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Cheap flights from San Francisco to Chicago from $183

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 30/5. Fares are subject to change and may not be available on all flights or dates of travel.
SFO — CHI
9 Jun — 16 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 10 May 2026.

Wed 3/605:05
SFO
-
ORD
Nonstop4h 24m
United Airlines
Tue 9/621:48
ORD
-
SFO
Nonstop4h 57m
United Airlines
Deal found 8/5$399
Thu 3/910:32
SFO
-
ORD
1 stop11h 25m
Alaska Airlines
Tue 8/919:59
ORD
-
SFO
1 stop14h 47m
Alaska Airlines
Deal found 7/5$400
Sat 30/506:15
SFO
-
ORD
1 stop6h 42m
Delta
Wed 3/607:45
ORD
-
SFO
1 stop6h 34m
Delta
Deal found 8/5$401
Sat 6/616:21
SFO
-
ORD
Nonstop4h 38m
United Airlines
Tue 9/621:48
ORD
-
SFO
Nonstop4h 57m
United Airlines
Deal found 6/5$403
Tue 29/910:00
SFO
-
ORD
1 stop6h 01m
Delta
Sat 3/1014:55
ORD
-
SFO
1 stop7h 24m
Delta
Deal found 8/5$407
Sat 18/714:27
SFO
-
ORD
Nonstop4h 34m
United Airlines
Wed 22/707:30
ORD
-
SFO
Nonstop4h 49m
United Airlines
Deal found 8/5$408
Wed 3/607:20
SFO
-
ORD
1 stop9h 30m
Alaska Airlines
Mon 8/619:59
ORD
-
SFO
1 stop15h 34m
Alaska Airlines
Deal found 5/5$412
Thu 4/623:30
SFO
-
ORD
Nonstop4h 23m
United Airlines
Sat 13/621:48
ORD
-
SFO
Nonstop4h 57m
United Airlines
Deal found 8/5$414
Thu 11/623:30
SFO
-
ORD
Nonstop4h 27m
United Airlines
Tue 16/612:46
ORD
-
SFO
Nonstop4h 49m
United Airlines
Deal found 7/5$415
Thu 27/818:38
SFO
-
ORD
Nonstop4h 21m
United Airlines
Mon 31/807:40
ORD
-
SFO
Nonstop4h 46m
United Airlines
Deal found 9/5$416
Wed 3/605:05
SFO
-
ORD
Nonstop4h 24m
United Airlines
Wed 10/607:30
ORD
-
SFO
Nonstop4h 49m
United Airlines
Deal found 6/5$421
Sat 7/1113:05
SFO
-
ORD
1 stop8h 41m
Delta
Sat 14/1115:50
ORD
-
SFO
1 stop6h 32m
Delta
Deal found 10/5$423

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 10 May 2026.

Round-trip from

$399

One-way from

$183

Popular in

March

Cheapest in

September

Average price

$603
United Airlines
  • United Airlines
  • 3/6-9/6
  • Nonstop
  • 9h 21m total
  • San Francisco to Chicago
Search Deals
United Airlines
  • United Airlines
  • 30/5
  • Nonstop
  • 4h 26m total
  • San Francisco to Chicago
Search Deals
Highest demand for flights based on searches. 3% potential increase in price ($25 potential increase over avg. return price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($13 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 10 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

Tue 29/9

06:15-16:48

1 stop8h 33m

Chicago O'Hare Intl

Wed 30/9

18:00-23:46

1 stop7h 46m

$407

San FranciscoChicago

SFO - ORD

SFOORD

San Francisco

Wed 3/6

06:15-16:51

1 stop8h 36m

Chicago O'Hare Intl

Mon 8/6

17:55-00:06

1 stop8h 11m

$448

San FranciscoChicago

SFO - ORD

SFOORD

San Francisco

Wed 15/7

18:34-00:59

Nonstop4h 25m

Chicago O'Hare Intl

Sun 19/7

06:10-08:47

Nonstop4h 37m

$458

San FranciscoChicago

SFO - ORD

SFOORD

San Francisco

Wed 27/5

07:20-18:50

2 stops9h 30m

Chicago O'Hare Intl

Tue 2/6

16:50-23:15

1 stop8h 25m

$495

San FranciscoChicago

SFO - ORD

SFOORD

San Francisco

Thu 28/5

13:15-23:55

2 stops8h 40m

Chicago O'Hare Intl

Tue 2/6

19:35-11:05

2 stops17h 30m

$536
Fastest return journey

San FranciscoChicago

SFO - ORD

SFOORD

San Francisco

Tue 16/6

05:05-11:29

Nonstop4h 24m

Chicago O'Hare Intl

Sun 21/6

06:13-08:50

Nonstop4h 37m

$558

San FranciscoChicago

SFO - ORD

SFOORD

San Francisco

Fri 4/9

07:05-19:03

1 stop9h 58m

Chicago O'Hare Intl

Tue 8/9

06:01-13:00

1 stop8h 59m

$564

San FranciscoChicago

SFO - ORD

SFOORD

San Francisco

Wed 3/6

05:55-18:50

2 stops10h 55m

Chicago O'Hare Intl

Tue 16/6

19:37-23:58

1 stop6h 21m

$614

San FranciscoChicago

SFO - ORD

SFOORD

San Francisco

Wed 3/6

00:50-07:16

Nonstop4h 26m

Chicago O'Hare Intl

Thu 11/6

06:13-08:50

Nonstop4h 37m

$623

San FranciscoChicago

SFO - ORD

SFOORD

San Francisco

Sat 13/6

22:35-04:58

Nonstop4h 23m

Chicago O'Hare Intl

Sun 21/6

07:30-10:19

Nonstop4h 49m

$623

Flights are sorted by cheapest return flights first.

Deals found on 9/5

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 $397). Flying from San Francisco to Chicago in January is currently the most expensive (average of $1,509). 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 10 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 10 May 2026.

The most flights from SFO to CHI are scheduled on a Sunday (94 on average). You will have fewer flight options on Monday, which is when the least amount of flights are scheduled (60 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 183 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 74 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 25m. Your travel time can differ by up to 5h 05m. 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 $397). Flying from San Francisco to Chicago in January is currently the most expensive (average of $1,509). 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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