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.
$123+ 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 1/31. Fares are subject to change and may not be available on all flights or dates of travel.
SFO — CHI
Dec 6 — Dec 131
1 adult, Economy
We work with more than 300 partners to bring you better travel deals
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 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
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 November 6, 2025.
Most accurate provider | eDreams 3 stars |
|---|---|
Most trusted provider | eDreams 3 stars |
Round-trip from | $288 (Delta) |
One-way from | $123 (Kiwi.com) |
Popular in | December |
Cheapest in | February |
Average price | $390 |
Good round-trip deal | $397 or less |
Good one-way deal | $184 or less |
Find flight deals from San Francisco to Chicago
Cheapest flights from San Francisco to ChicagoExplore 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 November 6, 2025.
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 November 6, 2025.
This Kiwi.com deal was found by Cheapflights users on 11/4. 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 11/226:00 pmSFO - ORD
1 stop9h 32mMultiple Airlines
Thu 12/46:50 amORD - SFO
1 stop16h 21mMultiple Airlines
Deal found 11/4![Multiple Airlines logo]()
$285
This Delta deal was found by Cheapflights users on 11/6. 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.
Sun 11/2312:30 amSFO - MDW
1 stop6h 31mDelta
Fri 12/55:13 pmMDW - SFO
1 stop8h 07mDelta
Deal found 11/6![Delta logo]()
$288
This Delta deal was found by Cheapflights users on 11/4. 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 12/910:30 amSFO - ORD
1 stop11h 29mDelta
Tue 12/1611:00 amORD - SFO
2 stops13h 31mDelta
Deal found 11/4![Delta logo]()
$288
This Kiwi.com deal was found by Cheapflights users on 11/4. 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 11/228:06 amSFO - ORD
2 stops14h 04mMultiple Airlines
Tue 12/28:18 pmORD - SFO
1 stop26h 53mMultiple Airlines
Deal found 11/4![Multiple Airlines logo]()
$289
This Delta deal was found by Cheapflights users on 11/4. 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 11/246:00 amSFO - ORD
1 stop9h 18mDelta
Wed 12/37:50 amORD - SFO
1 stop16h 41mDelta
Deal found 11/4![Delta logo]()
$290
This Kiwi.com deal was found by Cheapflights users on 11/4. 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.
Mon 12/16:32 pmSFO - MDW
2 stops12h 45mMultiple Airlines
Thu 12/47:23 pmMDW - SFO
1 stop19h 55mMultiple Airlines
Deal found 11/4![Multiple Airlines logo]()
$291
This Delta deal was found by Cheapflights users on 11/4. 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 12/812:30 amSFO - ORD
1 stop6h 10mDelta
Thu 12/187:50 amORD - SFO
1 stop10h 07mDelta
Deal found 11/4![Delta logo]()
$291
This Kiwi.com deal was found by Cheapflights users on 11/4. 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.
Mon 11/1010:23 pmSFO - ORD
1 stop10h 51mFrontier
Fri 11/218:59 amORD - SFO
2 stops16h 30mFrontier
Deal found 11/4![Frontier logo]()
$292
This Kiwi.com deal was found by Cheapflights users on 11/5. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/168:09 pmSFO - MDW
1 stop13h 21mFrontier
Thu 1/156:00 amMDW - SFO
1 stop9h 29mFrontier
Deal found 11/5![Frontier logo]()
$293
This Kiwi.com deal was found by Cheapflights users on 11/5. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/179:29 amSFO - ORD
2 stops12h 15mFrontier
Mon 1/127:51 pmORD - SFO
1 stop6h 34mFrontier
Deal found 11/5![Frontier logo]()
$293
This Delta deal was found by Cheapflights users on 11/5. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/210:30 amSFO - ORD
2 stops8h 51mDelta
Wed 12/37:50 amORD - SFO
2 stops10h 22mDelta
Deal found 11/5![Delta logo]()
$294
This Priceline deal was found by Cheapflights users on 11/4. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/16:32 amSFO - MDW
1 stop5h 59mFrontier
Fri 12/56:15 amMDW - SFO
1 stop9h 03mFrontier
Deal found 11/4![Frontier logo]()
$295
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 November 6, 2025.
Use the filters below to find and compare flights from San Francisco to Chicago that are best for you.
Fly from
San Francisco
Fly to
Chicago
Route
Depart
Return
Price
San FranciscoChicago
SFO - ORD
SFOORD
San Francisco
Wed 12/17
7:00 am-11:50 pm
1 stop14h 50m
Chicago O'Hare Intl
Thu 12/25
6:00 am-1:54 pm
1 stop9h 54m
$292
San FranciscoChicago
SFO - ORD
SFOORD
San Francisco
Thu 1/29
10:30 am-9:52 pm
2 stops9h 22m
Chicago O'Hare Intl
Mon 2/9
7:30 am-4:10 pm
2 stops10h 40m
$304
San FranciscoChicago
SFO - ORD
SFOORD
San Francisco
Wed 11/19
10:35 am-11:59 pm
1 stop11h 24m
Chicago O'Hare Intl
Tue 12/2
8:59 pm-8:06 am
1 stop13h 07m
$305
San FranciscoChicago
SFO - ORD
SFOORD
San Francisco
Sun 12/14
7:00 am-11:50 pm
1 stop14h 50m
Chicago O'Hare Intl
Thu 1/1
8:39 am-12:27 am
1 stop17h 48m
$307
San FranciscoChicago
SFO - ORD
SFOORD
San Francisco
Mon 12/1
10:40 pm-5:00 am
Nonstop4h 20m
Chicago O'Hare Intl
Wed 12/17
4:10 pm-7:00 pm
Nonstop4h 50m
$313
San FranciscoChicago
SFO - ORD
SFOORD
San Francisco
Mon 12/8
10:30 am-9:21 pm
2 stops8h 51m
Chicago O'Hare Intl
Sat 12/13
7:50 am-4:12 pm
2 stops10h 22m
$314
San FranciscoChicago
SFO - MDW
SFOMDW
San Francisco
Thu 11/27
5:20 am-2:25 pm
1 stop7h 05m
Chicago Midway
Wed 12/3
12:05 pm-5:25 pm
1 stop7h 20m
$318
San FranciscoChicago
SFO - MDW
SFOMDW
San Francisco
Thu 11/27
6:15 am-12:20 pm
Nonstop4h 05m
Chicago Midway
Thu 12/4
1:55 pm-9:20 pm
1 stop9h 25m
$320
San FranciscoChicago
SFO - MDW
SFOMDW
San Francisco
Wed 11/26
12:30 am-9:01 am
1 stop6h 31m
Chicago Midway
Thu 12/4
5:13 pm-11:20 pm
1 stop8h 07m
$320
San FranciscoChicago
SFO - MDW
SFOMDW
San Francisco
Thu 11/27
12:30 pm-11:40 pm
1 stop9h 10m
Chicago Midway
Wed 12/3
5:29 pm-12:20 am
1 stop8h 51m
$321
Showing 1-10 of 60 results
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 November.
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy2 stars | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*1 star | |
| Price Accuracy- | Trust Score*1 star | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy2 stars | Trust Score*2 stars | |
| Price Accuracy2 stars | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*2 stars | |
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy- | Trust Score*1 star |
- 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 October 31, 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 $111). Flying from San Francisco to Chicago in March is currently the most expensive (average of $194). 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 November 6, 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 November 2, 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 November 6, 2025.
The most flights from SFO to CHI are scheduled on a Thursday (69 on average). You will have fewer flight options on Sunday, which is when the least amount of flights are scheduled (40 on average).
How much does it cost to fly round-trip from San Francisco to Chicago?
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.
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 Airlines
![Alaska Airlines]()
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.
Airports
Our travel experts
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 November 6, 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.
Food
7.1
Crew
8.5
Overall
8.0
Entertainment
7.0
Comfort
7.8
Boarding
8.1
Reviews
1 / 20
6.0
GoodHannah,Aug 2025
SFO - SAN
Food
7.1
Crew
8.5
Overall
8.0
Entertainment
7.0
Comfort
7.8
Boarding
8.1
Reviews
1 / 20
6.0
GoodHannah,Aug 2025
SFO - SAN
Food
7.1
Crew
8.5
Overall
8.0
Entertainment
7.0
Comfort
7.8
Boarding
8.1
Reviews
1 / 20
6.0
GoodHannah,Aug 2025
SFO - SAN
Food
7.1
Crew
8.5
Overall
8.0
Entertainment
7.0
Comfort
7.8
Boarding
8.1
Reviews
1 / 20
6.0
GoodHannah,Aug 2025
SFO - SAN
Food
7.1
Crew
8.5
Overall
8.0
Entertainment
7.0
Comfort
7.8
Boarding
8.1
Reviews
1 / 20
6.0
GoodHannah,Aug 2025
SFO - SAN
Food
7.1
Crew
8.5
Overall
8.0
Entertainment
7.0
Comfort
7.8
Boarding
8.1
Reviews
1 / 20
6.0
GoodHannah,Aug 2025
SFO - SAN
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.
Traveling to a place near Chicago?
Book flights to Chicago if you plan to visit one of these locationsLansing
Hammond
Porter
Benton Harbor
Merrillville
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.
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 November 6, 2025.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$108 | Average$288 | FlexibilityNo cancel fee | On-time85% | |
| Cheapest$128 | Average$241 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$128 | Average$319 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$133 | Average$397 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$185 | Average$336 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$196 | Average$341 | FlexibilityNo cancel fee | On-time75% | |
| Cheapest$197 | Average$342 | FlexibilityNo cancel fee | On-time71% |