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$109+ 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 4/15. Fares are subject to change and may not be available on all flights or dates of travel.
SFO — CHI
Mar 10 — Mar 171
Tue 3/10
Tue 3/17
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 September or February, booked 52 days in advance, depart on a Wednesday or Tuesday 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 February 8, 2026.

This Kiwi.com deal was found by Cheapflights users on 2/8. 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.
Tue 4/76:29 pm
SFO
-
ORD
2 stops14h 48m
Multiple Airlines
Tue 4/215:01 am
ORD
-
SFO
1 stop13h 53m
Multiple Airlines
Deal found 2/8$243
This Kiwi.com deal was found by Cheapflights users on 2/7. 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.
Sun 3/810:40 pm
SFO
-
ORD
1 stop10h 16m
Frontier
Fri 3/135:01 am
ORD
-
SFO
1 stop16h 13m
Frontier
Deal found 2/7$244
This Southwest deal was found by Cheapflights users on 2/7. 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 4/711:55 am
SFO
-
MDW
1 stop7h 55m
Southwest
Mon 4/139:45 pm
MDW
-
SFO
Nonstop4h 35m
Southwest
Deal found 2/7$245
This Cheapflightsfares deal was found by Cheapflights users on 2/5. 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.
Tue 4/79:00 pm
SFO
-
ORD
1 stop15h 19m
Frontier
Sat 4/115:53 pm
ORD
-
SFO
1 stop8h 30m
Frontier
Deal found 2/5$245
This Frontier deal was found by Cheapflights users on 2/5. 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.
Fri 5/155:49 pm
SFO
-
ORD
1 stop10h 01m
Frontier
Tue 5/195:01 am
ORD
-
SFO
1 stop13h 53m
Frontier
Deal found 2/5$246
This Southwest deal was found by Cheapflights users on 2/5. 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.
Wed 4/15:40 am
SFO
-
MDW
Nonstop4h 00m
Southwest
Sat 4/49:40 pm
MDW
-
SFO
Nonstop4h 40m
Southwest
Deal found 2/5$247
This American Airlines deal was found by Cheapflights users on 2/8. 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.
Sat 5/21:28 pm
SFO
-
ORD
Nonstop4h 44m
American Airlines
Sat 5/97:04 am
ORD
-
SFO
1 stop10h 21m
American Airlines
Deal found 2/8$247
This Southwest deal was found by Cheapflights users on 2/5. 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.
Sat 5/910:10 am
SFO
-
MDW
1 stop9h 10m
Southwest
Wed 5/1312:50 pm
MDW
-
SFO
2 stops10h 35m
Southwest
Deal found 2/5$248
This United Airlines deal was found by Cheapflights users on 2/5. 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.
Fri 3/136:44 pm
SFO
-
ORD
Nonstop4h 15m
United Airlines
Wed 3/189:15 pm
ORD
-
SFO
Nonstop5h 01m
United Airlines
Deal found 2/5$248
This Kiwi.com deal was found by Cheapflights users on 2/7. 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.
Sun 2/2210:46 pm
SFO
-
ORD
1 stop10h 05m
Frontier
Sat 2/285:05 am
ORD
-
SFO
2 stops21h 23m
Frontier
Deal found 2/7$249
This Southwest deal was found by Cheapflights users on 2/7. 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.
Fri 3/1311:25 pm
SFO
-
MDW
Nonstop4h 05m
Southwest
Wed 3/189:05 pm
MDW
-
SFO
Nonstop4h 40m
Southwest
Deal found 2/7$250
This Alaska Airlines deal was found by Cheapflights users on 2/7. 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 3/411:34 am
SFO
-
ORD
1 stop10h 22m
Alaska Airlines
Thu 3/53:54 pm
ORD
-
SFO
1 stop10h 05m
Alaska Airlines
Deal found 2/7$250

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 February 8, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$243
(CheapOair)

One-way from

$109
(Southwest)

Popular in

November

Cheapest in

September

Average price

$297

Good round-trip deal

$324 or less

Good one-way deal

$154 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. 13% potential increase in price ($57 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($8 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in February 2026
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 February 8, 2026.
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

Sat 5/9

10:10 am-9:20 pm

1 stop9h 10m

Chicago Midway

Wed 5/13

12:50 pm-9:25 pm

2 stops10h 35m

$248

San FranciscoChicago

SFO - ORD

SFOORD

San Francisco

Wed 3/4

11:34 am-11:56 pm

1 stop10h 22m

Chicago O'Hare Intl

Thu 3/5

3:54 pm-11:59 pm

1 stop10h 05m

$250

San FranciscoChicago

SFO - MDW

SFOMDW

San Francisco

Sat 3/14

5:15 am-11:10 am

Nonstop3h 55m

Chicago Midway

Wed 3/18

9:05 pm-11:45 pm

Nonstop4h 40m

$250

San FranciscoChicago

SFO - MDW

SFOMDW

San Francisco

Mon 5/4

5:15 am-11:25 am

Nonstop4h 10m

Chicago Midway

Wed 5/6

9:00 pm-11:35 pm

Nonstop4h 35m

$250

San FranciscoChicago

SFO - MDW

SFOMDW

San Francisco

Fri 4/17

9:15 pm-7:55 am

1 stop8h 40m

Chicago Midway

Sat 4/25

3:15 pm-9:10 pm

1 stop7h 55m

$251

San FranciscoChicago

SFO - MDW

SFOMDW

San Francisco

Fri 3/20

11:25 pm-5:30 am

Nonstop4h 05m

Chicago Midway

Wed 3/25

6:05 am-1:45 pm

1 stop9h 40m

$260

San FranciscoChicago

SFO - MDW

SFOMDW

San Francisco

Fri 5/8

9:15 pm-7:55 am

1 stop8h 40m

Chicago Midway

Mon 5/11

9:45 pm-12:20 am

Nonstop4h 35m

$260

San FranciscoChicago

SFO - MDW

SFOMDW

San Francisco

Fri 3/13

11:25 pm-5:30 am

Nonstop4h 05m

Chicago Midway

Tue 3/17

3:35 pm-9:05 pm

1 stop7h 30m

$260

San FranciscoChicago

SFO - ORD

SFOORD

San Francisco

Thu 4/30

10:55 pm-5:25 am

Nonstop4h 30m

Chicago O'Hare Intl

Mon 5/4

10:45 pm-1:35 am

Nonstop4h 50m

$264

San FranciscoChicago

SFO - MDW

SFOMDW

San Francisco

Tue 3/17

5:40 am-11:40 am

Nonstop4h 00m

Chicago Midway

Tue 3/17

1:20 pm-10:05 pm

2 stops10h 45m

$265

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/8

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 February.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars
JustAirTicketPrice Accuracy-Trust Score*1 star
OvagoPrice Accuracy2 starsTrust Score*3 stars
Trip.comPrice Accuracy1 starTrust Score*3 stars
CheapflightsfaresPrice Accuracy2 starsTrust Score*2 stars
Kiwi.comPrice Accuracy3 starsTrust Score*3 stars
eDreamsPrice 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 FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on San Francisco-Chicago flight deals on Cheapflights vs. FlightHub >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 FlightHub the most. FlightHub 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 January 30, 2026.

The best time to book flights from San Francisco to Chicago is 52 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, October is the cheapest month in which you can book a flight from San Francisco to Chicago (average of $125). Flying from San Francisco to Chicago in December is currently the most expensive (average of $233). 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 February 8, 2026.

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 28% 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 February 7, 2026.

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.

What’s the top layover airport for flights from San Francisco to Chicago?

Share of 1-stop round-trip flights from San Francisco to Chicago chosen by Cheapflights users in the past 12 months, using the same layover each way.

Las Vegas (LAS) – chosen by Cheapflights users on 50% of 1-stop itineraries from San Francisco to Chicago on Cheapflights.

What’s the cheapest layover airport for flights from San Francisco to Chicago?

Average round-trip fare for 1-stop flights from San Francisco to Chicago, chosen by Cheapflights users in the past 12 months, with the same layover each way.

Denver (DEN) is the most affordable 1-stop option, with an average round-trip price of $153.

What’s the fastest layover option from San Francisco to Chicago?

Shortest average travel time for 1-stop one-way flights from San Francisco to Chicago, based on itineraries clicked by Cheapflights users over the past 12 months, grouped by layover airport.

Flights via San Diego (SAN) have the shortest average one-way travel time for 1-stop routes: 7h 01m.

Which airport typically offers the quickest layover for flights from San Francisco to Chicago?

Average layover duration for 1-stop one-way flights from San Francisco to Chicago, chosen by Cheapflights users in the last 12 months, grouped by stopover airport.

Flights via San Diego (SAN) offer the fastest connection on this route, with an average layover time of 0h 57m.

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 last year, American Airlines have had the lowest number of delays on this route, with just 10% 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
Our travel experts
Harriet Baskas

Harriet Baskas

Expert on United Airlines and SFO

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

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

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 February 8, 2026.
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
11,851 reviews

Boarding

8.1

Crew

8.5

Entertainment

7.0

Food

7.1

Overall

8.0

Comfort

7.8

Reviews

1 / 20
10.0
Excellent

Anonymous,Jan 2026

STS - LAX

Enjoyed staff assistance from ticking thru tsa , boarding and in the plane Couldn’t pick a seat except upgrading
Alaska Airlines
8.0
Very good
11,851 reviews
Alaska Airlines
8.0
Very good
11,851 reviews

Boarding

8.1

Crew

8.5

Entertainment

7.0

Food

7.1

Overall

8.0

Comfort

7.8

Reviews

1 / 20
10.0
Excellent

Anonymous,Jan 2026

STS - LAX

Enjoyed staff assistance from ticking thru tsa , boarding and in the plane Couldn’t pick a seat except upgrading
Southwest
8.0
Very good
4,280 reviews
Alaska Airlines
8.0
Very good
11,851 reviews

Boarding

8.1

Crew

8.5

Entertainment

7.0

Food

7.1

Overall

8.0

Comfort

7.8

Reviews

1 / 20
10.0
Excellent

Anonymous,Jan 2026

STS - LAX

Enjoyed staff assistance from ticking thru tsa , boarding and in the plane Couldn’t pick a seat except upgrading
United Airlines
7.4
Good
9,254 reviews
Alaska Airlines
8.0
Very good
11,851 reviews

Boarding

8.1

Crew

8.5

Entertainment

7.0

Food

7.1

Overall

8.0

Comfort

7.8

Reviews

1 / 20
10.0
Excellent

Anonymous,Jan 2026

STS - LAX

Enjoyed staff assistance from ticking thru tsa , boarding and in the plane Couldn’t pick a seat except upgrading
American Airlines
7.2
Good
11,249 reviews
Alaska Airlines
8.0
Very good
11,851 reviews

Boarding

8.1

Crew

8.5

Entertainment

7.0

Food

7.1

Overall

8.0

Comfort

7.8

Reviews

1 / 20
10.0
Excellent

Anonymous,Jan 2026

STS - LAX

Enjoyed staff assistance from ticking thru tsa , boarding and in the plane Couldn’t pick a seat except upgrading
Frontier
5.7
Fair
3,052 reviews
Alaska Airlines
8.0
Very good
11,851 reviews

Boarding

8.1

Crew

8.5

Entertainment

7.0

Food

7.1

Overall

8.0

Comfort

7.8

Reviews

1 / 20
10.0
Excellent

Anonymous,Jan 2026

STS - LAX

Enjoyed staff assistance from ticking thru tsa , boarding and in the plane Couldn’t pick a seat except upgrading

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 38 daily outbound flights to Chicago from 8 different airlines.

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

    Departing from San Francisco to Chicago will take you 4h 30m. The distance from San Francisco to Chicago is about 1841 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 71% 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 $72. However, be on the lookout for offers from JetBlue 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: Gulf Air (95%), Iberia (91%), Austrian Airlines (91%).

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

    Looking at all options, your cheapest flight can be booked for $108. While the most popular route (San Francisco - Chicago O'Hare Intl) can be booked for $192 on average, our data indicates $1,036 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, Stratosphere Tower, and Fountains of Bellagio are the most popular attractions in Las Vegas if you're in need of something to do during your layover. Fremont Street Experience, Stratosphere Tower, and Fountains of Bellagio can be visited by traveling about 5.9 mi, 4.3 mi, and 2.3 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 $54 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, October is the cheapest month in which you can book a flight from San Francisco to Chicago (average of $125). Flying from San Francisco to Chicago in December is currently the most expensive (average of $233). 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

Browse thousands of different options on Cheapflights for your next trip

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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 February 8, 2026.
AirlineCheapestAverageFlexibilityOn-time
Hawaiian AirlinesCheapest$101Average$277FlexibilityNo cancel feeOn-time85%
FrontierCheapest$126Average$240FlexibilityNo cancel feeOn-time62%
DeltaCheapest$128Average$323FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$133Average$407FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$185Average$351FlexibilityNo cancel feeOn-time63%
Alaska AirlinesCheapest$196Average$333FlexibilityNo cancel feeOn-time75%
American AirlinesCheapest$197Average$354FlexibilityNo cancel feeOn-time71%
JetBlueCheapest$234Average$275FlexibilityNo cancel feeOn-time62%

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