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$63+ 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
Nov 19 — Nov 261
Tue 11/19
Tue 11/26
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 November 14, 2024.

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 November 14, 2024.

This Frontier deal was found by Cheapflights users on 11/14. 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.
Fri 12/132:28 pmSJC - MDW
1 stop7h 45mFrontier
Sun 12/157:15 amMDW - SJC
1 stop6h 53mFrontier
Deal found 11/14$168
This FareScan deal was found by Cheapflights users on 11/13. 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 FareScan is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/109:51 pmSJC - ORD
2 stops29h 39mSpirit Airlines
Thu 12/129:53 pmORD - SJC
2 stops24h 22mSpirit Airlines
Deal found 11/13$168
This FlightHub deal was found by Cheapflights users on 11/13. 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 12/188:10 pmSJC - ORD
1 stop7h 20mMultiple Airlines
Mon 1/207:50 amORD - SJC
1 stop6h 21mMultiple Airlines
Deal found 11/13$172
This FlightHub deal was found by Cheapflights users on 11/12. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/211:41 pmSJC - ORD
1 stop20h 34mFrontier
Sat 11/239:49 pmORD - SJC
1 stop12h 03mFrontier
Deal found 11/12$190
This FlightHub deal was found by Cheapflights users on 11/13. 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.
Fri 12/2711:47 pmSFO - ORD
1 stop14h 20mFrontier
Tue 12/316:55 amORD - SFO
1 stop19h 26mFrontier
Deal found 11/13$209
This eDestinos deal was found by Cheapflights users on 11/13. 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/610:59 pmSFO - ORD
1 stop28h 31mMultiple Airlines
Sun 12/86:36 pmORD - SFO
2 stops27h 34mMultiple Airlines
Deal found 11/13$210
This eDestinos deal was found by Cheapflights users on 11/13. 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/611:48 amSFO - MDW
1 stop6h 26mFrontier
Sun 12/81:30 pmMDW - SFO
2 stops34h 31mFrontier
Deal found 11/13$214
This Alaska Airlines deal was found by Cheapflights users on 11/13. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/710:40 amSFO - ORD
Nonstop4h 19mAlaska Airlines
Thu 12/125:59 pmORD - SFO
Nonstop4h 59mAlaska Airlines
Deal found 11/13$217
This United Airlines deal was found by Cheapflights users on 11/12. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/2511:59 pmSFO - ORD
Nonstop4h 12mUnited Airlines
Sat 12/148:20 pmORD - SFO
Nonstop4h 48mUnited Airlines
Deal found 11/12$224
This Southwest deal was found by Cheapflights users on 11/14. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/118:15 amSFO - MDW
Nonstop4h 10mSouthwest
Thu 12/124:50 pmMDW - SFO
Nonstop4h 40mSouthwest
Deal found 11/14$228
This American Airlines deal was found by Cheapflights users on 11/14. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/1111:50 pmSFO - ORD
Nonstop4h 17mAmerican Airlines
Thu 12/128:45 pmORD - SFO
Nonstop5h 04mAmerican Airlines
Deal found 11/14$242
This Cheapflightsfares deal was found by Cheapflights users on 11/13. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/256:36 pmOAK - ORD
1 stop8h 54mSpirit Airlines
Wed 1/19:54 pmORD - OAK
1 stop13h 35mSpirit Airlines
Deal found 11/13$242

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 2,752,363 searches. Data last updated November 14, 2024.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

San JoseChicago

SJC - MDW

SJCMDW

San Jose

Fri 12/13

2:28 pm-12:13 am

1 stop7h 45m

Chicago Midway

Sun 12/15

7:15 am-12:08 pm

1 stop6h 53m

$168

San JoseChicago

SJC - ORD

SJCORD

San Jose

Thu 12/5

3:56 pm-5:30 am

1 stop11h 34m

Chicago O'Hare Intl

Sun 12/8

3:21 pm-1:30 pm

2 stops24h 09m

$169

San JoseChicago

SJC - ORD

SJCORD

San Jose

Thu 11/28

1:41 pm-12:15 pm

1 stop20h 34m

Chicago O'Hare Intl

Sat 12/7

9:10 pm-7:46 am

1 stop12h 36m

$203

San JoseChicago

SJC - ORD

SJCORD

San Jose

Fri 1/31

1:11 pm-12:32 am

1 stop9h 21m

Chicago O'Hare Intl

Mon 2/3

7:50 am-12:11 pm

1 stop6h 21m

$208

San FranciscoChicago

SFO - ORD

SFOORD

San Francisco

Fri 12/27

11:47 pm-4:07 pm

1 stop14h 20m

Chicago O'Hare Intl

Tue 12/31

6:55 am-12:21 am

1 stop19h 26m

$209

San FranciscoChicago

SFO - ORD

SFOORD

San Francisco

Fri 12/6

10:59 pm-5:30 am

1 stop28h 31m

Chicago O'Hare Intl

Sun 12/8

6:36 pm-8:10 pm

2 stops27h 34m

$210

San FranciscoChicago

SFO - ORD

SFOORD

San Francisco

Sat 12/7

10:40 am-4:59 pm

Nonstop4h 19m

Chicago O'Hare Intl

Fri 12/13

5:59 pm-8:58 pm

Nonstop4h 59m

$217

San FranciscoChicago

SFO - MDW

SFOMDW

San Francisco

Mon 1/6

11:47 pm-4:14 pm

1 stop14h 27m

Chicago Midway

Thu 1/9

12:43 pm-7:14 am

1 stop20h 31m

$218

San JoseChicago

SJC - MDW

SJCMDW

San Jose

Mon 12/30

2:27 pm-11:20 pm

2 stops30h 53m

Chicago Midway

Tue 1/7

8:15 am-3:34 pm

2 stops33h 19m

$222

San FranciscoChicago

SFO - ORD

SFOORD

San Francisco

Mon 11/25

11:59 pm-6:11 am

Nonstop4h 12m

Chicago O'Hare Intl

Sat 12/14

8:20 pm-11:08 pm

Nonstop4h 48m

$224

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/12

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.

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, September is the cheapest month in which you can book a flight from San Francisco Bay Area to Chicago (average of $232). Flying from San Francisco Bay Area to Chicago in June is currently the most expensive (average of $308). 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 November 14, 2024.

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 November 14, 2024.

The most flights from zzXIH to CHI are scheduled on a Thursday (69 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (28 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 November 14, 2024.
Get a feel of what it's like to fly with Spirit Airlines, Frontier and Alaska Airlines 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
5,045 reviews

Overall

8.1

Boarding

8.3

Crew

8.7

Comfort

8.1

Food

7.2

Entertainment

7.7

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
5,045 reviews
Southwest
8.1
Very good
5,045 reviews

Overall

8.1

Boarding

8.3

Crew

8.7

Comfort

8.1

Food

7.2

Entertainment

7.7

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
9,439 reviews
Southwest
8.1
Very good
5,045 reviews

Overall

8.1

Boarding

8.3

Crew

8.7

Comfort

8.1

Food

7.2

Entertainment

7.7

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
8,788 reviews
Southwest
8.1
Very good
5,045 reviews

Overall

8.1

Boarding

8.3

Crew

8.7

Comfort

8.1

Food

7.2

Entertainment

7.7

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
9,194 reviews
Southwest
8.1
Very good
5,045 reviews

Overall

8.1

Boarding

8.3

Crew

8.7

Comfort

8.1

Food

7.2

Entertainment

7.7

Reviews

1 / 10

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

WestJet
7.3
Good
2,804 reviews
Southwest
8.1
Very good
5,045 reviews

Overall

8.1

Boarding

8.3

Crew

8.7

Comfort

8.1

Food

7.2

Entertainment

7.7

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 Frontier, which is currently one of the cheapest options available, starting at $63. Spirit Airlines 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 Asiana Airlines (95%), Iberia (92%) or Royal Jordanian (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 $108. On average you can expect to pay $909. The most popular route, (San Francisco - Chicago O'Hare Intl), can usually be booked for $146.

  • 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, September is the cheapest month in which you can book a flight from San Francisco Bay Area to Chicago (average of $232). Flying from San Francisco Bay Area to Chicago in June is currently the most expensive (average of $308). 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

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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 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 2,752,363 searches. Data last updated November 14, 2024.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$72Average$228FlexibilityNo cancel feeOn-time62%
Alaska AirlinesCheapest$100Average$342FlexibilityNo cancel feeOn-time75%
Spirit AirlinesCheapest$111Average$267FlexibilityNo cancel feeOn-time65%
United AirlinesCheapest$185Average$443FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$192Average$516FlexibilityNo cancel feeOn-time71%
DeltaCheapest$204Average$419FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$210Average$433FlexibilityNo cancel feeOn-time63%
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