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Cheap flights from San Francisco Bay Area to Chicago from $92

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 Bay Area to Chicago departing on 1/15. 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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0 bags

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Cheap round-trip flights

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Frontier Logo
10:34 am - 9:03 pm
SJC
-
ORD
8h 29m1 stop
Frontier Logo
6:34 pm - 7:55 am
ORD
-
SJC
15h 21m1 stop
$204Frontier
Thu, Feb 19 - Thu, Feb 26
Multiple Airlines Logo
6:49 pm - 3:17 pm
SJC
-
ORD
42h 28m2 stops
Multiple Airlines Logo
6:34 pm - 7:55 am
ORD
-
SJC
15h 21m1 stop
$221Multiple Airlines
Thu, Feb 19 - Thu, Feb 26
Multiple Airlines Logo
11:14 am - 9:11 pm
SJC
-
ORD
7h 57m1 stop
Multiple Airlines Logo
8:00 am - 2:42 pm
ORD
-
SJC
8h 42m1 stop
$232Multiple Airlines
Thu, Jan 15 - Tue, Jan 20
Multiple Airlines Logo
7:31 pm - 10:38 pm
SJC
-
ORD
49h 07m2 stops
Multiple Airlines Logo
9:38 pm - 9:42 am
ORD
-
SJC
14h 04m1 stop
$233Multiple Airlines
Mon, Jan 19 - Sun, Jan 25
Southwest Logo
5:55 am - 12:00 pm
OAK
-
MDW
4h 05mnonstop
Southwest Logo
8:55 pm - 11:50 pm
MDW
-
OAK
4h 55mnonstop
$236Southwest
Sat, Feb 7 - Sat, Feb 14
Southwest Logo
11:10 am - 5:15 pm
OAK
-
MDW
4h 05mnonstop
Southwest Logo
5:05 am - 12:35 pm
MDW
-
OAK
9h 30m1 stop
$242Southwest
Wed, Feb 11 - Wed, Feb 18
Hawaiian Airlines Logo
3:36 pm - 2:38 pm
SJC
-
ORD
21h 02m1 stop
Hawaiian Airlines Logo
3:44 pm - 10:35 pm
ORD
-
SJC
8h 51m1 stop
$253Hawaiian Airlines
Thu, Jan 22 - Tue, Jan 27
Alaska Airlines Logo
6:35 am - 11:59 pm
SFO
-
ORD
15h 24m1 stop
Alaska Airlines Logo
4:10 pm - 10:52 pm
ORD
-
SFO
8h 42m1 stop
$259Alaska Airlines
Mon, Apr 13 - Tue, Apr 21
Alaska Airlines Logo
5:31 pm - 12:01 pm
OAK
-
ORD
16h 30m1 stop
Alaska Airlines Logo
3:54 pm - 10:49 pm
ORD
-
OAK
8h 55m1 stop
$259Alaska Airlines
Wed, Feb 18 - Fri, Feb 20
United Airlines Logo
11:56 pm - 6:25 am
SFO
-
ORD
4h 29mnonstop
United Airlines Logo
2:40 pm - 5:36 pm
ORD
-
SFO
4h 56mnonstop
$265United Airlines
Wed, Jan 21 - Thu, Jan 22

Delta flights from San Francisco Bay Area to Chicago

Our best Delta deals on San Francisco Bay Area to Chicago flight tickets
Delta
Feb 7
OAK12:33 pmOakland
7h 19m
1 stop
ORD9:52 pmChicago O'Hare Intl
Feb 14
ORD5:15 pmChicago O'Hare Intl
6h 31m
1 stop
OAK9:46 pmOakland
$256
Find similar
Delta
Jan 26
SFO1:20 pmSan Francisco
6h 32m
1 stop
ORD9:52 pmChicago O'Hare Intl
Jan 29
ORD5:30 amChicago O'Hare Intl
9h 25m
1 stop
SFO12:55 pmSan Francisco
$261
Find similar
Delta
Feb 6
SFO10:54 pmSan Francisco
7h 58m
1 stop
MDW8:52 amChicago Midway
Feb 9
MDW1:26 pmChicago Midway
7h 12m
1 stop
SFO6:38 pmSan Francisco
$262
Find similar

American Airlines flights from San Francisco Bay Area to Chicago

Our best American Airlines deals on San Francisco Bay Area to Chicago flight tickets
American Airlines
Feb 21
SFO11:30 pmSan Francisco
4h 08m
ORD5:38 amChicago O'Hare Intl
Mar 1
ORD1:46 pmChicago O'Hare Intl
4h 57m
SFO4:43 pmSan Francisco
$269
Find similar
American Airlines
Feb 18
SFO9:25 amSan Francisco
9h 40m
1 stop
ORD9:05 pmChicago O'Hare Intl
Feb 20
ORD7:42 pmChicago O'Hare Intl
4h 58m
SFO10:40 pmSan Francisco
$270
Find similar
American Airlines
Mar 26
SFO5:33 pmSan Francisco
4h 15m
ORD11:48 pmChicago O'Hare Intl
Mar 28
ORD7:34 pmChicago O'Hare Intl
4h 58m
SFO10:32 pmSan Francisco
$274
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from San Francisco Bay Area 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 January 1, 2026.
Use the filters below to find and compare flights from San Francisco Bay Area to Chicago that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

San JoseChicago

SJC - ORD

SJCORD

San Jose

Thu 2/19

10:34 am-9:03 pm

1 stop8h 29m

Chicago O'Hare Intl

Thu 2/26

6:34 pm-7:55 am

1 stop15h 21m

$204

San JoseChicago

SJC - ORD

SJCORD

San Jose

Thu 2/19

6:49 pm-3:17 pm

2 stops42h 28m

Chicago O'Hare Intl

Thu 2/26

6:34 pm-7:55 am

1 stop15h 21m

$221

San JoseChicago

SJC - ORD

SJCORD

San Jose

Thu 1/15

11:14 am-9:11 pm

1 stop7h 57m

Chicago O'Hare Intl

Tue 1/20

8:00 am-2:42 pm

1 stop8h 42m

$232

San JoseChicago

SJC - ORD

SJCORD

San Jose

Mon 1/19

7:31 pm-10:38 pm

2 stops49h 07m

Chicago O'Hare Intl

Sun 1/25

9:38 pm-9:42 am

1 stop14h 04m

$233

OaklandChicago

OAK - MDW

OAKMDW

Oakland

Sat 2/7

5:55 am-12:00 pm

Nonstop4h 05m

Chicago Midway

Sat 2/14

8:55 pm-11:50 pm

Nonstop4h 55m

$236

OaklandChicago

OAK - MDW

OAKMDW

Oakland

Wed 2/11

11:10 am-5:15 pm

Nonstop4h 05m

Chicago Midway

Wed 2/18

5:05 am-12:35 pm

1 stop9h 30m

$242

San JoseChicago

SJC - ORD

SJCORD

San Jose

Thu 1/22

3:36 pm-2:38 pm

1 stop21h 02m

Chicago O'Hare Intl

Tue 1/27

3:44 pm-10:35 pm

1 stop8h 51m

$253

San FranciscoChicago

SFO - ORD

SFOORD

San Francisco

Mon 4/13

6:35 am-11:59 pm

1 stop15h 24m

Chicago O'Hare Intl

Tue 4/21

4:10 pm-10:52 pm

1 stop8h 42m

$259

OaklandChicago

OAK - ORD

OAKORD

Oakland

Wed 2/18

5:31 pm-12:01 pm

1 stop16h 30m

Chicago O'Hare Intl

Fri 2/20

3:54 pm-10:49 pm

1 stop8h 55m

$259

San FranciscoChicago

SFO - ORD

SFOORD

San Francisco

Wed 1/21

11:56 pm-6:25 am

Nonstop4h 29m

Chicago O'Hare Intl

Thu 1/22

2:40 pm-5:36 pm

Nonstop4h 56m

$265

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 Bay Area 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 Bay Area, with most prices found around $283. If you’re not able to fly to Chicago in February, then September is your next best option. Flight prices from San Francisco Bay Area 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 $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 Bay Area to Chicago for around $495.

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 evening. Flights from San Francisco Bay Area to Chicago during this time can be as low as $410. In contrast, the most expensive time of day to depart to Chicago is at noon when prices are around $459.

What is the cheapest San Francisco Bay Area to Chicago flight route?

Fly from San Francisco to Chicago O'Hare Intl for the best San Francisco Bay Area - 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 Bay Area when booking weeks ahead of your departure date. In general, you can expect to find flights to Chicago for around $371 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 Bay Area for as low as $289 on momondo.

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

There are 4 cabin classes available to choose from on San Francisco Bay Area 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 Bay Area to Chicago flights?

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

Cheap San Francisco Bay Area to Chicago flight deals and tips

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

Fastest flight time

3h 55m

Direct flights

Every day

Airports in Chicago

3 airports
The fastest flight from San Francisco Bay Area to Chicago takes 3h 55m
Direct flights go from San Francisco Bay Area to Chicago every day.
There are 3 airports in Chicago. From San Francisco Bay Area there are direct flights to Chicago Midway (MDW).
Search flight deals

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

    Prices for flights from San Francisco Bay Area to Chicago are refreshed on a daily basis.

  • How many operators does momondo search for flights from San Francisco Bay Area to Chicago?

  • How old do you have to be to fly from San Francisco Bay Area 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 Bay Area to Chicago.

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

    The travel and health documents you'll need for your trip to Chicago may differ based on your itinerary and personal situation. Typically, you should have several documents on hand, such as a national ID card or driver's license and a passport that is valid for six months after your intended arrival at Chicago. It is always advisable to seek advice from your airline or a trusted third party, such as IATA.

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

Best airlines flying from San Francisco Bay Area to Chicago

Compare and see reviews for airlines that fly from San Francisco Bay Area to Chicago with momondo
Airline
Rating
Free Cancellation
Price
FrontierPriceFrom $65Free CancellationRating
5.7
3,067 reviews
Search Frontier flights
Spirit AirlinesPriceFrom $108Free CancellationRating
6.3
8,248 reviews
Search Spirit Airlines flights
Hawaiian AirlinesPriceFrom $108Free CancellationRating
7.8
2,822 reviews
Search Hawaiian Airlines flights
DeltaPriceFrom $128Free CancellationRating
7.9
8,012 reviews
Search Delta flights
United AirlinesPriceFrom $133Free CancellationRating
7.4
9,125 reviews
Search United Airlines flights
Alaska AirlinesPriceFrom $170Free CancellationRating
8.0
11,589 reviews
Search Alaska Airlines flights
SouthwestPriceFrom $185Free CancellationRating
8.0
4,250 reviews
Search Southwest flights
American AirlinesPriceFrom $197Free CancellationRating
7.2
11,069 reviews
Search American Airlines flights

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
Portage
Lansing
Schererville
Valparaiso
Munster
Crown Point
Chesterton
Monticello
Porter
Griffith
Saint John

Why use momondo?

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

It is quick and easy to find San Francisco Bay Area to Chicago flights on momondo. We search and return numerous flight options from various airlines and agents. You can then use our filters to narrow your search until you have found the most convenient flight to Chicago that suits you.

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

All flight searches from San Francisco Bay Area to Chicago on momondo can be filtered to show those which offer flexible booking policies.

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

momondo provides multiple filters to help you find the best flight to Chicago from San Francisco Bay Area. 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 Bay Area to Chicago right now. Can momondo alert me if prices change?

Of course. momondo tracks the price of San Francisco Bay Area to Chicago flights. All you need is a valid email address and we will do the rest; it is that quick and easy.

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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