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$101+ Cheap flights from San Francisco (SFO) to Chicago (CHI)

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 10/21. Fares are subject to change and may not be available on all flights or dates of travel.
SFO — CHI
Aug 2 — Aug 91
Sat 8/2
Sat 8/9
1 adult, Economy
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Cheapflights Tip: The best prices from San Francisco to Chicago are usually found in February or January, booked 34 days in advance, depart on a Wednesday or Tuesday and return on a Thursday

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 July 28, 2025.

Round-trip from

$207
(Southwest)

One-way from

$101
(American Airlines)

Popular in

December

Cheapest in

February

Average price

$357

Good round-trip deal

$237 or less

Good one-way deal

$154 or less
From San Francisco to Chicago (CHI)
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One-way flight from San Francisco to Chicago (CHI)
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Highest demand for flights based on searches. 5% potential increase in price ($20 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($9 potential savings vs. average RT price).
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Average for round-trip flights in July 2025
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Price to beat on a round-trip flight from San Francisco to Chicago (CHI).
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Price to beat on a one-way flight from San Francisco to Chicago (CHI).
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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 July 28, 2025.

This Southwest deal was found by Cheapflights users on 7/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/47:15 amSFO - MDW
Nonstop4h 05mSouthwest
Wed 9/103:50 pmMDW - SFO
Nonstop4h 35mSouthwest
Deal found 7/27$207
This American Airlines deal was found by Cheapflights users on 7/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/166:00 amSFO - ORD
Nonstop4h 18mAmerican Airlines
Fri 9/263:19 pmORD - SFO
Nonstop4h 42mAmerican Airlines
Deal found 7/27$207
This Southwest deal was found by Cheapflights users on 7/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/2612:45 pmSFO - ORD
1 stop7h 35mSouthwest
Sun 8/317:30 amORD - SFO
1 stop6h 25mSouthwest
Deal found 7/28$208
This Kiwi.com deal was found by Cheapflights users on 7/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/127:00 amSFO - ORD
1 stop9h 59mHawaiian Airlines
Sat 11/152:54 pmORD - SFO
1 stop9h 01mHawaiian Airlines
Deal found 7/28$215
This Alaska Airlines deal was found by Cheapflights users on 7/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/810:26 amSFO - ORD
1 stop11h 33mAlaska Airlines
Wed 10/158:20 amORD - SFO
1 stop7h 41mAlaska Airlines
Deal found 7/26$216
This Cheapflightsfares deal was found by Cheapflights users on 7/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/272:10 pmSFO - ORD
1 stop19h 38mFrontier
Wed 10/87:20 amORD - SFO
1 stop17h 07mFrontier
Deal found 7/26$235
This Frontier deal was found by Cheapflights users on 7/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/611:30 pmSFO - MDW
1 stop11h 59mFrontier
Tue 8/1211:39 amMDW - SFO
1 stop11h 08mFrontier
Deal found 7/27$238
This Delta deal was found by Cheapflights users on 7/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/2212:40 amSFO - MDW
1 stop6h 11mDelta
Wed 8/279:30 amMDW - SFO
1 stop6h 57mDelta
Deal found 7/28$257
This Delta deal was found by Cheapflights users on 7/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/196:00 amSFO - ORD
1 stop8h 45mDelta
Wed 8/277:15 amORD - SFO
1 stop9h 12mDelta
Deal found 7/28$257
This Orbitz deal was found by Cheapflights users on 7/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/1310:29 pmSFO - ORD
1 stop9h 56mMultiple Airlines
Tue 8/197:18 pmORD - SFO
Nonstop4h 48mMultiple Airlines
Deal found 7/26$263
This Mytrip deal was found by Cheapflights users on 7/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/76:12 pmSFO - RFD
2 stops18h 13mMultiple Airlines
Fri 9/1210:37 amRFD - SFO
2 stops26h 41mMultiple Airlines
Deal found 7/26$506

Cheapflights Fare Finder

 
Customize 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 2,558,603 searches. Data last updated July 28, 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 - MDW

SFOMDW

San Francisco

Thu 9/4

7:15 am-1:20 pm

Nonstop4h 05m

Chicago Midway

Wed 9/10

3:50 pm-6:25 pm

Nonstop4h 35m

$207

San FranciscoChicago

SFO - ORD

SFOORD

San Francisco

Tue 9/23

12:47 am-6:56 am

Nonstop4h 09m

Chicago O'Hare Intl

Sun 9/28

6:45 am-9:24 am

Nonstop4h 39m

$207

San FranciscoChicago

SFO - ORD

SFOORD

San Francisco

Tue 8/26

12:45 pm-10:20 pm

1 stop7h 35m

Chicago O'Hare Intl

Sun 8/31

7:30 am-11:55 am

1 stop6h 25m

$208

San FranciscoChicago

SFO - ORD

SFOORD

San Francisco

Tue 10/7

10:26 am-11:59 pm

1 stop11h 33m

Chicago O'Hare Intl

Wed 10/15

8:20 am-2:01 pm

1 stop7h 41m

$211

San FranciscoChicago

SFO - ORD

SFOORD

San Francisco

Wed 10/8

10:26 am-11:59 pm

1 stop11h 33m

Chicago O'Hare Intl

Tue 10/14

8:20 am-2:01 pm

1 stop7h 41m

$216

San FranciscoChicago

SFO - ORD

SFOORD

San Francisco

Wed 8/6

6:37 am-12:32 am

1 stop15h 55m

Chicago O'Hare Intl

Sat 8/9

1:39 pm-7:39 pm

1 stop8h 00m

$234

San FranciscoChicago

SFO - MDW

SFOMDW

San Francisco

Wed 8/6

11:30 pm-1:29 pm

1 stop11h 59m

Chicago Midway

Tue 8/12

11:39 am-8:47 pm

1 stop11h 08m

$238

San FranciscoChicago

SFO - MDW

SFOMDW

San Francisco

Fri 8/22

12:40 am-8:51 am

1 stop6h 11m

Chicago Midway

Sat 8/30

4:25 pm-10:25 pm

1 stop8h 00m

$257

San FranciscoChicago

SFO - ORD

SFOORD

San Francisco

Tue 8/19

12:35 am-8:24 am

1 stop5h 49m

Chicago O'Hare Intl

Tue 8/26

7:05 am-2:24 pm

1 stop9h 19m

$257

San FranciscoChicago

SFO - ORD

SFOORD

San Francisco

Wed 8/13

10:29 pm-10:25 am

1 stop9h 56m

Chicago O'Hare Intl

Tue 8/19

7:18 pm-10:06 pm

Nonstop4h 48m

$263

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/27

Showing 1-10 of 25 results
1
2
3

The best insider tips for San Francisco to Chicago flights

Snippets provided in this section are AI-generated based on a summarization of Cheapflights-commissioned articles. The articles are presented as-is, for general informational purposes only, and may not be up-to-date. The opinions contained in the articles are original to the author and reflect their authentic experience, which may vary significantly from the experience of others.
Cheapflights partnered with top experts to bring you the best recommendations for your San Francisco to Chicago trip
Airlines
United Airlines

United's Economy Plus offers extra legroom, ideal for comfort on medium-haul flights.


United's Polaris Lounges offer exclusive amenities like showers and dining, enhancing pre-flight comfort.

Read more about United Airlinesby Harriet Baskas
Alaska Airlines

Alaska's Premium Class offers extra legroom and free cocktails, enhancing comfort on medium-haul flights.


Alaska's Wi-Fi is a flat fee, ideal for business travelers needing connectivity during flights.

Read more about Alaska Airlinesby Robert Schrader
Airports
SFO

Save time by ordering meals for pickup via the SFO2Go program during busy times.

Read more about SFOby Harriet Baskas
ORD

For a quick city trip, take the “L” train from ORD to downtown Chicago, avoiding traffic delays.

Read more about ORDby Ramsey Qubein
Our travel experts
Harriet Baskas

Harriet Baskas

Expert on United Airlines and SFO

Harriet Baskas

Harriet Baskas

Harriet is an award-winning journalist who is happiest in an airport or an unusual museum. Her stories about airports, air travel, and the business of travel have appeared on NBC News, CNBC, USA TODAY, The Points Guy and other outlets. She is the creator of the StuckatTheAirport.com blog and the author of nine books. When not out on the road or exploring the latest airport amenities, she’s home in Seattle getting ready for the next adventure.

Read more
Robert Schrader

Robert Schrader

Expert on Alaska Airlines

Robert Schrader

Robert Schrader

One of the web's original travel bloggers, Robert launched his first site Leave Your Daily Hell in 2009. Since then, he's expanded into destination niche sites (one each for Japan, Thailand and Taiwan), in addition to having written for the inflight magazines of Singapore Airlines and Korean Air. Overall, he's visited nearly 100 countries, and flies business as often as possible.

Read more
Ramsey Qubein

Ramsey Qubein

Expert on ORD

Ramsey Qubein

Ramsey Qubein

An avid traveler and aviation expert who has visited 173 countries, all 50 states and seven continents, Ramsey Qubein flies nearly 400,000 miles a year. As a North Carolina-based freelance journalist for publications including Conde Nast Traveler, Forbes, USA Today and Bloomberg among others, he explores the latest trends in aviation, hospitality, cruises and business.

Read more

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 round-trip 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 round-trip flight from San Francisco to Chicago. Price data was last updated on July 25, 2025.

The best time to book flights from San Francisco to Chicago is 34 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, August is the cheapest month in which you can book a flight from San Francisco to Chicago (average of $245). Flying from San Francisco to Chicago in March is currently the most expensive (average of $321). 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 July 28, 2025.

One of the essential ways to save on airfare from San Francisco to Chicago is to remain as flexible as possible. Flights that are at noon tend to be the most expensive. A flight in the afternoon could potentially save you up to 14% on airfare.

What is the cheapest day to fly from San Francisco to Chicago?

Use this chart to determine the cheapest time to fly round-trip from San Francisco to Chicago. Price data was last updated on July 27, 2025.

Travelers seeking maximum savings on their San Francisco to Chicago flight should consider departing on Wednesday afternoons when fares are most often at their lowest. Sunday at noon flights should be avoided if possible as fares are typically the most expensive at this time.

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 July 28, 2025.

The most flights from SFO to CHI are scheduled on a Monday (94 on average). You will have fewer flight options on Wednesday, which is when the least amount of flights are scheduled (64 on average).

Reviews of airlines servicing Chicago

Get insights into the airlines that provide service to Chicago. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Chicago. Reviews last updated July 28, 2025.
Read through reviews of airlines operating flights from San Francisco to Chicago, such as Alaska Airlines, Southwest, and Delta. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Alaska Airlines
8.0
Very good
10,000 reviews

Comfort

7.8

Overall

8.0

Crew

8.5

Food

7.1

Boarding

8.1

Entertainment

7.1

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Alaska Airlines
8.0
Very good
10,000 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Comfort

7.8

Overall

8.0

Crew

8.5

Food

7.1

Boarding

8.1

Entertainment

7.1

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Southwest
8.0
Very good
4,238 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Comfort

7.8

Overall

8.0

Crew

8.5

Food

7.1

Boarding

8.1

Entertainment

7.1

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Delta
8.0
Very good
7,975 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Comfort

7.8

Overall

8.0

Crew

8.5

Food

7.1

Boarding

8.1

Entertainment

7.1

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Hawaiian Airlines
7.8
Good
2,604 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Comfort

7.8

Overall

8.0

Crew

8.5

Food

7.1

Boarding

8.1

Entertainment

7.1

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
United Airlines
7.4
Good
8,892 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Comfort

7.8

Overall

8.0

Crew

8.5

Food

7.1

Boarding

8.1

Entertainment

7.1

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.

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?

    Located just 11.8 mi from the city center, San Francisco is the airport most travelers will use when flying to Chicago from San Francisco. Booking flights from San Francisco (SFO) to Chicago should be relatively easy as there are 78 daily outbound flights to Chicago from 8 different airlines.

  • What are the cheapest airlines flying from San Francisco to Chicago round-trip?

    Southwest, at $207, was found to be the cheapest airline from San Francisco to Chicago.Alternate airlines to your destination round-trip include American Airlines and Hawaiian Airlines. These flights start at 38% lower than the current average price 3 months from now.

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

    The cheapest airline one-way is American Airlines, with whom users have recently found tickets for as low as $101. However, be on the lookout for offers from Frontier and Southwest, as they are both options that can get you from San Francisco to Chicago for a low price.

  • What are the most popular routes from San Francisco to Chicago?

    While some choose either San Francisco - Chicago Midway or San Francisco - Chicago Greater Rockford, San Francisco - Chicago O'Hare Intl is the most popular route from San Francisco to Chicago.

  • What are the most reliable airlines from San Francisco to Chicago?

    Looking for the most reliable airlines to get you to your destination on time? Our data shows these are most likely to get you from San Francisco to Chicago on time: Fiji Airways (100%), Asiana Airlines (88%), China Southern (82%).

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

    Looking at all options, your cheapest flight can be booked for $98. While the most popular route (San Francisco - Chicago O'Hare Intl) can be booked for $188 on average our data indicates $1,096 when flying from San Francisco to Chicago.

  • Where are the most common layover locations when flying from San Francisco to Chicago?

    San Francisco to Chicago flights have a layover in Las Vegas most often.

  • What are some popular things to do or see while on a layover in Las Vegas?

    Fremont Street Experience, The Colosseum at Caesars Palace, and Stratosphere Tower are the most popular attractions in Las Vegas if you're in need of something to do during your layover. Fremont Street Experience, The Colosseum at Caesars Palace, and Stratosphere Tower can be visited by traveling about 5.9 mi, 2.6 mi, and 4.3 mi respectively from Las Vegas Harry Reid Intl. Those looking to explore during their layover in Las Vegas can rent a car from Las Vegas Harry Reid Intl for about $62 per day.

  • Where are the least popular layover locations for San Francisco to Chicago flights?

    San Francisco to Chicago flights have a layover in Denver least often.

  • 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 vacation 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, August is the cheapest month in which you can book a flight from San Francisco to Chicago (average of $245). Flying from San Francisco to Chicago in March is currently the most expensive (average of $321). 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

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
Lansing
Hammond
Benton Harbor
Porter
Valparaiso
Chesterton

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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.
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Top 8 airlines flying from San Francisco to Chicago

Discover the top 8 airlines that operate flights from San Francisco to Chicago. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated July 28, 2025.
AirlineCheapestAverageFlexibilityOn-time
Hawaiian AirlinesCheapest$108Average$288FlexibilityNo cancel feeOn-time85%
FrontierCheapest$118Average$220FlexibilityNo cancel feeOn-time62%
DeltaCheapest$128Average$313FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$133Average$352FlexibilityNo cancel feeOn-time69%
Spirit AirlinesCheapest$143Average$221FlexibilityNo cancel feeOn-time65%
Alaska AirlinesCheapest$179Average$306FlexibilityNo cancel feeOn-time75%
SouthwestCheapest$185Average$348FlexibilityNo cancel feeOn-time63%
American AirlinesCheapest$197Average$342FlexibilityNo cancel feeOn-time71%

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