$59+ Cheap flights from San Francisco Bay Area 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 5/29. Fares are subject to change and may not be available on all flights or dates of travel.
Find cheap flights from San Francisco Bay Area 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.Cheap flight deals from San Francisco Bay Area to Chicago
Keep the following information in mind while searching for San Francisco Bay Area to Chicago flight deals. Data was last updated May 1, 2025.
Most accurate provider | Mytrip 3 stars |
|---|---|
Most trusted provider | Mytrip 3 stars |
Round-trip from | $210 (Frontier) |
One-way from | $59 (eDestinos) |
Popular in | December |
Cheapest in | February |
Average price | $343 |
Find flight deals from San Francisco Bay Area to Chicago
Cheapest flights from San Francisco Bay Area to ChicagoExplore the most affordable flight options available from San Francisco Bay Area to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on May 1, 2025.
Explore the most affordable flight options available from San Francisco Bay Area to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on May 1, 2025.
This Frontier deal was found by Cheapflights users on 4/30. 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.
This Frontier deal was found by Cheapflights users on 4/30. 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.
This Kiwi.com deal was found by Cheapflights users on 4/30. 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.
This Orbitz deal was found by Cheapflights users on 4/30. 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
This Southwest deal was found by Cheapflights users on 4/30. 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.
This Southwest deal was found by Cheapflights users on 4/30. 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.
This United Airlines deal was found by Cheapflights users on 4/30. 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.
This American Airlines deal was found by Cheapflights users on 4/30. 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.
This Alaska Airlines deal was found by Cheapflights users on 4/30. 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.
This Mytrip deal was found by Cheapflights users on 4/29. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
This Booking.com deal was found by Cheapflights users on 4/29. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
This CheapOair deal was found by Cheapflights users on 4/29. 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.
Cheapflights Fare Finder
Customize your flight search to find flights from San Francisco Bay Area 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 May 1, 2025.
Use the filters below to find and compare flights from San Francisco Bay Area to Chicago that are best for you.
Fly from
Fly to
Route
Depart
Return
Price
San FranciscoChicago
SFO - MDW
SFOMDW
San Francisco
Sun 5/25
6:15 am-8:53 pm
1 stop12h 38m
Chicago Midway
Sat 5/31
2:44 pm-12:09 am
1 stop11h 25m
San FranciscoChicago
SFO - ORD
SFOORD
San Francisco
Sun 5/25
6:15 am-11:52 pm
1 stop15h 37m
Chicago O'Hare Intl
Sat 5/31
6:00 am-5:19 pm
1 stop13h 19m
San FranciscoChicago
SFO - ORD
SFOORD
San Francisco
Tue 6/10
6:49 pm-5:40 am
1 stop8h 51m
Chicago O'Hare Intl
Sat 6/14
7:18 pm-10:06 pm
Nonstop4h 48m
San FranciscoChicago
SFO - ORD
SFOORD
San Francisco
Wed 5/14
11:45 pm-11:43 am
1 stop9h 58m
Chicago O'Hare Intl
Sat 5/31
7:59 pm-10:49 pm
Nonstop4h 50m
San FranciscoChicago
SFO - MDW
SFOMDW
San Francisco
Tue 6/3
6:35 pm-5:20 am
1 stop8h 45m
Chicago Midway
Tue 6/10
5:25 pm-11:30 pm
1 stop8h 05m
San FranciscoChicago
SFO - ORD
SFOORD
San Francisco
Tue 6/3
6:00 am-4:45 pm
1 stop8h 45m
Chicago O'Hare Intl
Tue 6/10
6:55 pm-11:30 pm
1 stop6h 35m
San FranciscoChicago
SFO - ORD
SFOORD
San Francisco
Mon 6/2
11:59 pm-6:19 am
Nonstop4h 20m
Chicago O'Hare Intl
Thu 6/5
2:33 pm-5:23 pm
Nonstop4h 50m
San FranciscoChicago
SFO - ORD
SFOORD
San Francisco
Fri 5/30
2:50 pm-9:23 pm
Nonstop4h 33m
Chicago O'Hare Intl
Sun 6/8
6:45 am-9:23 am
Nonstop4h 38m
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
San JoseChicago
SJC - ORD
SJCORD
San Jose
Fri 5/30
6:00 am-11:50 am
3 stops27h 50m
Chicago O'Hare Intl
Tue 6/3
9:02 pm-11:29 pm
1 stop28h 27m
Best time to book a flight from San Francisco Bay Area to Chicago
Have a flexible travel schedule? Discover the best time to fly to Chicago from San Francisco Bay Area with our price prediction graph.
Cheapflights Insights
Everything you need to know about your flight from San Francisco Bay Area to Chicago
What is the cheapest month to book a flight from San Francisco Bay Area to Chicago?
Currently, August is the cheapest month in which you can book a flight from San Francisco Bay Area to Chicago (average of $245). Flying from San Francisco Bay Area 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 XIH to CHI?
Find hourly flight availability from San Francisco Bay Area 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 May 1, 2025.
When flying from San Francisco Bay Area to Chicago, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.
Weekly flight availability from San Francisco Bay Area to Chicago
Explore weekly flight availability from San Francisco Bay Area 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 May 1, 2025.
The most flights from zzXIH to CHI are scheduled on a Thursday (82 on average). You will have fewer flight options on Monday, which is when the least amount of flights are scheduled (34 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 May 1, 2025.
Get a feel of what it's like to fly with Alaska Airlines, Southwest and Delta from San Francisco Bay Area 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
Overall
Entertainment
Crew
Comfort
Food
Reviews
James,Apr 2025
LAX - SFO
Boarding
Overall
Entertainment
Crew
Comfort
Food
Reviews
James,Apr 2025
LAX - SFO
Boarding
Overall
Entertainment
Crew
Comfort
Food
Reviews
James,Apr 2025
LAX - SFO
Boarding
Overall
Entertainment
Crew
Comfort
Food
Reviews
James,Apr 2025
LAX - SFO
Boarding
Overall
Entertainment
Crew
Comfort
Food
Reviews
James,Apr 2025
LAX - SFO
Boarding
Overall
Entertainment
Crew
Comfort
Food
Reviews
James,Apr 2025
LAX - SFO
Related info for your journey
Find useful and relevant information for your journey from San Francisco Bay Area 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 Bay Area?
Book flights to San Francisco Bay Area if you plan to visit one of these locationsBrowse thousands of different options on Cheapflights for your next trip
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Alternative routes for San Francisco Bay Area to Chicago
See prices for flight routes from nearby airports that may be better suited for you.
Top 8 airlines flying from San Francisco Bay Area to Chicago
Discover the top 8 airlines that operate flights from San Francisco Bay Area 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 May 1, 2025.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$55 | Average$238 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$113 | Average$264 | FlexibilityNo cancel fee | On-time65% | |
| Cheapest$138 | Average$381 | FlexibilityNo cancel fee | On-time75% | |
| Cheapest$138 | Average$337 | FlexibilityNo cancel fee | On-time85% | |
| Cheapest$185 | Average$399 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$197 | Average$458 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$208 | Average$449 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$235 | Average$405 | FlexibilityNo cancel fee | On-timeN/A |