NT$8,715 Cheap Flights from San Diego (SAN) to Chicago (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 NT$8,715 for one-way flights and for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Flights from San Diego (SAN) to Chicago (MDW)
Origin airport
San Diego Intl.
Destination airport
Midway Intl.
Distance
2761 km
Average flight time
6 hours 28 mins

San Diego to Chicago 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 San Diego to Chicago 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 Chicago.

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 SAN to MDW flights that won’t make your bank account wince. Ready to temporarily leave behind San Diego 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 MDW 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 San Diego Airport to MDW?
Based on fares quoted within the last 7 days on Expedia for flights departing within the next year, round-trip journeys from SAN to MDW start from . Book today to score the best price for your exciting 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 SAN to MDW?
Each air carrier has its own set of terms and conditions. If you do decide to cancel, follow the easy instructions on our Customer Service Portal.
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 Intl. Airport (MDW) flights, you’ll see a “no change fees” filter for you to select.
How far is the flight from San Diego Airport to Midway Airport?
You’ll be up above the clouds for a while, as the flight distance from San Diego to Chicago is 2,800 kilometers. Create a playlist of your favorite podcasts before leaving home to keep yourself entertained during the journey.
Which airlines fly direct from San Diego Airport to Midway Airport?
Operating 78 monthly flights, Southwest Airlines (WN) is a great choice when flying directly from SAN to Chicago Airport.
Are San Diego Intl. Airport (SAN) to Midway Airport flight tickets cheaper when they're purchased at the last minute?
Booking last minute from SAN to Chicago Airport can be hit-or-miss. You may be able to find a bargain, but then again, you could miss out! If you’d prefer to start planning ahead of time, Expedia compares flight deals up to a year in advance. Just remember that not all airlines list their prices that far in advance. Our top tip? Check back often as prices are updated regularly.
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