$42+ 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 3/25. Fares are subject to change and may not be available on all flights or dates of travel.
SFO — CHI
Feb 27 — Mar 61
1 adult, Economy
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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 February 22, 2025.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $116 (Cheapflightsfares) |
One-way from | $42 (FlightHub) |
Popular in | December |
Cheapest in | February |
Average price | $297 |
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 February 22, 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 February 22, 2025.
This Cheapflightsfares deal was found by Cheapflights users on 2/22. 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.
Mon 4/76:55 pmOAK - ORD
1 stop9h 47mSpirit Airlines
Wed 4/97:41 amORD - OAK
1 stop11h 53mSpirit Airlines
Deal found 2/22![Spirit Airlines logo]()
$116
This Delta deal was found by Cheapflights users on 2/22. 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 4/1511:45 amSJC - ORD
2 stops11h 08mDelta
Tue 4/222:15 pmORD - SJC
2 stops10h 34mDelta
Deal found 2/22![Delta logo]()
$194
This FlightHub deal was found by Cheapflights users on 2/21. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/2912:53 pmSJC - ORD
1 stop26h 57mSpirit Airlines
Sun 6/17:00 pmORD - SJC
1 stop18h 58mSpirit Airlines
Deal found 2/21![Spirit Airlines logo]()
$197
This Booking.com deal was found by Cheapflights users on 2/21. 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.
Fri 3/214:03 pmSJC - MDW
1 stop6h 14mFrontier
Mon 3/248:44 pmMDW - SJC
1 stop21h 50mFrontier
Deal found 2/21![Frontier logo]()
$200
This FlightHub deal was found by Cheapflights users on 2/21. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/210:17 pmSFO - MDW
1 stop9h 07mFrontier
Sun 4/66:45 amMDW - SFO
1 stop19h 59mFrontier
Deal found 2/21![Frontier logo]()
$202
This FlightHub deal was found by Cheapflights users on 2/21. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 3/2211:02 amSFO - ORD
1 stop11h 55mFrontier
Fri 3/286:30 amORD - SFO
1 stop9h 03mFrontier
Deal found 2/21![Frontier logo]()
$202
This American Airlines deal was found by Cheapflights users on 2/20. 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 3/155:00 amSFO - ORD
Nonstop4h 16mAmerican Airlines
Wed 3/198:20 pmORD - SFO
Nonstop4h 54mAmerican Airlines
Deal found 2/20![American Airlines logo]()
$207
This CheapOair deal was found by Cheapflights users on 2/21. 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 3/67:54 pmSJC - ORD
1 stop8h 48mMultiple Airlines
Mon 3/106:30 amORD - SJC
1 stop10h 33mMultiple Airlines
Deal found 2/21![Multiple Airlines logo]()
$208
This Orbitz deal was found by Cheapflights users on 2/21. 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.
Wed 3/122:53 pmSFO - ORD
1 stop7h 51mMultiple Airlines
Wed 3/196:56 pmORD - SFO
Nonstop4h 59mMultiple Airlines
Deal found 2/21![Multiple Airlines logo]()
$209
This Frontier deal was found by Cheapflights users on 2/21. 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 3/214:03 pmSJC - ORD
1 stop6h 41mFrontier
Fri 3/286:30 amORD - SJC
1 stop10h 33mFrontier
Deal found 2/21![Frontier logo]()
$210
This United Airlines deal was found by Cheapflights users on 2/21. 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 3/2111:59 pmSFO - ORD
Nonstop4h 18mUnited Airlines
Mon 3/246:15 pmORD - SFO
Nonstop4h 59mUnited Airlines
Deal found 2/21![United Airlines logo]()
$217
This Delta deal was found by Cheapflights users on 2/22. 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 4/2112:47 amSFO - ORD
1 stop5h 48mDelta
Wed 4/237:50 amORD - SFO
1 stop9h 56mDelta
Deal found 2/22![Delta logo]()
$220
Find flights from San Francisco Bay Area to Chicago within your budget
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 February 22, 2025.
Fly from
San Francisco Bay Area
Fly to
Chicago
Route
Depart
Return
Price
OaklandChicago
OAK - ORD
OAKORD
Oakland
Mon 4/7
6:55 pm-6:42 am
1 stop9h 47m
Chicago O'Hare Intl
Wed 4/9
7:41 am-5:34 pm
1 stop11h 53m
$116
San JoseChicago
SJC - ORD
SJCORD
San Jose
Tue 4/15
11:45 am-12:53 am
2 stops11h 08m
Chicago O'Hare Intl
Tue 4/22
2:15 pm-10:49 pm
2 stops10h 34m
$194
San JoseChicago
SJC - ORD
SJCORD
San Jose
Thu 5/29
12:53 pm-5:50 pm
1 stop26h 57m
Chicago O'Hare Intl
Sun 6/1
7:00 pm-11:58 am
1 stop18h 58m
$197
San JoseChicago
SJC - MDW
SJCMDW
San Jose
Fri 3/21
4:03 pm-12:17 am
1 stop6h 14m
Chicago Midway
Mon 3/24
8:44 pm-4:34 pm
1 stop21h 50m
$200
San FranciscoChicago
SFO - MDW
SFOMDW
San Francisco
Wed 4/2
10:17 pm-9:24 am
1 stop9h 07m
Chicago Midway
Sun 4/6
6:45 am-12:44 am
1 stop19h 59m
$202
San FranciscoChicago
SFO - ORD
SFOORD
San Francisco
Sat 3/22
11:02 am-12:57 am
1 stop11h 55m
Chicago O'Hare Intl
Fri 3/28
6:30 am-1:33 pm
1 stop9h 03m
$202
San FranciscoChicago
SFO - ORD
SFOORD
San Francisco
Sat 3/15
5:00 am-11:16 am
Nonstop4h 16m
Chicago O'Hare Intl
Wed 3/19
8:20 pm-11:14 pm
Nonstop4h 54m
$207
San JoseChicago
SJC - ORD
SJCORD
San Jose
Thu 3/6
7:54 pm-6:42 am
1 stop8h 48m
Chicago O'Hare Intl
Mon 3/10
6:30 am-3:03 pm
1 stop10h 33m
$208
San FranciscoChicago
SFO - ORD
SFOORD
San Francisco
Wed 3/12
2:53 pm-12:44 am
1 stop7h 51m
Chicago O'Hare Intl
Wed 3/19
6:56 pm-9:55 pm
Nonstop4h 59m
$209
San JoseChicago
SJC - ORD
SJCORD
San Jose
Fri 3/21
4:03 pm-12:44 am
1 stop6h 41m
Chicago O'Hare Intl
Fri 3/28
6:30 am-3:03 pm
1 stop10h 33m
$210
Showing 1-10 of 60 results
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.
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.
Travel insights for flights from San Francisco Bay Area to Chicago
Get recent, data-driven insights about flights from San Francisco Bay Area to Chicago including ideal travel times, pricing trends, and more.
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 February 22, 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 February 22, 2025.
The most flights from zzXIH to CHI are scheduled on a Monday (57 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (41 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 February 22, 2025.
Get a feel of what it's like to fly with Southwest, Alaska Airlines 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.
Food
7.1
Overall
8.1
Comfort
8.1
Crew
8.7
Boarding
8.2
Entertainment
7.6
Reviews
1 / 20
10.0
ExcellentArlene,May 2024
SAN - OAK
Food
7.1
Overall
8.1
Comfort
8.1
Crew
8.7
Boarding
8.2
Entertainment
7.6
Reviews
1 / 20
10.0
ExcellentArlene,May 2024
SAN - OAK
Food
7.1
Overall
8.1
Comfort
8.1
Crew
8.7
Boarding
8.2
Entertainment
7.6
Reviews
1 / 20
10.0
ExcellentArlene,May 2024
SAN - OAK
Food
7.1
Overall
8.1
Comfort
8.1
Crew
8.7
Boarding
8.2
Entertainment
7.6
Reviews
1 / 20
10.0
ExcellentArlene,May 2024
SAN - OAK
Food
7.1
Overall
8.1
Comfort
8.1
Crew
8.7
Boarding
8.2
Entertainment
7.6
Reviews
1 / 20
10.0
ExcellentArlene,May 2024
SAN - OAK
Food
7.1
Overall
8.1
Comfort
8.1
Crew
8.7
Boarding
8.2
Entertainment
7.6
Reviews
1 / 20
10.0
ExcellentArlene,May 2024
SAN - OAK
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 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 Bay Area to Chicago
See prices for flight routes from nearby airports that may be better suited for you.
Top 7 airlines flying from San Francisco Bay Area to Chicago
Discover the top 7 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 February 22, 2025.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$74 | Average$227 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$100 | Average$384 | FlexibilityNo cancel fee | On-time75% | |
| Cheapest$112 | Average$262 | FlexibilityNo cancel fee | On-time65% | |
| Cheapest$185 | Average$455 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$207 | Average$535 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$208 | Average$451 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$235 | Average$410 | FlexibilityNo cancel fee | On-timeN/A |