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Cheap flights from San Francisco to Chicago from $99

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 10/4. 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 round-trip flights

Frontier Logo
6:39 pm - 11:30 amSFO-MDW
14h 51m2 stops
Frontier Logo
1:37 pm - 9:11 pmMDW-SFO
9h 34m1 stop
$202Frontier
Find Deal
Sat, Nov 8 - Mon, Nov 10
Frontier Logo
10:25 pm - 12:58 pmSFO-ORD
12h 33m1 stop
Frontier Logo
6:00 am - 2:09 pmORD-SFO
10h 09m2 stops
$202Frontier
Find Deal
Thu, Oct 23 - Fri, Nov 7
Frontier Logo
8:00 am - 11:20 pmSFO-MDW
13h 20m2 stops
Frontier Logo
8:30 am - 4:43 pmMDW-SFO
10h 13m1 stop
$203Frontier
Find Deal
Sat, Oct 25 - Thu, Nov 6
Frontier Logo
10:49 am - 9:28 pmSFO-ORD
8h 39m1 stop
Frontier Logo
5:10 am - 6:19 pmORD-SFO
15h 09m2 stops
$203Frontier
Find Deal
Sat, Sep 20 - Mon, Sep 22
American Airlines Logo
11:25 pm - 5:34 amSFO-ORD
4h 09mnonstop
American Airlines Logo
6:45 am - 9:22 amORD-SFO
4h 37mnonstop
$217American Airlines
Find Deal
Fri, Oct 24 - Mon, Oct 27
American Airlines Logo
2:22 pm - 8:40 pmSFO-ORD
4h 18mnonstop
American Airlines Logo
7:15 pm - 10:09 pmORD-SFO
4h 54mnonstop
$218American Airlines
Find Deal
Fri, Oct 3 - Fri, Oct 10
Southwest Logo
9:25 am - 3:35 pmSFO-MDW
4h 10mnonstop
Southwest Logo
3:50 pm - 6:25 pmMDW-SFO
4h 35mnonstop
$218Southwest
Find Deal
Sun, Aug 31 - Tue, Sep 9
Southwest Logo
5:15 am - 1:15 pmSFO-MDW
6h 00m1 stop
Southwest Logo
6:50 pm - 11:20 pmMDW-SFO
6h 30m1 stop
$227Southwest
Find Deal
Tue, Sep 16 - Fri, Sep 19
United Airlines Logo
5:15 am - 11:46 amSFO-ORD
4h 31mnonstop
United Airlines Logo
7:43 pm - 10:34 pmORD-SFO
4h 51mnonstop
$233United Airlines
Find Deal
Thu, Sep 11 - Sat, Sep 13
Hawaiian Airlines Logo
8:19 pm - 7:03 amSFO-ORD
8h 44m1 stop
Hawaiian Airlines Logo
6:20 am - 1:44 pmORD-SFO
9h 24m1 stop
$236Hawaiian Airlines
Find Deal
Mon, Sep 15 - Wed, Sep 17

American Airlines flights from San Francisco to Chicago

Our best American Airlines deals on San Francisco to Chicago flight tickets
American Airlines
Oct 24
SFO11:25 pmSan Francisco
4h 09m
ORD5:34 amChicago O'Hare Intl
Oct 27
ORD6:45 amChicago O'Hare Intl
4h 37m
SFO9:22 amSan Francisco
$217
Find similar
American Airlines
Oct 3
SFO2:22 pmSan Francisco
4h 18m
ORD8:40 pmChicago O'Hare Intl
Oct 10
ORD7:15 pmChicago O'Hare Intl
4h 54m
SFO10:09 pmSan Francisco
$218
Find similar
American Airlines
Aug 31
SFO8:00 amSan Francisco
4h 20m
ORD2:20 pmChicago O'Hare Intl
Sep 9
ORD6:05 pmChicago O'Hare Intl
4h 50m
SFO8:55 pmSan Francisco
$228
Find similar

Frontier flights from San Francisco to Chicago

Our best Frontier deals on San Francisco to Chicago flight tickets
Frontier
Oct 23
SFO10:25 pmSan Francisco
12h 33m
1 stop
ORD12:58 pmChicago O'Hare Intl
Nov 7
ORD6:00 amChicago O'Hare Intl
10h 09m
2 stops
SFO2:09 pmSan Francisco
$202
Find similar
Frontier
Aug 25
SFO10:29 pmSan Francisco
13h 04m
1 stop
ORD1:33 pmChicago O'Hare Intl
Aug 28
ORD7:00 amChicago O'Hare Intl
7h 07m
1 stop
SFO12:07 pmSan Francisco
$203
Find similar
Frontier
Sep 12
SFO6:29 amSan Francisco
7h 24m
1 stop
MDW3:53 pmChicago Midway
Sep 15
MDW6:20 amChicago Midway
13h 59m
2 stops
SFO6:19 pmSan Francisco
$204
Find similar

momondo Fare Finder

 
Customize 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 832,500 searches. Data last updated August 20, 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 - MDW

SFOMDW

San Francisco

Sat 11/8

6:39 pm-11:30 am

2 stops14h 51m

Chicago Midway

Mon 11/10

1:37 pm-9:11 pm

1 stop9h 34m

$202

San FranciscoChicago

SFO - ORD

SFOORD

San Francisco

Thu 10/23

10:25 pm-12:58 pm

1 stop12h 33m

Chicago O'Hare Intl

Fri 11/7

6:00 am-2:09 pm

2 stops10h 09m

$202

San FranciscoChicago

SFO - MDW

SFOMDW

San Francisco

Sat 10/25

8:00 am-11:20 pm

2 stops13h 20m

Chicago Midway

Thu 11/6

8:30 am-4:43 pm

1 stop10h 13m

$203

San FranciscoChicago

SFO - ORD

SFOORD

San Francisco

Sat 9/20

10:49 am-9:28 pm

1 stop8h 39m

Chicago O'Hare Intl

Mon 9/22

5:10 am-6:19 pm

2 stops15h 09m

$203

San FranciscoChicago

SFO - ORD

SFOORD

San Francisco

Fri 10/24

11:25 pm-5:34 am

Nonstop4h 09m

Chicago O'Hare Intl

Mon 10/27

6:45 am-9:22 am

Nonstop4h 37m

$217

San FranciscoChicago

SFO - ORD

SFOORD

San Francisco

Fri 10/3

2:22 pm-8:40 pm

Nonstop4h 18m

Chicago O'Hare Intl

Fri 10/10

7:15 pm-10:09 pm

Nonstop4h 54m

$218

San FranciscoChicago

SFO - MDW

SFOMDW

San Francisco

Sun 8/31

9:25 am-3:35 pm

Nonstop4h 10m

Chicago Midway

Tue 9/9

3:50 pm-6:25 pm

Nonstop4h 35m

$218

San FranciscoChicago

SFO - MDW

SFOMDW

San Francisco

Tue 9/16

5:15 am-1:15 pm

1 stop6h 00m

Chicago Midway

Fri 9/19

6:50 pm-11:20 pm

1 stop6h 30m

$227

San FranciscoChicago

SFO - ORD

SFOORD

San Francisco

Thu 9/11

5:15 am-11:46 am

Nonstop4h 31m

Chicago O'Hare Intl

Sat 9/13

7:43 pm-10:34 pm

Nonstop4h 51m

$233

San FranciscoChicago

SFO - ORD

SFOORD

San Francisco

Mon 9/15

8:19 pm-7:03 am

1 stop8h 44m

Chicago O'Hare Intl

Wed 9/17

6:20 am-1:44 pm

1 stop9h 24m

$236

Flights are sorted by cheapest round-trip 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?

The month of February is, on average, the cheapest month to fly to Chicago from San Francisco, with most prices found around $286. 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 $307.

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 $404. 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 $512.

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 $415. In contrast, the most expensive time of day to depart to Chicago is at noon when prices are around $474.

What is the cheapest San Francisco to Chicago flight route?

Fly from San Francisco to Chicago O'Hare Intl 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 $365 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 $292 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 29% 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 August 2025, prices for San Francisco to Chicago flights are approximately 8% 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

$99

Fastest flight time

4h 00m

Direct flights

Every day

Airports in Chicago

3 airports
The best one-way flight to Chicago from San Francisco in the past 72 hours is $99. The best round-trip flight deal from San Francisco to Chicago found on momondo in the last 72 hours is $202.
The fastest flight from San Francisco to Chicago takes 4h 00m
Direct flights go from San Francisco to Chicago every day.
There are 3 airports near Chicago: Chicago O'Hare Intl (ORD), Chicago Midway (MDW), Chicago Greater Rockford (RFD)
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 05m 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?

  • 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?

  • 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
Airline
Rating
Free Cancellation
Price
Hawaiian AirlinesPriceFrom $108Free CancellationRating
7.8
2,668 reviews
Search Hawaiian Airlines flights
FrontierPriceFrom $118Free CancellationRating
5.8
3,207 reviews
Search Frontier flights
DeltaPriceFrom $128Free CancellationRating
7.9
7,982 reviews
Search Delta flights
United AirlinesPriceFrom $133Free CancellationRating
7.4
8,928 reviews
Search United Airlines flights
Spirit AirlinesPriceFrom $143Free CancellationRating
6.3
8,039 reviews
Search Spirit Airlines flights
SouthwestPriceFrom $185Free CancellationRating
8.0
4,246 reviews
Search Southwest flights
Alaska AirlinesPriceFrom $192Free CancellationRating
8.0
10,000 reviews
Search Alaska Airlines flights
American AirlinesPriceFrom $197Free CancellationRating
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 $337. 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 $356. United Airlines operates 51 flights to Chicago from San Francisco in an average week. Users have rated it 7.4/10 across 8,928 reviews.

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
New Buffalo
Hammond
Benton Harbor
Saint Joseph
Lansing
Portage
Schererville
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

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

Fly into one of these airports located in Chicago

Airports listed have a maximum distance of 78.5 mi from Chicago
Chicago Midway Airport
Chicago O'Hare Intl Airport
Chicago Greater Rockford Airport