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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 15/5. Fares are subject to change and may not be available on all flights or dates of travel.
SFO — CHI
29 Mar — 5 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 27 February 2026.

Mon 6/423:52
SFO
-
ORD
Nonstop4h 28m
United Airlines
Mon 13/422:45
ORD
-
SFO
Nonstop4h 50m
United Airlines
Deal found 26/2$325
Thu 9/405:50
SFO
-
ORD
1 stop8h 53m
Delta
Wed 15/407:15
ORD
-
SFO
1 stop8h 50m
Delta
Deal found 26/2$330
Wed 6/510:32
SFO
-
ORD
2 stops8h 46m
Delta
Tue 12/512:47
ORD
-
SFO
1 stop9h 00m
Delta
Deal found 26/2$334
Mon 6/418:29
SFO
-
ORD
Nonstop4h 30m
United Airlines
Fri 10/407:40
ORD
-
SFO
Nonstop4h 58m
United Airlines
Deal found 24/2$337
Wed 18/322:45
SFO
-
ORD
Nonstop4h 22m
United Airlines
Wed 25/306:17
ORD
-
SFO
Nonstop5h 05m
United Airlines
Deal found 24/2$344
Wed 25/323:59
SFO
-
ORD
Nonstop4h 20m
United Airlines
Sat 16/506:20
ORD
-
SFO
Nonstop4h 51m
United Airlines
Deal found 25/2$346
Sun 5/419:00
SFO
-
ORD
Nonstop4h 28m
United Airlines
Wed 8/406:25
ORD
-
SFO
Nonstop4h 51m
United Airlines
Deal found 24/2$349
Sat 9/513:50
SFO
-
ORD
1 stop6h 30m
Southwest
Tue 12/507:45
ORD
-
SFO
2 stops9h 35m
Southwest
Deal found 27/2$350
Tue 31/313:25
SFO
-
ORD
1 stop6h 09m
Delta
Thu 2/406:15
ORD
-
SFO
1 stop9h 12m
Delta
Deal found 27/2$353
Tue 24/315:15
SFO
-
ORD
Nonstop4h 22m
United Airlines
Tue 31/309:25
ORD
-
SFO
Nonstop4h 42m
United Airlines
Deal found 24/2$356
Mon 18/519:00
SFO
-
ORD
Nonstop4h 28m
United Airlines
Fri 22/515:57
ORD
-
SFO
Nonstop4h 52m
United Airlines
Deal found 24/2$358

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 27 February 2026.

Round-trip from

$325

One-way from

$155

Popular in

November

Cheapest in

September

Average price

$523

Good one-way deal

$88 or less
United Airlines
  • United Airlines
  • 1/5-3/5
  • Nonstop
  • 9h 15m total
  • San Francisco to Chicago
Search Deals
United Airlines
  • United Airlines
  • 15/5
  • Nonstop
  • 4h 28m total
  • San Francisco to Chicago
Search Deals
Highest demand for flights based on searches. 12% potential increase in price ($100 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 February 2026
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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 27 February 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

San FranciscoChicago

SFO - ORD

SFOORD

San Francisco

Tue 31/3

06:00-19:49

2 stops11h 49m

Chicago O'Hare Intl

Thu 2/4

19:10-23:59

1 stop6h 49m

$433

San FranciscoChicago

SFO - ORD

SFOORD

San Francisco

Sun 29/3

18:29-00:59

Nonstop4h 30m

Chicago O'Hare Intl

Tue 7/4

21:25-00:24

Nonstop4h 59m

$443

San FranciscoChicago

SFO - ORD

SFOORD

San Francisco

Tue 19/5

10:57-23:59

2 stops11h 02m

Chicago O'Hare Intl

Thu 4/6

09:00-17:01

1 stop10h 01m

$467

San FranciscoChicago

SFO - ORD

SFOORD

San Francisco

Tue 9/6

10:50-22:55

2 stops10h 05m

Chicago O'Hare Intl

Tue 16/6

06:05-14:15

2 stops10h 10m

$485

San FranciscoChicago

SFO - ORD

SFOORD

San Francisco

Tue 31/3

18:29-00:59

Nonstop4h 30m

Chicago O'Hare Intl

Sat 4/4

21:25-00:24

Nonstop4h 59m

$485

San FranciscoChicago

SFO - ORD

SFOORD

San Francisco

Thu 28/5

13:15-23:55

2 stops8h 40m

Chicago O'Hare Intl

Mon 1/6

13:35-22:25

2 stops10h 50m

$499

San FranciscoChicago

SFO - ORD

SFOORD

San Francisco

Sat 9/5

10:10-22:20

2 stops10h 10m

Chicago O'Hare Intl

Sat 16/5

06:15-16:10

2 stops11h 55m

$499

San FranciscoChicago

SFO - ORD

SFOORD

San Francisco

Tue 2/6

11:25-22:55

2 stops9h 30m

Chicago O'Hare Intl

Fri 5/6

18:00-00:50

2 stops8h 50m

$510

San FranciscoChicago

SFO - ORD

SFOORD

San Francisco

Sat 11/4

11:45-23:25

2 stops9h 40m

Chicago O'Hare Intl

Sat 18/4

06:15-17:25

2 stops13h 10m

$519

San FranciscoChicago

SFO - ORD

SFOORD

San Francisco

Mon 13/7

22:50-13:15

1 stop12h 25m

Chicago O'Hare Intl

Mon 20/7

18:25-07:45

2 stops15h 20m

$531

Flights are sorted by cheapest return flights first.

Deals found on 24/2

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
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 20 February 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 $173). Flying from San Francisco to Chicago in December is currently the most expensive (average of $327). 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 27 February 2026.

Unlike at midday, when flights are generally more expensive, you can save up to 62% 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 27 February 2026.

The most flights from SFO to CHI are scheduled on a Friday (72 on average). You will have fewer flight options on Tuesday, 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 188 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, United 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 58 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?

    Delta, United Airlines, and Southwest can get you from San Francisco to Chicago in just under 4h 30m. Your travel time can differ by up to 5h 35m. 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: Iberia (95%), Qatar Airways (95%), Gulf Air( 94%).

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

    On average you can expect to pay $219 for a flight from San Francisco to Chicago. The cheapest flight overall is $88 while the most popular route, (San Francisco - Chicago O'Hare Intl) is currently priced at $306.

  • 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 $173). Flying from San Francisco to Chicago in December is currently the most expensive (average of $327). 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.
Los Angeles to O'Hare Intl flights
San Francisco 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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