Cheap Flights from Chicago (ORD) to San Diego (MYF)

Popular airlines from Chicago O'Hare Intl. Airport (ORD) to San Diego, CA (MYF-Montgomery Field)

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Frequently asked questions

How much does a flight from O'Hare Intl. Airport (ORD) to San Diego, CA (MYF-Montgomery Field) cost?
Snag a cheap one-way flight or cheap return flight from O'Hare Intl. Airport (ORD) to San Diego, CA (MYF-Montgomery Field) with Expedia. Enter your travel dates and sort by "Price (lowest to highest)" to find our cheapest flight deals on this route.
What is the cheapest month to fly from O'Hare Intl. Airport (ORD) to San Diego, CA (MYF-Montgomery Field)?
The cheapest month to fly from ORD to MYF is , when demand is low. Off-peak months are typically when you'll find lower airfares between these airports.
What is the cheapest airline that flies from O'Hare Intl. Airport (ORD) to San Diego, CA (MYF-Montgomery Field)?
To find the cheapest airline that'll fly you from ORD to MYF, use Expedia's filter tool. Customize your search based on your travel needs, such as preferred carriers and seat class. You can then sort your results by "Price (lowest to highest)" to see the most affordable options first.
How many flights per day from O'Hare Intl. Airport (ORD) to San Diego, CA (MYF-Montgomery Field)?
There aren't any daily nonstop flights departing from O'Hare Intl. Airport (ORD) to San Diego, CA (MYF-Montgomery Field). But you can book flights with layovers. Filter your search on Expedia to include one or more stops, and you'll be soaring above the clouds in no time at all.
What day of the week has the most flights from ORD to MYF?
Generally you'll have the most choice when it comes to flights on a Friday. Tuesdays tend to be the quietest.* However, this can vary depending on the season, airline and other factors.*Busiest/quietest day to travel is based on Expedia flight demand through January to December 2024.
What is the best time to fly from O'Hare Intl. Airport (ORD) to San Diego, CA (MYF-Montgomery Field)?
Select a flight from O'Hare Intl. Airport (ORD) to San Diego, CA (MYF-Montgomery Field) that leaves before 3 PM to reduce the risk of delays and cancellations. Departures after this hour are on average 22% more likely to be canceled.**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 San Diego County from O'Hare Intl. Airport (ORD)?
If you're boarding a direct flight from O'Hare Intl. Airport (ORD) to San Diego County, San Diego Intl. Airport (SAN) is the only airport you can land at.
Is it cheaper to buy a plane ticket from O'Hare Intl. Airport (ORD) to San Diego, CA (MYF-Montgomery Field) last-minute?
Holding off until right before your break to book your flight from ORD to MYF generally means paying more. While you may find some last-minute offers, there's no guarantee. Allow some flexibility in your schedule to maximize your chances of getting a bargain.
Is it cheaper to book an ORD to MYF flight and hotel package?
Compared with arranging hotels and flights separately, booking an ORD to MYF flight and hotel package with Expedia could result in significant savings. Better still, having everything in one easy place will take the hassle out of planning your trip. Simply pick your flights and select from our wide range of hotels, then personalize your trip with other add-ons like activities and car rentals.
Can I cancel or change the date of my flight from O'Hare Intl. Airport (ORD) to San Diego, CA (MYF-Montgomery Field)?
Generally, it's possible to reschedule or cancel your ORD to MYF flight. However, if it's been more than 24 hours since booking, additional fees may apply. Refer to your airline's policies in your itinerary to see what changes are allowed and if any costs are involved. You'll also find further details on our Customer Service portal.

Travel information

Travel information

Origin airport
O'Hare Intl.
Destination airport
Montgomery Field
Distance
1714 mi

Book with confidence

Book with confidence

Chicago to San Diego Flights

The cheapest times to fly from Chicago to San Diego

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 Chicago to San Diego are during the month of . You can find some of the cheapest flights from Chicago to San Diego with Expedia's search tool and vast selection of airlines.

 

The best time to book a flight from Chicago to San Diego

Sunday is one of the best days to book for cheap flights from Chicago to San Diego: 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 Chicago to San Diego

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 Chicago to San Diego in 2025. You can also book with separate airlines for your outbound and return journeys, from 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 Chicago to San Diego 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 Chicago to San Diego 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.

 

Chicago to San Diego Flights

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*Available to One Key members.