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Cheap flights from San Francisco to Chicago from $177

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 14/4. Fares are subject to change and may not be available on all flights or dates of travel.
SFO — CHI
12 Feb — 19 Feb1
1 adult
1 adult, Economy, 0 bags

Cheap 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 13 January 2026.

Round-trip from

$371

One-way from

$177

Popular in

November

Cheapest in

February

Average price

$510
Alaska Airlines
  • Alaska Airlines
  • 2/2-4/2
  • 2 total stops
  • 24h 09m total
  • San Francisco to Chicago
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Alaska Airlines
  • Alaska Airlines
  • 14/4
  • 1 total stop
  • 10h 05m total
  • San Francisco to Chicago
Search Deals
Highest demand for flights based on searches. 15% potential increase in price ($137 potential increase over avg. return price).
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Cheapest flight prices on average. 2% potential price decrease ($19 potential savings vs. average return price).
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Average for round-trip flights in January 2026
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Find 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 13 January 2026.

Mon 2/207:00
SFO
-
ORD
1 stop14h 37m
Alaska Airlines
Wed 4/209:00
ORD
-
SFO
1 stop9h 32m
Alaska Airlines
Deal found 12/1$371
Wed 22/407:15
SFO
-
ORD
1 stop9h 48m
Alaska Airlines
Tue 28/408:50
ORD
-
SFO
1 stop16h 58m
Alaska Airlines
Deal found 12/1$373
Wed 6/507:15
SFO
-
ORD
1 stop9h 48m
Alaska Airlines
Wed 13/509:00
ORD
-
SFO
1 stop10h 01m
Alaska Airlines
Deal found 12/1$377
Wed 11/212:25
SFO
-
ORD
Nonstop4h 23m
United Airlines
Wed 18/220:20
ORD
-
SFO
Nonstop5h 04m
United Airlines
Deal found 12/1$380
Wed 25/217:44
SFO
-
ORD
Nonstop4h 15m
American Airlines
Wed 4/319:42
ORD
-
SFO
Nonstop4h 58m
American Airlines
Deal found 11/1$382
Sat 7/221:30
SFO
-
ORD
1 stop10h 35m
Delta
Sat 14/215:21
ORD
-
SFO
1 stop10h 28m
Delta
Deal found 12/1$383
Mon 2/214:30
SFO
-
ORD
1 stop7h 20m
Alaska Airlines
Tue 3/215:44
ORD
-
SFO
1 stop9h 03m
Alaska Airlines
Deal found 12/1$386
Wed 22/407:15
SFO
-
ORD
1 stop9h 48m
Alaska Airlines
Fri 24/415:52
ORD
-
SFO
1 stop9h 56m
Alaska Airlines
Deal found 12/1$388
Wed 22/407:15
SFO
-
ORD
1 stop9h 48m
Alaska Airlines
Thu 23/415:52
ORD
-
SFO
1 stop9h 56m
Alaska Airlines
Deal found 12/1$389
Fri 6/207:00
SFO
-
ORD
1 stop8h 10m
Alaska Airlines
Mon 9/215:44
ORD
-
SFO
1 stop9h 03m
Alaska Airlines
Deal found 12/1$392
Tue 3/214:52
SFO
-
ORD
1 stop6h 45m
Alaska Airlines
Tue 10/214:06
ORD
-
SFO
2 stops10h 57m
Alaska Airlines
Deal found 12/1$394
Sat 14/217:03
SFO
-
ORD
Nonstop4h 23m
United Airlines
Sun 22/206:25
ORD
-
SFO
Nonstop5h 05m
United Airlines
Deal found 12/1$401

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

Fly from

San Francisco

Fly to

Chicago

Route

Depart

Return

Price

San FranciscoChicago

SFO - ORD

SFOORD

San Francisco

Wed 6/5

07:15-19:03

1 stop9h 48m

Chicago O'Hare Intl

Sat 9/5

08:50-19:38

1 stop12h 48m

$377

San FranciscoChicago

SFO - ORD

SFOORD

San Francisco

Sat 14/2

17:03-23:26

Nonstop4h 23m

Chicago O'Hare Intl

Sat 28/2

18:17-21:20

Nonstop5h 03m

$380

San FranciscoChicago

SFO - ORD

SFOORD

San Francisco

Sat 7/2

06:45-13:10

Nonstop4h 25m

Chicago O'Hare Intl

Tue 10/2

09:00-12:10

Nonstop5h 10m

$380

San FranciscoChicago

SFO - ORD

SFOORD

San Francisco

Fri 6/2

00:40-10:25

1 stop7h 45m

Chicago O'Hare Intl

Sat 7/2

17:35-23:25

1 stop7h 50m

$383

San FranciscoChicago

SFO - ORD

SFOORD

San Francisco

Sat 7/2

22:54-09:41

1 stop8h 47m

Chicago O'Hare Intl

Tue 10/2

18:00-23:25

1 stop7h 25m

$383

San FranciscoChicago

SFO - ORD

SFOORD

San Francisco

Fri 1/5

21:10-06:40

1 stop7h 30m

Chicago O'Hare Intl

Tue 5/5

14:19-19:49

1 stop7h 30m

$392

San FranciscoChicago

SFO - ORD

SFOORD

San Francisco

Thu 12/2

00:40-08:40

1 stop6h 00m

Chicago O'Hare Intl

Fri 20/2

14:20-22:41

1 stop10h 21m

$392

San FranciscoChicago

SFO - ORD

SFOORD

San Francisco

Tue 3/3

23:59-06:19

Nonstop4h 20m

Chicago O'Hare Intl

Sun 8/3

06:17-09:22

Nonstop5h 05m

$401

San FranciscoChicago

SFO - ORD

SFOORD

San Francisco

Sat 14/2

17:03-23:26

Nonstop4h 23m

Chicago O'Hare Intl

Thu 19/2

07:40-10:50

Nonstop5h 10m

$401

San FranciscoChicago

SFO - ORD

SFOORD

San Francisco

Wed 18/2

23:59-06:19

Nonstop4h 20m

Chicago O'Hare Intl

Fri 20/2

06:25-09:27

Nonstop5h 02m

$401

Flights are sorted by cheapest return flights first.

Deals found on 11/1

Showing 1-10 of 24 results
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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 9 January 2026.

The best time to book flights from San Francisco to Chicago is 52 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, October is the cheapest month in which you can book a flight from San Francisco to Chicago (average of $186). Flying from San Francisco to Chicago in December is currently the most expensive (average of $347). 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 13 January 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 13 January 2026.

The most flights from SFO to CHI are scheduled on a Friday (62 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (39 on average).

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 182 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 9% 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 50 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?

    Alaska Airlines, United Airlines, and American Airlines can get you from San Francisco to Chicago in just under 4h 15m. Your travel time can differ by up to 10h 22m. 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: Gulf Air (100%), Qatar Airways (97%), Iberia( 93%).

  • 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, October is the cheapest month in which you can book a flight from San Francisco to Chicago (average of $186). Flying from San Francisco to Chicago in December is currently the most expensive (average of $347). 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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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

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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.

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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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