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$100+ 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 6/11. Fares are subject to change and may not be available on all flights or dates of travel.
SFO — CHI
May 4 — May 111
Sun 5/4
Sun 5/11
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”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

Cheapflights Tip: The best prices from San Francisco to Chicago are usually found in February or January, booked 76 days in advance, depart on a Wednesday or Tuesday and return on a Wednesday

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 April 29, 2025.

Most accurate provider

Mytrip
3 stars

Most trusted provider

Mytrip
3 stars

Round-trip from

$208
(Frontier)

One-way from

$100
(American Airlines)

Popular in

December

Cheapest in

February

Average price

$314

Good round-trip deal

$311 or less

Good one-way deal

$155 or less
Provider with most accurate pricing for San Francisco-Chicago (CHI) flight deals.
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Provider most trusted by Cheapflights users for San Francisco-Chicago (CHI) flights.
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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. 6% potential increase in price ($22 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 April 2025
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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).
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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 April 29, 2025.

This Frontier deal was found by Cheapflights users on 4/28. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/3110:19 pmSFO - MDW
1 stop8h 44mFrontier
Sun 6/19:12 pmMDW - SFO
1 stop15h 11mFrontier
Deal found 4/28$208
This CheapOair deal was found by Cheapflights users on 4/28. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/19:50 pmSFO - ORD
1 stop29h 20mFrontier
Sat 5/3111:55 amORD - SFO
1 stop12h 28mFrontier
Deal found 4/28$211
This United Airlines deal was found by Cheapflights users on 4/27. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/155:04 amSFO - ORD
Nonstop4h 22mUnited Airlines
Sat 5/246:15 pmORD - SFO
Nonstop4h 49mUnited Airlines
Deal found 4/27$212
This Trip.com deal was found by Cheapflights users on 4/27. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/295:45 amSFO - ORD
1 stop21h 40mMultiple Airlines
Mon 6/29:56 pmORD - SFO
1 stop25h 25mMultiple Airlines
Deal found 4/27$214
This Southwest deal was found by Cheapflights users on 4/28. 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.
Wed 6/45:40 amSFO - MDW
1 stop6h 15mSouthwest
Sat 6/77:00 pmMDW - SFO
1 stop6h 10mSouthwest
Deal found 4/28$216
This Alaska Airlines deal was found by Cheapflights users on 4/28. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/278:49 pmSFO - ORD
1 stop6h 51mAlaska Airlines
Wed 6/117:59 pmORD - SFO
Nonstop4h 50mAlaska Airlines
Deal found 4/28$217
This Southwest deal was found by Cheapflights users on 4/28. 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 6/36:00 amSFO - ORD
1 stop8h 45mSouthwest
Wed 6/182:50 pmORD - SFO
1 stop10h 35mSouthwest
Deal found 4/28$222
This American Airlines deal was found by Cheapflights users on 4/28. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/2011:55 pmSFO - ORD
Nonstop4h 15mAmerican Airlines
Sat 6/218:05 amORD - SFO
1 stop8h 28mAmerican Airlines
Deal found 4/28$244
This Delta deal was found by Cheapflights users on 4/28. 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.
Mon 5/2612:40 amSFO - MDW
1 stop5h 56mDelta
Mon 6/97:21 pmMDW - SFO
1 stop6h 16mDelta
Deal found 4/28$257
This Delta deal was found by Cheapflights users on 4/28. 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.
Mon 5/2612:40 amSFO - ORD
1 stop9h 07mDelta
Tue 6/107:40 amORD - SFO
1 stop6h 32mDelta
Deal found 4/28$257
This Sun Country Air deal was found by Cheapflights users on 4/28. 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 Sun Country Air is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/1311:59 pmSFO - ORD
1 stop19h 40mSun Country Air
Mon 6/166:20 pmORD - SFO
1 stop6h 33mSun Country Air
Deal found 4/28$275
This Hawaiian Airlines deal was found by Cheapflights users on 4/28. 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 Hawaiian Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/68:00 amSFO - ORD
1 stop8h 01mHawaiian Airlines
Wed 5/79:00 amORD - SFO
1 stop8h 53mHawaiian Airlines
Deal found 4/28$276

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 April 29, 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

Sat 5/31

10:19 pm-9:03 am

1 stop8h 44m

Chicago Midway

Sun 6/1

9:12 pm-10:23 am

1 stop15h 11m

$208

San FranciscoChicago

SFO - ORD

SFOORD

San Francisco

Thu 5/1

9:50 pm-5:10 am

1 stop29h 20m

Chicago O'Hare Intl

Sat 5/31

11:55 am-10:23 pm

1 stop12h 28m

$211

San FranciscoChicago

SFO - ORD

SFOORD

San Francisco

Thu 5/15

5:04 am-11:26 am

Nonstop4h 22m

Chicago O'Hare Intl

Sat 5/24

6:15 pm-9:04 pm

Nonstop4h 49m

$212

San FranciscoChicago

SFO - ORD

SFOORD

San Francisco

Thu 5/29

5:45 am-5:25 am

1 stop21h 40m

Chicago O'Hare Intl

Mon 6/2

9:56 pm-9:21 pm

1 stop25h 25m

$214

San FranciscoChicago

SFO - MDW

SFOMDW

San Francisco

Wed 6/4

5:40 am-1:55 pm

1 stop6h 15m

Chicago Midway

Sat 6/7

7:00 pm-11:10 pm

1 stop6h 10m

$216

San FranciscoChicago

SFO - ORD

SFOORD

San Francisco

Tue 5/27

8:49 pm-5:40 am

1 stop6h 51m

Chicago O'Hare Intl

Wed 6/11

7:59 pm-10:49 pm

Nonstop4h 50m

$217

San FranciscoChicago

SFO - ORD

SFOORD

San Francisco

Tue 6/3

6:00 am-4:45 pm

1 stop8h 45m

Chicago O'Hare Intl

Wed 6/18

2:50 pm-11:25 pm

1 stop10h 35m

$222

San FranciscoChicago

SFO - ORD

SFOORD

San Francisco

Fri 6/20

11:55 pm-6:10 am

Nonstop4h 15m

Chicago O'Hare Intl

Sat 6/21

8:05 am-2:33 pm

1 stop8h 28m

$244

San FranciscoChicago

SFO - MDW

SFOMDW

San Francisco

Mon 5/26

12:40 am-8:36 am

1 stop5h 56m

Chicago Midway

Mon 6/9

7:21 pm-11:37 pm

1 stop6h 16m

$257

San FranciscoChicago

SFO - ORD

SFOORD

San Francisco

Mon 5/26

12:40 am-11:47 am

1 stop9h 07m

Chicago O'Hare Intl

Tue 6/10

7:40 am-12:12 pm

1 stop6h 32m

$257

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/28

Showing 1-10 of 26 results
1
2
3

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 April.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*2 stars
eDreamsPrice Accuracy3 starsTrust Score*3 stars
Kiwi.comPrice Accuracy3 starsTrust Score*3 stars
PricelinePrice Accuracy1 starTrust Score*3 stars
Trip.comPrice Accuracy1 starTrust Score*3 stars
CheapflightsfaresPrice Accuracy3 starsTrust Score*2 stars
MytripPrice Accuracy3 starsTrust Score*3 stars
CheapOairPrice Accuracy1 starTrust Score*3 stars
JustAirTicketPrice Accuracy-Trust Score*3 stars

*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 Mytrip to be most consistent on Cheapflights vs. Mytrip Users can find the same prices on San Francisco-Chicago flight deals on Cheapflights vs. Mytrip >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 Mytrip the most. Mytrip 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.

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 at SFO by using the SFO2Go program to order meals for pickup during busy times.

Read more about SFOby Harriet Baskas
ORD

For a quick city transfer from ORD, consider taking the “L” train from the airport to downtown Chicago.

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 April 25, 2025.

The best time to book flights from San Francisco to Chicago is 76 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 April 29, 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 32% 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 March 30, 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 April 29, 2025.

The most flights from SFO to CHI are scheduled on a Wednesday (80 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (56 on average).

Rainfall in Chicago by month

Plan your trip to Chicago by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Chicago ranges from 1.7 - 4.9 inches per month. August is typically the wettest month, when rainfall can reach 4.9 in. January is typically the driest time to visit Chicago when rainfall is around 1.7 in.

Temperature in Chicago by month

Plan your trip to Chicago by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Chicago, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 73.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 23.0 F).

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 April 29, 2025.
Get a feel of what it's like to fly with Alaska Airlines, Southwest and Delta from San Francisco to Chicago by reading reviews from past customers. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
Alaska Airlines
8.0
Very good
9,949 reviews

Boarding

8.2

Crew

8.5

Comfort

7.9

Overall

8.0

Entertainment

7.1

Food

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
9,949 reviews
Alaska Airlines
8.0
Very good
9,949 reviews

Boarding

8.2

Crew

8.5

Comfort

7.9

Overall

8.0

Entertainment

7.1

Food

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
4,292 reviews
Alaska Airlines
8.0
Very good
9,949 reviews

Boarding

8.2

Crew

8.5

Comfort

7.9

Overall

8.0

Entertainment

7.1

Food

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
7,929 reviews
Alaska Airlines
8.0
Very good
9,949 reviews

Boarding

8.2

Crew

8.5

Comfort

7.9

Overall

8.0

Entertainment

7.1

Food

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
7.9
Good
2,402 reviews
Alaska Airlines
8.0
Very good
9,949 reviews

Boarding

8.2

Crew

8.5

Comfort

7.9

Overall

8.0

Entertainment

7.1

Food

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
8,696 reviews
Alaska Airlines
8.0
Very good
9,949 reviews

Boarding

8.2

Crew

8.5

Comfort

7.9

Overall

8.0

Entertainment

7.1

Food

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 69 daily outbound flights to Chicago from 8 different airlines.

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

    Frontier, at $208, was found to be the cheapest airline from San Francisco to Chicago.Alternate airlines to your destination round-trip include American Airlines and Southwest. 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 $100. However, be on the lookout for offers from Frontier and Hawaiian 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: Royal Jordanian (97%), Brussels Airlines (92%), Austrian Airlines (90%).

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

    Looking at all options, your cheapest flight can be booked for $99. While the most popular route (San Francisco - Chicago O'Hare Intl) can be booked for $178 on average our data indicates $860 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 $61 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 San Francisco?

Book flights to San Francisco if you plan to visit one of these locations
Merrillville
Hammond
Benton Harbor
Porter
Lansing
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.
Los Angeles to O'Hare Intl flights
San Francisco to O'Hare Intl flights
San Francisco to Midway flights
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Burbank to Midway flights
Santa Ana to St. Louis flights
San Diego to St. Louis flights
Long Beach to O'Hare Intl flights
Las Vegas to St. Louis flights
Burbank to St. Louis flights
Fresno to Midway flights
Sacramento to St. Louis flights
Santa Barbara to O'Hare Intl flights
San Jose to St. Louis flights
San Diego to Moline flights
Oakland to St. Louis flights
Long Beach to Midway flights
Reno to Midway flights
Palm Springs to Midway flights
Long Beach to St. Louis flights
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Santa Ana to Moline flights
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Bakersfield to O'Hare Intl flights
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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 April 29, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$58Average$231FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$113Average$239FlexibilityNo cancel feeOn-time65%
Hawaiian AirlinesCheapest$138Average$287FlexibilityNo cancel feeOn-time85%
Alaska AirlinesCheapest$175Average$311FlexibilityNo cancel feeOn-time75%
United AirlinesCheapest$185Average$369FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$197Average$353FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$208Average$393FlexibilityNo cancel feeOn-time63%
DeltaCheapest$236Average$336FlexibilityNo cancel feeOn-timeN/A

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