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Cheap flights from San Francisco Bay Area to Chicago (CHI)

SFO — CHI
يونيو 20 — يونيو 271
س 6/20
س 6/27
1 adult, Economy
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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 مايو 21, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$282
(Delta)

One-way from

$129
(Southwest)

Popular in

March

Cheapest in

September

Average price

$453
Provider with most accurate pricing for San Francisco-Chicago (CHI) flight deals.
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Provider most trusted by Cheapflights users for San Francisco-Chicago (CHI) flights.
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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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Highest demand for flights based on searches. 3% potential increase in price ($12 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease ($6 potential savings vs. average RT price).
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Average for round-trip flights in May 2026
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Cheapflights Insights

Everything you need to know about your flight from San Francisco Bay Area to Chicago

How far ahead should I book a flight from San Francisco Bay Area to Chicago?

To ensure you get the cheapest price possible for a flight from San Francisco Bay Area to Chicago, you should look to book at least 66 days in advance of your intended travel date. The price of your flight may increase if you delay and leave booking until a week or so before departure.

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 $277). Flying from San Francisco Bay Area to Chicago in January is currently the most expensive (average of $825). 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 مايو 21, 2026.

It’s optimal to fly from San Francisco Bay Area to Chicago in the afternoon. By choosing this option you can save up to 23% 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 May 16, 2026.

Travelers seeking maximum savings on their San Francisco Bay Area to Chicago flight should consider departing on Saturday afternoons when fares are most often at their lowest. Sunday at noon 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 مايو 21, 2026.
See what other customers who have flown with Alaska Airlines,Southwest, andUnited 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
7.9
Good
12,390 reviews

Overall

7.9

Boarding

8.1

Entertainment

7.0

Crew

8.5

Food

7.0

Comfort

7.8

Reviews

1 / 20
10.0
Excellent

Franzi,Mar 2026

SFO - PDX

I love flying with Alaska. I think they sre the best airline.
Alaska Airlines
7.9
Good
12,390 reviews
Alaska Airlines
7.9
Good
12,390 reviews

Overall

7.9

Boarding

8.1

Entertainment

7.0

Crew

8.5

Food

7.0

Comfort

7.8

Reviews

1 / 20
10.0
Excellent

Franzi,Mar 2026

SFO - PDX

I love flying with Alaska. I think they sre the best airline.
Southwest
7.9
Good
4,282 reviews
Alaska Airlines
7.9
Good
12,390 reviews

Overall

7.9

Boarding

8.1

Entertainment

7.0

Crew

8.5

Food

7.0

Comfort

7.8

Reviews

1 / 20
10.0
Excellent

Franzi,Mar 2026

SFO - PDX

I love flying with Alaska. I think they sre the best airline.
United Airlines
7.4
Good
9,749 reviews
Alaska Airlines
7.9
Good
12,390 reviews

Overall

7.9

Boarding

8.1

Entertainment

7.0

Crew

8.5

Food

7.0

Comfort

7.8

Reviews

1 / 20
10.0
Excellent

Franzi,Mar 2026

SFO - PDX

I love flying with Alaska. I think they sre the best airline.
American Airlines
7.1
Good
11,644 reviews
Alaska Airlines
7.9
Good
12,390 reviews

Overall

7.9

Boarding

8.1

Entertainment

7.0

Crew

8.5

Food

7.0

Comfort

7.8

Reviews

1 / 20
10.0
Excellent

Franzi,Mar 2026

SFO - PDX

I love flying with Alaska. I think they sre the best airline.
Frontier
5.7
Fair
2,945 reviews
Alaska Airlines
7.9
Good
12,390 reviews

Overall

7.9

Boarding

8.1

Entertainment

7.0

Crew

8.5

Food

7.0

Comfort

7.8

Reviews

1 / 20
10.0
Excellent

Franzi,Mar 2026

SFO - PDX

I love flying with Alaska. I think they sre the best airline.

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, Southwest, and Delta can get you from San Francisco Bay Area to Chicago in just under 4h 15m. Your travel time can differ by up to 14h 45m. There are 1849 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 $76 while deals on JetBlue start at $96 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 ITA Airways (100%), Brussels Airlines (89%) or Austrian Airlines (85%) 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 $142. On average you can expect to pay $1,120. The most popular route, (San Francisco - Chicago O'Hare Intl), can usually be booked for $122.

  • 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 $277). Flying from San Francisco Bay Area to Chicago in January is currently the most expensive (average of $825). 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
Benton Harbor
Lansing
Merrillville
Hammond
Porter

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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 9 airlines flying from San Francisco Bay Area to Chicago

Discover the top 9 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 مايو 21, 2026.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$97Average$230FlexibilityNo cancel feeOn-time65%
Hawaiian AirlinesCheapest$108Average$217FlexibilityNo cancel feeOn-time85%
DeltaCheapest$122Average$384FlexibilityNo cancel feeOn-timeN/A
FrontierCheapest$130Average$277FlexibilityNo cancel feeOn-time62%
Alaska AirlinesCheapest$179Average$385FlexibilityNo cancel feeOn-time75%
SouthwestCheapest$185Average$432FlexibilityNo cancel feeOn-time63%
American AirlinesCheapest$200Average$403FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$207Average$461FlexibilityNo cancel feeOn-time69%
JetBlueCheapest$224Average$321FlexibilityNo cancel feeOn-time62%

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