S$173 Cheap Flights from San Diego to Chicago

View S$173 flight on Wed, 4 Jun, 2025Opens in a new window

Featured airlines

Singapore Airlines
AirAsia
Scoot
Philippine Airlines
Malaysia Airlines
Thai Airways International
Asiana Airlines
Qatar Airways
Air India

  • 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 San Diego to Chicago (SAN-MDW)

Prices were available within the past 7 days and start at S$173 for one-way flights and S$371 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Delta
Fri, 25 Jul - Tue, 29 Jul
SAN
San Diego
MDW
Chicago
S$371 Return, found 2 days ago
S$371
Return
found 2 days ago
Select Delta flight, departing Fri, 25 Jul from San Diego to Chicago, returning Tue, 29 Jul, priced at S$371 found 2 days ago
Delta
Fri, 25 Jul - Tue, 29 Jul
SAN
San Diego
MDW
Chicago
S$426 Return, found 2 days ago
S$426
Return
found 2 days ago
Select Delta flight, departing Fri, 25 Jul from San Diego to Chicago, returning Tue, 29 Jul, priced at S$426 found 2 days ago
San Diego to Chicago route information
Origin airport
San Diego Intl.
Destination airport
Midway Intl.
Return price
S$371
Distance
2761 km

Flights from San Diego to Chicago

When looking for plane tickets from San Diego to Chicago, the ease and convenience of using Expedia simply can’t be beat. With tons of departure points and flights options from the top airline carriers, Expedia gives you the widest array of cheap flights to Chicago. Look for SAN to MDW airfare with the assurance that you have the largest online travel agency working for you.

Expedia lets you search across the largest number of airlines and Chicago flights, which means that you’ll be able to find a great flight deal at the perfect travel date and time. Our simple-to-use booking engine makes looking for terrific bargains easy and hassle-free; just enter your travel dates and departure city, and let Expedia do the rest! Adjust your travel dates and explore connecting flights to find an even better deal on your San Diego Chicago flight!

Browse through dozens of options and rest 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 San Diego to Chicago trip. There’s simply no substitute for great prices suited to your travel needs and backed by excellent customer support.

Combine your Chicago flight with a hotel and/or car rental for a package deal designed to save you even more money! Discover additional savings by booking in advance or find a last minute deal. There are tons of ways to save on your flights from San Diego to Chicago with Expedia. Use us as your stop travel destination and have the confidence that you’re getting a bargain!

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 S$371. 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 kilometres. Create a playlist of your favourite 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.

Explore a world of travel with Expedia

Chicago Airports

Chicago

San Diego to O'Hare Intl.
S$370.60
*Available to Expedia members.