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Cheap flights from San Francisco Bay Area to Chicago from $124

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 12/5. 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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Find the cheapest flights from San Francisco Bay Area to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
Multiple Airlines Logo
7:00 am - 12:13 amSTS-ORD
15h 13m1 stop
Multiple Airlines Logo
3:05 pm - 10:54 pmORD-STS
9h 49m1 stop
$239Multiple Airlines
Find Deal
Mon, Dec 8 - Tue, Dec 16
Southwest Logo
5:55 am - 12:00 pmOAK-MDW
4h 05mnonstop
Southwest Logo
7:40 pm - 10:35 pmMDW-OAK
4h 55mnonstop
$255Southwest
Find Deal
Sat, Jan 10 - Sat, Jan 17
Multiple Airlines Logo
8:10 am - 8:57 pmOAK-ORD
34h 47m2 stops
Multiple Airlines Logo
8:00 am - 4:28 pmORD-OAK
10h 28m1 stop
$263Multiple Airlines
Find Deal
Sat, Jan 10 - Sat, Jan 17
Alaska Airlines Logo
2:31 pm - 11:59 pmOAK-ORD
7h 28m1 stop
Alaska Airlines Logo
3:35 pm - 11:59 pmORD-OAK
10h 24m1 stop
$271Alaska Airlines
Find Deal
Wed, Dec 3 - Tue, Dec 9
Delta Logo
5:55 am - 1:38 pmOAK-ORD
5h 43m1 stop
Delta Logo
7:20 am - 11:57 amORD-OAK
6h 37m1 stop
$275Delta
Find Deal
Wed, Jan 14 - Sat, Jan 17
Delta Logo
12:30 pm - 9:21 pmOAK-ORD
6h 51m1 stop
Delta Logo
7:40 pm - 12:08 amORD-OAK
6h 28m1 stop
$277Delta
Find Deal
Sat, Dec 13 - Wed, Dec 17
Alaska Airlines Logo
6:15 am - 4:33 pmOAK-ORD
8h 18m1 stop
Alaska Airlines Logo
7:00 am - 4:37 pmORD-OAK
11h 37m1 stop
$281Alaska Airlines
Find Deal
Tue, Mar 3 - Wed, Mar 4
Frontier Logo
4:07 pm - 11:08 amSFO-MDW
17h 01m1 stop
Frontier Logo
6:15 am - 1:18 pmMDW-SFO
9h 03m1 stop
$297Frontier
Find Deal
Thu, Dec 4 - Sun, Dec 7
Frontier Logo
6:30 am - 11:08 amSFO-MDW
26h 38m1 stop
Frontier Logo
9:15 am - 11:52 pmMDW-SFO
40h 37m2 stops
$300Frontier
Find Deal
Sat, Dec 13 - Sat, Dec 27
Hawaiian Airlines Logo
8:00 pm - 8:02 pmSJC-ORD
22h 02m1 stop
Hawaiian Airlines Logo
8:39 am - 2:16 pmORD-SJC
7h 37m1 stop
$307Hawaiian Airlines
Find Deal
Tue, Dec 30 - Tue, Jan 6

Alaska Airlines flights from San Francisco Bay Area to Chicago

Our best Alaska Airlines deals on San Francisco Bay Area to Chicago flight tickets
Alaska Airlines
Dec 3
OAK2:31 pmOakland
7h 28m
1 stop
ORD11:59 pmChicago O'Hare Intl
Dec 9
ORD3:35 pmChicago O'Hare Intl
10h 24m
1 stop
OAK11:59 pmOakland
$271
Find similar
Alaska Airlines
Mar 3
OAK6:15 amOakland
8h 18m
1 stop
ORD4:33 pmChicago O'Hare Intl
Mar 4
ORD7:00 amChicago O'Hare Intl
11h 37m
1 stop
OAK4:37 pmOakland
$281
Find similar
Alaska Airlines
Dec 3
OAK2:31 pmOakland
7h 28m
1 stop
ORD11:59 pmChicago O'Hare Intl
Dec 8
ORD5:51 pmChicago O'Hare Intl
8h 08m
1 stop
OAK11:59 pmOakland
$282
Find similar

Delta flights from San Francisco Bay Area to Chicago

Our best Delta deals on San Francisco Bay Area to Chicago flight tickets
Delta
Jan 14
OAK5:55 amOakland
5h 43m
1 stop
ORD1:38 pmChicago O'Hare Intl
Jan 17
ORD7:20 amChicago O'Hare Intl
6h 37m
1 stop
OAK11:57 amOakland
$275
Find similar
Delta
Dec 13
OAK12:30 pmOakland
6h 51m
1 stop
ORD9:21 pmChicago O'Hare Intl
Dec 17
ORD7:40 pmChicago O'Hare Intl
6h 28m
1 stop
OAK12:08 amOakland
$277
Find similar
Delta
Jan 14
OAK5:55 amOakland
10h 00m
2 stops
ORD5:55 pmChicago O'Hare Intl
Jan 17
ORD7:20 amChicago O'Hare Intl
6h 37m
1 stop
OAK11:57 amOakland
$280
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 November 17, 2025.
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

Santa RosaChicago

STS - ORD

STSORD

Santa Rosa Sonoma County

Mon 12/8

7:00 am-12:13 am

1 stop15h 13m

Chicago O'Hare Intl

Tue 12/16

3:05 pm-10:54 pm

1 stop9h 49m

$239

OaklandChicago

OAK - MDW

OAKMDW

Oakland

Sat 1/10

5:55 am-12:00 pm

Nonstop4h 05m

Chicago Midway

Sat 1/17

7:40 pm-10:35 pm

Nonstop4h 55m

$255

OaklandChicago

OAK - ORD

OAKORD

Oakland

Sat 1/10

8:10 am-8:57 pm

2 stops34h 47m

Chicago O'Hare Intl

Sat 1/17

8:00 am-4:28 pm

1 stop10h 28m

$263

OaklandChicago

OAK - ORD

OAKORD

Oakland

Wed 12/3

2:31 pm-11:59 pm

1 stop7h 28m

Chicago O'Hare Intl

Tue 12/9

3:35 pm-11:59 pm

1 stop10h 24m

$271

OaklandChicago

OAK - ORD

OAKORD

Oakland

Wed 1/14

5:55 am-1:38 pm

1 stop5h 43m

Chicago O'Hare Intl

Sat 1/17

7:20 am-11:57 am

1 stop6h 37m

$275

OaklandChicago

OAK - ORD

OAKORD

Oakland

Sat 12/13

12:30 pm-9:21 pm

1 stop6h 51m

Chicago O'Hare Intl

Wed 12/17

7:40 pm-12:08 am

1 stop6h 28m

$277

OaklandChicago

OAK - ORD

OAKORD

Oakland

Tue 3/3

6:15 am-4:33 pm

1 stop8h 18m

Chicago O'Hare Intl

Wed 3/4

7:00 am-4:37 pm

1 stop11h 37m

$281

San FranciscoChicago

SFO - MDW

SFOMDW

San Francisco

Thu 12/4

4:07 pm-11:08 am

1 stop17h 01m

Chicago Midway

Sun 12/7

6:15 am-1:18 pm

1 stop9h 03m

$297

San FranciscoChicago

SFO - MDW

SFOMDW

San Francisco

Sat 12/13

6:30 am-11:08 am

1 stop26h 38m

Chicago Midway

Sat 12/27

9:15 am-11:52 pm

2 stops40h 37m

$300

San JoseChicago

SJC - ORD

SJCORD

San Jose

Tue 12/30

8:00 pm-8:02 pm

1 stop22h 02m

Chicago O'Hare Intl

Tue 1/6

8:39 am-2:16 pm

1 stop7h 37m

$307

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 $282. 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 $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 Bay Area 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 Bay Area 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 Bay Area to Chicago flight route?

Fly from San Francisco to Chicago Midway 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 $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 Bay Area for as low as $293 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

4h 00m

Direct flights

Every day

Airports in Chicago

1 airport
The fastest flight from San Francisco Bay Area to Chicago takes 4h 00m
Direct flights go from San Francisco Bay Area to Chicago every day.
There is 1 airport near Chicago: 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 $98Free CancellationRating
5.8
3,106 reviews
Search Frontier flights
Spirit AirlinesPriceFrom $108Free CancellationRating
6.3
8,144 reviews
Search Spirit Airlines flights
Hawaiian AirlinesPriceFrom $108Free CancellationRating
7.8
2,809 reviews
Search Hawaiian Airlines flights
DeltaPriceFrom $128Free CancellationRating
7.9
8,006 reviews
Search Delta flights
United AirlinesPriceFrom $133Free CancellationRating
7.4
9,014 reviews
Search United Airlines flights
Alaska AirlinesPriceFrom $170Free CancellationRating
8.0
11,309 reviews
Search Alaska Airlines flights
SouthwestPriceFrom $185Free CancellationRating
8.0
4,244 reviews
Search Southwest flights
American AirlinesPriceFrom $197Free CancellationRating
7.2
11,048 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
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 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