Featured Airlines
- Be in the knowGet alerts if flight prices drop or rise*
- Book smarterSave up to 40% on select hotels after you book a flight*
Plan, book, fly with confidence
Cheap Flights from San Diego to Chicago (SAN-ORD)
Prices were available within the past 7 days and start at S$160 for one-way flights and S$318 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.
Fri, 17 May - Sun, 26 May
SAN
San Diego
ORD
Chicago
S$318 Return, found 5 days ago
S$318
Return
found 5 days ago
Tue, 7 May - Sun, 26 May
SAN
San Diego
ORD
Chicago
S$331 Return, found 4 days ago
S$331
Return
found 4 days ago
Fri, 17 May - Sun, 26 May
SAN
San Diego
ORD
Chicago
S$340 Return, found 5 days ago
S$340
Return
found 5 days ago
Fri, 17 May - Sun, 26 May
SAN
San Diego
ORD
Chicago
S$345 Return, found 5 days ago
S$345
Return
found 5 days ago
Tue, 23 Apr - Tue, 7 May
SAN
San Diego
ORD
Chicago
S$346 Return, found 4 days ago
S$346
Return
found 4 days ago
Wed, 8 May - Sun, 26 May
SAN
San Diego
ORD
Chicago
S$357 Return, found 4 days ago
S$357
Return
found 4 days ago
Sat, 18 May - Sun, 26 May
SAN
San Diego
ORD
Chicago
S$362 Return, found 3 days ago
S$362
Return
found 3 days ago
Fri, 17 May - Sun, 26 May
SAN
San Diego
ORD
Chicago
S$367 Return, found 5 days ago
S$367
Return
found 5 days ago
Mon, 22 Apr - Tue, 7 May
SAN
San Diego
ORD
Chicago
S$371 Return, found 4 days ago
S$371
Return
found 4 days ago
Sat, 20 Apr - Sat, 27 Apr
SAN
San Diego
ORD
Chicago
S$374 Return, found 6 days ago
S$374
Return
found 6 days ago
Origin airport | San Diego Intl. |
Destination airport | O'Hare Intl. |
Return price | S$318 |
Distance | 2752 km |
Average flight time | 6 hours 3 mins |
Perfect flights from San Diego to Chicago
Your Journey from San Diego to Chicago
Start your unforgettable journey with Expedia. Our broad selection of flights from San Diego to Chicago caters to every travel need. Whether you're yearning for a romantic escape, a solo adventure, or a cultural immersion, we've got you covered.
Choosing Your Ideal Flight
With Expedia, you have access to a wide range of airlines, including Delta, United. Our selection of flights from San Diego Intl. to O'Hare Intl. caters to every traveler's requirements, ensuring your journey aligns with your schedule. With options from 20 airlines, you're bound to find the perfect flight.
Maximizing Value with San Diego to Chicago Flights
Experience the joy of finding cheap flights from San Diego Intl. to O'Hare Intl. that fit your budget. Keep an eye out for our special deals and discounts, and check our flexible one-way fares from S$160 and roundtrip prices from S$318*.
Pre-Flight Essentials
Ensure a smooth journey from San Diego to Chicago with Expedia. From information about check-in times and in-flight amenities to guidance on baggage policies, we provide all the essentials to prepare you for your flight.
Experience the Vibrant Chicago
Picture yourself stepping off the plane in Chicago and immersing yourself in the unique atmosphere of Chicago. From local markets to cultural festivals, each city offers its distinct charm. Make the most of your trip by exploring local attractions and indulging in the local cuisine. With Expedia, explore all this and more, tailored to your budget.
Added Convenience on Your San Diego to Chicago Flight
Traveling with Expedia is more than just a flight. We offer details about in-flight amenities, baggage policies, and more to ensure a smooth and hassle-free journey. Choose from our variety of airlines and embark on a memorable journey from San Diego to Chicago.
Beyond the Flight – Exploring Chicago
With Expedia, your adventure extends beyond the flight. Explore Chicago at your own pace by renting a car or booking a hotel. Discover hidden gems off the beaten path and create unforgettable memories.
Book Your Flight from San Diego to Chicago with Confidence
Planning your next great adventure is a breeze with Expedia. Our user-friendly platform, unbeatable prices, and round-the-clock customer support make your travel experience seamless and stress-free. Embark on your journey from San Diego to Chicago with confidence. Book your travel arrangements with Expedia today.
*Note: Prices may vary based on availability and are subject to change.
Frequently asked questions
- Trending Routes
- Trending Flights
- Top Flights Destinations
- More Carriers
- Nearby Airports
- Cheap Flights from Other Airports
- Expedia's Latest Trends
Popular flights from San Diego
- San Diego to Mexico City (SAN - MEX)
- San Diego to Los Angeles (SAN - LAX)
- San Diego to Washington (SAN - DCA)
- San Diego to Kelowna (SAN - YLW)
- San Diego to San José del Cabo (SAN - SJD)
- San Diego to Seattle (SAN - SEA)
- San Diego to Tokyo (SAN - NRT)
- San Diego to Singapore (SAN - SIN)
- San Diego to Tokyo (SAN - HND)
- San Diego to Las Vegas (SAN - LAS)
Popular flights to Chicago
- Newark to Chicago (EWR - ORD)
- Mumbai to Chicago (BOM - ORD)
- Mexico City to Chicago (MEX - ORD)
- Bangkok to Chicago (BKK - ORD)
- Washington to Chicago (DCA - ORD)
- Hong Kong to Chicago (HKG - ORD)
- New York to Chicago (LGA - ORD)
- Boston to Chicago (BOS - ORD)
- Paris to Chicago (CDG - ORD)
- Delhi to Chicago (DEL - ORD)
- Washington to Chicago (IAD - ORD)
- New York to Chicago (JFK - ORD)
Popular flights from San Diego
Popular flights to Chicago
Top Flight Destinations Near Here
- Flights to Las Vegas
- Flights to New York
- Flights to Orlando
- Flights to Miami
- Flights to Panama City Beach
- Flights to Los Angeles
- Flights to San Diego
- Flights to Chicago
- Flights to Myrtle Beach
- Flights to Fort Lauderdale
- Flights to Destin
- Flights to Nashville
- Flights to Key West
- Flights to New Orleans
- Flights to Palm Springs
- Flights to Honolulu
- Flights to Boston
- Flights to Phoenix
- Flights to San Antonio
- Flights to Houston
Chicago Airports
Chicago
S$317.80
Nearby Airports
- Montgomery Field Airport (MYF)
- McClellan-Palomar Airport (CLD)
- John Wayne Airport (SNA)
- Palm Springs Intl. Airport (PSP)
- Jacqueline Cochran Regional Airport (TRM)
- Bermuda Dunes Airport (UDD)
- Fullerton Municipal Airport (FUL)
- Long Beach Municipal Airport (LGB)
- Imperial County Airport (IPL)
- San Bernardino Intl. Airport (SBD)
Flights
Los Angeles to Baltimore (LAX - BWI)Boston to San Francisco (BOS - SFO)Singapore to Seattle (SIN - SEA)Kelowna to Los Angeles (YLW - LAX)San Francisco to Los Angeles (SFO - LAX)Singapore to Philadelphia (SIN - PHL)Singapore to Chicago (SIN - ORD)San Francisco to Chicago (SFO - ORD)San Francisco to New York (SFO - JFK)San Diego to Las Vegas (SAN - LAS)Los Angeles to Honolulu (LAX - HNL)Chicago to New York (ORD - LGA)Boston to Singapore (BOS - SIN)Los Angeles to San Francisco (LAX - SFO)Newark to San Francisco (EWR - SFO)New York to Cancun (NYC - CUN)Singapore to Los Angeles (SIN - LAX)Singapore to Boston (SIN - BOS)San Francisco to Las Vegas (SFO - LAS)Chicago to Singapore (ORD - SIN)Singapore to Dallas (SIN - DFW)Pittsburgh to Newark (PIT - EWR)Singapore to St. Louis (SIN - STL)San Francisco to Singapore (SFO - SIN)Los Angeles to Singapore (LAX - SIN)Singapore to San Francisco (SIN - SFO)Los Angeles to New York (LAX - NYC)Singapore to San Diego (SIN - SAN)Singapore to Las Vegas (SIN - LAS)New York to Los Angeles (NYC - LAX)
*Available to Expedia members.