HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Chicago

$120+ 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 11/11. Fares are subject to change and may not be available on all flights or dates of travel.
SFO — CHI
Nov 29 — Dec 61
Sat 11/29
Sat 12/6
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

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.

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 October 30, 2025.

This Alaska Airlines deal was found by Cheapflights users on 10/27. 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 12/107:00 amSJC - ORD
1 stop10h 54mAlaska Airlines
Wed 12/178:59 pmORD - SJC
1 stop16h 12mAlaska Airlines
Deal found 10/27$249
This Alaska Airlines deal was found by Cheapflights users on 10/28. 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.
Thu 12/117:00 amSJC - ORD
1 stop14h 50mAlaska Airlines
Tue 12/168:59 pmORD - SJC
1 stop19h 33mAlaska Airlines
Deal found 10/28$250
This Kiwi.com deal was found by Cheapflights users on 10/28. 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.
Fri 12/58:08 pmSJC - ORD
1 stop7h 56mMultiple Airlines
Sat 12/64:47 pmORD - SJC
2 stops28h 26mMultiple Airlines
Deal found 10/28$253
This Kiwi.com deal was found by Cheapflights users on 10/29. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/217:48 pmSJC - ORD
1 stop8h 17mMultiple Airlines
Wed 1/77:44 pmORD - SJC
1 stop16h 48mMultiple Airlines
Deal found 10/29$259
This Alaska Airlines deal was found by Cheapflights users on 10/28. 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.
Thu 12/117:00 amSJC - ORD
1 stop10h 54mAlaska Airlines
Sun 12/148:59 pmORD - SJC
1 stop19h 33mAlaska Airlines
Deal found 10/28$263
This Orbitz deal was found by Cheapflights users on 10/28. 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.
Tue 12/93:09 pmSJC - ORD
1 stop6h 41mAlaska Airlines
Sat 12/133:05 pmORD - SJC
1 stop22h 53mAlaska Airlines
Deal found 10/28$269
This Alaska Airlines deal was found by Cheapflights users on 10/30. 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.
Sat 12/63:09 pmSJC - ORD
1 stop6h 41mAlaska Airlines
Sun 12/73:05 pmORD - SJC
1 stop20h 46mAlaska Airlines
Deal found 10/30$270
This Alaska Airlines deal was found by Cheapflights users on 10/29. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/187:00 amSJC - ORD
1 stop14h 59mAlaska Airlines
Wed 1/79:00 amORD - SJC
1 stop26h 47mAlaska Airlines
Deal found 10/29$272
This Kiwi.com deal was found by Cheapflights users on 10/29. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/128:08 pmSJC - ORD
2 stops22h 01mMultiple Airlines
Sun 12/146:50 amORD - SJC
1 stop9h 42mMultiple Airlines
Deal found 10/29$273
This Kiwi.com deal was found by Cheapflights users on 10/28. 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 11/810:23 pmSFO - ORD
1 stop10h 15mFrontier
Sat 11/156:00 amORD - SFO
2 stops18h 27mFrontier
Deal found 10/28$275
This Kiwi.com deal was found by Cheapflights users on 10/28. 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.
Tue 12/910:10 pmSFO - ORD
1 stop29h 54mMultiple Airlines
Thu 12/256:00 amORD - SFO
1 stop9h 13mMultiple Airlines
Deal found 10/28$276
This Kiwi.com deal was found by Cheapflights users on 10/27. 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 11/55:28 pmSFO - ORD
1 stop12h 00mMultiple Airlines
Wed 11/126:05 pmORD - SFO
1 stop17h 28mMultiple Airlines
Deal found 10/27$277

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 October 30, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$248
(KAYAK)

One-way from

$120
(Kiwi.com)

Popular in

December

Cheapest in

February

Average price

$389
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. 9% potential increase in price ($36 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($9 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in October 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 October 30, 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

San JoseChicago

SJC - ORD

SJCORD

San Jose

Wed 12/17

12:35 pm-11:50 pm

1 stop9h 15m

Chicago O'Hare Intl

Thu 1/8

9:00 am-2:21 pm

1 stop7h 21m

$250

San JoseChicago

SJC - ORD

SJCORD

San Jose

Mon 12/15

5:45 pm-7:54 pm

1 stop24h 09m

Chicago O'Hare Intl

Thu 12/18

8:39 am-2:16 pm

1 stop7h 37m

$250

San JoseChicago

SJC - ORD

SJCORD

San Jose

Thu 12/11

7:00 am-7:54 pm

1 stop10h 54m

Chicago O'Hare Intl

Sun 12/14

3:05 pm-9:51 am

1 stop20h 46m

$263

San JoseChicago

SJC - ORD

SJCORD

San Jose

Tue 12/9

12:35 pm-11:50 pm

1 stop9h 15m

Chicago O'Hare Intl

Thu 12/11

8:55 am-5:08 pm

1 stop10h 13m

$270

San FranciscoChicago

SFO - ORD

SFOORD

San Francisco

Fri 12/5

7:00 am-7:54 pm

1 stop10h 54m

Chicago O'Hare Intl

Mon 12/8

8:59 pm-9:10 am

1 stop14h 11m

$283

Santa RosaChicago

STS - ORD

STSORD

Santa Rosa Sonoma County

Mon 3/9

6:58 am-11:10 pm

1 stop14h 12m

Chicago O'Hare Intl

Tue 3/10

2:59 pm-10:46 pm

1 stop9h 47m

$287

San FranciscoChicago

SFO - ORD

SFOORD

San Francisco

Tue 12/2

11:35 am-11:50 pm

2 stops10h 15m

Chicago O'Hare Intl

Fri 12/5

3:05 pm-8:06 am

1 stop19h 01m

$289

San FranciscoChicago

SFO - ORD

SFOORD

San Francisco

Sun 11/23

7:00 am-11:32 pm

1 stop14h 32m

Chicago O'Hare Intl

Tue 12/2

8:59 pm-8:06 am

1 stop13h 07m

$293

San FranciscoChicago

SFO - ORD

SFOORD

San Francisco

Sat 12/6

1:30 pm-7:42 pm

Nonstop4h 12m

Chicago O'Hare Intl

Tue 12/16

12:45 pm-3:35 pm

Nonstop4h 50m

$298

San FranciscoChicago

SFO - ORD

SFOORD

San Francisco

Wed 1/28

12:47 am-8:40 am

1 stop5h 53m

Chicago O'Hare Intl

Tue 2/3

2:20 pm-10:57 pm

1 stop10h 37m

$300

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/30

Showing 1-10 of 60 results
1
2
3
...
6

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 $111). Flying from San Francisco Bay Area to Chicago in March is currently the most expensive (average of $194). 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 October 30, 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 22% on the cost of your flight, compared to a flight in the evening.

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. Sunday mornings flights should be avoided if possible as fares are typically the most expensive at this time.

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 October 30, 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
11,220 reviews

Crew

8.5

Comfort

7.8

Food

7.1

Entertainment

7.0

Boarding

8.1

Overall

8.0

Reviews

1 / 20
6.0
Good

Hannah,Aug 2025

SFO - SAN

Ticket said TSA pre check, but then the TSA agent said that Alaska Airlines has not actually entered the pre check information for the ticket, so I had to use regular security. During boarding, I have a disability and need to board early. The Alaska Airlines employee announced disability boarding, but then immediately announced 2 other groups to board, so I still had to fight the crowds. On the plane, the stewardess was brusk and rude. Seats were very uncomfortable, especially on lower back.
Alaska Airlines
8.0
Very good
11,220 reviews
Alaska Airlines
8.0
Very good
11,220 reviews

Crew

8.5

Comfort

7.8

Food

7.1

Entertainment

7.0

Boarding

8.1

Overall

8.0

Reviews

1 / 20
6.0
Good

Hannah,Aug 2025

SFO - SAN

Ticket said TSA pre check, but then the TSA agent said that Alaska Airlines has not actually entered the pre check information for the ticket, so I had to use regular security. During boarding, I have a disability and need to board early. The Alaska Airlines employee announced disability boarding, but then immediately announced 2 other groups to board, so I still had to fight the crowds. On the plane, the stewardess was brusk and rude. Seats were very uncomfortable, especially on lower back.
Southwest
8.0
Very good
4,243 reviews
Alaska Airlines
8.0
Very good
11,220 reviews

Crew

8.5

Comfort

7.8

Food

7.1

Entertainment

7.0

Boarding

8.1

Overall

8.0

Reviews

1 / 20
6.0
Good

Hannah,Aug 2025

SFO - SAN

Ticket said TSA pre check, but then the TSA agent said that Alaska Airlines has not actually entered the pre check information for the ticket, so I had to use regular security. During boarding, I have a disability and need to board early. The Alaska Airlines employee announced disability boarding, but then immediately announced 2 other groups to board, so I still had to fight the crowds. On the plane, the stewardess was brusk and rude. Seats were very uncomfortable, especially on lower back.
United Airlines
7.4
Good
8,996 reviews
Alaska Airlines
8.0
Very good
11,220 reviews

Crew

8.5

Comfort

7.8

Food

7.1

Entertainment

7.0

Boarding

8.1

Overall

8.0

Reviews

1 / 20
6.0
Good

Hannah,Aug 2025

SFO - SAN

Ticket said TSA pre check, but then the TSA agent said that Alaska Airlines has not actually entered the pre check information for the ticket, so I had to use regular security. During boarding, I have a disability and need to board early. The Alaska Airlines employee announced disability boarding, but then immediately announced 2 other groups to board, so I still had to fight the crowds. On the plane, the stewardess was brusk and rude. Seats were very uncomfortable, especially on lower back.
American Airlines
7.2
Good
11,034 reviews
Alaska Airlines
8.0
Very good
11,220 reviews

Crew

8.5

Comfort

7.8

Food

7.1

Entertainment

7.0

Boarding

8.1

Overall

8.0

Reviews

1 / 20
6.0
Good

Hannah,Aug 2025

SFO - SAN

Ticket said TSA pre check, but then the TSA agent said that Alaska Airlines has not actually entered the pre check information for the ticket, so I had to use regular security. During boarding, I have a disability and need to board early. The Alaska Airlines employee announced disability boarding, but then immediately announced 2 other groups to board, so I still had to fight the crowds. On the plane, the stewardess was brusk and rude. Seats were very uncomfortable, especially on lower back.
Frontier
5.8
Fair
3,123 reviews
Alaska Airlines
8.0
Very good
11,220 reviews

Crew

8.5

Comfort

7.8

Food

7.1

Entertainment

7.0

Boarding

8.1

Overall

8.0

Reviews

1 / 20
6.0
Good

Hannah,Aug 2025

SFO - SAN

Ticket said TSA pre check, but then the TSA agent said that Alaska Airlines has not actually entered the pre check information for the ticket, so I had to use regular security. During boarding, I have a disability and need to board early. The Alaska Airlines employee announced disability boarding, but then immediately announced 2 other groups to board, so I still had to fight the crowds. On the plane, the stewardess was brusk and rude. Seats were very uncomfortable, especially on lower back.

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?

    Alaska Airlines, United Airlines, and Delta can get you from San Francisco Bay Area to Chicago in just under 4h 12m. Your travel time can differ by up to 5h 03m. There are 1841 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 Alaska Airlines, which is currently one of the cheapest options available, starting at $121. Frontier flights start at $122 while deals on Southwest start at $127 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 China Southern (100%), ITA Airways (90%) or Asiana Airlines (90%) 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 $130. On average you can expect to pay $1,024. The most popular route, (San Francisco - Chicago O'Hare Intl), can usually be booked for $164.

  • 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 $111). Flying from San Francisco Bay Area to Chicago in March is currently the most expensive (average of $194). 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
Porter
Benton Harbor

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for San Francisco Bay Area to Chicago

See prices for flight routes from nearby airports that may be better suited for you.
Los Angeles to O'Hare Intl flights
San Francisco to O'Hare Intl flights
Ontario to O'Hare Intl flights
Los Angeles to Midway flights
San Francisco to Midway flights
Santa Ana to O'Hare Intl flights
San Diego to O'Hare Intl flights
Sacramento to O'Hare Intl flights
San Jose to O'Hare Intl flights
Burbank to O'Hare Intl flights
Oakland to O'Hare Intl flights
Los Angeles to St. Louis flights
Las Vegas to O'Hare Intl flights
San Francisco to St. Louis flights
San Diego to Midway flights
Sacramento to Midway flights
Ontario to St. Louis flights
Oakland to Midway flights
Reno to O'Hare Intl flights
Santa Ana to Midway flights
Las Vegas to Midway flights
Fresno to O'Hare Intl flights
San Diego to St. Louis flights
Palm Springs to O'Hare Intl flights
Burbank to Midway flights
Las Vegas to St. Louis flights
Ontario to Midway flights
Long Beach to O'Hare Intl flights
Burbank to St. Louis flights
Fresno to Midway flights
San Jose to Midway flights
Oakland to St. Louis flights
Santa Ana to St. Louis flights
San Jose to St. Louis flights
Monterey to O'Hare Intl flights
Santa Barbara to O'Hare Intl flights
Sacramento to St. Louis flights
Los Angeles to Moline flights
Reno to Midway flights
Los Angeles to Rockford flights
Long Beach to St. Louis flights
Santa Ana to Moline flights
San Luis Obispo to O'Hare Intl flights
Los Angeles to Peoria flights
Long Beach to Midway flights
Santa Ana to Bloomington flights
Palm Springs to Midway flights
San Francisco to Rockford flights
Las Vegas to Moline flights
San Diego to Peoria flights

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 October 30, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$98Average$251FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$108Average$240FlexibilityNo cancel feeOn-time65%
Hawaiian AirlinesCheapest$108Average$288FlexibilityNo cancel feeOn-time85%
DeltaCheapest$128Average$339FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$133Average$417FlexibilityNo cancel feeOn-time69%
Alaska AirlinesCheapest$170Average$384FlexibilityNo cancel feeOn-time75%
SouthwestCheapest$185Average$423FlexibilityNo cancel feeOn-time63%
American AirlinesCheapest$197Average$423FlexibilityNo cancel feeOn-time71%

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.