Popular airlines from San Diego Intl. Airport (SAN) to Chicago O'Hare Intl. Airport (ORD)

Cheap Flights from San Diego to Chicago (SAN-ORD)

Prices were available within the past 7 days and start at $43 for one-way flights and $86 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Spirit Airlines
Wed, Aug 13 - Sat, Aug 16
SAN
San Diego
ORD
Chicago
$86 Roundtrip, found 2 hours ago
$86
Roundtrip
found 2 hours ago
Select Spirit Airlines flight, departing Wed, Aug 13 from San Diego to Chicago, returning Sat, Aug 16, priced at $86 found 2 hours ago
Spirit Airlines
Sat, Aug 9 - Wed, Aug 13
SAN
San Diego
ORD
Chicago
$88 Roundtrip, found 2 hours ago
$88
Roundtrip
found 2 hours ago
Select Spirit Airlines flight, departing Sat, Aug 9 from San Diego to Chicago, returning Wed, Aug 13, priced at $88 found 2 hours ago
Spirit Airlines
Wed, Aug 13 - Wed, Aug 20
SAN
San Diego
ORD
Chicago
$99 Roundtrip, found 3 hours ago
$99
Roundtrip
found 3 hours ago
Select Spirit Airlines flight, departing Wed, Aug 13 from San Diego to Chicago, returning Wed, Aug 20, priced at $99 found 3 hours ago
Spirit Airlines
Sat, Aug 9 - Wed, Aug 20
SAN
San Diego
ORD
Chicago
$100 Roundtrip, found 4 hours ago
$100
Roundtrip
found 4 hours ago
Select Spirit Airlines flight, departing Sat, Aug 9 from San Diego to Chicago, returning Wed, Aug 20, priced at $100 found 4 hours ago
Spirit Airlines
Sat, Aug 9 - Tue, Aug 12
SAN
San Diego
ORD
Chicago
$102 Roundtrip, found 4 hours ago
$102
Roundtrip
found 4 hours ago
Select Spirit Airlines flight, departing Sat, Aug 9 from San Diego to Chicago, returning Tue, Aug 12, priced at $102 found 4 hours ago
Spirit Airlines
Wed, Aug 13 - Tue, Aug 19
SAN
San Diego
ORD
Chicago
$108 Roundtrip, found 3 hours ago
$108
Roundtrip
found 3 hours ago
Select Spirit Airlines flight, departing Wed, Aug 13 from San Diego to Chicago, returning Tue, Aug 19, priced at $108 found 3 hours ago
United
Thu, Aug 7 - Sat, Aug 16
SAN
San Diego
ORD
Chicago
$129 Roundtrip, just found
$129
Roundtrip
just found
Select United flight, departing Thu, Aug 7 from San Diego to Chicago, returning Sat, Aug 16, priced at $129 just found
American Airlines
Wed, Sep 24 - Sat, Sep 27
SAN
San Diego
ORD
Chicago
$139 Roundtrip, just found
$139
Roundtrip
just found
Select American Airlines flight, departing Wed, Sep 24 from San Diego to Chicago, returning Sat, Sep 27, priced at $139 just found
Frontier Airlines
Sat, Aug 9 - Wed, Aug 13
SAN
San Diego
ORD
Chicago
$149 Roundtrip, found 2 hours ago
$149
Roundtrip
found 2 hours ago
Select Frontier Airlines flight, departing Sat, Aug 9 from San Diego to Chicago, returning Wed, Aug 13, priced at $149 found 2 hours ago
Hawaiian Airlines
Tue, Oct 28 - Tue, Nov 4
SAN
San Diego
ORD
Chicago
$171 Roundtrip, found 2 days ago
$171
Roundtrip
found 2 days ago
Select Hawaiian Airlines flight, departing Tue, Oct 28 from San Diego to Chicago, returning Tue, Nov 4, priced at $171 found 2 days ago

Find the cheapest month to fly from San Diego (SAN) to Chicago (ORD)

September is typically the cheapest month to fly

From $89 - $156 per traveler.

Graph displaying average flight prices per month

Alternative airports near Chicago

Prices were available within the past 7 days. Prices and availability are subject to change.

Select flight to Midway Intl. MDW. Closest option available. Average driving time to city center is 16 minutes. Flights from $329
MDW
Midway Intl.
Closest
Average driving time to city center16 min
Flights from $329
Flights from San Diego (SAN) to Chicago (ORD)
Origin airport
San Diego Intl.
Destination airport
O'Hare Intl.
Airlines serving
Alaska Airlines, American Airlines, Delta, Frontier Airlines, JetBlue Airways, Southwest Airlines, Spirit Airlines, Sun Country Airlines, United
Roundtrip price
$86
Distance
1720 mi
Average flight time
6 hours 17 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 August. 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 2025. You can also book with separate airlines for your outbound and return journeys, from $43 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.

 

Frequently asked questions

How much does a flight from San Diego Intl. Airport (SAN) to O'Hare Intl. Airport (ORD) cost?
You can book cheap return fares starting at $171 from San Diego Intl. Airport (SAN) to O'Hare Intl. Airport (ORD). This information is based on the cheapest price found on Expedia for this return journey departing within the next three months. This airfare is for a Alaska Airlines flight leaving SAN on August 12 2025 and touching down at ORD. The price was last updated on July 16 2025 and has not changed since.
What is the cheapest month to fly from SAN to ORD?
The cheapest flights from SAN to ORD are usually during off-peak season, when demand is lower. To save money, avoid flying during public holidays, school breaks and major local events.
Which airlines fly direct from San Diego Intl. Airport (SAN) to O'Hare Intl. Airport (ORD)?
Fly directly from San Diego Intl. Airport (SAN) to O'Hare Intl. Airport (ORD) on a United Airlines flight.
What is the cheapest airline that flies from SAN to ORD?
Book a flight from SAN to ORD with Alaska Airlines. This carrier currently offers the lowest one-way fare on this route, starting from $86. This fare is based on the lowest price found on Expedia departing within the next three months. The flight takes off from SAN on October 11 2025. Prices were last updated on July 16 2025 and have not changed since.
How many flights per day from San Diego Intl. Airport (SAN) to O'Hare Intl. Airport (ORD)?
When jetting out of San Diego Intl. Airport (SAN), you can pick from an average of 5 daily nonstop flights to O'Hare Intl. Airport (ORD).
What are the most popular departure times for flights from San Diego Intl. Airport (SAN) to O'Hare Intl. Airport (ORD)?
The 10 AM departures from SAN to ORD are the busiest. Greater demand means you'll likely pay more for these departures. If you're hoping to save money, pick a less crowded time to fly.
What day of the week has the most flights from SAN to ORD?
Depart on a Sunday if you're searching for the best selection of flights from San Diego Intl. Airport (SAN) to O'Hare Intl. Airport (ORD).
What is the earliest flight from San Diego Intl. Airport (SAN) to O'Hare Intl. Airport (ORD)?
Catch the earliest flight at around 6:40AM UTC-8, departing from San Diego Intl. Airport (SAN). You'll be in the air for roughly 4h 8m, landing at O'Hare Intl. Airport (ORD) at approximately 12:48PM UTC-6.
How long does it take to fly from San Diego Intl. Airport (SAN) to O'Hare Intl. Airport (ORD)?
It usually takes 4 hours and 9 minutes to fly the 1,700 mi from SAN to ORD.
What airline has the least delays from SAN to ORD?
With 89% of flights usually arriving on time, American Airlines has the best on-time performance for nonstop flights from San Diego Intl. Airport (SAN) to O'Hare Intl. Airport (ORD). To check your flight status and get notifications about any changes, simply head to the Expedia App.
What is the best time to fly from San Diego Intl. Airport (SAN) to O'Hare Intl. Airport (ORD)?
To arrive at O'Hare Intl. Airport (ORD) without delays, opt for a flight that leaves from San Diego Intl. Airport (SAN) before 3 PM. The likelihood of cancellations is 22% higher, on average, for departures after this hour.**Most reliable time of the day and month to travel recommendation is based on January through August 2024 flight status data sourced from OAG's global flight data platform.
What airports do you fly into for Chicago from San Diego Intl. Airport (SAN)?
You'll land at O'Hare Intl. Airport (ORD) or Midway Intl. Airport (MDW) when traveling to Chicago on a direct flight from San Diego Intl. Airport (SAN).
Is it cheaper to buy a plane ticket from San Diego Intl. Airport (SAN) to O'Hare Intl. Airport (ORD) last-minute?
Last-minute fares from SAN to ORD are typically more expensive. To lock in the best prices, start looking for flights well in advance. That being said, if you're flexible with your travel dates, it's possible to score a cheap fare right before your trip.
Is it cheaper to book a SAN to ORD flight and hotel package?
Compared with arranging hotels and flights separately, booking a SAN to ORD flight and hotel package with Expedia could result in significant savings. Better still, having everything in one convenient place will take the stress out of travel planning. Just secure your flights and select from our wide range of hotels, then tailor your trip with other add-ons like activities and car rentals.
Can I cancel or change the date of my flight from San Diego Intl. Airport (SAN) to O'Hare Intl. Airport (ORD)?
In most instances, you can modify or cancel your SAN to ORD flight. However, additional charges may apply, especially if your booking was made over 24 hours ago. Check your itinerary for the airline's fees and rules on flight changes, or if you'd like more information, head to our Customer Service portal.

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*Available to One Key members.