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Chicago – San Diego (and vice versa). $135 (Basic Economy) / $225 (Regular Economy). Roundtrip, including all Taxes – The Flight Deal

Miles@Flyingfrugal by Miles@Flyingfrugal
September 24, 2025
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Catch a fantastic deal for nonstop flights to and from San Diego!

According to Matrix Airfare Search by ITA Software, fares start at $225 for Regular Economy. When booking with United, the price may drop to $135 for Basic Economy and $225 for Regular Economy.

The $225 fare allows for advance seat selection and a standard size carry-on.

United’s $135 fare is for Basic Economy, which does not include advance seat assignments. Seats will be allocated randomly during check-in. Additionally, a normal-sized carry-on that doesn’t fit under the seat incurs a $35 fee each way, plus any applicable gate check fees (this fee is waived if you have a United co-branded credit card or elite status).

Sign up for our Real-Time Newsletter to receive economy class deals tailored to your city about an hour before they’re posted on our website and social media channels—all for just a nickel a day.


Looking for Business Class, First Class, or Premium Economy deals? Subscribe to our Premium Newsletter for about a quarter a day.

Scripps Pier – Photo: SD Dirk via Flickr, used under Creative Commons License (By 2.0)

Sample Travel Dates:

  • This is just ONE SAMPLE travel date. For more availability, please refer to the “Fare Availability” and “How to Search for Availability” instructions below.

Fare Availability:

  • Valid for travel from late October to early November, or early December to January 2026 through February 2026, with departures and returns on Tuesdays, Wednesdays, and Saturdays. Availability is limited. A purchase is required at least 7 days prior to departure.
  • Note: This fare is valid at the time of posting, but if this post is more than two days old, the fare may no longer be available.

How to Search for Availability:

  • This section is for searching availability only. To purchase tickets, scroll down to the “How to Buy” section of this post.
  • The Matrix Airfare Search by ITA Software should look like the example provided once all values are input.

  • You cannot purchase tickets directly using the Matrix Airfare Search by ITA Software. Follow the instructions in the “How to Buy” section to complete your purchase.

Fare Class:

  • N (Basic Economy)
  • G (Regular Economy)

Elite Qualifying Dollars:

Routing:

  • ORD – SAN (San Diego) – ORD

Mileage:

  • Miles Flown: 3,438 miles, averaging 3.9 cents per mile (Basic Economy) or 6.5 cents per mile (Regular Economy)
  • Redeemable Miles: 904 miles

How to Buy:

  • Book through United using the dates identified on Matrix Airfare Search by ITA Software.

Accommodations

  • TripAdvisor – One of the top hotel comparison engines, helping you find the best rates from over 200 sites.

Car Rentals

  • Rental Cars – A leading agency for car rentals, featuring top brands like Hertz, Avis, Budget, Dollar, and Enterprise.

Activities and Tours

  • Viator – The largest marketplace for activities and tours at your destination.

For more of the latest cheap flights from Chicago:

* The Flight Deal earns a commission when you use our affiliate links for bookings or apply for credit cards through our site. Your support is appreciated!

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Stay updated with our latest deals by liking The Flight Deal on Facebook, following us on Twitter @TheFlightDeal, Threads @TheFlightDeal, or joining The Flight Deal WhatsApp channel. You can also subscribe to The Flight Deal RSS Feed or sign up for email updates (once a day).

Please note that The Flight Deal does not sell travel products or services but provides information on third-party travel suppliers’ offers and links to their platforms. While the information is accurate at publication, we do not guarantee the availability of offers as they may change without notice. Always check the suppliers’ sites for the most current offers and terms.


Tags: BasicChicagodealDiegoEconomyflightincludingRegularRoundtripSanTaxesversavice
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