
Popular airlines from San Francisco Intl. Airport (SFO) to Chicago
- Alaska Airlines
Alaska Airlines
- Frontier Airlines
Frontier Airlines
- Delta
Delta
- Southwest Airlines
Southwest Airlines
- United
United
- American Airlines
American Airlines
- JetBlue Airways
JetBlue Airways
- Plan, book, fly with confidence
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Today's featured flight deals from San Francisco Intl. Airport (SFO) to Chicago
- San Francisco (SFO) to Chicago (MDW).Southwest Airlines, nonstop.Departing on Thu, Aug 7 at 7:15am from San Francisco, arriving at 1:20pm in Chicago.Returning on Mon, Aug 11 at 7:17pm from Chicago, arriving at 11:55pm in San Francisco.Select Southwest Airlines flight departing on Thu, Aug 7 at 7:15am from San Francisco, returning on Mon, Aug 11 at 7:17pm from Chicago priced at $53925% less than typical$539
- San Francisco (SFO) to Chicago (ORD).American Airlines, nonstop.Departing on Thu, Sep 11 at 2:22pm from San Francisco, arriving at 8:40pm in Chicago.Returning on Mon, Sep 15 at 6:55pm from Chicago, arriving at 11:10pm in San Francisco.Select American Airlines flight departing on Thu, Sep 11 at 2:22pm from San Francisco, returning on Mon, Sep 15 at 6:55pm from Chicago priced at $22735% less than typical$227
- San Francisco (SFO) to Chicago (ORD).American Airlines, nonstop.Departing on Thu, Sep 11 at 1:21pm from San Francisco, arriving at 7:45pm in Chicago.Returning on Mon, Sep 15 at 6:55pm from Chicago, arriving at 11:10pm in San Francisco.Select American Airlines flight departing on Thu, Sep 11 at 1:21pm from San Francisco, returning on Mon, Sep 15 at 6:55pm from Chicago priced at $22735% less than typical$227
- San Francisco (SFO) to Chicago (ORD).American Airlines, nonstop.Departing on Mon, Aug 25 at 6:10am from San Francisco, arriving at 12:30pm in Chicago.Returning on Sat, Aug 30 at 6:45am from Chicago, arriving at 9:18am in San Francisco.Select American Airlines flight departing on Mon, Aug 25 at 6:10am from San Francisco, returning on Sat, Aug 30 at 6:45am from Chicago priced at $19835% less than typical$198
- San Francisco (SFO) to Chicago (ORD).American Airlines, nonstop.Departing on Tue, Aug 26 at 8:00am from San Francisco, arriving at 2:20pm in Chicago.Returning on Sat, Aug 30 at 5:39pm from Chicago, arriving at 8:13pm in San Francisco.Select American Airlines flight departing on Tue, Aug 26 at 8:00am from San Francisco, returning on Sat, Aug 30 at 5:39pm from Chicago priced at $18835% less than typical$188
- San Francisco (SFO) to Chicago (ORD).American Airlines, nonstop.Departing on Tue, Sep 9 at 10:14am from San Francisco, arriving at 4:36pm in Chicago.Returning on Sat, Sep 13 at 3:19pm from Chicago, arriving at 6:01pm in San Francisco.Select American Airlines flight departing on Tue, Sep 9 at 10:14am from San Francisco, returning on Sat, Sep 13 at 3:19pm from Chicago priced at $19725% less than typical$197
Cheap Flights from San Francisco to Chicago (SFO-CHI)
Prices were available within the past 7 days and start at $90 for one-way flights and $179 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.










Find the cheapest month to fly from San Francisco (SFO) to Chicago (CHI)
September is typically the cheapest month to fly
Graph displaying average flight prices per month
Alternative airports near Chicago
Prices were available within the past 7 days. Prices and availability are subject to change.
Origin airport | San Francisco Intl. |
Destination airport | O'Hare Intl. |
Roundtrip price | $179 |
Distance | 1842 mi |
San Francisco to Chicago Flights
The cheapest times to fly from San Francisco to Chicago
On average, Thursday can be the cheapest time to fly, according to data from the Airlines Reporting Corporation (ARC), one of the world's biggest databases for global airline sales. The data reveals that you could save up to 16% by flying on a Thursday—the cheapest day to travel on average—instead of a Sunday—the most expensive. Some of the most affordable flights from San Francisco to Chicago are during the month of August. You can find some of the cheapest flights from San Francisco to Chicago with Expedia's search tool and vast selection of airlines.
The best time to book a flight from San Francisco to Chicago
Sunday is one of the best days to book for cheap flights from San Francisco to Chicago: Tickets reserved on a Sunday cost between 6% and 13% less than those reserved on a Friday, according to ARC data. The data also suggests booking early can also lead to cheaper airfares. You could save 24% by buying your tickets for domestic flights at least a month in advance and 10% by booking international flights 2 months in advance.
How to find cheap round-trip tickets from San Francisco to Chicago
Being flexible with your dates and using Expedia's Price Drop Protection and Price Tracking features are some of the best ways of finding a cheap ticket from San Francisco to Chicago in 2025. You can also book with separate airlines for your outbound and return journeys, from $90 one-way. Expedia also offers Price Drop Protection, so if the cost of your airfare goes down after booking, you'll receive a credit for the difference*. This is available for a small fee, and is free to One Key Gold and Platinum tier members.
Expedia's Price Tracking feature means you can stay on top of airfares without manually checking every day. It sends you automated price alerts for cheap San Francisco to Chicago flights and uses historical data to indicate when the best time to book is. Download Expedia's free app to activate this handy tool in a few easy taps.
You could also save big by booking one of Expedia's vacation packages. Bundling together your San Francisco to Chicago airfare with your accommodations and car rental is often cheaper than booking everything separately. There’s also One Key, Expedia's generous rewards program. Join for free and you could earn One Key cash on most bookings to save on future adventures.
*Terms apply.
Disclaimer: ARC The statistics are based on average round-trip ticket prices between January and August 2023. The percentages you see are averages.
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