "no change fees" filter for you to select.
How many hours is the flight from San Diego Airport to Midway Intl. Airport (MDW)?
The average flight time between San Diego Airport and Midway Intl. Airport (MDW) is 3 hours and 58 minutes. If you get peckish on longer flights, pack some fruit or snacks in your carry-on bag.
How far is the flight from San Diego Airport to Midway Intl. Airport (MDW)?
The flight distance from SAN to Chicago Airport is 2,800 kilometers. Pack yourself a drink, some snacks and a good movie. Keep yourself occupied and time will zip by.
Which airlines fly direct from San Diego Airport to Midway Airport?
You won't find any airlines flying directly between SAN and MDW, so be prepared to make at least one stop on your journey. A layover can be a welcome way to break up a trip!
Are San Diego Intl. Airport (SAN) to Chicago Airport flight tickets cheaper when they're purchased at the last minute?
It is possible to get an awesome last-minute deal from SAN to MDW, but it can also be hit-or-miss. As many airlines release prices up to a year in advance, it's worthwhile keeping an eye on fares early and being ready to book when you see a bargain. Expedia compares air carrier prices and updates flight deals often, so you can rest easy knowing you're always seeing the latest offers.

Travel information

Origin airport
San Diego Intl.
Destination airport
Midway Intl.
Roundtrip price
￥58,270
Distance
2761 km
Average flight time
6 hours 48 mins
*Available to Expedia members.