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Cheap flights from San Francisco to Chicago from $280

SFO — CHI
15 Nov — 22 Nov1
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

Tue 10/1112:13 -
1 stop9h 46m
Sat 14/1114:07 -
1 stop7h 42m
Deal found 16/10$565
Fri 6/1107:04 -
1 stop9h 55m
Sat 14/1109:30 -
2 stops11h 40m
Deal found 12/10$572
Wed 18/1118:28 -
2 stops12h 36m
Thu 19/1114:32 -
1 stop8h 51m
Deal found 13/10$574
Fri 13/1107:05 -
1 stop14h 50m
Mon 16/1107:45 -
1 stop15h 38m
Deal found 14/10$575
Wed 18/1111:44 -
1 stop10h 11m
Sun 22/1106:40 -
1 stop8h 35m
Deal found 13/10$577
Sat 12/1216:35 -
2 stops13h 24m
Thu 17/1207:45 -
1 stop17h 15m
Deal found 12/10$584
Fri 11/1209:58 -
2 stops12h 01m
Wed 16/1215:19 -
1 stop8h 29m
Deal found 12/10$590
Fri 13/1106:40 -
2 stops21h 00m
Sat 14/1114:07 -
2 stops11h 20m
Deal found 14/10$593
Mon 16/1120:58 -
1 stop16h 02m
Wed 18/1107:00 -
2 stops12h 21m
Deal found 16/10$597
Tue 17/1111:44 -
1 stop10h 11m
Sat 21/1117:55 -
1 stop7h 38m
Deal found 13/10$598
Mon 30/1100:10 -
Nonstop4h 18m
Mon 21/1214:35 -
Nonstop5h 00m
Deal found 15/10$600

Find flight deals from San Francisco to Chicago

Round-trip from

$565

One-way from

$280

Popular in

July

Cheapest in

February

Average price

$743
Alaska Airlines
  • Alaska Airlines
  • 10/11-14/11
  • 2 total stops
  • 17h 28m total
  • San Francisco to Chicago
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Delta
  • Delta
  • 13/11-31/12
  • 1 total stop
  • 14h 50m total
  • San Francisco to Chicago
Search Deals
Highest demand for flights based on searches. 6% potential increase in price ($97 potential increase over avg. return price).
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Cheapest flight prices on average. 1% potential price decrease ($15 potential savings vs. average return price).
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Average for round-trip flights in October 2026
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Cheapflights Fare Finder

 
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

San FranciscoChicago

SFO San Francisco - ORD Chicago O'Hare Intl

SFOORD

San Francisco

Wed 11/11

18:28-13:37

1 stop17h 09m

Chicago O'Hare Intl

Wed 31/12

00:00-22:00

Nonstop0h 00m

$280

San FranciscoChicago

SFO San Francisco - ORD Chicago O'Hare Intl

SFOORD

San Francisco

Mon 23/11

05:00-11:24

Nonstop4h 24m

Chicago O'Hare Intl

Wed 31/12

00:00-22:00

Nonstop0h 00m

$301

San FranciscoChicago

SFO San Francisco - ORD Chicago O'Hare Intl

SFOORD

San Francisco

Mon 16/11

06:35-12:59

Nonstop4h 24m

Chicago O'Hare Intl

Wed 31/12

00:00-22:00

Nonstop0h 00m

$312

San FranciscoChicago

SFO San Francisco - ORD Chicago O'Hare Intl

SFOORD

San Francisco

Fri 1/1

06:20-14:49

1 stop6h 29m

Chicago O'Hare Intl

Wed 31/12

00:00-22:00

Nonstop0h 00m

$319

San FranciscoChicago

SFO San Francisco - ORD Chicago O'Hare Intl

SFOORD

San Francisco

Thu 8/4

13:05-23:46

1 stop8h 41m

Chicago O'Hare Intl

Wed 31/12

00:00-22:00

Nonstop0h 00m

$344

San FranciscoChicago

SFO San Francisco - ORD Chicago O'Hare Intl

SFOORD

San Francisco

Thu 12/11

14:44-23:49

1 stop7h 05m

Chicago O'Hare Intl

Wed 31/12

00:00-22:00

Nonstop0h 00m

$356

San FranciscoChicago

SFO San Francisco - ORD Chicago O'Hare Intl

SFOORD

San Francisco

Sat 27/3

13:05-23:46

1 stop8h 41m

Chicago O'Hare Intl

Wed 31/12

00:00-22:00

Nonstop0h 00m

$362
Fastest return journey

San FranciscoChicago

SFO San Francisco - ORD Chicago O'Hare Intl

SFOORD

San Francisco

Sat 19/12

18:53-01:16

Nonstop4h 23m

Chicago O'Hare Intl

Wed 31/12

00:00-22:00

Nonstop0h 00m

$378

San FranciscoChicago

SFO San Francisco - ORD Chicago O'Hare Intl

SFOORD

San Francisco

Thu 31/12

06:34-13:03

Nonstop4h 29m

Chicago O'Hare Intl

Wed 31/12

00:00-22:00

Nonstop0h 00m

$408

San FranciscoChicago

SFO San Francisco - ORD Chicago O'Hare Intl

SFOORD

San Francisco

Fri 1/1

18:53-01:16

Nonstop4h 23m

Chicago O'Hare Intl

Wed 31/12

00:00-22:00

Nonstop0h 00m

$408

Flights are sorted by cheapest return flights first.

Deals found on 13/10

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

Cheapflights Insights

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

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

Currently, February is the cheapest month in which you can book a flight from San Francisco to Chicago (average of $657). Flying from San Francisco to Chicago in June is currently the most expensive (average of $862). 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?

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

The most flights from SFO to CHI are scheduled on a Wednesday (92 on average). You will have fewer flight options on Monday, which is when the least amount of flights are scheduled (76 on average).

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

Airfare is below average for this route at the moment.
San Francisco to Chicago flights typically cost between $593 and $1,005 in November.
The cheapest return price found within the last 5 days was $565 on Alaska Airlines (10 Nov–14 Nov).

How often are flights from San Francisco to Chicago delayed?

About 9% of weekly flights between San Francisco and Chicago have experienced delays in the past year, with the average delay time being 185 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 Monday 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.

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 55 days in advance of your trip. Fares are likely to increase a fortnight or so before your departure date.

Related info for your journey

  • 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 83 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 $686, Alaska Airlines can have you in Chicago from San Francisco in 8h 37m. 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 (90%), Aer Lingus (83%), 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.

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

    Currently, February is the cheapest month in which you can book a flight from San Francisco to Chicago (average of $657). Flying from San Francisco to Chicago in June is currently the most expensive (average of $862). 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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