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Cheap flights from San Francisco to Chicago from $238

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 9/6. Fares are subject to change and may not be available on all flights or dates of travel.
SFO — CHI
16 Jun — 23 Jun1
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 17 May 2026.

Mon 16/1111:53
SFO
-
ORD
1 stop9h 56m
Alaska Airlines
Fri 4/1217:55
ORD
-
SFO
1 stop8h 04m
Alaska Airlines
Deal found 13/5$514
Tue 2/600:50
SFO
-
ORD
Nonstop4h 26m
United Airlines
Fri 5/612:45
ORD
-
SFO
Nonstop4h 43m
United Airlines
Deal found 12/5$522
Wed 10/614:40
SFO
-
ORD
Nonstop4h 24m
United Airlines
Wed 17/612:45
ORD
-
SFO
Nonstop4h 43m
United Airlines
Deal found 13/5$524
Thu 6/813:30
SFO
-
ORD
1 stop6h 28m
Delta
Thu 13/819:44
ORD
-
SFO
1 stop6h 08m
Delta
Deal found 14/5$526
Tue 9/600:50
SFO
-
ORD
Nonstop4h 26m
United Airlines
Tue 16/612:45
ORD
-
SFO
Nonstop4h 43m
United Airlines
Deal found 13/5$527
Sat 6/605:05
SFO
-
ORD
Nonstop4h 24m
United Airlines
Sat 27/607:30
ORD
-
SFO
Nonstop4h 49m
United Airlines
Deal found 13/5$532
Sat 6/606:16
SFO
-
ORD
1 stop10h 34m
Alaska Airlines
Mon 8/619:59
ORD
-
SFO
1 stop15h 34m
Alaska Airlines
Deal found 16/5$538
Mon 6/707:55
SFO
-
ORD
1 stop9h 02m
Alaska Airlines
Sat 18/717:59
ORD
-
SFO
1 stop7h 09m
Alaska Airlines
Deal found 14/5$539
Tue 9/613:38
SFO
-
ORD
1 stop8h 01m
Delta
Sat 20/611:15
ORD
-
SFO
1 stop8h 58m
Delta
Deal found 13/5$541
Thu 27/806:00
SFO
-
ORD
1 stop8h 54m
Delta
Mon 31/818:00
ORD
-
SFO
1 stop7h 46m
Delta
Deal found 12/5$543
Mon 8/622:55
SFO
-
ORD
1 stop7h 10m
Delta
Tue 16/607:01
ORD
-
SFO
1 stop9h 15m
Delta
Deal found 13/5$544
Fri 28/815:00
SFO
-
ORD
1 stop6h 41m
Alaska Airlines
Sat 5/907:00
ORD
-
SFO
1 stop7h 39m
Alaska Airlines
Deal found 14/5$548

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 17 May 2026.

Round-trip from

$514

One-way from

$238

Popular in

March

Cheapest in

September

Average price

$776
Alaska Airlines
  • Alaska Airlines
  • 28/8-31/8
  • 2 total stops
  • 22h 23m total
  • San Francisco to Chicago
Search Deals
Delta
  • Delta
  • 24/6
  • 1 total stop
  • 7h 03m total
  • San Francisco to Chicago
Search Deals
Highest demand for flights based on searches. 2% potential increase in price ($33 potential increase over avg. return price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($19 potential savings vs. average return price).
Search Deals
Average for round-trip flights in May 2026
Search Deals

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 17 May 2026.
Use the filters below to find and compare flights from San Francisco to Chicago that are best for you.

Fly from

Fly to

Route

Departure

Return

Price

Cheapest return flight
Fastest return journey

San FranciscoChicago

SFO - ORD

SFOORD

San Francisco

Tue 30/6

15:10-21:34

Nonstop4h 24m

Chicago O'Hare Intl

Fri 3/7

06:10-08:47

Nonstop4h 37m

$522

San FranciscoChicago

SFO - ORD

SFOORD

San Francisco

Sat 1/8

16:21-22:59

Nonstop4h 38m

Chicago O'Hare Intl

Sat 8/8

06:10-08:47

Nonstop4h 37m

$532

San FranciscoChicago

SFO - ORD

SFOORD

San Francisco

Mon 9/11

23:50-06:18

Nonstop4h 28m

Chicago O'Hare Intl

Thu 19/11

21:30-00:29

Nonstop4h 59m

$532

San FranciscoChicago

SFO - ORD

SFOORD

San Francisco

Sat 18/7

14:30-23:18

1 stop6h 48m

Chicago O'Hare Intl

Tue 21/7

08:27-13:09

1 stop6h 42m

$541

San FranciscoChicago

SFO - ORD

SFOORD

San Francisco

Wed 22/7

13:38-23:38

1 stop8h 00m

Chicago O'Hare Intl

Mon 27/7

17:54-23:46

1 stop7h 52m

$541

San FranciscoChicago

SFO - ORD

SFOORD

San Francisco

Sun 6/9

14:45-23:41

1 stop6h 56m

Chicago O'Hare Intl

Wed 9/9

07:00-12:39

1 stop7h 39m

$568

San FranciscoChicago

SFO - ORD

SFOORD

San Francisco

Wed 22/7

18:34-00:59

Nonstop4h 25m

Chicago O'Hare Intl

Mon 27/7

21:35-00:32

Nonstop4h 57m

$568

San FranciscoChicago

SFO - ORD

SFOORD

San Francisco

Sat 3/10

18:38-00:59

Nonstop4h 21m

Chicago O'Hare Intl

Sun 4/10

06:02-08:45

Nonstop4h 43m

$594

San FranciscoChicago

SFO - ORD

SFOORD

San Francisco

Mon 10/8

00:55-07:16

Nonstop4h 21m

Chicago O'Hare Intl

Wed 12/8

16:20-19:12

Nonstop4h 52m

$611

San FranciscoChicago

SFO - ORD

SFOORD

San Francisco

Wed 15/7

18:34-00:59

Nonstop4h 25m

Chicago O'Hare Intl

Tue 21/7

21:35-00:32

Nonstop4h 57m

$611

Flights are sorted by cheapest return flights first.

Deals found on 14/5

Showing 1-10 of 23 resultsSorted by cheapest first
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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?

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 66 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, September is the cheapest month in which you can book a flight from San Francisco to Chicago (average of $495). Flying from San Francisco to Chicago in January is currently the most expensive (average of $1,919). 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 17 May 2026.

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 17 May 2026.

The most flights from SFO to CHI are scheduled on a Sunday (91 on average). You will have fewer flight options on Thursday, which is when the least amount of flights are scheduled (2 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 183 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, American Airlines have had the lowest number of delays on this route, with just 10% 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 17.7 km from the centre of San Francisco. There are 62 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 $522, 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: ITA Airways (100%), Brussels Airlines (89%), Austrian Airlines (85%).

  • 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, September is the cheapest month in which you can book a flight from San Francisco to Chicago (average of $495). Flying from San Francisco to Chicago in January is currently the most expensive (average of $1,919). 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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