San Francisco – Chicago (and vice versa). $123 (Basic Economy) / $213 (Regular Economy). Roundtrip, including all Taxes – The Flight Deal

Exciting airfare options to or from Chicago!

The Matrix Airfare Search by ITA Software lists this fare at $247 for Regular Economy. If you use those dates on United, you’ll find prices dropping to $123 (Basic Economy) and $213 (Regular Economy).

The $213 fare is for Regular Economy, which includes advance seat selection and a regular-sized carry-on.

Although United offers a $123 fare for Basic Economy, this option does not allow for advance seat assignments; seats will be randomly allocated at check-in. Additionally, a regular-sized carry-on that exceeds under-seat dimensions incurs a $35 fee each way + any applicable gate check fees (this fee can be waived with a United co-branded credit card or elite status).

Millennium Park, Chicago, Illinois – Photo: Dhilung Kirat via Flickr, used under Creative Commons License (By 2.0)

Sample Travel Dates:

• January 21st – 28th, 2026

• This is just ONE SAMPLE travel date; please refer to the “Fare Availability” and “How to Search for Availability” sections below for more options.

Fare Availability:

• Valid for travel between January 2026 – February 2026 on Tuesdays and Wednesdays. Availability is limited. Tickets must be purchased at least 7 days before departure, by December 4th (TODAY).

• Please note that while this fare is valid at the time of posting, it is likely to change if this post is older than two days.

How to Search for Availability:

• This section is for checking availability. To purchase tickets, please see the “How to Buy” section below.

• The Matrix Airfare Search by ITA Software should appear as shown after entering all required information.

• You cannot purchase tickets directly through Matrix Airfare Search by ITA Software. Please follow the instructions in the “How to Buy” section below.

Fare Class:

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

Elite Qualifying Dollars:

Routing:

• SFO – ORD (Chicago) – SFO

Mileage:

• Miles Flown: 3,680 miles or 3.3 cents per mile (Basic Economy) / 5.8 cents per mile (Regular Economy)
  
• Redeemable Miles: 848 miles

How to Buy:

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

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Check out more of the latest cheap flight deals to Chicago:

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The Flight Deal itself does not sell travel products or services. We aim to provide you with insights into offers from third-party travel suppliers and connect you to their platforms. Please note that the information available is accurate at the time of publication but may change without our control. Always verify with suppliers for the most recent offer details and applicable terms.