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Cheap flights from San Francisco to Chicago from $221

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 15/2. Fares are subject to change and may not be available on all flights or dates of travel.
SFO — CHI
19 Jan — 26 Jan1
1 adult
1 adult, Economy, 0 bags

Cheap 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 20 December 2025.

Wed 31/1205:00SFO - ORD
Nonstop4h 25mUnited Airlines
Thu 1/106:15ORD - SFO
Nonstop4h 53mUnited Airlines
Deal found 19/12$590
Thu 25/1213:19SFO - ORD
1 stop6h 17mDelta
Mon 5/113:35ORD - SFO
1 stop6h 43mDelta
Deal found 18/12$620
Thu 25/1205:30SFO - ORD
1 stop7h 55mSouthwest
Fri 9/116:25ORD - SFO
1 stop7h 25mSouthwest
Deal found 17/12$623
Wed 31/1223:05SFO - ORD
Nonstop4h 22mUnited Airlines
Sun 4/106:15ORD - SFO
Nonstop4h 57mUnited Airlines
Deal found 18/12$682
Wed 31/1205:30SFO - ORD
1 stop7h 55mSouthwest
Sat 3/115:45ORD - SFO
1 stop6h 25mSouthwest
Deal found 20/12$698
Wed 31/1223:05SFO - ORD
Nonstop4h 22mUnited Airlines
Sat 3/106:15ORD - SFO
Nonstop4h 57mUnited Airlines
Deal found 20/12$755
Thu 25/1205:00SFO - ORD
Nonstop4h 25mUnited Airlines
Thu 25/1216:20ORD - SFO
Nonstop4h 56mUnited Airlines
Deal found 18/12$778
Sat 27/1205:00SFO - ORD
Nonstop4h 25mUnited Airlines
Sat 10/119:58ORD - SFO
Nonstop5h 02mUnited Airlines
Deal found 19/12$783
Wed 31/1205:30SFO - ORD
1 stop7h 55mSouthwest
Sun 4/114:15ORD - SFO
1 stop11h 40mSouthwest
Deal found 18/12$788

Find 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 20 December 2025.

Round-trip from

$460

One-way from

$221

Popular in

December

Cheapest in

February

Average price

$795
Delta
  • Delta
  • 31/1-2/2
  • 3 total stops
  • 18h 54m total
  • San Francisco to Chicago
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Delta
  • Delta
  • 7/2
  • 2 total stops
  • 9h 22m total
  • San Francisco to Chicago
Search Deals
Highest demand for flights based on searches. 14% potential increase in price ($175 potential increase over avg. return price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($32 potential savings vs. average return price).
Search Deals
Average for round-trip flights in December 2025
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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 20 December 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 24/2

08:11-23:59

1 stop13h 48m

Chicago O'Hare Intl

Wed 25/2

15:07-08:46

2 stops19h 39m

$465

San FranciscoChicago

SFO - ORD

SFOORD

San Francisco

Tue 20/1

14:52-23:37

1 stop6h 45m

Chicago O'Hare Intl

Fri 23/1

14:06-21:58

2 stops9h 52m

$469

San FranciscoChicago

SFO - ORD

SFOORD

San Francisco

Sat 14/2

14:39-23:52

1 stop7h 13m

Chicago O'Hare Intl

Wed 18/2

06:15-15:56

2 stops11h 41m

$478

San FranciscoChicago

SFO - ORD

SFOORD

San Francisco

Sun 1/2

05:45-16:38

1 stop8h 53m

Chicago O'Hare Intl

Tue 3/2

14:20-22:54

2 stops10h 34m

$479

San FranciscoChicago

SFO - ORD

SFOORD

San Francisco

Fri 27/2

23:59-06:19

Nonstop4h 20m

Chicago O'Hare Intl

Mon 2/3

16:20-19:19

Nonstop4h 59m

$484

San FranciscoChicago

SFO - ORD

SFOORD

San Francisco

Fri 6/2

16:55-23:14

Nonstop4h 19m

Chicago O'Hare Intl

Sun 8/2

06:47-09:40

Nonstop4h 53m

$484

San FranciscoChicago

SFO - ORD

SFOORD

San Francisco

Sun 25/1

23:56-06:25

Nonstop4h 29m

Chicago O'Hare Intl

Sun 1/2

06:47-09:40

Nonstop4h 53m

$484

San FranciscoChicago

SFO - ORD

SFOORD

San Francisco

Thu 5/3

23:59-06:19

Nonstop4h 20m

Chicago O'Hare Intl

Mon 9/3

21:15-00:16

Nonstop5h 01m

$484

San FranciscoChicago

SFO - ORD

SFOORD

San Francisco

Fri 9/1

14:39-23:53

1 stop7h 14m

Chicago O'Hare Intl

Sun 11/1

13:50-23:28

2 stops11h 38m

$497

San FranciscoChicago

SFO - ORD

SFOORD

San Francisco

Thu 5/3

06:05-21:41

2 stops13h 36m

Chicago O'Hare Intl

Sun 8/3

17:39-23:01

1 stop7h 22m

$497

Flights are sorted by cheapest return flights first.

Deals found on 18/12

Showing 1-10 of 24 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 12 December 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 $186). Flying from San Francisco to Chicago in November is currently the most expensive (average of $365). 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 20 December 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 20 December 2025.

The most flights from SFO to CHI are scheduled on a Friday (71 on average). You will have fewer flight options on Wednesday, which is when the least amount of flights are scheduled (50 on average).

How much does it cost for a return flight from San Francisco to Chicago?

How often are flights from San Francisco to Chicago delayed?

About 10% of weekly flights between San Francisco and Chicago have experienced delays in the past year, with the average delay time being 182 minutes.

What is the most punctual flight time for San Francisco to Chicago flights?

Historically, flights departing in the morning are less likely to be delayed, whereas flights leaving in the evening tend to experience delays more often.

What day of the week experiences the fewest flight delays on this route?

Tuesday tends to have the lowest number of delays on this route, whereas Sunday has historically faced a higher average of delays compared to other days of the week.

Which airline has the best punctuality record on San Francisco to Chicago flights?

Over the past year, United Airlines have had the lowest number of delays on this route, with just 9% of flights being delayed.

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 57 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 $478, Alaska Airlines can have you in Chicago from San Francisco in 7h 13m. 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: Fiji Airways (100%), Royal Jordanian (92%), China Southern (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 $186). Flying from San Francisco to Chicago in November is currently the most expensive (average of $365). 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?

Yes! Cheapflights helps users easily find flights from San Francisco to Chicago with no change fees.

Can Cheapflights notify me if prices for flights from San Francisco to Chicago become cheaper?

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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