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Cheap flights from San Francisco to Chicago from $219

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 9/12. Fares are subject to change and may not be available on all flights or dates of travel.
SFO — CHI
6 Dec — 13 Dec1
1 adult
1 adult, Economy, 0 bags

Cheap flight deals from San Francisco to Chicago

Discover tips and strategies to find the most affordable flight options for your journey from San Francisco (SFO) to Chicago (CHI). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated 6 November 2025.

Round-trip from

$509

One-way from

$219

Popular in

December

Cheapest in

February

Average price

$690
Delta
  • Delta
  • 9/12-13/12
  • 3 total stops
  • 21h 10m total
  • San Francisco to Chicago
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Alaska Airlines
  • Alaska Airlines
  • 9/12
  • 2 total stops
  • 10h 15m total
  • San Francisco to Chicago
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Highest demand for flights based on searches. 9% potential increase in price ($110 potential increase over avg. return price).
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Cheapest flight prices on average. 2% potential price decrease ($28 potential savings vs. average return price).
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Average for round-trip flights in November 2025
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Find flight deals from San Francisco to Chicago

Enter your travel dates to find the best prices.

Cheapest flights from San Francisco to Chicago
Explore the most affordable flight options available from San Francisco to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on 6 November 2025.

Tue 9/1219:37SFO - ORD
2 stops11h 03mDelta
Sat 13/1207:50ORD - SFO
1 stop10h 07mDelta
Deal found 4/11$509
Mon 24/1106:00SFO - ORD
1 stop9h 18mDelta
Wed 3/1207:50ORD - SFO
1 stop16h 41mDelta
Deal found 4/11$513
Mon 8/1200:30SFO - ORD
1 stop6h 10mDelta
Fri 12/1214:14ORD - SFO
1 stop10h 17mDelta
Deal found 4/11$515
Fri 12/1208:09SFO - ORD
1 stop13h 41mAlaska Airlines
Sun 14/1208:55ORD - SFO
1 stop14h 51mAlaska Airlines
Deal found 4/11$517
Fri 5/1208:09SFO - ORD
1 stop13h 41mAlaska Airlines
Mon 8/1220:59ORD - SFO
1 stop13h 07mAlaska Airlines
Deal found 4/11$518
Tue 2/1210:30SFO - ORD
2 stops8h 51mDelta
Wed 3/1207:50ORD - SFO
2 stops10h 22mDelta
Deal found 5/11$520
Thu 27/1106:00SFO - ORD
1 stop9h 21mDelta
Wed 3/1207:50ORD - SFO
2 stops10h 22mDelta
Deal found 5/11$522
Thu 11/1212:37SFO - ORD
1 stop9h 24mDelta
Mon 15/1207:20ORD - SFO
2 stops10h 37mDelta
Deal found 4/11$524
Thu 11/1213:58SFO - ORD
1 stop8h 01mDelta
Wed 17/1207:20ORD - SFO
2 stops10h 37mDelta
Deal found 4/11$527
Fri 5/1200:30SFO - ORD
1 stop9h 13mDelta
Tue 9/1215:50ORD - SFO
1 stop6h 38mDelta
Deal found 3/11$529
Wed 31/1200:10SFO - ORD
1 stop7h 15mDelta
Sat 31/107:30ORD - SFO
1 stop8h 13mDelta
Deal found 3/11$531
Fri 5/1200:30SFO - ORD
1 stop8h 03mDelta
Mon 8/1214:14ORD - SFO
1 stop10h 17mDelta
Deal found 4/11$532

Cheapflights Fare Finder

 
Customise your flight search to find flights from San Francisco to Chicago that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 134,765 searches. Data last updated 6 November 2025.
Use the filters below to find and compare flights from San Francisco to Chicago that are best for you.

Fly from

San Francisco

Fly to

Chicago

Route

Departure

Return

Price

San FranciscoChicago

SFO - ORD

SFOORD

San Francisco

Tue 16/12

09:00-23:50

2 stops12h 50m

Chicago O'Hare Intl

Mon 22/12

15:33-23:54

1 stop10h 21m

$527

San FranciscoChicago

SFO - ORD

SFOORD

San Francisco

Sat 6/12

06:00-12:24

Nonstop4h 24m

Chicago O'Hare Intl

Sat 13/12

16:10-19:00

Nonstop4h 50m

$529

San FranciscoChicago

SFO - ORD

SFOORD

San Francisco

Tue 2/12

05:10-13:30

1 stop6h 20m

Chicago O'Hare Intl

Wed 3/12

07:15-17:25

1 stop12h 10m

$538

San FranciscoChicago

SFO - ORD

SFOORD

San Francisco

Mon 8/12

10:30-21:21

2 stops8h 51m

Chicago O'Hare Intl

Sat 13/12

07:50-16:12

2 stops10h 22m

$555

San FranciscoChicago

SFO - ORD

SFOORD

San Francisco

Wed 10/12

14:50-23:50

1 stop7h 00m

Chicago O'Hare Intl

Fri 12/12

15:05-21:46

1 stop8h 41m

$561

San FranciscoChicago

SFO - ORD

SFOORD

San Francisco

Tue 10/3

22:50-05:03

Nonstop4h 13m

Chicago O'Hare Intl

Wed 11/3

12:55-16:00

Nonstop5h 05m

$578

San FranciscoChicago

SFO - ORD

SFOORD

San Francisco

Mon 15/12

23:44-06:02

Nonstop4h 18m

Chicago O'Hare Intl

Tue 6/1

06:47-09:40

Nonstop4h 53m

$582

San FranciscoChicago

SFO - ORD

SFOORD

San Francisco

Wed 17/12

05:45-18:45

2 stops11h 00m

Chicago O'Hare Intl

Sun 18/1

08:50-17:49

2 stops10h 59m

$626

San FranciscoChicago

SFO - ORD

SFOORD

San Francisco

Thu 18/12

10:46-23:59

2 stops11h 13m

Chicago O'Hare Intl

Mon 22/12

15:33-23:54

1 stop10h 21m

$640

San FranciscoChicago

SFO - ORD

SFOORD

San Francisco

Tue 16/12

19:37-08:40

2 stops11h 03m

Chicago O'Hare Intl

Mon 22/12

13:59-00:32

2 stops12h 33m

$644

Flights are sorted by cheapest return flights first.

Deals found on 5/11

Showing 1-10 of 23 results
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Best time to book a flight from San Francisco to Chicago

Have a flexible travel schedule? Discover the best time to fly to Chicago from San Francisco with our price prediction graph.
Estimated return price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from San Francisco to Chicago

How far ahead should I book a flight from San Francisco to Chicago?

Use this chart to determine the optimal time to book a return flight from San Francisco to Chicago. Price data was last updated on 31 October 2025.

The price you pay for your flight from San Francisco to Chicago may vary depending on when you book. For the best chance of a lower fare, look to book 71 days in advance of your trip. Fares are likely to increase a fortnight or so before your departure date.

What is the cheapest month to book a flight from San Francisco to Chicago?

Currently, December is the cheapest month in which you can book a flight from San Francisco to Chicago (average of $196). Flying from San Francisco to Chicago in March is currently the most expensive (average of $343). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

What is the cheapest time of day to fly from SFO to CHI?

Find hourly flight availability from San Francisco to Chicago. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated 6 November 2025.

When flying from San Francisco to Chicago, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

Weekly flight availability from San Francisco to Chicago

Explore weekly flight availability from San Francisco to Chicago. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated 6 November 2025.

The most flights from SFO to CHI are scheduled on a Thursday (69 on average). You will have fewer flight options on Sunday, which is when the least amount of flights are scheduled (40 on average).

Related info for your journey

Find useful and relevant information for your journey from San Francisco to Chicago. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What airport do you fly from for flights from San Francisco to Chicago?

    If you book a flight to Chicago from San Francisco, you will be flying from San Francisco, which is the city’s only airport. San Francisco (SFO) is located 19.0 km from the centre of San Francisco. There are 51 flights from San Francisco to Chicago per day from 0 different airlines.

  • How long is the flight from San Francisco to Chicago?

    For as low as $529, United Airlines can have you in Chicago from San Francisco in 4h 24m. San Francisco and Chicago are separated by a distance of 2963 km. Both multi-stop and direct flights can be found to your destination and back.

  • What are the most reliable airlines from San Francisco to Chicago?

    Looking for the most reliable airlines to get you to your destination on time? Our data shows these are most likely to get you from San Francisco to Chicago on time: China Southern (100%), Fiji Airways (92%), Asiana Airlines (91%).

  • Can I find deals for flights from San Francisco to Chicago that include hotel bookings?

    Yes. In addition to deals on San Francisco to Chicago flights, Cheapflights offers holiday packages that include both flights and hotel.

  • How can I find direct flights from San Francisco to Chicago?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from San Francisco to Chicago.

  • Can I find deals for business class flights from San Francisco to Chicago?

    Yes. Cheapflights offers flight deals from San Francisco to Chicago by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from San Francisco to Chicago?

    Currently, December is the cheapest month in which you can book a flight from San Francisco to Chicago (average of $196). Flying from San Francisco to Chicago in March is currently the most expensive (average of $343). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

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It’s simple! Cheapflights, which is free to use for everyone, saves millions of users time and money every year by helping them find the cheapest and most suitable flights from San Francisco to Chicago.

Can Cheapflights find flights from San Francisco to Chicago with no change fees?

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Yes, and it’s super simple to set up. Click the bell icon next to the flight deals above and provide a valid email address to enable Price Alerts. That’s it!

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