¥18,160 Cheap Flights from San Diego (SAN) to Chicago (MDW)

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

  • Be in the know

    Get alerts if flight prices drop or rise*
  • Book smarter

    Save up to 40% on select hotels after you book a flight*
  • Earn twice

    Earn your airline miles on top of our rewards

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

Prices were available within the past 7 days and start at ¥18,160 for one-way flights and ¥36,210 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Delta
Delta
Delta
Delta
Delta
Delta
Delta
Delta
Delta
Delta

Alternative airports near Chicago

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

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

January is typically the cheapest month to fly

From ¥18,421 - ¥100,469 per traveler.

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 ¥36,210. 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
¥36,210
Distance
2761 km
Average flight time
5 hours 55 mins

Book with confidence

*Available to Expedia members.