Cheap flights from San Francisco to Chicago from $153

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 1/1. Fares are subject to change and may not be available on all flights or dates of travel.
SFO — CHI
8 Sep — 15 Sep1
1 adult

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 3 September 2025.

Round-trip from

$323

One-way from

$153

Popular in

December

Cheapest in

February

Average price

$471

Good one-way deal

$361 or less
Frontier
  • Frontier
  • 3/10-10/10
  • 2 total stops
  • 29h 05m total
  • San Francisco to Chicago
United Airlines
  • United Airlines
  • 24/11
  • Nonstop
  • 4h 18m total
  • San Francisco to Chicago
Highest demand for flights based on searches. 6% potential increase in price ($55 potential increase over avg. return price).
Cheapest flight prices on average. 2% potential price decrease ($21 potential savings vs. average return price).
Average for round-trip flights in September 2025
Price to beat on a one-way flight from San Francisco to Chicago (CHI).

Find flight deals from San Francisco to Chicago

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 3 September 2025.

Tue 7/1010:26SFO - ORD
1 stop11h 33mAlaska Airlines
Tue 14/1015:50ORD - SFO
1 stop21h 16mAlaska Airlines
Deal found 3/9$340
Wed 12/1107:00SFO - ORD
1 stop14h 59mAlaska Airlines
Wed 19/1114:54ORD - SFO
1 stop9h 07mAlaska Airlines
Deal found 1/9$343
Mon 20/1006:45SFO - ORD
1 stop15h 14mAlaska Airlines
Wed 22/1008:20ORD - SFO
1 stop7h 41mAlaska Airlines
Deal found 3/9$357
Wed 1/1023:00SFO - ORD
Nonstop4h 13mUnited Airlines
Wed 8/1006:15ORD - SFO
Nonstop4h 38mUnited Airlines
Deal found 1/9$366
Wed 24/914:42SFO - ORD
1 stop7h 21mAlaska Airlines
Wed 8/1008:20ORD - SFO
1 stop7h 41mAlaska Airlines
Deal found 3/9$368
Tue 21/1010:26SFO - ORD
1 stop11h 33mAlaska Airlines
Sat 8/1109:20ORD - SFO
1 stop14h 35mAlaska Airlines
Deal found 2/9$371
Thu 9/1006:45SFO - ORD
1 stop15h 14mAlaska Airlines
Tue 14/1019:59ORD - SFO
1 stop20h 02mAlaska Airlines
Deal found 3/9$373
Tue 4/1107:00SFO - ORD
1 stop9h 59mAlaska Airlines
Sat 8/1109:20ORD - SFO
1 stop14h 35mAlaska Airlines
Deal found 2/9$374
Sat 18/1006:30SFO - ORD
Nonstop4h 35mUnited Airlines
Wed 22/1021:13ORD - SFO
Nonstop4h 46mUnited Airlines
Deal found 1/9$376
Wed 24/923:59SFO - ORD
Nonstop4h 16mUnited Airlines
Thu 25/918:32ORD - SFO
Nonstop4h 51mUnited Airlines
Deal found 1/9$379
Tue 21/1010:26SFO - ORD
1 stop11h 33mAlaska Airlines
Mon 27/1014:54ORD - SFO
1 stop9h 07mAlaska Airlines
Deal found 3/9$380
Wed 22/1008:45SFO - ORD
1 stop8h 14mAlaska Airlines
Tue 11/1109:20ORD - SFO
1 stop14h 41mAlaska Airlines
Deal found 2/9$383

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 3 September 2025.
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

Sat 18/10

08:41-23:59

1 stop13h 18m

Chicago O'Hare Intl

Tue 21/10

19:59-11:06

1 stop17h 07m

$343

San FranciscoChicago

SFO - ORD

SFOORD

San Francisco

Wed 15/10

10:26-23:59

1 stop11h 33m

Chicago O'Hare Intl

Wed 22/10

08:20-17:45

1 stop11h 25m

$343

San FranciscoChicago

SFO - ORD

SFOORD

San Francisco

Wed 8/10

10:26-23:59

1 stop11h 33m

Chicago O'Hare Intl

Wed 15/10

08:20-14:01

1 stop7h 41m

$343

San FranciscoChicago

SFO - ORD

SFOORD

San Francisco

Mon 20/10

06:45-23:59

1 stop15h 14m

Chicago O'Hare Intl

Tue 28/10

09:20-22:01

1 stop14h 41m

$357

San FranciscoChicago

SFO - ORD

SFOORD

San Francisco

Wed 1/10

23:00-05:13

Nonstop4h 13m

Chicago O'Hare Intl

Wed 8/10

06:15-08:53

Nonstop4h 38m

$366

San FranciscoChicago

SFO - ORD

SFOORD

San Francisco

Tue 23/9

06:30-13:01

Nonstop4h 31m

Chicago O'Hare Intl

Tue 30/9

15:47-18:28

Nonstop4h 41m

$366

San FranciscoChicago

SFO - ORD

SFOORD

San Francisco

Tue 11/11

23:44-06:02

Nonstop4h 18m

Chicago O'Hare Intl

Tue 18/11

09:10-11:56

Nonstop4h 46m

$366

San FranciscoChicago

SFO - ORD

SFOORD

San Francisco

Tue 21/10

10:26-23:59

1 stop11h 33m

Chicago O'Hare Intl

Sat 8/11

09:20-21:55

1 stop14h 35m

$371

San FranciscoChicago

SFO - ORD

SFOORD

San Francisco

Sat 18/10

08:41-23:59

1 stop13h 18m

Chicago O'Hare Intl

Tue 28/10

09:20-22:01

1 stop14h 41m

$371

San FranciscoChicago

SFO - ORD

SFOORD

San Francisco

Tue 21/10

10:26-23:59

1 stop11h 33m

Chicago O'Hare Intl

Tue 11/11

14:54-22:01

1 stop9h 07m

$371

Flights are sorted by cheapest return flights first.

Deals found on 1/9

Showing 1-10 of 18 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 29 August 2025.

The best time to book flights from San Francisco to Chicago is 71 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 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 3 September 2025.

When flying from San Francisco to Chicago, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

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 3 September 2025.

The most flights from SFO to CHI are scheduled on a Tuesday (85 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (26 on average).

How much does it cost for a return flight from San Francisco to Chicago?

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 44 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 and United Airlines can get you from San Francisco to Chicago in just under 4h 18m. Your travel time can differ by up to 7h 15m. The distance between San Francisco and Chicago is about 2963 km. This flight may include one or multiple stops.

  • What are the cheapest airlines to fly from San Francisco to Chicago one-way?

    For one-way options, check prices for United Airlines. According to our data, you can fly for as low as $153. Users have also found prices from $169 and $179 on Southwest and Alaska Airlines, respectively.

  • 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: Asiana Airlines (82%), Qatar Airways (81%), Air Canada( 79%).

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

    On average you can expect to pay $373 for a flight from San Francisco to Chicago. The cheapest flight overall is $272 while the most popular route, (San Francisco - Chicago O'Hare Intl) is currently priced at $376.

  • 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.

See more FAQs

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Alternative routes for San Francisco to Chicago

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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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