Popular airlines from San Diego Intl. Airport (SAN) to Chicago O'Hare Intl. Airport (ORD)
Alaska AirlinesAlaska Airlines
American AirlinesAmerican Airlines
UnitedUnited
DeltaDelta
Southwest AirlinesSouthwest Airlines
Frontier AirlinesFrontier Airlines
JetBlue AirwaysJetBlue Airways
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Today's featured flight deals from San Diego Intl. Airport (SAN) to Chicago O'Hare Intl. Airport (ORD)
- San Diego (SAN) to Chicago (ORD).Alaska Airlines, nonstop.Departing on Thu, Dec 25 at 1:30pm from San Diego, arriving at 8:02pm in Chicago.Returning on Fri, Jan 2 at 8:58pm from Chicago, arriving at 11:44pm in San Diego.Select Alaska Airlines flight departing on Thu, Dec 25 at 1:30pm from San Diego, returning on Fri, Jan 2 at 8:58pm from Chicago priced at $31260% less than typical$312
- San Diego (SAN) to Chicago (ORD).American Airlines, nonstop.Departing on Wed, Jan 7 at 6:20am from San Diego, arriving at 12:29pm in Chicago.Returning on Sun, Jan 11 at 9:00am from Chicago, arriving at 11:43am in San Diego.Select American Airlines flight departing on Wed, Jan 7 at 6:20am from San Diego, returning on Sun, Jan 11 at 9:00am from Chicago priced at $16750% less than typical$167
- San Diego (SAN) to Chicago (ORD).American Airlines, nonstop.Departing on Fri, Jan 9 at 6:20am from San Diego, arriving at 12:29pm in Chicago.Returning on Mon, Jan 12 at 7:50pm from Chicago, arriving at 10:26pm in San Diego.Select American Airlines flight departing on Fri, Jan 9 at 6:20am from San Diego, returning on Mon, Jan 12 at 7:50pm from Chicago priced at $17745% less than typical$177
- San Diego (SAN) to Chicago (ORD).American Airlines, nonstop.Departing on Sat, Jan 10 at 6:20am from San Diego, arriving at 12:29pm in Chicago.Returning on Sat, Jan 17 at 3:44pm from Chicago, arriving at 6:26pm in San Diego.Select American Airlines flight departing on Sat, Jan 10 at 6:20am from San Diego, returning on Sat, Jan 17 at 3:44pm from Chicago priced at $15745% less than typical$157
- San Diego (SAN) to Chicago (ORD).Alaska Airlines, nonstop.Departing on Wed, Jan 7 at 5:10pm from San Diego, arriving at 11:37pm in Chicago.Returning on Sun, Jan 11 at 9:00am from Chicago, arriving at 11:43am in San Diego.Select Alaska Airlines flight departing on Wed, Jan 7 at 5:10pm from San Diego, returning on Sun, Jan 11 at 9:00am from Chicago priced at $16750% less than typical$167
- San Diego (SAN) to Chicago (ORD).American Airlines, nonstop.Departing on Wed, Jan 7 at 6:20am from San Diego, arriving at 12:29pm in Chicago.Returning on Sun, Jan 11 at 7:50pm from Chicago, arriving at 10:26pm in San Diego.Select American Airlines flight departing on Wed, Jan 7 at 6:20am from San Diego, returning on Sun, Jan 11 at 7:50pm from Chicago priced at $16750% less than typical$167
- San Diego (SAN) to Chicago (ORD).Alaska Airlines, nonstop.Departing on Tue, Jan 13 at 5:10pm from San Diego, arriving at 11:37pm in Chicago.Returning on Sun, Jan 18 at 3:44pm from Chicago, arriving at 6:26pm in San Diego.Select Alaska Airlines flight departing on Tue, Jan 13 at 5:10pm from San Diego, returning on Sun, Jan 18 at 3:44pm from Chicago priced at $15750% less than typical$157
- San Diego (SAN) to Chicago (ORD).Alaska Airlines, nonstop.Departing on Sun, Jan 18 at 8:00am from San Diego, arriving at 2:29pm in Chicago.Returning on Tue, Jan 27 at 9:00am from Chicago, arriving at 11:43am in San Diego.Select Alaska Airlines flight departing on Sun, Jan 18 at 8:00am from San Diego, returning on Tue, Jan 27 at 9:00am from Chicago priced at $15750% less than typical$157
- San Diego (SAN) to Chicago (ORD).Alaska Airlines, nonstop.Departing on Tue, Jan 20 at 5:10pm from San Diego, arriving at 11:37pm in Chicago.Returning on Sat, Jan 24 at 9:00am from Chicago, arriving at 11:43am in San Diego.Select Alaska Airlines flight departing on Tue, Jan 20 at 5:10pm from San Diego, returning on Sat, Jan 24 at 9:00am from Chicago priced at $15740% less than typical$157
Cheap Flights from San Diego to Chicago (SAN-ORD)
Prices were available within the past 7 days and start at $74 for one-way flights and $151 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.
Find the cheapest month to fly from San Diego (SAN) to Chicago (ORD)
February is typically the cheapest month to fly
Alternative airports near Chicago
Prices were available within the past 7 days. Prices and availability are subject to change.
Origin airport | San Diego Intl. |
|---|---|
Destination airport | O'Hare Intl. |
Airlines serving | Alaska Airlines, American Airlines, Delta, Frontier Airlines, JetBlue Airways, Southwest Airlines, Sun Country Airlines, United |
Roundtrip price | $151 |
Distance | 1720 mi |
Average flight time | 6 hours 9 mins |
San Diego to Chicago Flights
The cheapest times to fly from San Diego to Chicago
On average, Thursday can be the cheapest time to fly, according to data from the Airlines Reporting Corporation (ARC), one of the world's biggest databases for global airline sales. The data reveals that you could save up to 16% by flying on a Thursday—the cheapest day to travel on average—instead of a Sunday—the most expensive. Some of the most affordable flights from San Diego to Chicago are during the month of January. You can find some of the cheapest flights from San Diego to Chicago with Expedia's search tool and vast selection of airlines.
The best time to book a flight from San Diego to Chicago
Sunday is one of the best days to book for cheap flights from San Diego to Chicago: Tickets reserved on a Sunday cost between 6% and 13% less than those reserved on a Friday, according to ARC data. The data also suggests booking early can also lead to cheaper airfares. You could save 24% by buying your tickets for domestic flights at least a month in advance and 10% by booking international flights 2 months in advance.
How to find cheap round-trip tickets from San Diego to Chicago
Being flexible with your dates and using Expedia's Price Drop Protection and Price Tracking features are some of the best ways of finding a cheap ticket from San Diego to Chicago in 2026. You can also book with separate airlines for your outbound and return journeys, from $74 one-way. Expedia also offers Price Drop Protection, so if the cost of your airfare goes down after booking, you'll receive a credit for the difference*. This is available for a small fee, and is free to One Key Gold and Platinum tier members.
Expedia's Price Tracking feature means you can stay on top of airfares without manually checking every day. It sends you automated price alerts for cheap San Diego to Chicago flights and uses historical data to indicate when the best time to book is. Download Expedia's free app to activate this handy tool in a few easy taps.
You could also save big by booking one of Expedia's vacation packages. Bundling together your San Diego to Chicago airfare with your accommodations and car rental is often cheaper than booking everything separately. There’s also One Key, Expedia's generous rewards program. Join for free and you could earn One Key cash on most bookings to save on future adventures.
*Terms apply.
Disclaimer: ARC The statistics are based on average round-trip ticket prices between January and August 2023. The percentages you see are averages.
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