What is the cheapest airline that flies from San Francisco to Chicago?

Frontier, Hawaiian Airlines, and Alaska Airlines are the most popular carriers operating from San Francisco to Chicago

How many flights depart from San Francisco to Chicago on average per week?

The number of flights available between San Francisco and Chicago is 566 per week as of September 2025. The most frequent departure day is Mon, with 17% of weekly flights leaving on this day.

How many flights depart from San Francisco to Chicago on average per day?

80 flights are operational daily from San Francisco to Chicago as of September 2025. The most popular departure time for this route is 8:00AM, with 48% of flights per day taking off at noon.

Which layover airport offers the lowest fares from San Francisco to Chicago?

Flights via Denver (DEN) offer the lowest average round-trip price of $202.

Which layover airport has the shortest connection time from San Francisco to Chicago?

Minneapolis (MSP) has the shortest average layover time for this route: 1h 00m.

Which airport is the most popular layover for flights between San Francisco and Chicago?

Denver (DEN) was the most common stop: 59% of momondo users choosing 1-stop flights on this route connected there.

Which layover airport has the shortest travel time from San Francisco to Chicago?

Flights connecting via Minneapolis (MSP) have the shortest average one-way travel time: 6h 15m.

What airlines fly to Chicago?

United Airlines, American Airlines and Southwest are the top three most popular airlines that fly to Chicago from San Francisco according to our data. United Airlines is the first choice among our users, with 48% of people opting to fly with this airline when traveling to Chicago. Keep in mind that there are 8 different airlines that fly to Chicago on a routine basis, so you have a few additional options to choose from.

When did momondo last update prices for flights from San Francisco Airport to Chicago?

Prices for flights from San Francisco Airport to Chicago are updated daily.

How many operators does momondo search for flights from San Francisco Airport to Chicago?

As of September 2025, there are 7 operators available to choose from for flights from San Francisco Airport to Chicago.

How old do you have to be to fly from San Francisco Airport to Chicago?

The minimum age for a child to fly alone is five, but airlines offering an unaccompanied minor (UNMR) service may have their age restrictions, such as regulations concerning flight duration, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from San Francisco Airport to Chicago.

What documentation or ID do you need to fly to Chicago?

The travel and health documents required for your trip to Chicago can vary based on your itinerary and personal situation. As a rule, consider having multiple documents such as a national ID card or driver’s license, and a passport valid for six-months after you plan to arrive at Chicago. We always recommend checking with your airline or a trusted third party such as IATA to get advice.

$100 Cheap Flights from San Francisco to Chicago in 2025/26

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Round-trip

One-way

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Cheap round-trip flights

9:55 pm - 2:57 pmSFO-MDW

15h 02m1 stop

1:37 pm - 9:11 pmMDW-SFO

9h 34m1 stop

$206Frontier

Find Deal

Fri, Oct 31 - Fri, Nov 7

6:00 am - 6:14 pmSFO-ORD

10h 14m1 stop

6:40 am - 9:22 pmORD-SFO

16h 42m1 stop

$206Multiple Airlines

Find Deal

Sat, Oct 4 - Tue, Oct 7

6:33 pm - 11:30 amSFO-MDW

14h 57m2 stops

12:30 pm - 12:14 amMDW-SFO

13h 44m1 stop

$207Frontier

Find Deal

Thu, Nov 13 - Sun, Nov 16

10:23 pm - 10:38 amSFO-ORD

10h 15m1 stop

9:20 am - 3:47 pmORD-SFO

8h 27m1 stop

$207Multiple Airlines

Find Deal

Sat, Nov 15 - Tue, Nov 18

8:55 pm - 1:57 pmSFO-MDW

15h 02m1 stop

1:37 pm - 9:11 pmMDW-SFO

9h 34m1 stop

$208Frontier

Find Deal

Fri, Nov 14 - Mon, Nov 17

11:57 pm - 10:40 amSFO-ORD

8h 43m1 stop

7:14 am - 10:27 pmORD-SFO

17h 13m1 stop

$208Frontier

Find Deal

Mon, Sep 29 - Tue, Oct 28

7:00 am - 7:55 pmSFO-ORD

10h 55m1 stop

2:54 pm - 9:55 pmORD-SFO

9h 01m1 stop

$218Alaska Airlines

Find Deal

Tue, Nov 11 - Sat, Nov 15

10:26 am - 11:59 pmSFO-ORD

11h 33m1 stop

2:54 pm - 10:01 pmORD-SFO

9h 07m1 stop

$238Alaska Airlines

Find Deal

Wed, Oct 22 - Wed, Nov 12

7:00 am - 7:55 pmSFO-ORD

10h 55m1 stop

9:20 am - 10:01 pmORD-SFO

14h 41m1 stop

$241Alaska Airlines

Find Deal

Mon, Nov 10 - Wed, Nov 19

9:17 pm - 2:50 pmSFO-ORD

15h 33m1 stop

8:20 am - 2:01 pmORD-SFO

7h 41m1 stop

$250Alaska Airlines

Find Deal

Mon, Oct 13 - Tue, Oct 21

Frontier flights from San Francisco to Chicago

Our best Frontier deals on San Francisco to Chicago flight tickets

Frontier

Oct 31

SFO9:55 pmSan Francisco

15h 02m

1 stop

MDW2:57 pmChicago Midway

Nov 7

MDW1:37 pmChicago Midway

9h 34m

1 stop

SFO9:11 pmSan Francisco

$206

Find similar

Frontier

Nov 13

SFO6:33 pmSan Francisco

14h 57m

2 stops

MDW11:30 amChicago Midway

Nov 16

MDW12:30 pmChicago Midway

13h 44m

1 stop

SFO12:14 amSan Francisco

$207

Find similar

Frontier

Sep 29

SFO11:57 pmSan Francisco

8h 43m

1 stop

ORD10:40 amChicago O'Hare Intl

Oct 28

ORD7:14 amChicago O'Hare Intl

17h 13m

1 stop

SFO10:27 pmSan Francisco

$208

Find similar

Alaska Airlines flights from San Francisco to Chicago

Our best Alaska Airlines deals on San Francisco to Chicago flight tickets

Alaska Airlines

Nov 11

SFO7:00 amSan Francisco

10h 55m

1 stop

ORD7:55 pmChicago O'Hare Intl

Nov 15

ORD2:54 pmChicago O'Hare Intl

9h 01m

1 stop

SFO9:55 pmSan Francisco

$218

Find similar

Alaska Airlines

Oct 22

SFO10:26 amSan Francisco

11h 33m

1 stop

ORD11:59 pmChicago O'Hare Intl

Nov 12

ORD2:54 pmChicago O'Hare Intl

9h 07m

1 stop

SFO10:01 pmSan Francisco

$238

Find similar

Alaska Airlines

Nov 10

SFO7:00 amSan Francisco

10h 55m

1 stop

ORD7:55 pmChicago O'Hare Intl

Nov 19

ORD9:20 amChicago O'Hare Intl

14h 41m

1 stop

SFO10:01 pmSan Francisco

$241

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Fly from

Fly to

Route

Depart

Return

Price

San FranciscoChicago

SFO - MDW

SFOMDW

San Francisco

Fri 10/31

9:55 pm-2:57 pm

1 stop15h 02m

Chicago Midway

Fri 11/7

1:37 pm-9:11 pm

1 stop9h 34m

$206

San FranciscoChicago

SFO - ORD

SFOORD

San Francisco

Sat 10/4

6:00 am-6:14 pm

1 stop10h 14m

Chicago O'Hare Intl

Tue 10/7

6:40 am-9:22 pm

1 stop16h 42m

$206

San FranciscoChicago

SFO - MDW

SFOMDW

San Francisco

Thu 11/13

6:33 pm-11:30 am

2 stops14h 57m

Chicago Midway

Sun 11/16

12:30 pm-12:14 am

1 stop13h 44m

$207

San FranciscoChicago

SFO - ORD

SFOORD

San Francisco

Sat 11/15

10:23 pm-10:38 am

1 stop10h 15m

Chicago O'Hare Intl

Tue 11/18

9:20 am-3:47 pm

1 stop8h 27m

$207

San FranciscoChicago

SFO - MDW

SFOMDW

San Francisco

Fri 11/14

8:55 pm-1:57 pm

1 stop15h 02m

Chicago Midway

Mon 11/17

1:37 pm-9:11 pm

1 stop9h 34m

$208

San FranciscoChicago

SFO - ORD

SFOORD

San Francisco

Mon 9/29

11:57 pm-10:40 am

1 stop8h 43m

Chicago O'Hare Intl

Tue 10/28

7:14 am-10:27 pm

1 stop17h 13m

$208

San FranciscoChicago

SFO - ORD

SFOORD

San Francisco

Tue 11/11

7:00 am-7:55 pm

1 stop10h 55m

Chicago O'Hare Intl

Sat 11/15

2:54 pm-9:55 pm

1 stop9h 01m

$218

San FranciscoChicago

SFO - ORD

SFOORD

San Francisco

Wed 10/22

10:26 am-11:59 pm

1 stop11h 33m

Chicago O'Hare Intl

Wed 11/12

2:54 pm-10:01 pm

1 stop9h 07m

$238

San FranciscoChicago

SFO - ORD

SFOORD

San Francisco

Mon 11/10

7:00 am-7:55 pm

1 stop10h 55m

Chicago O'Hare Intl

Wed 11/19

9:20 am-10:01 pm

1 stop14h 41m

$241

San FranciscoChicago

SFO - ORD

SFOORD

San Francisco

Mon 10/13

9:17 pm-2:50 pm

1 stop15h 33m

Chicago O'Hare Intl

Tue 10/21

8:20 am-2:01 pm

1 stop7h 41m

$250

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How to get the cheapest flight ticket from San Francisco to Chicago

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

Prices

Airlines

Layovers

Other information

What is the cheapest month to fly to Chicago?

The month of February is, on average, the cheapest month to fly to Chicago from San Francisco, with most prices found around $284. If you’re not able to fly to Chicago in February, then January is your next best option. Flight prices from San Francisco to Chicago during January average around $308.

What is the cheapest day to depart on your flight to Chicago?

The cheapest day to depart on your flight to Chicago is on a Wednesday when prices can be found for as low as $403. This is often the case because there is less demand to fly during this day of the week. When flying out on a Sunday, the most expensive travel day of the week, you can expect to see flight prices from San Francisco to Chicago for around $514.

What is the cheapest time of day to depart on your flight to Chicago?

Our most recent data shows that the best time of day to fly to Chicago is in the afternoon. Flights from San Francisco to Chicago during this time can be as low as $413. In contrast, the most expensive time of day to depart to Chicago is at noon when prices are around $466.

What is the cheapest San Francisco to Chicago flight route?

Fly from San Francisco to Chicago Midway for the best San Francisco - Chicago flight prices

How far in advance should I book a flight to Chicago?

You are more likely to see cheaper flights to Chicago from San Francisco when booking weeks ahead of your departure date. In general, you can expect to find flights to Chicago for around $367 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Chicago from San Francisco for as low as $301 on momondo.

What cabin class options are available on San Francisco to Chicago flights?

There are 4 cabin classes available to choose from on San Francisco to Chicago flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

Can stopping save me money on San Francisco to Chicago flights?

You could potentially save up to 22% on your flight if you consider stops on a San Francisco to Chicago flight.

How have San Francisco to Chicago flight prices changed over time?

As of September 2025, prices for San Francisco to Chicago flights are approximately 48% more expensive when compared to flights at the same time last year.

When to book flights from San Francisco to Chicago

Are you open to changing your travel dates? Check out the ideal times to fly from San Francisco to Chicago according to our flight data. Find out which month and days have the cheapest flights.

Estimated round-trip price

Cheap San Francisco to Chicago (SFO to CHI) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from San Francisco to Chicago

Best Price Found	$160
Fastest flight time	4h 00m
Direct flights	Every day
Airports in Chicago	1 airport

The best one-way flight to Chicago from San Francisco in the past 72 hours is $160. The best round-trip flight deal from San Francisco to Chicago found on momondo in the last 72 hours is $317.

The fastest flight from San Francisco to Chicago takes 4h 00m

Direct flights go from San Francisco to Chicago every day.

There is 1 airport near Chicago: Chicago Midway (MDW)

Search flight deals

How far is San Francisco to Chicago by plane?
A flight from San Francisco to Chicago will travel around 1852.8 mi. Typically, this will take 7h 11m by plane in normal conditions.
When did momondo last update prices for flights from San Francisco Airport to Chicago?
Prices for flights from San Francisco Airport to Chicago are updated daily.
How many operators does momondo search for flights from San Francisco Airport to Chicago?
As of September 2025, there are 7 operators available to choose from for flights from San Francisco Airport to Chicago.
How old do you have to be to fly from San Francisco Airport to Chicago?
The minimum age for a child to fly alone is five, but airlines offering an unaccompanied minor (UNMR) service may have their age restrictions, such as regulations concerning flight duration, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from San Francisco Airport to Chicago.
What documentation or ID do you need to fly to Chicago?
The travel and health documents required for your trip to Chicago can vary based on your itinerary and personal situation. As a rule, consider having multiple documents such as a national ID card or driver’s license, and a passport valid for six-months after you plan to arrive at Chicago. We always recommend checking with your airline or a trusted third party such as IATA to get advice.
What is the most popular plane model from San Francisco to Chicago?
Based on momondo bookings for flights between San Francisco and Chicago, the leading plane model is Boeing 737-800, making up 16.51% of the total bookings. Other popular models include Boeing 757-300 with 16.19%, Airbus A321neo with 15.79%, and Boeing 777 with 14.83%.
What is the most popular airline from San Francisco to Chicago?
Based on momondo bookings for flights between San Francisco and Chicago, the leading airline is United Airlines, making up 40% of the total bookings. Other popular airlines include American Airlines with 34%, Alaska Airlines with 12%, and Frontier with 7%.

Best airlines flying from San Francisco to Chicago

Compare and see reviews for airlines that fly from San Francisco to Chicago with momondo

Airline	Rating	Free Cancellation	Price
Hawaiian Airlines	PriceFrom $108	Free Cancellation	Rating 7.8 2,729 reviews	Search Hawaiian Airlines flights
Frontier	PriceFrom $127	Free Cancellation	Rating 5.8 3,173 reviews	Search Frontier flights
Delta	PriceFrom $128	Free Cancellation	Rating 7.9 7,961 reviews	Search Delta flights
United Airlines	PriceFrom $133	Free Cancellation	Rating 7.4 8,926 reviews	Search United Airlines flights
Southwest	PriceFrom $185	Free Cancellation	Rating 8.0 4,242 reviews	Search Southwest flights
Alaska Airlines	PriceFrom $196	Free Cancellation	Rating 8.0 10,000 reviews	Search Alaska Airlines flights
American Airlines	PriceFrom $197	Free Cancellation	Rating 7.2 10,000 reviews	Search American Airlines flights

Southwest Flights From San Francisco to Chicago
The lowest priced Southwest flight from San Francisco to Chicago from the last 72 hours was $185. Generally, Southwest has 8 flights on this route every week with an average price of $336. Southwest is rated 8.0/10 by our users.
United Airlines Flights From San Francisco to Chicago
United Airlines is also a popular choice for this route. United Airlines flight deals for San Francisco to Chicago start from as low as $133 round-trip, depending on your selected dates, with average United Airlines deals seen on momondo around $360. United Airlines operates 79 flights to Chicago from San Francisco in an average week. Users have rated it 7.4/10 across 8,926 reviews.

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Saint Joseph

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Crown Point

Munster

Chesterton

Monticello

Porter

Griffith

Saint John

Why use momondo?

Why should I use momondo to find a flight deal from San Francisco to Chicago?

momondo compares prices from hundreds of airlines and agents so you can find and book the best deal on flights from San Francisco to Chicago. Millions of users trust and use momondo every year so you are in good hands.

Can I find flights from San Francisco to Chicago with flexible booking policies on momondo?

Yes. All flights to Chicago from San Francisco on momondo can be compared and filtered by various policies on offer, including flexible booking.

How can momondo help me find flights from San Francisco to Chicago?

momondo provides multiple filters to help you find the best flight to Chicago from San Francisco. Filter by price, airline, airports, cabin, aircraft, payment method, number of stops and more.

I’m not ready to book a flight from San Francisco to Chicago right now. Can momondo alert me if prices change?

If you are not ready to book a flight from San Francisco to Chicago now, use our insights above to find helpful tips or alternatively set up a price alert, where momondo will track prices on flights to Chicago and let you know when they change.

An easier way to manage your Chicago trip

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.

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Find better results for your trip to the United States

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Chicago Midway Airport

Chicago O'Hare Intl Airport

Chicago Greater Rockford Airport

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Flights to Denverfrom $63

Cheap flights from San Francisco to Chicago from $100

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from San Francisco to Chicago departing on 11/9. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.

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Big names and deals

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Filter for what you want

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Frontier flights from San Francisco to Chicago

Our best Frontier deals on San Francisco to Chicago flight tickets

Alaska Airlines flights from San Francisco to Chicago

Our best Alaska Airlines deals on San Francisco to Chicago flight tickets

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See travel insights to Chicago from

How to get the cheapest flight ticket from San Francisco to Chicago

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

What is the cheapest month to fly to Chicago?

What is the cheapest day to depart on your flight to Chicago?

What is the cheapest time of day to depart on your flight to Chicago?

Our most recent data shows that the best time of day to fly to Chicago is in the afternoon. Flights from San Francisco to Chicago during this time can be as low as $413. In contrast, the most expensive time of day to depart to Chicago is at noon when prices are around $466.

What is the cheapest San Francisco to Chicago flight route?

Fly from San Francisco to Chicago Midway for the best San Francisco - Chicago flight prices

How far in advance should I book a flight to Chicago?

What cabin class options are available on San Francisco to Chicago flights?

There are 4 cabin classes available to choose from on San Francisco to Chicago flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

Can stopping save me money on San Francisco to Chicago flights?

You could potentially save up to 22% on your flight if you consider stops on a San Francisco to Chicago flight.

How have San Francisco to Chicago flight prices changed over time?

As of September 2025, prices for San Francisco to Chicago flights are approximately 48% more expensive when compared to flights at the same time last year.

What is the cheapest airline that flies from San Francisco to Chicago?

Frontier, Hawaiian Airlines, and Alaska Airlines are the most popular carriers operating from San Francisco to Chicago

What airlines fly to Chicago?

Which airport is the most popular layover for flights between San Francisco and Chicago?

Denver (DEN) was the most common stop: 59% of momondo users choosing 1-stop flights on this route connected there.

Which layover airport offers the lowest fares from San Francisco to Chicago?

Flights via Denver (DEN) offer the lowest average round-trip price of $202.

Which layover airport has the shortest travel time from San Francisco to Chicago?

Flights connecting via Minneapolis (MSP) have the shortest average one-way travel time: 6h 15m.

Which layover airport has the shortest connection time from San Francisco to Chicago?

Minneapolis (MSP) has the shortest average layover time for this route: 1h 00m.

How many flights depart from San Francisco to Chicago on average per day?

80 flights are operational daily from San Francisco to Chicago as of September 2025. The most popular departure time for this route is 8:00AM, with 48% of flights per day taking off at noon.

How many flights depart from San Francisco to Chicago on average per week?

The number of flights available between San Francisco and Chicago is 566 per week as of September 2025. The most frequent departure day is Mon, with 17% of weekly flights leaving on this day.

When to book flights from San Francisco to Chicago

Cheap San Francisco to Chicago (SFO to CHI) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from San Francisco to Chicago

Best Price Found

Fastest flight time

Direct flights

Airports in Chicago

How far is San Francisco to Chicago by plane?

When did momondo last update prices for flights from San Francisco Airport to Chicago?

How many operators does momondo search for flights from San Francisco Airport to Chicago?

How old do you have to be to fly from San Francisco Airport to Chicago?

What documentation or ID do you need to fly to Chicago?

What is the most popular plane model from San Francisco to Chicago?

What is the most popular airline from San Francisco to Chicago?

Best airlines flying from San Francisco to Chicago

Compare and see reviews for airlines that fly from San Francisco to Chicago with momondo

Southwest Flights From San Francisco to Chicago

United Airlines Flights From San Francisco to Chicago

Traveling to a place near Chicago?

Why use momondo?

Why should I use momondo to find a flight deal from San Francisco to Chicago?

Can I find flights from San Francisco to Chicago with flexible booking policies on momondo?

How can momondo help me find flights from San Francisco to Chicago?

I’m not ready to book a flight from San Francisco to Chicago right now. Can momondo alert me if prices change?

An easier way to manage your Chicago trip

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.