Great flight deals to and from Chicago are available for summer travel!
According to the Matrix Airfare Search by ITA Software, prices start at $287 for Regular Economy. If you book with United, expect prices to drop to $197 for Basic Economy and remain at $287 for Regular Economy.
The $287 fare includes advance seat assignments and a standard-sized carry-on bag.
While United offers a Basic Economy fare for $187, it’s important to note that this fare does not allow for advance seat selection; seats are randomly assigned during check-in. Also, if your carry-on doesn’t fit under the seat, a fee of $35 will apply both ways, plus any applicable gate check fees (this fee is waived if you possess a United co-branded credit card or have United elite status).
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Millennium Park, Chicago, Illinois – Photo by Dhilung Kirat via Flickr, used under Creative Commons License (By 2.0)
Sample Travel Date:
- This is just a SINGLE SAMPLE travel date; for additional availability, please refer to the “Fare Availability” and “How to Search for Availability” sections below.
Fare Availability:
- Flights are available from March to mid-December on Tuesdays, Wednesdays, or Saturdays, with limited availability. Tickets must be purchased at least 7 days prior to departure.
- Note: While this fare is valid at the time of publication, it may no longer be available if this post is older than two days.
How to Search for Availability:
- This section is only for checking availability. For purchasing tickets, please scroll to the “How to Buy” section below.
- Ensure that your Matrix Airfare Search by ITA Software page is set up as shown below after all values are entered.

- Tickets cannot be purchased directly through the Matrix Airfare Search by ITA Software. To buy your tickets, 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 5.4 cents per mile (Basic Economy) / 7.8 cents per mile (Regular Economy)
- Redeemable Miles: 1,192 miles
How to Buy:
- Make your booking on United with the dates available in the Matrix Airfare Search by ITA Software.

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For the latest cheap flight deals to Chicago:
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The Flight Deal doesn’t sell travel products or services directly. We provide information on offers from third-party travel suppliers and link you to their sites. The information shared is valid at the time of posting, but we have no control over the suppliers’ prices and availability. Please check their sites for the most accurate offers and terms.