Exciting fare deals for trips to/from Chicago!
Using Matrix Airfare Search by ITA Software, you can find prices starting at $278 for Regular Economy. When searching with United, you may see a fare of $188 for Basic Economy and $278 for Regular Economy.
The $278 fare includes advance seat selection and standard carry-on luggage.
While United offers a $188 fare for Basic Economy, please note that this option does not permit advance seat selections, and your seat will be randomly assigned at check-in. Additionally, a normal-sized carry-on that does not fit under the seat incurs a fee of $35 each way plus any applicable gate check fees (this fee is waived if you have a United co-branded credit card or United elite status).
Subscribe to our Real-Time Newsletter to get economy class deals for your city before they’re publicly shared—available for just a nickel a day.
If you’re interested in Business Class, First Class, or Premium Economy deals, sign up for our Premium Newsletter for around a quarter a day.

Millennium Park, Chicago, Illinois – Photo: Dhilung Kirat via Flickr, used under Creative Commons License (By 2.0)
Sample Travel Date:
- This is just one example of a potential travel date. For further options, please refer to the “Fare Availability” and “How to Search for Availability” sections below.
Fare Availability:
- Valid for travel in late May or late August. Availability is limited, and you must purchase at least 7 days in advance of departure.
- Please keep in mind that while this fare is available at the time of posting, if this post is older than two days, the fare may no longer be accessible.
How to Search for Availability:
- This section is for finding availability only. To purchase your tickets, please proceed to the “How to Buy” section below.
- Make sure the Matrix Airfare Search by ITA Software shows the following criteria once all values are filled in.

- Note that you cannot purchase tickets through Matrix Airfare Search by ITA Software. Follow the instructions in the “How to Buy” section below to complete your purchase.
Fare Class:
- N (Basic Economy)
- G (Regular Economy)
Elite Qualifying Dollars:
Routing:
- SFO – ORD (Chicago) – SFO
Mileage:
- Miles Flown: 3,680 miles or 5.1 cents per mile (Basic Economy) / 7.6 cents per mile (Regular Economy)
- Redeemable Miles: 1,150 miles
How to Buy:
- Book through United using the dates you find on Matrix Airfare Search by ITA Software.

Accommodations
- TripAdvisor – Discover the best hotel prices from over 200 websites through one of the leading hotel meta-search engines.
Car Rentals
- Rental Cars – Access a wide range of rental options from reputable companies like Hertz, Avis, Budget, Dollar, Enterprise, and more.
Activities and Tours
- Viator – Explore the largest marketplace for destination activities and tours.
To stay updated on the latest cheap flight deals to Chicago:
For more affordable flight deals in the San Francisco/Bay Area:
* The Flight Deal may earn a commission if you click on one of the accommodation, car rental, activities, or travel insurance links and make a booking or apply for a credit card through our link. Thank you for your support!
=====
To ensure you receive our latest deals, LIKE our The Flight Deal Facebook Page, follow us on Twitter @TheFlightDeal, on Threads @TheFlightDeal, or through The Flight Deal WhatsApp channel. You can also subscribe to The Flight Deal RSS Feed or through email (once a day).
Note that The Flight Deal does not sell travel products or services. We provide information about third-party travel suppliers’ offers and link to their websites. The information shared by The Flight Deal is accurate at the time of publication, but we have no control over the suppliers, and therefore cannot guarantee that their offers will remain available. Please check their websites for the latest offers and applicable terms and conditions.


Stay Updated on the Latest Deals
Sign up for The Flight Deal Daily DealsLetter to keep track of the newest and best flight deals available!