San Francisco – Chicago (and vice versa). $157 (Basic Economy) / $247 (Regular Economy). Roundtrip, including all Taxes – The Flight Deal

Great fare options to and from Chicago!

Using Matrix Airfare Search by ITA Software, you can find tickets priced at $247 (Regular Economy). If you book with United, it can drop to $157 (Basic Economy) or stay at $247 (Regular Economy).

The $247 fare includes advance seat selection and allows for a standard carry-on bag.

United’s $157 fare is classified as Basic Economy, which does not include advance seat assignments; you’ll receive a randomly assigned seat at check-in. Additionally, if your carry-on does not fit under the seat, a $35 fee will apply each way + applicable gate check fees (these fees may be waived for United co-branded credit card holders or United elite members).

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

Sample Travel Date:

• January 17th – 20th, 2026

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

Fare Availability:

• Valid for travel in early December or from January to February 2026 with departures and returns on Tuesday, Wednesday, and Saturday. Availability is limited. Must purchase at least 7 days in advance and by October 23rd (TODAY).

• Please note that while this fare is valid at the time of posting, if this post is more than two days old, the fare might no longer be available.

How to Search for Availability:

• The following instructions are for checking availability. To purchase tickets, please scroll down to the “How to Buy” section.

• The Matrix Airfare Search by ITA Software should display values as shown below after you input the relevant details.

• You cannot purchase tickets directly through Matrix Airfare Search by ITA Software. To buy your tickets, 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 4.3 cents per mile (Basic Economy) / 6.7 cents per mile (Regular Economy)
  
• Redeemable Miles: 1,006 miles

How to Buy:

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

Accommodations

• TripAdvisor – A top hotel meta-search engine, comparing prices from over 200 sites.

Car Rentals

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Activities and Tours

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

Stay current on the latest cheap flight deals to Chicago:

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The Flight Deal does not sell travel products or services. We provide information about third-party travel suppliers’ offers and link to their sites. While the information is accurate at publication, we do not control these suppliers and cannot guarantee their offers will remain available. For up-to-date offer information and terms, please refer directly to their sites.