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

Flights via Denver (DEN) offer the lowest average round-trip price of $174.

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?

53 flights are operational daily from San Francisco to Chicago as of November 2025. The most popular departure time for this route is 6:00AM, with 46% of flights per day taking off at noon.

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.

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

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

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

Denver (DEN) was the most common stop: 63% of momondo users choosing 1-stop flights on this route connected there.

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

The number of flights available between San Francisco and Chicago is 375 per week as of November 2025. The most frequent departure day is Wed, with 18% of weekly flights leaving on this day.

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 November 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.

$125 Cheap Flights from San Francisco to Chicago in 2025/26

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12:47 am - 9:08 amSFO-MDW

6h 21m1 stop

9:34 am - 5:49 pmMDW-SFO

10h 15m2 stops

$286Delta

Find Deal

Sun, Jan 4 - Fri, Jan 9

5:50 am - 4:22 pmSFO-ORD

8h 32m1 stop

7:20 am - 3:57 pmORD-SFO

10h 37m2 stops

$286Delta

Find Deal

Fri, Dec 12 - Mon, Dec 15

6:00 am - 12:24 pmSFO-ORD

4h 24mnonstop

8:35 am - 11:26 amORD-SFO

4h 51mnonstop

$287American Airlines

Find Deal

Thu, Dec 4 - Tue, Dec 9

2:54 pm - 12:10 amSFO-ORD

7h 16m1 stop

6:11 am - 1:18 pmORD-SFO

9h 07m1 stop

$288Frontier

Find Deal

Sun, Nov 23 - Fri, Dec 5

12:30 am - 9:01 amSFO-MDW

6h 31m1 stop

6:00 am - 12:25 pmMDW-SFO

8h 25m1 stop

$288Delta

Find Deal

Wed, Nov 26 - Sat, Dec 6

8:42 am - 11:56 pmSFO-ORD

13h 14m1 stop

6:50 pm - 10:31 amORD-SFO

17h 41m1 stop

$289Alaska Airlines

Find Deal

Mon, Mar 16 - Wed, Mar 18

7:00 am - 11:50 pmSFO-ORD

14h 50m1 stop

8:58 pm - 8:15 amORD-SFO

13h 17m1 stop

$290Alaska Airlines

Find Deal

Tue, Dec 16 - Sun, Dec 21

11:38 am - 12:10 amSFO-ORD

10h 32m2 stops

6:00 am - 7:23 pmORD-SFO

15h 23m1 stop

$291Frontier

Find Deal

Mon, Nov 24 - Wed, Nov 26

10:10 am - 4:10 pmSFO-MDW

4h 00mnonstop

8:15 am - 11:00 amMDW-SFO

4h 45mnonstop

$292Southwest

Find Deal

Sat, Dec 6 - Wed, Dec 10

5:55 am - 11:55 amSFO-MDW

4h 00mnonstop

10:05 am - 5:05 pmMDW-SFO

9h 00m1 stop

$293Southwest

Find Deal

Fri, Feb 20 - Tue, Feb 24

Alaska Airlines flights from San Francisco to Chicago

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

Alaska Airlines

Dec 12

SFO7:00 amSan Francisco

29h 09m

1 stop

ORD2:09 pmChicago O'Hare Intl

Dec 19

ORD6:00 amChicago O'Hare Intl

11h 46m

1 stop

SFO3:46 pmSan Francisco

$286

Find similar

Alaska Airlines

Mar 16

SFO8:42 amSan Francisco

13h 14m

1 stop

ORD11:56 pmChicago O'Hare Intl

Mar 18

ORD6:50 pmChicago O'Hare Intl

17h 41m

1 stop

SFO10:31 amSan Francisco

$289

Find similar

Alaska Airlines

Dec 16

SFO7:00 amSan Francisco

14h 50m

1 stop

ORD11:50 pmChicago O'Hare Intl

Dec 21

ORD8:58 pmChicago O'Hare Intl

13h 17m

1 stop

SFO8:15 amSan Francisco

$290

Find similar

Delta flights from San Francisco to Chicago

Our best Delta deals on San Francisco to Chicago flight tickets

Delta

Jan 4

SFO12:47 amSan Francisco

6h 21m

1 stop

MDW9:08 amChicago Midway

Jan 9

MDW9:34 amChicago Midway

10h 15m

2 stops

SFO5:49 pmSan Francisco

$286

Find similar

Delta

Nov 26

SFO12:30 amSan Francisco

6h 31m

1 stop

MDW9:01 amChicago Midway

Dec 6

MDW6:00 amChicago Midway

8h 25m

1 stop

SFO12:25 pmSan Francisco

$288

Find similar

Delta

Dec 3

SFO12:37 pmSan Francisco

9h 10m

1 stop

MDW11:47 pmChicago Midway

Dec 10

MDW6:00 amChicago Midway

8h 36m

1 stop

SFO12:36 pmSan Francisco

$289

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Fly from

Fly to

Route

Depart

Return

Price

San FranciscoChicago

SFO - MDW

SFOMDW

San Francisco

Sun 1/4

12:47 am-9:08 am

1 stop6h 21m

Chicago Midway

Fri 1/9

9:34 am-5:49 pm

2 stops10h 15m

$286

San FranciscoChicago

SFO - ORD

SFOORD

San Francisco

Fri 12/12

5:50 am-4:22 pm

1 stop8h 32m

Chicago O'Hare Intl

Mon 12/15

7:20 am-3:57 pm

2 stops10h 37m

$286

San FranciscoChicago

SFO - ORD

SFOORD

San Francisco

Thu 12/4

6:00 am-12:24 pm

Nonstop4h 24m

Chicago O'Hare Intl

Tue 12/9

8:35 am-11:26 am

Nonstop4h 51m

$287

San FranciscoChicago

SFO - ORD

SFOORD

San Francisco

Sun 11/23

2:54 pm-12:10 am

1 stop7h 16m

Chicago O'Hare Intl

Fri 12/5

6:11 am-1:18 pm

1 stop9h 07m

$288

San FranciscoChicago

SFO - MDW

SFOMDW

San Francisco

Wed 11/26

12:30 am-9:01 am

1 stop6h 31m

Chicago Midway

Sat 12/6

6:00 am-12:25 pm

1 stop8h 25m

$288

San FranciscoChicago

SFO - ORD

SFOORD

San Francisco

Mon 3/16

8:42 am-11:56 pm

1 stop13h 14m

Chicago O'Hare Intl

Wed 3/18

6:50 pm-10:31 am

1 stop17h 41m

$289

San FranciscoChicago

SFO - ORD

SFOORD

San Francisco

Tue 12/16

7:00 am-11:50 pm

1 stop14h 50m

Chicago O'Hare Intl

Sun 12/21

8:58 pm-8:15 am

1 stop13h 17m

$290

San FranciscoChicago

SFO - ORD

SFOORD

San Francisco

Mon 11/24

11:38 am-12:10 am

2 stops10h 32m

Chicago O'Hare Intl

Wed 11/26

6:00 am-7:23 pm

1 stop15h 23m

$291

San FranciscoChicago

SFO - MDW

SFOMDW

San Francisco

Sat 12/6

10:10 am-4:10 pm

Nonstop4h 00m

Chicago Midway

Wed 12/10

8:15 am-11:00 am

Nonstop4h 45m

$292

San FranciscoChicago

SFO - MDW

SFOMDW

San Francisco

Fri 2/20

5:55 am-11:55 am

Nonstop4h 00m

Chicago Midway

Tue 2/24

10:05 am-5:05 pm

1 stop9h 00m

$293

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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 $282. If you’re not able to fly to Chicago in February, then September is your next best option. Flight prices from San Francisco to Chicago during September average around $291.

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 $405. 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 $506.

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 $412. In contrast, the most expensive time of day to depart to Chicago is at noon when prices are around $467.

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 $372 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 $293 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?

No. A direct flight is the cheapest option for a flight between San Francisco to Chicago.

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

As of November 2025, prices for San Francisco to Chicago flights are approximately 40% 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	$184
Fastest flight time	3h 55m
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 $184. The best round-trip flight deal from San Francisco to Chicago found on momondo in the last 72 hours is $397.

The fastest flight from San Francisco to Chicago takes 3h 55m

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 4h 00m 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 November 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 Airbus A321neo, making up 17.28% of the total bookings. Other popular models include Boeing 757-300 with 16.88%, Boeing 737-800 with 16.47%, and Boeing 737-900 with 11.71%.
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 36%, Alaska Airlines with 10%, 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 2,809 reviews	Search Hawaiian Airlines flights
Frontier	PriceFrom $128	Free Cancellation	Rating 5.8 3,112 reviews	Search Frontier flights
Delta	PriceFrom $128	Free Cancellation	Rating 7.9 8,008 reviews	Search Delta flights
United Airlines	PriceFrom $133	Free Cancellation	Rating 7.4 9,016 reviews	Search United Airlines flights
Southwest	PriceFrom $185	Free Cancellation	Rating 8.0 4,236 reviews	Search Southwest flights
Alaska Airlines	PriceFrom $196	Free Cancellation	Rating 8.0 11,282 reviews	Search Alaska Airlines flights
American Airlines	PriceFrom $197	Free Cancellation	Rating 7.2 11,050 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 6 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 $397. United Airlines operates 50 flights to Chicago from San Francisco in an average week. Users have rated it 7.4/10 across 9,016 reviews.

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Saint Joseph

Portage

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Valparaiso

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

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Find better results for your trip to the United States

Fly into one of these airports located in Chicago

Chicago Midway Airport

Chicago O'Hare Intl Airport

Chicago Greater Rockford Airport

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Flights to Denverfrom $58

Cheap flights from San Francisco to Chicago from $125

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 12/11. 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

Trusted and free

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Alaska Airlines flights from San Francisco to Chicago

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

Delta flights from San Francisco to Chicago

Our best Delta deals on San Francisco to Chicago flight tickets

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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

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 $412. In contrast, the most expensive time of day to depart to Chicago is at noon when prices are around $467.

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?

No. A direct flight is the cheapest option for a flight between San Francisco to Chicago.

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

As of November 2025, prices for San Francisco to Chicago flights are approximately 40% 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, Alaska Airlines, and Southwest 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: 63% 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 $174.

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?

53 flights are operational daily from San Francisco to Chicago as of November 2025. The most popular departure time for this route is 6:00AM, with 46% 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 375 per week as of November 2025. The most frequent departure day is Wed, with 18% 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.