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$91+ 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 1/15. Fares are subject to change and may not be available on all flights or dates of travel.
SFO — CHI
Jan 20 — Jan 271
Tue 1/20
Tue 1/27
1 adult, Economy
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Cheap 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 December 21, 2025.

This Kiwi.com deal was found by Cheapflights users on 12/20. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/286:00 amSFO - ORD
1 stop13h 39mFrontier
Mon 1/125:50 amORD - SFO
1 stop9h 28mFrontier
Deal found 12/20$264
This Kiwi.com deal was found by Cheapflights users on 12/20. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/276:24 amSFO - ORD
1 stop15h 48mFrontier
Sat 1/176:02 pmORD - SFO
1 stop17h 53mFrontier
Deal found 12/20$285
This Kiwi.com deal was found by Cheapflights users on 12/20. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/276:24 amSFO - ORD
1 stop15h 48mFrontier
Mon 1/127:50 pmORD - SFO
1 stop6h 34mFrontier
Deal found 12/20$289
This Kiwi.com deal was found by Cheapflights users on 12/20. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/286:00 amSFO - ORD
1 stop13h 39mFrontier
Thu 1/1510:41 pmORD - SFO
1 stop11h 07mFrontier
Deal found 12/20$291
This Kiwi.com deal was found by Cheapflights users on 12/20. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/316:24 amSFO - ORD
1 stop15h 48mMultiple Airlines
Wed 1/142:18 pmORD - SFO
2 stops19h 30mMultiple Airlines
Deal found 12/20$294
This Kiwi.com deal was found by Cheapflights users on 12/19. 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.
Wed 12/316:24 amSFO - ORD
1 stop15h 48mMultiple Airlines
Mon 1/57:44 pmORD - SFO
1 stop29h 15mMultiple Airlines
Deal found 12/19$297
This Kiwi.com deal was found by Cheapflights users on 12/20. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/286:00 amSFO - ORD
1 stop13h 39mFrontier
Sun 1/115:50 amORD - SFO
1 stop9h 28mFrontier
Deal found 12/20$299
This Kiwi.com deal was found by Cheapflights users on 12/20. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/286:00 amSFO - ORD
1 stop13h 39mMultiple Airlines
Tue 1/139:00 amORD - SFO
1 stop7h 02mMultiple Airlines
Deal found 12/20$306
This United Airlines deal was found by Cheapflights users on 12/20. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/313:15 pmSFO - ORD
Nonstop4h 17mUnited Airlines
Sat 1/176:47 amORD - SFO
Nonstop4h 53mUnited Airlines
Deal found 12/20$307
This Kiwi.com deal was found by Cheapflights users on 12/20. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/286:00 amSFO - ORD
1 stop13h 39mMultiple Airlines
Wed 1/142:18 pmORD - SFO
2 stops19h 30mMultiple Airlines
Deal found 12/20$309
This Kiwi.com deal was found by Cheapflights users on 12/20. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/276:24 amSFO - ORD
1 stop15h 48mFrontier
Thu 1/1510:41 pmORD - SFO
1 stop11h 07mFrontier
Deal found 12/20$316
This Kiwi.com deal was found by Cheapflights users on 12/20. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/316:24 amSFO - ORD
1 stop15h 48mFrontier
Sun 1/115:50 amORD - SFO
1 stop9h 28mFrontier
Deal found 12/20$319

Find 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 December 21, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$232
(Southwest)

One-way from

$91
(Priceline)

Popular in

December

Cheapest in

February

Average price

$460
Provider with most accurate pricing for San Francisco-Chicago (CHI) flight deals.
Search Deals
Provider most trusted by Cheapflights users for San Francisco-Chicago (CHI) flights.
Search Deals
From San Francisco Bay Area to Chicago (CHI)
Search Deals
One-way flight from San Francisco Bay Area to Chicago (CHI)
Search Deals
Highest demand for flights based on searches. 14% potential increase in price ($57 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($11 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 2025
Search 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 December 21, 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 - MDW

OAKMDW

Oakland

Tue 1/20

11:10 am-5:15 pm

Nonstop4h 05m

Chicago Midway

Tue 1/27

3:40 pm-9:25 pm

1 stop7h 45m

$242

OaklandChicago

OAK - ORD

OAKORD

Oakland

Tue 1/20

8:10 am-2:38 pm

1 stop28h 28m

Chicago O'Hare Intl

Tue 1/27

6:06 pm-4:23 pm

1 stop24h 17m

$242

OaklandChicago

OAK - ORD

OAKORD

Oakland

Tue 2/24

6:15 am-11:56 pm

1 stop15h 41m

Chicago O'Hare Intl

Wed 2/25

7:00 am-4:37 pm

1 stop11h 37m

$242

OaklandChicago

OAK - ORD

OAKORD

Oakland

Fri 1/30

8:10 am-11:50 pm

1 stop13h 40m

Chicago O'Hare Intl

Mon 2/2

8:00 am-11:03 am

1 stop29h 03m

$242

OaklandChicago

OAK - ORD

OAKORD

Oakland

Fri 3/13

5:31 pm-4:33 pm

1 stop21h 02m

Chicago O'Hare Intl

Tue 3/17

7:00 am-10:49 pm

1 stop17h 49m

$242

OaklandChicago

OAK - MDW

OAKMDW

Oakland

Sat 2/14

5:15 am-1:30 pm

1 stop6h 15m

Chicago Midway

Tue 2/17

2:05 pm-8:15 pm

1 stop8h 10m

$249

OaklandChicago

OAK - MDW

OAKMDW

Oakland

Sat 2/14

8:45 pm-5:05 am

1 stop6h 20m

Chicago Midway

Sat 2/21

8:10 am-1:20 pm

1 stop7h 10m

$256

OaklandChicago

OAK - ORD

OAKORD

Oakland

Thu 1/15

5:17 pm-11:50 pm

1 stop28h 33m

Chicago O'Hare Intl

Tue 1/20

6:06 pm-10:28 am

1 stop18h 22m

$259

San FranciscoChicago

SFO - MDW

SFOMDW

San Francisco

Fri 2/20

12:40 am-11:03 am

1 stop8h 23m

Chicago Midway

Tue 2/24

1:26 pm-10:41 pm

2 stops11h 15m

$265

San FranciscoChicago

SFO - ORD

SFOORD

San Francisco

Sat 1/31

2:35 pm-11:53 pm

1 stop7h 18m

Chicago O'Hare Intl

Mon 2/2

2:20 pm-11:56 pm

2 stops11h 36m

$265

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/21

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, December is the cheapest month in which you can book a flight from San Francisco Bay Area to Chicago (average of $107). Flying from San Francisco Bay Area to Chicago in November is currently the most expensive (average of $210). 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 December 21, 2025.

It’s optimal to fly from San Francisco Bay Area to Chicago in the afternoon. By choosing this option you can save up to 18% on the cost of your flight, compared to a flight at noon.

What is the cheapest day to fly from San Francisco Bay Area to Chicago?

Use this chart to determine the cheapest time to fly round-trip from San Francisco Bay Area to Chicago. Price data was last updated on December 16, 2024.

Travelers seeking maximum savings on their San Francisco Bay Area to Chicago flight should consider departing on Wednesday afternoons when fares are most often at their lowest. Wednesday evenings flights should be avoided if possible as fares are typically the most expensive at this time.

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 December 21, 2025.

The most flights from zzXIH to CHI are scheduled on a Friday (75 on average). You will have fewer flight options on Wednesday, which is when the least amount of flights are scheduled (50 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 December 21, 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.
Alaska Airlines
8.0
Very good
11,496 reviews

Crew

8.5

Entertainment

7.0

Boarding

8.1

Comfort

7.8

Overall

8.0

Food

7.1

Reviews

1 / 20
2.0
Mediocre

Art,Dec 2025

SAN - OGG

It was a five hour flight and my seat did not recline. I have had three back surgeries and I’m solid bone for my L3 vertebrae all the way to my tailbone. My body has never hurt so much. There was no TV on this flight and only a small can of soda was free.
Alaska Airlines
8.0
Very good
11,496 reviews
Alaska Airlines
8.0
Very good
11,496 reviews

Crew

8.5

Entertainment

7.0

Boarding

8.1

Comfort

7.8

Overall

8.0

Food

7.1

Reviews

1 / 20
2.0
Mediocre

Art,Dec 2025

SAN - OGG

It was a five hour flight and my seat did not recline. I have had three back surgeries and I’m solid bone for my L3 vertebrae all the way to my tailbone. My body has never hurt so much. There was no TV on this flight and only a small can of soda was free.
Southwest
8.0
Very good
4,254 reviews
Alaska Airlines
8.0
Very good
11,496 reviews

Crew

8.5

Entertainment

7.0

Boarding

8.1

Comfort

7.8

Overall

8.0

Food

7.1

Reviews

1 / 20
2.0
Mediocre

Art,Dec 2025

SAN - OGG

It was a five hour flight and my seat did not recline. I have had three back surgeries and I’m solid bone for my L3 vertebrae all the way to my tailbone. My body has never hurt so much. There was no TV on this flight and only a small can of soda was free.
United Airlines
7.4
Good
9,102 reviews
Alaska Airlines
8.0
Very good
11,496 reviews

Crew

8.5

Entertainment

7.0

Boarding

8.1

Comfort

7.8

Overall

8.0

Food

7.1

Reviews

1 / 20
2.0
Mediocre

Art,Dec 2025

SAN - OGG

It was a five hour flight and my seat did not recline. I have had three back surgeries and I’m solid bone for my L3 vertebrae all the way to my tailbone. My body has never hurt so much. There was no TV on this flight and only a small can of soda was free.
American Airlines
7.2
Good
11,051 reviews
Alaska Airlines
8.0
Very good
11,496 reviews

Crew

8.5

Entertainment

7.0

Boarding

8.1

Comfort

7.8

Overall

8.0

Food

7.1

Reviews

1 / 20
2.0
Mediocre

Art,Dec 2025

SAN - OGG

It was a five hour flight and my seat did not recline. I have had three back surgeries and I’m solid bone for my L3 vertebrae all the way to my tailbone. My body has never hurt so much. There was no TV on this flight and only a small can of soda was free.
Frontier
5.8
Fair
3,079 reviews
Alaska Airlines
8.0
Very good
11,496 reviews

Crew

8.5

Entertainment

7.0

Boarding

8.1

Comfort

7.8

Overall

8.0

Food

7.1

Reviews

1 / 20
2.0
Mediocre

Art,Dec 2025

SAN - OGG

It was a five hour flight and my seat did not recline. I have had three back surgeries and I’m solid bone for my L3 vertebrae all the way to my tailbone. My body has never hurt so much. There was no TV on this flight and only a small can of soda was free.

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.

  • How long is the flight from San Francisco Bay Area to Chicago?

    Southwest, Alaska Airlines, and Delta can get you from San Francisco Bay Area to Chicago in just under 4h 05m. Your travel time can differ by up to 24h 23m. There are 1839 mi between San Francisco Bay Area and Chicago. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

  • 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 $60. Frontier flights start at $65 while deals on Alaska Airlines start at $98 one-way.

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

    The most popular flight routes from San Francisco Bay Area to Chicago are San Francisco - Chicago O'Hare Intl, San Francisco - Chicago Midway and San Jose - Chicago O'Hare Intl.

  • 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%), Royal Jordanian (92%) or China Southern (91%) 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 $127. On average you can expect to pay $1,155. The most popular route, (San Francisco - Chicago O'Hare Intl), can usually be booked for $183.

  • 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, December is the cheapest month in which you can book a flight from San Francisco Bay Area to Chicago (average of $107). Flying from San Francisco Bay Area to Chicago in November is currently the most expensive (average of $210). 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
Lansing
Merrillville
Hammond
Porter
Benton Harbor

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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.
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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 December 21, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$65Average$241FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$108Average$226FlexibilityNo cancel feeOn-time65%
Hawaiian AirlinesCheapest$108Average$288FlexibilityNo cancel feeOn-time85%
DeltaCheapest$128Average$340FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$133Average$427FlexibilityNo cancel feeOn-time69%
Alaska AirlinesCheapest$170Average$397FlexibilityNo cancel feeOn-time75%
SouthwestCheapest$185Average$422FlexibilityNo cancel feeOn-time63%
American AirlinesCheapest$197Average$405FlexibilityNo cancel feeOn-time71%

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