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Cheap flights from San Francisco to Chicago from $165

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 16/12. 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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Cheap return flights

Alaska Airlines Logo
21:57 - 18:54SFO-ORD
18h 57m1 stop
Alaska Airlines Logo
19:59 - 08:06ORD-SFO
14h 07m1 stop
$330Alaska Airlines
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Mon, 8 Dec - Wed, 10 Dec
Alaska Airlines Logo
10:26 - 23:59SFO-ORD
11h 33m1 stop
Alaska Airlines Logo
19:59 - 11:01ORD-SFO
17h 02m1 stop
$361Alaska Airlines
Find Deal
Tue, 21 Oct - Tue, 28 Oct
Alaska Airlines Logo
10:26 - 23:59SFO-ORD
11h 33m1 stop
Alaska Airlines Logo
09:20 - 18:14ORD-SFO
10h 54m1 stop
$365Alaska Airlines
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Wed, 22 Oct - Sun, 26 Oct
Alaska Airlines Logo
08:00 - 23:10SFO-ORD
13h 10m2 stops
Alaska Airlines Logo
09:00 - 19:27ORD-SFO
12h 27m2 stops
$386Alaska Airlines
Find Deal
Thu, 19 Feb - Mon, 23 Feb
Alaska Airlines Logo
10:26 - 23:59SFO-ORD
11h 33m1 stop
Alaska Airlines Logo
14:54 - 22:18ORD-SFO
9h 24m1 stop
$389Alaska Airlines
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Tue, 21 Oct - Fri, 7 Nov
Hawaiian Airlines Logo
14:30 - 23:10SFO-ORD
6h 40m1 stop
Hawaiian Airlines Logo
09:00 - 16:05ORD-SFO
9h 05m1 stop
$427Hawaiian Airlines
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Wed, 21 Jan - Sat, 31 Jan
United Airlines Logo
18:35 - 00:54SFO-ORD
4h 19mdirect
United Airlines Logo
21:13 - 23:59ORD-SFO
4h 46mdirect
$435United Airlines
Find Deal
Wed, 15 Oct - Mon, 20 Oct
Hawaiian Airlines Logo
20:43 - 06:22SFO-ORD
7h 39m1 stop
Hawaiian Airlines Logo
14:54 - 22:01ORD-SFO
9h 07m1 stop
$450Hawaiian Airlines
Find Deal
Fri, 31 Oct - Tue, 4 Nov
United Airlines Logo
05:10 - 11:30SFO-ORD
4h 20mdirect
United Airlines Logo
12:45 - 15:35ORD-SFO
4h 50mdirect
$453United Airlines
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Mon, 27 Oct - Wed, 19 Nov
Delta Logo
00:35 - 11:35SFO-ORD
9h 00m1 stop
Delta Logo
07:37 - 16:05ORD-SFO
10h 28m1 stop
$465Delta
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Mon, 20 Oct - Thu, 23 Oct

Alaska Airlines flights from San Francisco to Chicago

Our best Alaska Airlines deals on San Francisco to Chicago flight tickets
Alaska Airlines
8 Dec
SFO21:57San Francisco
18h 57m
1 stop
ORD18:54Chicago O'Hare Intl
10 Dec
ORD19:59Chicago O'Hare Intl
14h 07m
1 stop
SFO08:06San Francisco
$330
Find similar
Alaska Airlines
21 Oct
SFO10:26San Francisco
11h 33m
1 stop
ORD23:59Chicago O'Hare Intl
28 Oct
ORD19:59Chicago O'Hare Intl
17h 02m
1 stop
SFO11:01San Francisco
$361
Find similar
Alaska Airlines
22 Oct
SFO10:26San Francisco
11h 33m
1 stop
ORD23:59Chicago O'Hare Intl
26 Oct
ORD09:20Chicago O'Hare Intl
10h 54m
1 stop
SFO18:14San Francisco
$365
Find similar

United Airlines flights from San Francisco to Chicago

Our best United Airlines deals on San Francisco to Chicago flight tickets
United Airlines
15 Oct
SFO18:35San Francisco
4h 19m
ORD00:54Chicago O'Hare Intl
20 Oct
ORD21:13Chicago O'Hare Intl
4h 46m
SFO23:59San Francisco
$435
Find similar
United Airlines
27 Oct
SFO05:10San Francisco
4h 20m
ORD11:30Chicago O'Hare Intl
19 Nov
ORD12:45Chicago O'Hare Intl
4h 50m
SFO15:35San Francisco
$453
Find similar
United Airlines
6 Nov
SFO05:10San Francisco
4h 20m
ORD11:30Chicago O'Hare Intl
10 Nov
ORD06:15Chicago O'Hare Intl
4h 49m
SFO09:04San Francisco
$456
Find similar

momondo Fare Finder

 
Customise your flight search to find flights from San Francisco 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, momondo users made 78,305 searches. Data last updated 21 September 2025.
Use the filters below to find and compare flights from San Francisco to Chicago that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

San FranciscoChicago

SFO - ORD

SFOORD

San Francisco

Mon 8/12

21:57-18:54

1 stop18h 57m

Chicago O'Hare Intl

Wed 10/12

19:59-08:06

1 stop14h 07m

$330

San FranciscoChicago

SFO - ORD

SFOORD

San Francisco

Tue 21/10

10:26-23:59

1 stop11h 33m

Chicago O'Hare Intl

Tue 28/10

19:59-11:01

1 stop17h 02m

$361

San FranciscoChicago

SFO - ORD

SFOORD

San Francisco

Wed 22/10

10:26-23:59

1 stop11h 33m

Chicago O'Hare Intl

Sun 26/10

09:20-18:14

1 stop10h 54m

$365

San FranciscoChicago

SFO - ORD

SFOORD

San Francisco

Thu 19/2

08:00-23:10

2 stops13h 10m

Chicago O'Hare Intl

Mon 23/2

09:00-19:27

2 stops12h 27m

$386

San FranciscoChicago

SFO - ORD

SFOORD

San Francisco

Tue 21/10

10:26-23:59

1 stop11h 33m

Chicago O'Hare Intl

Fri 7/11

14:54-22:18

1 stop9h 24m

$389

San FranciscoChicago

SFO - ORD

SFOORD

San Francisco

Wed 21/1

14:30-23:10

1 stop6h 40m

Chicago O'Hare Intl

Sat 31/1

09:00-16:05

1 stop9h 05m

$427

San FranciscoChicago

SFO - ORD

SFOORD

San Francisco

Wed 15/10

18:35-00:54

Nonstop4h 19m

Chicago O'Hare Intl

Mon 20/10

21:13-23:59

Nonstop4h 46m

$435

San FranciscoChicago

SFO - ORD

SFOORD

San Francisco

Fri 31/10

20:43-06:22

1 stop7h 39m

Chicago O'Hare Intl

Tue 4/11

14:54-22:01

1 stop9h 07m

$450

San FranciscoChicago

SFO - ORD

SFOORD

San Francisco

Mon 27/10

05:10-11:30

Nonstop4h 20m

Chicago O'Hare Intl

Wed 19/11

12:45-15:35

Nonstop4h 50m

$453

San FranciscoChicago

SFO - ORD

SFOORD

San Francisco

Mon 20/10

00:35-11:35

1 stop9h 00m

Chicago O'Hare Intl

Thu 23/10

07:37-16:05

1 stop10h 28m

$465

Flights are sorted by cheapest return flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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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?

If you don’t want to visit Chicago in February, then you should wait until January to fly from San Francisco, when ticket prices are also cheap, with an average price of $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 $557 when searching weeks before you fly. 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 $461 on momondo.

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

There are 3 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 45% 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 return 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

Fastest flight time

4h 08m

Direct flights

Every day

Airports in Chicago

1 airport
The fastest flight from San Francisco to Chicago takes 4h 08m
Direct flights go from San Francisco to Chicago every day.
There is 1 airport near Chicago: Chicago O'Hare Intl (ORD)
Search flight deals

  • How far is San Francisco to Chicago by plane?

    The straight-line distance from San Francisco to Chicago is 2981.9 km. A reasonable flight in good conditions will take 4h 19m.

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

    Prices for flights from San Francisco Airport to Chicago were last updated today.

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

    Although the minimum age for a child to fly alone is five, airlines that offer an unaccompanied minor (UMNR) service may have their own age limits, which could be impacted by factors such as flight length, timing, and stopovers. 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 licence, 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?

Why use momondo?

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

momondo collates all your flight options in one place and lets you filter them to find the perfect flight from San Francisco to Chicago. momondo saves you time and could save you money on your trip.

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

momondo does allow users to show only those flights to Chicago from San Francisco which offer a flexible booking policy as well as other useful filters and features.

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

momondo helps you find the best flight between San Francisco and Chicago by providing filters to narrow your choice of flights to those matching your criteria. You can select flights based on numerous factors such as price, departure and landing times, airport and airline.

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

Yes momondo offers price alerts on flights to Chicago from San Francisco. After performing a search on this page you should be able to see the price alert set up feature. Simply provide a valid email address and momondo will instantly alert you when prices change.

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Find better results for your trip to the United States

Fly into one of these airports located in Chicago

Airports listed have a maximum distance of 25.6 km from Chicago
Chicago Midway Airport
Chicago O'Hare Intl Airport