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Cheap flights from San Francisco to Chicago from $155

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 18/4. Fares are subject to change and may not be available on all flights or dates of travel.
SFO — CHI
11 Apr — 18 Apr1
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 12 March 2026.

Wed 6/514:50
SFO
-
ORD
1 stop7h 05m
Southwest
Sat 9/507:00
ORD
-
SFO
1 stop6h 50m
Southwest
Deal found 9/3$327
Thu 9/419:00
SFO
-
ORD
Nonstop4h 28m
United Airlines
Sat 18/407:40
ORD
-
SFO
Nonstop4h 58m
United Airlines
Deal found 8/3$328
Thu 23/407:15
SFO
-
ORD
1 stop9h 48m
Alaska Airlines
Tue 28/415:52
ORD
-
SFO
1 stop9h 09m
Alaska Airlines
Deal found 9/3$330
Fri 10/400:10
SFO
-
ORD
1 stop6h 42m
Delta
Wed 15/418:00
ORD
-
SFO
1 stop7h 37m
Delta
Deal found 9/3$331
Sat 16/513:35
SFO
-
ORD
1 stop8h 22m
Delta
Tue 26/519:45
ORD
-
SFO
1 stop6h 12m
Delta
Deal found 9/3$338
Wed 22/407:20
SFO
-
ORD
2 stops9h 30m
Southwest
Sat 25/407:00
ORD
-
SFO
1 stop6h 50m
Southwest
Deal found 8/3$341
Wed 22/413:28
SFO
-
ORD
Nonstop4h 44m
American Airlines
Sat 25/408:05
ORD
-
SFO
Nonstop4h 57m
American Airlines
Deal found 8/3$344
Wed 27/500:05
SFO
-
ORD
1 stop6h 31m
Delta
Thu 28/514:00
ORD
-
SFO
1 stop10h 21m
Delta
Deal found 9/3$345
Fri 10/400:10
SFO
-
ORD
1 stop6h 42m
Delta
Sat 18/407:15
ORD
-
SFO
2 stops10h 50m
Delta
Deal found 8/3$347
Wed 15/410:30
SFO
-
ORD
2 stops10h 25m
Southwest
Sat 18/407:00
ORD
-
SFO
2 stops11h 10m
Southwest
Deal found 8/3$348
Tue 31/322:40
SFO
-
ORD
1 stop8h 30m
Delta
Sun 5/406:15
ORD
-
SFO
1 stop7h 10m
Delta
Deal found 9/3$351

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 12 March 2026.

Round-trip from

$327

One-way from

$155

Popular in

November

Cheapest in

September

Average price

$555

Good one-way deal

$87 or less
Southwest
  • Southwest
  • 6/5-9/5
  • 2 total stops
  • 13h 55m total
  • San Francisco to Chicago
Search Deals
Southwest
  • Southwest
  • 18/4
  • 1 total stop
  • 9h 15m total
  • San Francisco to Chicago
Search Deals
Highest demand for flights based on searches. 12% potential increase in price ($96 potential increase over avg. return price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($15 potential savings vs. average return price).
Search Deals
Average for round-trip flights in March 2026
Search Deals
Price to beat on a one-way flight from San Francisco to Chicago (CHI).
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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 647,157 searches. Data last updated 12 March 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

Depart

Return

Price

Cheapest return flight

San FranciscoChicago

SFO - ORD

SFOORD

San Francisco

Wed 22/4

07:20-18:50

2 stops9h 30m

Chicago O'Hare Intl

Sat 25/4

07:00-11:50

1 stop6h 50m

$341

San FranciscoChicago

SFO - ORD

SFOORD

San Francisco

Tue 14/4

23:39-10:09

1 stop8h 30m

Chicago O'Hare Intl

Sat 18/4

07:15-16:05

2 stops10h 50m

$370

San FranciscoChicago

SFO - ORD

SFOORD

San Francisco

Wed 15/4

10:05-22:55

2 stops10h 50m

Chicago O'Hare Intl

Mon 20/4

19:35-11:05

2 stops17h 30m

$402

San FranciscoChicago

SFO - ORD

SFOORD

San Francisco

Sat 25/4

11:45-22:20

2 stops8h 35m

Chicago O'Hare Intl

Sat 2/5

06:15-16:10

2 stops11h 55m

$412

San FranciscoChicago

SFO - ORD

SFOORD

San Francisco

Wed 3/6

11:25-22:55

2 stops9h 30m

Chicago O'Hare Intl

Thu 11/6

13:35-21:50

2 stops10h 15m

$442

San FranciscoChicago

SFO - ORD

SFOORD

San Francisco

Thu 2/4

06:40-19:00

2 stops10h 20m

Chicago O'Hare Intl

Mon 6/4

19:20-00:50

1 stop7h 30m

$462

San FranciscoChicago

SFO - ORD

SFOORD

San Francisco

Thu 9/7

07:00-17:30

1 stop8h 30m

Chicago O'Hare Intl

Tue 14/7

07:00-11:59

1 stop6h 59m

$465

San FranciscoChicago

SFO - ORD

SFOORD

San Francisco

Sun 10/5

06:45-18:50

2 stops10h 05m

Chicago O'Hare Intl

Fri 15/5

16:15-23:45

2 stops9h 30m

$492

San FranciscoChicago

SFO - ORD

SFOORD

San Francisco

Fri 12/6

22:50-12:50

1 stop12h 00m

Chicago O'Hare Intl

Tue 16/6

14:40-22:15

2 stops9h 35m

$496
Fastest return journey

San FranciscoChicago

SFO - ORD

SFOORD

San Francisco

Sat 23/5

15:01-21:35

Nonstop4h 34m

Chicago O'Hare Intl

Mon 25/5

07:40-10:29

Nonstop4h 49m

$502

Flights are sorted by cheapest return flights first.

Deals found on 8/3

Showing 1-10 of 22 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?

Use this chart to determine the optimal time to book a return flight from San Francisco to Chicago. Price data was last updated on 6 March 2026.

The best time to book flights from San Francisco to Chicago is 84 days before your desired departure date. The cost of your flight will likely increase significantly if you book two weeks in advance of your flight.

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

Currently, April is the cheapest month in which you can book a flight from San Francisco to Chicago (average of $156). Flying from San Francisco to Chicago in December is currently the most expensive (average of $326). 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 12 March 2026.

Unlike at midday, when flights are generally more expensive, you can save up to 59% on flights from San Francisco to Chicago by exploring options for tickets in the afternoon.

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 12 March 2026.

The most flights from SFO to CHI are scheduled on a Wednesday (79 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (48 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 187 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?

    San Francisco (SFO) is the airport you will fly out of if you book a flight from San Francisco to Chicago. You should not have trouble finding flights to Chicago from San Francisco; the airport handles an average of 62 outbound flights to Chicago per day. You should also have plenty of airline options to choose from since 0 airlines have flights from the San Francisco airport to Chicago. It is only a 19.0 km journey to San Francisco (SFO) from San Francisco’s city centre.

  • How long is the flight from San Francisco to Chicago?

    Southwest and Delta can get you from San Francisco to Chicago in just under 8h 30m. Your travel time can differ by up to 1h. The distance between San Francisco and Chicago is about 2963 km. This flight may include one or multiple stops.

  • What are the most reliable airlines from San Francisco to Chicago?

    Before booking your flight to Chicago from San Francisco, have a look at the most reliable airlines to get you to your destination on time: Royal Jordanian (94%), Austrian Airlines (93%), Gulf Air( 93%).

  • What are the cheapest flights from San Francisco to Chicago?

    On average you can expect to pay $217 for a flight from San Francisco to Chicago. The cheapest flight overall is $87 while the most popular route, (San Francisco - Chicago O'Hare Intl) is currently priced at $323.

  • 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, April is the cheapest month in which you can book a flight from San Francisco to Chicago (average of $156). Flying from San Francisco to Chicago in December is currently the most expensive (average of $326). 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

Browse thousands of different options on Cheapflights for your next trip

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Alternative routes for San Francisco to Chicago

See prices for flight routes from nearby airports that may be better suited for you.
San Francisco to O'Hare Intl flights
Los Angeles to O'Hare Intl flights

Fly with Cheapflights

Find the best flight deals on Cheapflights, where travellers can enjoy low prices and a wide availability of flights to their desired destinations.

How does Cheapflights help users find flights from San Francisco to Chicago?

Cheapflights makes it easy to find San Francisco to Chicago flights by helping our users search from 900+ travel sites for deals. We also provide you with filters for cabin, price, airline, airports, number of stops, and many more to narrow down that perfect flight.

Why should you use Cheapflights to find cheap flight tickets from San Francisco to Chicago?

Cheapflights taps into our reliable network of hundreds of airlines and travel agencies to find the best deals for flights from San Francisco to Chicago for you. Better yet — we are completely free to use.

Can Cheapflights find flights from San Francisco to Chicago with no change fees?

Users can book flights with no change fees policies with our dedicated filters. Book flights from San Francisco to Chicago flexibly with Cheapflights today.

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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