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$46+ 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 2/26. Fares are subject to change and may not be available on all flights or dates of travel.
SFO — CHI
Jan 28 — Feb 41
Tue 1/28
Tue 2/4
1 adult, Economy
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Cheap flight deals from San Francisco Bay Area to Chicago

Discover tips and strategies to find the most affordable flight options for your journey from San Francisco Bay Area (zzXIH) to Chicago (CHI). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated January 23, 2025.

Round-trip from

$113
(Cheapflightsfares)

One-way from

$46
(FlightHub)
From San Francisco Bay Area to Chicago (CHI)
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One-way flight from San Francisco Bay Area to Chicago (CHI)
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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 January 23, 2025.

This Cheapflightsfares deal was found by Cheapflights users on 1/22. 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.
Tue 2/117:02 pmOAK - ORD
1 stop9h 05mSpirit Airlines
Sat 2/224:30 pmORD - OAK
1 stop9h 47mSpirit Airlines
Deal found 1/22$132
This Booking.com deal was found by Cheapflights users on 1/22. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 2/214:03 pmSJC - MDW
1 stop6h 14mFrontier
Sun 2/238:44 pmMDW - SJC
1 stop22h 02mFrontier
Deal found 1/22$180
This Booking.com deal was found by Cheapflights users on 1/23. 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.
Thu 5/12:35 pmSJC - ORD
1 stop12h 35mMultiple Airlines
Wed 5/76:45 amORD - SJC
1 stop6h 27mMultiple Airlines
Deal found 1/23$181
This Mytrip deal was found by Cheapflights users on 1/22. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/411:19 amSJC - ORD
2 stops15h 26mSpirit Airlines
Wed 3/57:41 amORD - SJC
2 stops18h 34mSpirit Airlines
Deal found 1/22$182
This Alaska Airlines deal was found by Cheapflights users on 1/23. 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 2/1910:46 amSFO - ORD
Nonstop4h 12mAlaska Airlines
Tue 3/47:00 pmORD - SFO
Nonstop5h 10mAlaska Airlines
Deal found 1/23$197
This United Airlines deal was found by Cheapflights users on 1/21. 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.
Sat 2/226:05 amSFO - ORD
Nonstop4h 23mUnited Airlines
Fri 2/288:05 pmORD - SFO
Nonstop4h 54mUnited Airlines
Deal found 1/21$198
This American Airlines deal was found by Cheapflights users on 1/23. 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 2/225:15 amSFO - ORD
Nonstop4h 06mAmerican Airlines
Sat 3/112:25 pmORD - SFO
Nonstop4h 54mAmerican Airlines
Deal found 1/23$199
This Orbitz deal was found by Cheapflights users on 1/22. 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/2711:53 pmSFO - MDW
1 stop11h 36mFrontier
Fri 5/22:45 pmMDW - SFO
1 stop10h 21mFrontier
Deal found 1/22$200
This Lucky2Go deal was found by Cheapflights users on 1/23. 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 Lucky2Go is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/1510:59 pmSFO - ORD
1 stop28h 06mMultiple Airlines
Sat 2/227:00 pmORD - SFO
Nonstop5h 10mMultiple Airlines
Deal found 1/23$201
This FlightHub deal was found by Cheapflights users on 1/23. 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.
Mon 4/143:58 pmSJC - ORD
1 stop6h 44mFrontier
Thu 4/177:44 pmORD - SJC
1 stop25h 38mFrontier
Deal found 1/23$201
This Cheapflightsfares deal was found by Cheapflights users on 1/23. 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.
Thu 2/1310:59 pmSFO - ORD
1 stop28h 01mFrontier
Mon 2/177:54 pmORD - SFO
1 stop15h 48mFrontier
Deal found 1/23$203
This Southwest deal was found by Cheapflights users on 1/23. 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.
Sat 3/16:10 amSFO - MDW
Nonstop4h 10mSouthwest
Thu 3/66:20 pmMDW - SFO
Nonstop4h 40mSouthwest
Deal found 1/23$207

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 January 23, 2025.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

OaklandChicago

OAK - ORD

OAKORD

Oakland

Tue 2/11

7:02 pm-6:07 am

1 stop9h 05m

Chicago O'Hare Intl

Sat 2/22

4:30 pm-12:17 am

1 stop9h 47m

$132

San JoseChicago

SJC - MDW

SJCMDW

San Jose

Fri 2/28

4:03 pm-12:17 am

1 stop6h 14m

Chicago Midway

Sun 3/2

8:44 pm-7:12 pm

1 stop24h 28m

$180

San JoseChicago

SJC - ORD

SJCORD

San Jose

Thu 5/1

2:35 pm-5:10 am

1 stop12h 35m

Chicago O'Hare Intl

Wed 5/7

6:45 am-11:12 am

1 stop6h 27m

$181

San JoseChicago

SJC - ORD

SJCORD

San Jose

Tue 3/4

11:19 am-4:45 am

2 stops15h 26m

Chicago O'Hare Intl

Wed 3/5

7:41 am-12:15 am

2 stops18h 34m

$182

San FranciscoChicago

SFO - ORD

SFOORD

San Francisco

Wed 2/19

10:46 am-4:58 pm

Nonstop4h 12m

Chicago O'Hare Intl

Wed 2/26

7:00 pm-10:10 pm

Nonstop5h 10m

$197

San FranciscoChicago

SFO - ORD

SFOORD

San Francisco

Wed 2/12

6:15 am-12:42 pm

Nonstop4h 27m

Chicago O'Hare Intl

Sat 2/15

3:40 pm-8:40 pm

1 stop7h 00m

$198

San FranciscoChicago

SFO - ORD

SFOORD

San Francisco

Mon 2/10

6:05 am-2:11 pm

1 stop6h 06m

Chicago O'Hare Intl

Thu 2/27

7:00 pm-10:10 pm

Nonstop5h 10m

$199

San FranciscoChicago

SFO - MDW

SFOMDW

San Francisco

Sun 4/27

11:53 pm-1:29 pm

1 stop11h 36m

Chicago Midway

Fri 5/2

2:45 pm-11:06 pm

1 stop10h 21m

$200

San FranciscoChicago

SFO - ORD

SFOORD

San Francisco

Sun 3/16

8:10 pm-12:44 am

1 stop26h 34m

Chicago O'Hare Intl

Fri 4/4

9:14 am-10:49 pm

1 stop15h 35m

$200

San JoseChicago

SJC - ORD

SJCORD

San Jose

Mon 4/14

3:58 pm-12:42 am

1 stop6h 44m

Chicago O'Hare Intl

Thu 4/17

7:44 pm-7:22 pm

1 stop25h 38m

$201

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/23

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.

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 $322). 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 January 23, 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 January 23, 2025.

The most flights from zzXIH to CHI are scheduled on a Monday (58 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (35 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 January 23, 2025.
Get a feel of what it's like to fly with Spirit Airlines, United Airlines and Frontier 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.
Southwest
8.1
Very good
4,647 reviews

Food

7.2

Entertainment

7.7

Overall

8.1

Comfort

8.1

Boarding

8.2

Crew

8.7

Reviews

1 / 10

My original flight was delayed so they found this flight for me so I could arrive at a reasonable time

Southwest
8.1
Very good
4,647 reviews
Southwest
8.1
Very good
4,647 reviews

Food

7.2

Entertainment

7.7

Overall

8.1

Comfort

8.1

Boarding

8.2

Crew

8.7

Reviews

1 / 10

My original flight was delayed so they found this flight for me so I could arrive at a reasonable time

Alaska Airlines
8.0
Very good
9,699 reviews
Southwest
8.1
Very good
4,647 reviews

Food

7.2

Entertainment

7.7

Overall

8.1

Comfort

8.1

Boarding

8.2

Crew

8.7

Reviews

1 / 10

My original flight was delayed so they found this flight for me so I could arrive at a reasonable time

Delta
8.0
Very good
8,508 reviews
Southwest
8.1
Very good
4,647 reviews

Food

7.2

Entertainment

7.7

Overall

8.1

Comfort

8.1

Boarding

8.2

Crew

8.7

Reviews

1 / 10

My original flight was delayed so they found this flight for me so I could arrive at a reasonable time

United Airlines
7.4
Good
8,971 reviews
Southwest
8.1
Very good
4,647 reviews

Food

7.2

Entertainment

7.7

Overall

8.1

Comfort

8.1

Boarding

8.2

Crew

8.7

Reviews

1 / 10

My original flight was delayed so they found this flight for me so I could arrive at a reasonable time

American Airlines
7.2
Good
10,000 reviews
Southwest
8.1
Very good
4,647 reviews

Food

7.2

Entertainment

7.7

Overall

8.1

Comfort

8.1

Boarding

8.2

Crew

8.7

Reviews

1 / 10

My original flight was delayed so they found this flight for me so I could arrive at a reasonable time

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 $46. Frontier flights start at $65 while deals on Southwest start at $99 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 (97%), Royal Jordanian (90%) or Iberia (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 $98. On average you can expect to pay $910. The most popular route, (San Francisco - Chicago O'Hare Intl), can usually be booked for $141.

  • 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 $322). 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 San Francisco Bay Area?

Book flights to San Francisco Bay Area if you plan to visit one of these locations
Merrillville
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.
Los Angeles to O'Hare Intl flights
San Francisco to O'Hare Intl flights
Los Angeles to Midway flights
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Las Vegas to Midway flights
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Las Vegas to St. Louis flights
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Burbank to Midway flights
Long Beach to O'Hare Intl flights
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Sacramento to St. Louis flights
Sacramento to Midway flights
Santa Ana to St. Louis flights
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Long Beach to Midway flights
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Palm Springs to Midway flights
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Fresno to St. Louis flights
San Luis Obispo to O'Hare Intl flights
Palm Springs to St. Louis flights
Las Vegas to Rockford flights
Bakersfield to St. Louis flights
San Francisco to Moline flights

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 January 23, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$77Average$230FlexibilityNo cancel feeOn-time62%
Alaska AirlinesCheapest$100Average$383FlexibilityNo cancel feeOn-time75%
Spirit AirlinesCheapest$112Average$263FlexibilityNo cancel feeOn-time65%
United AirlinesCheapest$185Average$447FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$206Average$536FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$208Average$465FlexibilityNo cancel feeOn-time63%
DeltaCheapest$235Average$415FlexibilityNo cancel feeOn-timeN/A
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