
Popular airlines from Chicago Midway Airport (MDW) to San Diego Intl. Airport (SAN)
- Delta
Delta
- Plan, book, fly with confidence
trending down icon Be in the knowGet alerts if flight prices drop or rise*bex rewards loyalty icon Book smarterSave up to 15% on select hotels after you book a flight*payments icon
Cheap flights from Chicago to San Diego (MDW-SAN)
Prices were available within the past 7 days and start at €113 for one-way flights and €276 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Wed, 2 Jul - Fri, 4 Jul
MDW
Chicago
SAN
San Diego
€276 Return, found 3 days ago
€276
Return
found 3 days ago

Wed, 13 Aug - Sun, 17 Aug
MDW
Chicago
SAN
San Diego
€277 Return, found 5 days ago
€277
Return
found 5 days ago

Wed, 2 Jul - Wed, 9 Jul
MDW
Chicago
SAN
San Diego
€295 Return, found 4 days ago
€295
Return
found 4 days ago

Thu, 10 Jul - Sat, 12 Jul
MDW
Chicago
SAN
San Diego
€325 Return, found 1 day ago
€325
Return
found 1 day ago

Wed, 9 Jul - Fri, 11 Jul
MDW
Chicago
SAN
San Diego
€328 Return, found 2 days ago
€328
Return
found 2 days ago

Wed, 2 Jul - Fri, 4 Jul
MDW
Chicago
SAN
San Diego
€337 Return, found 3 days ago
€337
Return
found 3 days ago

Wed, 9 Jul - Sat, 12 Jul
MDW
Chicago
SAN
San Diego
€342 Return, found 1 day ago
€342
Return
found 1 day ago

Wed, 9 Jul - Fri, 11 Jul
MDW
Chicago
SAN
San Diego
€346 Return, found 2 days ago
€346
Return
found 2 days ago

Wed, 2 Jul - Fri, 4 Jul
MDW
Chicago
SAN
San Diego
€354 Return, found 3 days ago
€354
Return
found 3 days ago

Wed, 13 Aug - Sun, 17 Aug
MDW
Chicago
SAN
San Diego
€356 Return, found 5 days ago
€356
Return
found 5 days ago
Find the cheapest month to fly from Chicago (MDW) to San Diego (SAN)
September is typically the cheapest month to fly
From €102 - €378 per traveller.
Graph displaying average flight prices per month
Origin airport | Midway Intl. |
Destination airport | San Diego Intl. |
Airlines serving | Delta |
Return price | €276 |
Distance | 2761 km |
Average flight time | 3 hours 6 mins |
Perfect flights from Chicago to San Diego
Embark on an unforgettable journey without breaking the bank with Expedia's incredible deals on cheap flights from Chicago to San Diego. Whether you're aching for a romantic escape with your partner, craving an adventurous solo expedition, or yearning to immerse yourself in the local history and culture, we've got you covered.
Picture yourself strolling through the streets of San Diego, surrounded by breathtaking architecture and absorbing the vibrant atmosphere of this captivating city. Indulge in the mouth-watering local specialties, from tantalizing street food to exquisite fine dining. With Expedia, you can experience all of this and more, without sacrificing your budget.
Our flexible Midway Intl. to San Diego Intl. ticket options cater to your travel preferences, with incredible one-way fares from €113 and roundtrip prices from €276. Whether you're planning a short city break or a longer adventure, our dynamic pricing ensures that you find the best deals for your journey.
But the magic doesn't stop there. Expedia offers a range of partner services to enhance your trip. Rent a car at San Diego Intl. and explore San Diego and its surrounding areas at your own pace. Discover hidden gems off the beaten path, and create unforgettable memories. We also provide a handpicked selection of accommodations, from charming bed and breakfasts to luxury hotels, ensuring that you have a comfortable and memorable stay.
Planning your next great adventure is a breeze with Expedia. Our user-friendly platform, unbeatable prices, and round-the-clock customer support are designed to make your travel experience seamless and stress-free. So, why wait? Book your MDW to SAN travel arrangements today and embark on the journey of a lifetime in San Diego.
Frequently asked questions
Explore a world of travel with Expedia
- Trending Routes
- Top Flights Destinations
- More Airlines
- Cheap Flights from Other Airports
- Expedia's Latest Trends
Top Routes from Chicago
Top Routes to San Diego
- Newark Liberty Intl. Airport to San Diego (EWR - SAN)
- Boston to San Diego (BOS - SAN)
- Fort Lauderdale to San Diego (FLL - SAN)
- New York to San Diego (LGA - SAN)
- Cork to San Diego (ORK - SAN)
- Denver to San Diego (DEN - SAN)
- New York to San Diego (JFK - SAN)
- Dublin to San Diego (DUB - SAN)
- Budapest to San Diego (BUD - SAN)
- Shannon to San Diego (SNN - SAN)
- Vancouver to San Diego (YVR - SAN)
- London to San Diego (LHR - SAN)
Top Flight Destinations
- Flights to Las Vegas
- Flights to New York
- Flights to Orlando
- Flights to Myrtle Beach
- Flights to Chicago
- Flights to San Diego
- Flights to Panama City Beach
- Flights to Destin
- Flights to Los Angeles
- Flights to Miami
- Flights to Boston
- Flights to Gulf Shores
- Flights to Nashville
- Flights to Ocean City
- Flights to San Francisco
- Flights to Pigeon Forge
- Flights to Atlanta
- Flights to Honolulu
- Flights to Houston
- Flights to Orange Beach
Expedia's Latest Trends
Flights
Flights from Las Vegas (LAS) to Los Angeles (LAX)Flights from San Francisco (SFO) to Las Vegas (LAS)Flights from Los Angeles (LAX) to Las Vegas (LAS)Flights from Boston (BOS) to Dublin (DUB)Flights from Los Angeles (LAX) to Dublin (DUB)Flights from Dublin (DUB) to Pittsburgh (PIT)Flights from Las Vegas (LAS) to Dublin (DUB)Flights from Shannon (SNN) to Boston (BOS)Flights from London (LHR) to Los Angeles (LAX)Flights from Dublin (DUB) to San Francisco (SFO)Flights from Dublin (DUB) to St. Louis (STL)Flights from New York (JFK) to Boston (BOS)Flights from Shannon (SNN) to San Francisco (SFO)Flights from LON-All Airports to NYC-All AirportsFlights from San Francisco (SFO) to Dublin (DUB)Flights from Los Angeles (LAX) to Shannon (SNN)Flights from London (LHR) to San Francisco (SFO)Flights from Shannon (SNN) to Las Vegas (LAS)Flights from Cork (ORK) to Las Vegas (LAS)Flights from Dublin (DUB) to Fort Lauderdale (FLL)Flights from Dublin (DUB) to Philadelphia (PHL)Flights from Cork (ORK) to San Francisco (SFO)Flights from Dublin (DUB) to Los Angeles (LAX)Flights from Shannon (SNN) to Seattle (SEA)Flights from Boston (BOS) to New York (JFK)Flights from London (LHR) to Las Vegas (LAS)Flights from Dublin (DUB) to Boston (BOS)Flights from Dublin (DUB) to Seattle (SEA)Flights from Dublin (DUB) to Dallas (DFW)Flights from Dublin (DUB) to Las Vegas (LAS)
*Available to Expedia members.