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Cheap flights from San Francisco to Chicago from $186

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 2/6. Fares are subject to change and may not be available on all flights or dates of travel.
SFO — CHI
4 Jun — 11 Jun1
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 5 May 2026.

Tue 23/618:34
SFO
-
ORD
Nonstop4h 25m
United Airlines
Tue 30/621:35
ORD
-
SFO
Nonstop4h 57m
United Airlines
Deal found 1/5$392
Mon 25/506:15
SFO
-
ORD
1 stop6h 42m
Delta
Sat 30/512:47
ORD
-
SFO
1 stop9h 00m
Delta
Deal found 2/5$397
Tue 9/618:34
SFO
-
ORD
Nonstop4h 25m
United Airlines
Sat 13/621:33
ORD
-
SFO
Nonstop4h 57m
United Airlines
Deal found 30/4$398
Wed 3/606:00
SFO
-
ORD
1 stop8h 48m
Alaska Airlines
Mon 8/619:59
ORD
-
SFO
1 stop15h 34m
Alaska Airlines
Deal found 4/5$402
Mon 1/607:25
SFO
-
ORD
1 stop9h 25m
Southwest
Wed 3/610:30
ORD
-
SFO
2 stops10h 00m
Southwest
Deal found 4/5$404
Thu 28/511:10
SFO
-
ORD
1 stop10h 45m
Southwest
Tue 2/610:30
ORD
-
SFO
2 stops11h 25m
Southwest
Deal found 5/5$406
Wed 27/518:34
SFO
-
ORD
Nonstop4h 25m
United Airlines
Fri 29/506:13
ORD
-
SFO
Nonstop4h 37m
United Airlines
Deal found 30/4$410
Wed 17/615:54
SFO
-
ORD
1 stop6h 34m
American Airlines
Wed 24/606:29
ORD
-
SFO
Nonstop4h 58m
American Airlines
Deal found 3/5$416
Fri 5/600:50
SFO
-
ORD
Nonstop4h 26m
United Airlines
Thu 11/606:13
ORD
-
SFO
Nonstop4h 37m
United Airlines
Deal found 4/5$417
Wed 10/605:05
SFO
-
ORD
Nonstop4h 24m
United Airlines
Wed 17/606:13
ORD
-
SFO
Nonstop4h 37m
United Airlines
Deal found 4/5$422
Wed 24/605:05
SFO
-
ORD
Nonstop4h 26m
United Airlines
Wed 1/707:40
ORD
-
SFO
Nonstop4h 49m
United Airlines
Deal found 30/4$424

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 5 May 2026.

Round-trip from

$392

One-way from

$186

Popular in

March

Cheapest in

September

Average price

$529
United Airlines
  • United Airlines
  • 23/6-30/6
  • Nonstop
  • 9h 22m total
  • San Francisco to Chicago
Search Deals
Southwest
  • Southwest
  • 2/6
  • 1 total stop
  • 12h 00m total
  • San Francisco to Chicago
Search Deals
Highest demand for flights based on searches. 4% potential increase in price ($36 potential increase over avg. return price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($14 potential savings vs. average return price).
Search Deals
Average for round-trip flights in May 2026
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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 5 May 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

Mon 8/6

14:30-23:18

1 stop6h 48m

Chicago O'Hare Intl

Wed 10/6

19:37-23:58

1 stop6h 21m

$438

San FranciscoChicago

SFO - ORD

SFOORD

San Francisco

Fri 29/5

23:59-08:45

1 stop6h 46m

Chicago O'Hare Intl

Mon 1/6

19:45-00:12

1 stop6h 27m

$458

San FranciscoChicago

SFO - ORD

SFOORD

San Francisco

Wed 23/9

00:50-07:16

Nonstop4h 26m

Chicago O'Hare Intl

Mon 28/9

21:39-00:34

Nonstop4h 55m

$466

San FranciscoChicago

SFO - ORD

SFOORD

San Francisco

Thu 27/8

18:34-00:55

Nonstop4h 21m

Chicago O'Hare Intl

Mon 31/8

07:40-10:26

Nonstop4h 46m

$466

San FranciscoChicago

SFO - ORD

SFOORD

San Francisco

Sun 24/5

10:10-23:55

2 stops11h 45m

Chicago O'Hare Intl

Sat 30/5

07:00-17:15

1 stop12h 15m

$495

San FranciscoChicago

SFO - ORD

SFOORD

San Francisco

Wed 27/5

10:30-22:55

2 stops10h 25m

Chicago O'Hare Intl

Fri 29/5

13:35-22:25

2 stops10h 50m

$515

San FranciscoChicago

SFO - ORD

SFOORD

San Francisco

Fri 5/6

18:34-00:59

Nonstop4h 25m

Chicago O'Hare Intl

Tue 9/6

21:48-00:45

Nonstop4h 57m

$523
Fastest return journey

San FranciscoChicago

SFO - ORD

SFOORD

San Francisco

Mon 3/8

22:38-05:01

Nonstop4h 23m

Chicago O'Hare Intl

Sun 9/8

06:10-08:47

Nonstop4h 37m

$530

San FranciscoChicago

SFO - ORD

SFOORD

San Francisco

Tue 26/5

23:29-08:32

1 stop7h 03m

Chicago O'Hare Intl

Thu 28/5

06:45-09:25

Nonstop4h 40m

$570

San FranciscoChicago

SFO - ORD

SFOORD

San Francisco

Fri 17/7

18:34-00:59

Nonstop4h 25m

Chicago O'Hare Intl

Thu 23/7

07:30-10:19

Nonstop4h 49m

$577

Flights are sorted by cheapest return flights first.

Deals found on 2/5

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?

The best time to book flights from San Francisco to Chicago is 66 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, September is the cheapest month in which you can book a flight from San Francisco to Chicago (average of $401). Flying from San Francisco to Chicago in January is currently the most expensive (average of $1,522). 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 5 May 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 5 May 2026.

The most flights from SFO to CHI are scheduled on a Friday (96 on average). You will have fewer flight options on Wednesday, which is when the least amount of flights are scheduled (66 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 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 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 81 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 17.7 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 26m. Your travel time can differ by up to 7h 19m. 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: Brussels Airlines (85%), Air Canada (84%), Asiana Airlines( 83%).

  • 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, September is the cheapest month in which you can book a flight from San Francisco to Chicago (average of $401). Flying from San Francisco to Chicago in January is currently the most expensive (average of $1,522). 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

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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