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Cheap flights from San Francisco to Chicago from $218

SFO — CHI
15 Oct — 22 Oct1
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

Fri 13/1114:44 -
1 stop7h 05m
Mon 16/1119:57 -
1 stop14h 55m
Deal found 15/9$450
Thu 17/1223:30 -
Nonstop4h 26m
Tue 22/1220:17 -
Nonstop5h 08m
Deal found 14/9$455
Fri 6/1118:42 -
Nonstop4h 17m
Sat 7/1121:57 -
Nonstop4h 56m
Deal found 14/9$457
Wed 21/1000:10 -
1 stop6h 43m
Sat 24/1015:30 -
1 stop7h 10m
Deal found 14/9$462
Fri 30/1006:07 -
1 stop8h 43m
Fri 30/1019:16 -
1 stop15h 33m
Deal found 15/9$479
Wed 14/1000:35 -
Nonstop4h 21m
Mon 26/1021:57 -
Nonstop4h 56m
Deal found 14/9$483
Fri 16/1022:42 -
Nonstop4h 19m
Mon 19/1021:40 -
Nonstop4h 50m
Deal found 15/9$484
Wed 28/1013:25 -
2 stops14h 15m
Tue 3/1107:20 -
1 stop8h 36m
Deal found 15/9$486
Mon 5/1014:15 -
1 stop7h 42m
Thu 8/1006:35 -
1 stop8h 33m
Deal found 15/9$490
Fri 27/1106:17 -
1 stop8h 30m
Sat 5/1210:32 -
1 stop8h 53m
Deal found 15/9$491
Thu 29/1022:17 -
1 stop9h 00m
Thu 5/1106:30 -
1 stop6h 47m
Deal found 13/9$495
Mon 26/1016:51 -
2 stops10h 49m
Thu 29/1017:46 -
1 stop8h 06m
Deal found 15/9$497

Find flight deals from San Francisco to Chicago

Round-trip from

$450

One-way from

$218

Popular in

July

Cheapest in

February

Average price

$645
Alaska Airlines
  • Alaska Airlines
  • 13/11-16/11
  • 2 total stops
  • 22h 00m total
  • San Francisco to Chicago
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Delta
  • Delta
  • 14/10-31/12
  • 1 total stop
  • 7h 19m total
  • San Francisco to Chicago
Search Deals
Highest demand for flights based on searches. 7% potential increase in price ($104 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 September 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

Tue 15/12

09:58-23:59

2 stops12h 01m

Chicago O'Hare Intl

Wed 31/12

00:00-22:00

Nonstop0h 00m

$287

San FranciscoChicago

SFO San Francisco - ORD Chicago O'Hare Intl

SFOORD

San Francisco

Fri 11/12

00:10-06:28

Nonstop4h 18m

Chicago O'Hare Intl

Wed 31/12

00:00-22:00

Nonstop0h 00m

$287
Fastest return journey

San FranciscoChicago

SFO San Francisco - ORD Chicago O'Hare Intl

SFOORD

San Francisco

Sat 7/11

18:42-00:59

Nonstop4h 17m

Chicago O'Hare Intl

Wed 31/12

00:00-22:00

Nonstop0h 00m

$299

San FranciscoChicago

SFO San Francisco - ORD Chicago O'Hare Intl

SFOORD

San Francisco

Thu 15/10

05:00-11:25

Nonstop4h 25m

Chicago O'Hare Intl

Wed 31/12

00:00-22:00

Nonstop0h 00m

$313

San FranciscoChicago

SFO San Francisco - ORD Chicago O'Hare Intl

SFOORD

San Francisco

Wed 11/11

08:43-23:59

2 stops13h 16m

Chicago O'Hare Intl

Wed 31/12

00:00-22:00

Nonstop0h 00m

$324

San FranciscoChicago

SFO San Francisco - ORD Chicago O'Hare Intl

SFOORD

San Francisco

Fri 12/3

15:00-21:38

Nonstop4h 38m

Chicago O'Hare Intl

Wed 31/12

00:00-22:00

Nonstop0h 00m

$332

San FranciscoChicago

SFO San Francisco - ORD Chicago O'Hare Intl

SFOORD

San Francisco

Tue 1/12

07:05-17:31

1 stop8h 26m

Chicago O'Hare Intl

Wed 31/12

00:00-22:00

Nonstop0h 00m

$334

San FranciscoChicago

SFO San Francisco - ORD Chicago O'Hare Intl

SFOORD

San Francisco

Fri 27/11

06:17-16:47

1 stop8h 30m

Chicago O'Hare Intl

Wed 31/12

00:00-22:00

Nonstop0h 00m

$349

San FranciscoChicago

SFO San Francisco - ORD Chicago O'Hare Intl

SFOORD

San Francisco

Sun 11/10

05:00-11:22

Nonstop4h 22m

Chicago O'Hare Intl

Wed 31/12

00:00-22:00

Nonstop0h 00m

$362

San FranciscoChicago

SFO San Francisco - ORD Chicago O'Hare Intl

SFOORD

San Francisco

Sun 8/11

00:55-07:13

Nonstop4h 18m

Chicago O'Hare Intl

Wed 31/12

00:00-22:00

Nonstop0h 00m

$386

Flights are sorted by cheapest return flights first.

Deals found on 15/9

Showing 1-10 of 24 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 $638). Flying from San Francisco to Chicago in June is currently the most expensive (average of $837). 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 Monday (94 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (53 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 $512 and $881 in November.
The cheapest return price found within the last 5 days was $450 on Alaska Airlines (13 Nov–16 Nov).

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 186 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 66 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 72 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 $455, United Airlines can have you in Chicago from San Francisco in 4h 35m. 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 (92%), Austrian Airlines (76%), Brussels Airlines (74%).

  • 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 $638). Flying from San Francisco to Chicago in June is currently the most expensive (average of $837). 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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