Chicago

$51+ 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 9/10. Fares are subject to change and may not be available on all flights or dates of travel.
SFO — CHI
Aug 19 — Aug 261
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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 August 14, 2025.

Round-trip from

$203
(Frontier)

One-way from

$51
(Cheapflightsfares)

Popular in

December

Cheapest in

February

Average price

$366
From San Francisco Bay Area to Chicago (CHI)
One-way flight from San Francisco Bay Area to Chicago (CHI)
Highest demand for flights based on searches. 6% potential increase in price ($25 potential increase over avg. RT price).
Cheapest flight prices on average. 2% potential price decrease ($9 potential savings vs. average RT price).
Average for round-trip flights in August 2025

Find flight deals from San Francisco Bay Area to Chicago

Cheapest flights from San Francisco Bay Area to Chicago
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 August 14, 2025.

This Frontier deal was found by Cheapflights users on 8/13. 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.
Thu 9/410:19 amSFO - MDW
1 stop9h 39mFrontier
Sat 9/611:23 amMDW - SFO
2 stops11h 58mFrontier
Deal found 8/13$203
This Frontier deal was found by Cheapflights users on 8/14. 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 9/2111:00 pmSFO - ORD
1 stop9h 31mFrontier
Wed 9/246:44 pmORD - SFO
2 stops16h 00mFrontier
Deal found 8/14$203
This CheapOair deal was found by Cheapflights users on 8/14. 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.
Fri 9/1911:57 pmSFO - MDW
1 stop8h 31mFrontier
Mon 9/226:20 amMDW - SFO
1 stop17h 01mFrontier
Deal found 8/14$204
This Alaska Airlines deal was found by Cheapflights users on 8/12. 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.
Wed 10/2210:26 amSFO - ORD
1 stop11h 33mAlaska Airlines
Wed 11/59:20 amORD - SFO
1 stop14h 41mAlaska Airlines
Deal found 8/12$204
This Frontier deal was found by Cheapflights users on 8/14. 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.
Thu 9/185:45 amSFO - MDW
2 stops14h 13mFrontier
Fri 9/193:48 pmMDW - SFO
1 stop10h 28mFrontier
Deal found 8/14$205
This Trip.com deal was found by Cheapflights users on 8/12. 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 9/42:17 pmSFO - ORD
1 stop6h 58mMultiple Airlines
Wed 9/1011:15 amORD - SFO
1 stop12h 06mMultiple Airlines
Deal found 8/12$205
This Cheapflightsfares deal was found by Cheapflights users on 8/12. 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.
Fri 9/266:30 amOAK - ORD
1 stop8h 29mSpirit Airlines
Tue 9/309:00 amORD - OAK
1 stop6h 34mSpirit Airlines
Deal found 8/12$205
This FlightHub deal was found by Cheapflights users on 8/14. 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 9/410:45 amSFO - MDW
1 stop27h 08mFrontier
Sun 9/76:20 amMDW - SFO
1 stop17h 01mFrontier
Deal found 8/14$206
This Kiwi.com deal was found by Cheapflights users on 8/11. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/181:14 pmSFO - ORD
1 stop6h 55mFrontier
Mon 10/207:35 amORD - SFO
1 stop7h 09mFrontier
Deal found 8/11$206
This FlightHub deal was found by Cheapflights users on 8/13. 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 9/310:44 amOAK - ORD
2 stops16h 06mSpirit Airlines
Fri 9/56:05 pmORD - OAK
2 stops17h 56mSpirit Airlines
Deal found 8/13$206
This Southwest deal was found by Cheapflights users on 8/13. 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.
Mon 10/276:00 amSFO - MDW
Nonstop4h 05mSouthwest
Sat 11/158:15 amMDW - SFO
Nonstop4h 45mSouthwest
Deal found 8/13$207
This United Airlines deal was found by Cheapflights users on 8/13. 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.
Tue 9/163:00 pmSFO - ORD
Nonstop4h 24mUnited Airlines
Fri 9/269:13 pmORD - SFO
Nonstop4h 46mUnited Airlines
Deal found 8/13$207

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 August 14, 2025.
Use the filters below to find and compare flights from San Francisco Bay Area to Chicago that are best for you.

Fly from

San Francisco Bay Area

Fly to

Chicago

Route

Depart

Return

Price

OaklandChicago

OAK - ORD

OAKORD

Oakland

Wed 9/10

6:30 am-6:51 pm

1 stop10h 21m

Chicago O'Hare Intl

Thu 9/11

9:00 am-1:34 pm

1 stop6h 34m

$205

OaklandChicago

OAK - ORD

OAKORD

Oakland

Tue 9/2

6:00 am-5:15 pm

1 stop9h 15m

Chicago O'Hare Intl

Thu 9/4

8:01 pm-10:01 am

2 stops16h 00m

$205

OaklandChicago

OAK - ORD

OAKORD

Oakland

Thu 9/18

6:30 am-9:32 pm

1 stop13h 02m

Chicago O'Hare Intl

Tue 9/23

9:00 am-1:34 pm

1 stop6h 34m

$205

OaklandChicago

OAK - ORD

OAKORD

Oakland

Fri 9/26

6:30 am-4:59 pm

1 stop8h 29m

Chicago O'Hare Intl

Tue 9/30

9:00 am-1:34 pm

1 stop6h 34m

$205

OaklandChicago

OAK - ORD

OAKORD

Oakland

Wed 9/3

10:44 am-4:50 am

2 stops16h 06m

Chicago O'Hare Intl

Fri 9/5

6:05 pm-10:01 am

2 stops17h 56m

$206

OaklandChicago

OAK - ORD

OAKORD

Oakland

Thu 9/25

6:30 am-9:32 pm

1 stop13h 02m

Chicago O'Hare Intl

Mon 9/29

9:00 am-1:34 pm

1 stop6h 34m

$206

San FranciscoChicago

SFO - MDW

SFOMDW

San Francisco

Sat 11/8

12:35 pm-8:25 pm

1 stop5h 50m

Chicago Midway

Tue 11/11

8:15 am-11:00 am

Nonstop4h 45m

$207

San FranciscoChicago

SFO - ORD

SFOORD

San Francisco

Thu 9/25

11:00 pm-5:13 am

Nonstop4h 13m

Chicago O'Hare Intl

Wed 10/1

6:15 am-8:53 am

Nonstop4h 38m

$207

San FranciscoChicago

SFO - MDW

SFOMDW

San Francisco

Mon 11/17

6:10 am-12:15 pm

Nonstop4h 05m

Chicago Midway

Wed 11/19

8:15 am-11:00 am

Nonstop4h 45m

$207

San FranciscoChicago

SFO - ORD

SFOORD

San Francisco

Wed 10/29

7:00 am-1:23 pm

Nonstop4h 23m

Chicago O'Hare Intl

Sun 11/2

5:15 am-8:04 am

Nonstop4h 49m

$207

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/12

Showing 1-10 of 60 results
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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.

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 August 14, 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 August 14, 2025.

The most flights from zzXIH to CHI are scheduled on a Thursday (94 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (34 on average).

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 August 14, 2025.
See what other customers who have flown with Alaska Airlines, Southwest, and United Airlines from San Francisco Bay Area to Chicago have to say. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.

Entertainment

7.0

Overall

8.0

Comfort

7.8

Crew

8.5

Boarding

8.1

Food

7.1

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.

Entertainment

7.0

Overall

8.0

Comfort

7.8

Crew

8.5

Boarding

8.1

Food

7.1

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.

Entertainment

7.0

Overall

8.0

Comfort

7.8

Crew

8.5

Boarding

8.1

Food

7.1

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.

Entertainment

7.0

Overall

8.0

Comfort

7.8

Crew

8.5

Boarding

8.1

Food

7.1

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.

Entertainment

7.0

Overall

8.0

Comfort

7.8

Crew

8.5

Boarding

8.1

Food

7.1

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.

Entertainment

7.0

Overall

8.0

Comfort

7.8

Crew

8.5

Boarding

8.1

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 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.
  • What are the cheapest airlines to fly from San Francisco Bay Area to Chicago one-way?

    To fly one-way, consider booking your trip with Spirit Airlines, which is currently one of the cheapest options available, starting at $51. Southwest flights start at $99 while deals on United Airlines start at $99 one-way.

  • What are the most popular routes from San Francisco Bay Area to Chicago?

  • What are the most reliable airlines from San Francisco Bay Area to Chicago?

    No one likes to see their flight delayed. When booking a flight from San Francisco Bay Area to Chicago consider choosing Fiji Airways (100%), Asiana Airlines (85%) or Austrian Airlines (81%) as they are the most reliable in getting you off to your destination on time.

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

    The cheapest flight price from San Francisco Bay Area to Chicago is $98. On average you can expect to pay $898. The most popular route, (San Francisco - Chicago O'Hare Intl), can usually be booked for $197.

  • Can I find deals for flights from San Francisco Bay Area to Chicago that include hotel bookings?

    Yes. In addition to deals on San Francisco Bay Area to Chicago flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from San Francisco Bay Area 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 Bay Area to Chicago.

  • Can I find deals for business class flights from San Francisco Bay Area to Chicago?

    Yes. Cheapflights offers flight deals from San Francisco Bay Area 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 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.

See more FAQs

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
Lansing
Hammond
Benton Harbor
Porter
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 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 August 14, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$98Average$232FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$100Average$219FlexibilityNo cancel feeOn-time65%
Hawaiian AirlinesCheapest$108Average$288FlexibilityNo cancel feeOn-time85%
DeltaCheapest$128Average$330FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$133Average$380FlexibilityNo cancel feeOn-time69%
Alaska AirlinesCheapest$138Average$358FlexibilityNo cancel feeOn-time75%
SouthwestCheapest$185Average$411FlexibilityNo cancel feeOn-time63%
American AirlinesCheapest$197Average$403FlexibilityNo cancel feeOn-time71%

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