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$126+ 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 1/11. Fares are subject to change and may not be available on all flights or dates of travel.
SFO — CHI
Jan 22 — Jan 291
Thu 1/22
Thu 1/29
1 adult, Economy
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Find cheap flights from San Francisco to Chicago with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

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3. Compare prices and book

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Cheapflights Tip: The best prices from San Francisco to Chicago are usually found in February or September, booked 71 days in advance, depart on a Wednesday or Saturday and return on a Thursday

Cheap 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 December 23, 2025.

This Kiwi.com deal was found by Cheapflights users on 12/22. 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 12/319:30 pmSFO - ORD
2 stops24h 42mFrontier
Sun 1/256:41 amORD - SFO
1 stop13h 13mFrontier
Deal found 12/22$285
This Delta deal was found by Cheapflights users on 12/22. 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.
Wed 12/312:35 pmSFO - ORD
1 stop7h 24mDelta
Mon 1/195:35 pmORD - SFO
1 stop7h 50mDelta
Deal found 12/22$286
This Kiwi.com deal was found by Cheapflights users on 12/22. 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 12/311:29 pmSFO - ORD
2 stops28h 54mFrontier
Thu 1/227:41 pmORD - SFO
1 stop6h 47mFrontier
Deal found 12/22$293
This Kiwi.com deal was found by Cheapflights users on 12/22. 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 12/319:30 pmSFO - ORD
2 stops24h 42mFrontier
Fri 1/2312:07 pmORD - SFO
1 stop14h 21mFrontier
Deal found 12/22$296
This Kiwi.com deal was found by Cheapflights users on 12/22. 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 12/316:00 amSFO - ORD
2 stops22h 05mMultiple Airlines
Sat 1/176:02 pmORD - SFO
1 stop17h 53mMultiple Airlines
Deal found 12/22$303
This American Airlines deal was found by Cheapflights users on 12/22. 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.
Wed 12/3110:49 pmSFO - ORD
Nonstop4h 18mAmerican Airlines
Sat 1/177:05 amORD - SFO
1 stop7h 31mAmerican Airlines
Deal found 12/22$304
This United Airlines deal was found by Cheapflights users on 12/22. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/313:15 pmSFO - ORD
Nonstop4h 17mUnited Airlines
Tue 1/207:58 pmORD - SFO
Nonstop5h 02mUnited Airlines
Deal found 12/22$307
This Frontier deal was found by Cheapflights users on 12/22. 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.
Sun 12/289:56 pmSFO - ORD
1 stop12h 26mFrontier
Thu 1/227:41 pmORD - SFO
1 stop6h 47mFrontier
Deal found 12/22$312
This Kiwi.com deal was found by Cheapflights users on 12/21. 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.
Sat 12/276:24 amSFO - ORD
1 stop15h 48mFrontier
Sat 1/176:02 pmORD - SFO
1 stop17h 53mFrontier
Deal found 12/21$318
This Kiwi.com deal was found by Cheapflights users on 12/22. 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.
Sat 12/276:24 amSFO - ORD
1 stop15h 48mFrontier
Thu 1/227:41 pmORD - SFO
1 stop6h 47mFrontier
Deal found 12/22$319
This United Airlines deal was found by Cheapflights users on 12/22. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/314:55 pmSFO - ORD
Nonstop4h 19mUnited Airlines
Wed 1/216:29 pmORD - SFO
Nonstop5h 01mUnited Airlines
Deal found 12/22$322
This United Airlines deal was found by Cheapflights users on 12/22. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/314:55 pmSFO - ORD
Nonstop4h 19mUnited Airlines
Sat 1/242:40 pmORD - SFO
Nonstop4h 56mUnited Airlines
Deal found 12/22$326

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 December 23, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$257
(Delta)

One-way from

$126
(Frontier)

Popular in

December

Cheapest in

February

Average price

$460

Good round-trip deal

$374 or less

Good one-way deal

$190 or less
Provider with most accurate pricing for San Francisco-Chicago (CHI) flight deals.
Search Deals
Provider most trusted by Cheapflights users for San Francisco-Chicago (CHI) flights.
Search Deals
From San Francisco to Chicago (CHI)
Search Deals
One-way flight from San Francisco to Chicago (CHI)
Search Deals
Highest demand for flights based on searches. 14% potential increase in price ($57 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($11 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 2025
Search Deals
Price to beat on a round-trip flight from San Francisco to Chicago (CHI).
Search Deals
Price to beat on a one-way flight from San Francisco to Chicago (CHI).
Search Deals

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 December 23, 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 1/29

10:54 pm-8:52 am

1 stop7h 58m

Chicago Midway

Mon 2/2

1:51 pm-8:59 pm

1 stop9h 08m

$259

San FranciscoChicago

SFO - MDW

SFOMDW

San Francisco

Sat 2/21

6:55 am-12:55 pm

Nonstop4h 00m

Chicago Midway

Tue 2/24

2:10 pm-8:15 pm

1 stop8h 05m

$265

San FranciscoChicago

SFO - MDW

SFOMDW

San Francisco

Wed 1/28

10:54 pm-8:52 am

1 stop7h 58m

Chicago Midway

Wed 2/4

1:51 pm-11:30 pm

2 stops11h 39m

$265

San FranciscoChicago

SFO - MDW

SFOMDW

San Francisco

Fri 2/20

12:40 am-11:03 am

1 stop8h 23m

Chicago Midway

Tue 2/24

1:26 pm-10:41 pm

2 stops11h 15m

$265

San FranciscoChicago

SFO - ORD

SFOORD

San Francisco

Sat 1/31

2:05 pm-11:56 pm

1 stop7h 51m

Chicago O'Hare Intl

Mon 2/2

2:20 pm-10:54 pm

2 stops10h 34m

$265

San FranciscoChicago

SFO - ORD

SFOORD

San Francisco

Wed 1/21

10:54 pm-9:41 am

1 stop8h 47m

Chicago O'Hare Intl

Fri 1/23

2:20 pm-10:54 pm

2 stops10h 34m

$265

San FranciscoChicago

SFO - ORD

SFOORD

San Francisco

Tue 1/20

2:35 pm-11:53 pm

1 stop7h 18m

Chicago O'Hare Intl

Tue 1/27

2:20 pm-10:54 pm

2 stops10h 34m

$265

San FranciscoChicago

SFO - ORD

SFOORD

San Francisco

Wed 1/21

4:55 pm-11:14 pm

Nonstop4h 19m

Chicago O'Hare Intl

Fri 1/23

12:45 pm-3:35 pm

Nonstop4h 50m

$267

San FranciscoChicago

SFO - ORD

SFOORD

San Francisco

Sat 3/21

5:40 am-3:18 pm

1 stop7h 38m

Chicago O'Hare Intl

Tue 3/24

7:25 am-4:04 pm

1 stop10h 39m

$269

San FranciscoChicago

SFO - ORD

SFOORD

San Francisco

Sat 1/17

2:25 pm-10:35 pm

1 stop6h 10m

Chicago O'Hare Intl

Sat 1/24

7:15 am-3:35 pm

2 stops10h 20m

$270

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/22

Showing 1-10 of 58 results
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Compare providers for flights from San Francisco to Chicago

Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from San Francisco to Chicago in December.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy2 starsTrust Score*3 stars
eDreamsPrice Accuracy3 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*1 star
JustAirTicketPrice Accuracy-Trust Score*1 star
OvagoPrice Accuracy2 starsTrust Score*2 stars
Trip.comPrice Accuracy2 starsTrust Score*3 stars
CheapflightsfaresPrice Accuracy3 starsTrust Score*2 stars
Kiwi.comPrice Accuracy3 starsTrust Score*3 stars
PricelinePrice Accuracy1 starTrust Score*3 stars
CheapfaremartPrice Accuracy-Trust Score*1 star

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

  • Most accurate provider: When it comes to deals on San Francisco-Chicago flights, users find the pricing of eDreams to be most consistent on Cheapflights vs. eDreams Users can find the same prices on San Francisco-Chicago flight deals on Cheapflights vs. eDreams >95% of the time. Price accuracy is based on data collected from San Francisco-Chicago flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on San Francisco-Chicago flights, Cheapflights users trust eDreams the most. eDreams has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for San Francisco-Chicago flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

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 December 19, 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 month to book a flight from San Francisco to Chicago?

Currently, December is the cheapest month in which you can book a flight from San Francisco to Chicago (average of $107). Flying from San Francisco to Chicago in November is currently the most expensive (average of $210). 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 December 23, 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 morning could potentially save you up to 15% 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 December 20, 2025.

Travelers seeking maximum savings on their San Francisco to Chicago flight should consider departing on Saturday 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 December 23, 2025.

The most flights from SFO to CHI are scheduled on a Friday (72 on average). You will have fewer flight options on Wednesday, which is when the least amount of flights are scheduled (52 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 last year, United Airlines have had the lowest number of delays on this route, with just 9% of flights being delayed.

The best insider tips for San Francisco to Chicago flights

AI-powered summary based on content written by travel experts. AI can make mistakes.
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

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 December 23, 2025.
Read through reviews of airlines operating flights from San Francisco to Chicago, such as Alaska Airlines, Southwest, and United Airlines. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Alaska Airlines
8.0
Very good
11,506 reviews

Entertainment

7.0

Boarding

8.1

Food

7.1

Comfort

7.8

Crew

8.5

Overall

8.0

Reviews

1 / 20
2.0
Mediocre

Art,Dec 2025

SAN - OGG

It was a five hour flight and my seat did not recline. I have had three back surgeries and I’m solid bone for my L3 vertebrae all the way to my tailbone. My body has never hurt so much. There was no TV on this flight and only a small can of soda was free.
Alaska Airlines
8.0
Very good
11,506 reviews
Alaska Airlines
8.0
Very good
11,506 reviews

Entertainment

7.0

Boarding

8.1

Food

7.1

Comfort

7.8

Crew

8.5

Overall

8.0

Reviews

1 / 20
2.0
Mediocre

Art,Dec 2025

SAN - OGG

It was a five hour flight and my seat did not recline. I have had three back surgeries and I’m solid bone for my L3 vertebrae all the way to my tailbone. My body has never hurt so much. There was no TV on this flight and only a small can of soda was free.
Southwest
8.0
Very good
4,253 reviews
Alaska Airlines
8.0
Very good
11,506 reviews

Entertainment

7.0

Boarding

8.1

Food

7.1

Comfort

7.8

Crew

8.5

Overall

8.0

Reviews

1 / 20
2.0
Mediocre

Art,Dec 2025

SAN - OGG

It was a five hour flight and my seat did not recline. I have had three back surgeries and I’m solid bone for my L3 vertebrae all the way to my tailbone. My body has never hurt so much. There was no TV on this flight and only a small can of soda was free.
United Airlines
7.4
Good
9,103 reviews
Alaska Airlines
8.0
Very good
11,506 reviews

Entertainment

7.0

Boarding

8.1

Food

7.1

Comfort

7.8

Crew

8.5

Overall

8.0

Reviews

1 / 20
2.0
Mediocre

Art,Dec 2025

SAN - OGG

It was a five hour flight and my seat did not recline. I have had three back surgeries and I’m solid bone for my L3 vertebrae all the way to my tailbone. My body has never hurt so much. There was no TV on this flight and only a small can of soda was free.
American Airlines
7.2
Good
11,053 reviews
Alaska Airlines
8.0
Very good
11,506 reviews

Entertainment

7.0

Boarding

8.1

Food

7.1

Comfort

7.8

Crew

8.5

Overall

8.0

Reviews

1 / 20
2.0
Mediocre

Art,Dec 2025

SAN - OGG

It was a five hour flight and my seat did not recline. I have had three back surgeries and I’m solid bone for my L3 vertebrae all the way to my tailbone. My body has never hurt so much. There was no TV on this flight and only a small can of soda was free.
Frontier
5.8
Fair
3,076 reviews
Alaska Airlines
8.0
Very good
11,506 reviews

Entertainment

7.0

Boarding

8.1

Food

7.1

Comfort

7.8

Crew

8.5

Overall

8.0

Reviews

1 / 20
2.0
Mediocre

Art,Dec 2025

SAN - OGG

It was a five hour flight and my seat did not recline. I have had three back surgeries and I’m solid bone for my L3 vertebrae all the way to my tailbone. My body has never hurt so much. There was no TV on this flight and only a small can of soda was free.

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 61 daily outbound flights to Chicago from 7 different airlines.

  • How long is the flight from San Francisco to Chicago?

    Departing from San Francisco to Chicago will take you 4h. The distance from San Francisco to Chicago is about 1849 mi. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

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

    Hawaiian Airlines, at $101, was found to be the cheapest airline from San Francisco to Chicago.Alternate airlines to your destination round-trip include Frontier and Delta. These flights start at 70% 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 Frontier, with whom users have recently found tickets for as low as $71. However, be on the lookout for offers from Hawaiian Airlines and Alaska Airlines, 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%), Royal Jordanian (92%), China Southern (91%).

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

    Looking at all options, your cheapest flight can be booked for $127. While the most popular route (San Francisco - Chicago O'Hare Intl) can be booked for $183 on average, our data indicates $1,155 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, Fountains of Bellagio, 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, Fountains of Bellagio, and Stratosphere Tower can be visited by traveling about 5.9 mi, 2.3 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 $48 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, December is the cheapest month in which you can book a flight from San Francisco to Chicago (average of $107). Flying from San Francisco to Chicago in November is currently the most expensive (average of $210). 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
Lansing
Merrillville
Hammond
Porter
Benton Harbor

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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 7 airlines flying from San Francisco to Chicago

Discover the top 7 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 December 23, 2025.
AirlineCheapestAverageFlexibilityOn-time
Hawaiian AirlinesCheapest$108Average$288FlexibilityNo cancel feeOn-time85%
FrontierCheapest$128Average$240FlexibilityNo cancel feeOn-time62%
DeltaCheapest$128Average$320FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$133Average$407FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$185Average$349FlexibilityNo cancel feeOn-time63%
Alaska AirlinesCheapest$196Average$327FlexibilityNo cancel feeOn-time75%
American AirlinesCheapest$197Average$343FlexibilityNo cancel feeOn-time71%

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