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.
$99+ 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 5/18. Fares are subject to change and may not be available on all flights or dates of travel.
SFO — CHI
Apr 16 — Apr 231
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 April, 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 11, 2025.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $208 (Frontier) |
One-way from | $99 (Frontier) |
Popular in | December |
Cheapest in | February |
Average price | $305 |
Good round-trip deal | $298 or less |
Good one-way deal | $156 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 April 11, 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 April 11, 2025.
This Frontier deal was found by Cheapflights users on 4/9. 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 4/2712:11 amSFO - MDW
1 stop13h 23mFrontier
Wed 5/72:12 pmMDW - SFO
1 stop10h 10mFrontier
Deal found 4/9![Frontier logo]()
$208
This Frontier deal was found by Cheapflights users on 4/10. 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 5/311:50 pmSFO - ORD
1 stop9h 10mFrontier
Thu 5/87:35 amORD - SFO
1 stop10h 09mFrontier
Deal found 4/10![Frontier logo]()
$208
This Alaska Airlines deal was found by Cheapflights users on 4/10. 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.
Sat 5/106:30 amSFO - ORD
1 stop8h 30mAlaska Airlines
Sat 5/107:13 pmORD - SFO
Nonstop4h 59mAlaska Airlines
Deal found 4/10![Alaska Airlines logo]()
$211
This Southwest deal was found by Cheapflights users on 4/10. 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 5/106:45 amSFO - MDW
Nonstop4h 10mSouthwest
Sat 5/172:25 pmMDW - SFO
1 stop10h 05mSouthwest
Deal found 4/10![Southwest logo]()
$212
This Expedia deal was found by Cheapflights users on 4/10. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/211:03 amSFO - ORD
1 stop6h 39mMultiple Airlines
Mon 5/56:58 pmORD - SFO
Nonstop4h 59mMultiple Airlines
Deal found 4/10![Multiple Airlines logo]()
$213
This Southwest deal was found by Cheapflights users on 4/10. 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 5/611:50 amSFO - ORD
1 stop8h 30mSouthwest
Wed 5/76:15 amORD - SFO
1 stop6h 50mSouthwest
Deal found 4/10![Southwest logo]()
$216
This United Airlines deal was found by Cheapflights users on 4/10. 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 5/22:50 pmSFO - ORD
Nonstop4h 26mUnited Airlines
Sun 5/46:30 amORD - SFO
Nonstop4h 50mUnited Airlines
Deal found 4/10![United Airlines logo]()
$217
This American Airlines deal was found by Cheapflights users on 4/10. 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.
Thu 8/2811:47 pmSFO - ORD
Nonstop4h 18mAmerican Airlines
Sun 8/316:45 amORD - SFO
Nonstop4h 33mAmerican Airlines
Deal found 4/10![American Airlines logo]()
$234
This Hawaiian Airlines deal was found by Cheapflights users on 4/10. 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.
Fri 5/27:00 amSFO - ORD
1 stop9h 01mHawaiian Airlines
Tue 5/612:00 pmORD - SFO
1 stop10h 13mHawaiian Airlines
Deal found 4/10![Hawaiian Airlines logo]()
$236
This Delta deal was found by Cheapflights users on 4/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/2312:40 amSFO - MDW
1 stop5h 56mDelta
Tue 5/271:55 pmMDW - SFO
1 stop7h 49mDelta
Deal found 4/11![Delta logo]()
$257
This Delta deal was found by Cheapflights users on 4/10. 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.
Thu 6/1212:49 amSFO - ORD
1 stop5h 36mDelta
Sun 6/157:40 amORD - SFO
1 stop6h 32mDelta
Deal found 4/10![Delta logo]()
$257
This Sun Country Air deal was found by Cheapflights users on 4/10. 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 6/166:11 pmORD - SFO
1 stop18h 57mSun Country Air
Deal found 4/10![Sun Country Air logo]()
$275
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 11, 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
Sun 4/27
12:11 am-3:34 pm
1 stop13h 23m
Chicago Midway
Wed 5/7
2:12 pm-10:22 pm
1 stop10h 10m
$208
San FranciscoChicago
SFO - ORD
SFOORD
San Francisco
Sat 5/3
11:50 pm-11:00 am
1 stop9h 10m
Chicago O'Hare Intl
Mon 5/5
7:35 am-7:02 pm
1 stop13h 27m
$208
San FranciscoChicago
SFO - ORD
SFOORD
San Francisco
Sat 5/10
6:30 am-5:00 pm
1 stop8h 30m
Chicago O'Hare Intl
Sat 5/10
7:13 pm-10:12 pm
Nonstop4h 59m
$211
San FranciscoChicago
SFO - MDW
SFOMDW
San Francisco
Sat 5/10
6:45 am-12:55 pm
Nonstop4h 10m
Chicago Midway
Sat 5/17
2:25 pm-10:30 pm
1 stop10h 05m
$212
San FranciscoChicago
SFO - ORD
SFOORD
San Francisco
Fri 5/2
11:03 am-7:42 pm
1 stop6h 39m
Chicago O'Hare Intl
Mon 5/5
6:58 pm-9:57 pm
Nonstop4h 59m
$213
San FranciscoChicago
SFO - ORD
SFOORD
San Francisco
Tue 5/6
11:50 am-10:20 pm
1 stop8h 30m
Chicago O'Hare Intl
Wed 5/7
6:15 am-11:05 am
1 stop6h 50m
$216
San FranciscoChicago
SFO - ORD
SFOORD
San Francisco
Fri 5/2
2:50 pm-9:16 pm
Nonstop4h 26m
Chicago O'Hare Intl
Sun 5/4
6:30 am-9:20 am
Nonstop4h 50m
$217
San FranciscoChicago
SFO - ORD
SFOORD
San Francisco
Fri 5/2
7:00 am-6:01 pm
1 stop9h 01m
Chicago O'Hare Intl
Tue 5/6
12:00 pm-8:13 pm
1 stop10h 13m
$236
San FranciscoChicago
SFO - MDW
SFOMDW
San Francisco
Fri 5/23
12:40 am-8:36 am
1 stop5h 56m
Chicago Midway
Tue 5/27
1:55 pm-7:44 pm
1 stop7h 49m
$257
San FranciscoChicago
SFO - ORD
SFOORD
San Francisco
Thu 6/12
12:49 am-8:25 am
1 stop5h 36m
Chicago O'Hare Intl
Sun 6/15
7:40 am-12:12 pm
1 stop6h 32m
$257
Showing 1-10 of 27 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 April.
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*2 stars | |
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*2 stars | |
| Price Accuracy- | Trust Score*3 stars | |
| Price Accuracy1 star | Trust Score*3 stars |
- 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.
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
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 4, 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 11, 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 11, 2025.
The most flights from SFO to CHI are scheduled on a Wednesday (84 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (52 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 11, 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.
Boarding
8.2
Overall
8.0
Comfort
7.9
Entertainment
7.1
Food
7.1
Crew
8.5
Reviews
1 / 20
10.0
ExcellentCheri,Jan 2025
FAT - SEA
Boarding
8.2
Overall
8.0
Comfort
7.9
Entertainment
7.1
Food
7.1
Crew
8.5
Reviews
1 / 20
10.0
ExcellentCheri,Jan 2025
FAT - SEA
Boarding
8.2
Overall
8.0
Comfort
7.9
Entertainment
7.1
Food
7.1
Crew
8.5
Reviews
1 / 20
10.0
ExcellentCheri,Jan 2025
FAT - SEA
Boarding
8.2
Overall
8.0
Comfort
7.9
Entertainment
7.1
Food
7.1
Crew
8.5
Reviews
1 / 20
10.0
ExcellentCheri,Jan 2025
FAT - SEA
Boarding
8.2
Overall
8.0
Comfort
7.9
Entertainment
7.1
Food
7.1
Crew
8.5
Reviews
1 / 20
10.0
ExcellentCheri,Jan 2025
FAT - SEA
Boarding
8.2
Overall
8.0
Comfort
7.9
Entertainment
7.1
Food
7.1
Crew
8.5
Reviews
1 / 20
10.0
ExcellentCheri,Jan 2025
FAT - SEA
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 San Francisco?
Book flights to San Francisco if you plan to visit one of these locationsMerrillville
New Buffalo
Hammond
Benton Harbor
Porter
Lansing
Valparaiso
Chesterton
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 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 11, 2025.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$63 | Average$230 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$113 | Average$239 | FlexibilityNo cancel fee | On-time65% | |
| Cheapest$115 | Average$309 | FlexibilityNo cancel fee | On-time75% | |
| Cheapest$138 | Average$318 | FlexibilityNo cancel fee | On-time85% | |
| Cheapest$185 | Average$379 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$205 | Average$376 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$208 | Average$396 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$236 | Average$333 | FlexibilityNo cancel fee | On-timeN/A |