Cheap flights from San Francisco to Chicago from $169

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 24/11. Fares are subject to change and may not be available on all flights or dates of travel.
SFO — CHI
7 Sep — 14 Sep1
1 adult

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 2 September 2025.

Round-trip from

$379

One-way from

$169

Popular in

December

Cheapest in

February

Average price

$520
Alaska Airlines
  • Alaska Airlines
  • 12/11-18/11
  • 2 total stops
  • 24h 06m total
  • San Francisco to Chicago
United Airlines
  • United Airlines
  • 24/11
  • Nonstop
  • 4h 18m total
  • San Francisco to Chicago
Highest demand for flights based on searches. 6% potential increase in price ($67 potential increase over avg. return price).
Cheapest flight prices on average. 2% potential price decrease ($26 potential savings vs. average return price).
Average for round-trip flights in September 2025

Find flight deals from San Francisco to Chicago

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 2 September 2025.

Wed 12/1107:00SFO - ORD
1 stop14h 59mAlaska Airlines
Tue 18/1114:54ORD - SFO
1 stop9h 07mAlaska Airlines
Deal found 1/9$379
Sat 25/1023:00SFO - ORD
Nonstop4h 13mUnited Airlines
Fri 31/1017:16ORD - SFO
Nonstop4h 52mUnited Airlines
Deal found 31/8$381
Tue 23/906:30SFO - ORD
Nonstop4h 31mUnited Airlines
Wed 1/1021:13ORD - SFO
Nonstop4h 46mUnited Airlines
Deal found 31/8$405
Tue 4/1107:00SFO - ORD
1 stop9h 59mAlaska Airlines
Sat 8/1109:20ORD - SFO
1 stop14h 35mAlaska Airlines
Deal found 2/9$413
Sat 18/1005:15SFO - ORD
Nonstop4h 31mUnited Airlines
Tue 21/1015:47ORD - SFO
Nonstop4h 41mUnited Airlines
Deal found 2/9$415
Thu 2/1005:15SFO - ORD
Nonstop4h 31mUnited Airlines
Tue 7/1014:35ORD - SFO
Nonstop4h 45mUnited Airlines
Deal found 1/9$418
Thu 27/1107:00SFO - ORD
Nonstop4h 23mUnited Airlines
Thu 4/1209:00ORD - SFO
Nonstop4h 49mUnited Airlines
Deal found 1/9$423
Sat 25/1013:00SFO - ORD
2 stops8h 05mSouthwest
Fri 31/1006:15ORD - SFO
1 stop6h 20mSouthwest
Deal found 2/9$427
Thu 2/1018:35SFO - ORD
Nonstop4h 19mUnited Airlines
Sat 4/1015:47ORD - SFO
Nonstop4h 41mUnited Airlines
Deal found 31/8$429
Sat 18/1008:41SFO - ORD
1 stop13h 18mAlaska Airlines
Tue 21/1019:59ORD - SFO
1 stop20h 02mAlaska Airlines
Deal found 30/8$430
Thu 25/916:55SFO - ORD
Nonstop4h 17mUnited Airlines
Mon 29/916:25ORD - SFO
Nonstop4h 38mUnited Airlines
Deal found 1/9$432
Sat 27/914:42SFO - ORD
1 stop7h 21mAlaska Airlines
Wed 8/1008:20ORD - SFO
1 stop7h 41mAlaska Airlines
Deal found 2/9$435

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 2 September 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

Sat 18/10

08:41-23:59

1 stop13h 18m

Chicago O'Hare Intl

Tue 21/10

19:59-11:06

1 stop17h 07m

$379

San FranciscoChicago

SFO - ORD

SFOORD

San Francisco

Wed 15/10

10:26-23:59

1 stop11h 33m

Chicago O'Hare Intl

Wed 22/10

08:20-17:45

1 stop11h 25m

$379

San FranciscoChicago

SFO - ORD

SFOORD

San Francisco

Wed 5/11

07:00-23:59

1 stop14h 59m

Chicago O'Hare Intl

Wed 12/11

09:20-22:01

1 stop14h 41m

$379

San FranciscoChicago

SFO - ORD

SFOORD

San Francisco

Wed 8/10

10:26-23:59

1 stop11h 33m

Chicago O'Hare Intl

Wed 15/10

08:20-14:01

1 stop7h 41m

$379

San FranciscoChicago

SFO - ORD

SFOORD

San Francisco

Wed 1/10

23:00-05:13

Nonstop4h 13m

Chicago O'Hare Intl

Wed 8/10

06:15-08:53

Nonstop4h 38m

$405

San FranciscoChicago

SFO - ORD

SFOORD

San Francisco

Tue 23/9

06:30-13:01

Nonstop4h 31m

Chicago O'Hare Intl

Tue 30/9

15:47-18:28

Nonstop4h 41m

$405

San FranciscoChicago

SFO - ORD

SFOORD

San Francisco

Tue 11/11

23:44-06:02

Nonstop4h 18m

Chicago O'Hare Intl

Tue 18/11

09:10-11:56

Nonstop4h 46m

$405

San FranciscoChicago

SFO - ORD

SFOORD

San Francisco

Wed 8/10

23:00-05:13

Nonstop4h 13m

Chicago O'Hare Intl

Wed 15/10

06:15-08:54

Nonstop4h 39m

$405

San FranciscoChicago

SFO - ORD

SFOORD

San Francisco

Wed 25/2

18:40-00:59

Nonstop4h 19m

Chicago O'Hare Intl

Wed 4/3

06:30-09:20

Nonstop4h 50m

$405

San FranciscoChicago

SFO - ORD

SFOORD

San Francisco

Mon 20/10

21:17-14:50

1 stop15h 33m

Chicago O'Hare Intl

Tue 21/10

19:59-11:06

1 stop17h 07m

$413

Flights are sorted by cheapest return flights first.

Deals found on 31/8

Showing 1-10 of 21 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 29 August 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 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 2 September 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 2 September 2025.

The most flights from SFO to CHI are scheduled on a Monday (88 on average). You will have fewer flight options on Wednesday, which is when the least amount of flights are scheduled (27 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 60 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 $405, Alaska Airlines can have you in Chicago from San Francisco in 4h 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: Asiana Airlines (82%), Austrian Airlines (79%), Brussels Airlines (77%).

  • 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.

See more FAQs

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