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Cheap flights from San Francisco Bay Area to Chicago from $127

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 12/17. 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

Enter your travel dates to find the best prices.
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
Southwest Logo
11:10 am - 5:15 pmOAK-MDW
4h 05mnonstop
Southwest Logo
8:25 am - 3:05 pmMDW-OAK
8h 40m1 stop
$265Southwest
Find Deal
Wed, Jan 7 - Sat, Jan 10
Southwest Logo
11:10 am - 5:15 pmOAK-MDW
4h 05mnonstop
Southwest Logo
7:40 pm - 10:35 pmMDW-OAK
4h 55mnonstop
$267Southwest
Find Deal
Wed, Jan 7 - Sat, Jan 10
Southwest Logo
8:30 pm - 5:05 amOAK-MDW
6h 35m1 stop
Southwest Logo
8:25 am - 3:05 pmMDW-OAK
8h 40m1 stop
$275Southwest
Find Deal
Wed, Jan 7 - Sat, Jan 10
Southwest Logo
5:25 am - 11:30 amOAK-MDW
4h 05mnonstop
Southwest Logo
3:10 pm - 8:05 pmMDW-OAK
6h 55m1 stop
$277Southwest
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Sun, Dec 7 - Tue, Dec 9
Delta Logo
5:55 am - 6:18 pmOAK-MDW
10h 23m2 stops
Delta Logo
1:14 pm - 10:00 pmMDW-OAK
10h 46m2 stops
$285Delta
Find Deal
Wed, Dec 3 - Sat, Dec 6
Delta Logo
2:00 pm - 11:47 pmSFO-MDW
7h 47m1 stop
Delta Logo
1:49 pm - 11:30 pmMDW-SFO
11h 41m2 stops
$294Delta
Find Deal
Tue, Dec 9 - Sun, Jan 18
Delta Logo
7:15 am - 4:39 pmSFO-MDW
7h 24m1 stop
Delta Logo
6:00 am - 2:47 pmMDW-SFO
10h 47m1 stop
$296Delta
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Thu, Nov 27 - Sat, Dec 6
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
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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

Southwest flights from San Francisco Bay Area to Chicago Midway Airport

Our best Southwest deals on San Francisco Bay Area to Chicago Midway Airport flight tickets
Southwest
Jan 10
OAK5:55 amOakland
4h 05m
MDW12:00 pmChicago Midway
Jan 17
MDW7:40 pmChicago Midway
4h 55m
OAK10:35 pmOakland
$255
Find similar
Southwest
Jan 7
OAK11:10 amOakland
4h 05m
MDW5:15 pmChicago Midway
Jan 10
MDW8:25 amChicago Midway
8h 40m
1 stop
OAK3:05 pmOakland
$265
Find similar
Southwest
Jan 7
OAK11:10 amOakland
4h 05m
MDW5:15 pmChicago Midway
Jan 10
MDW7:40 pmChicago Midway
4h 55m
OAK10:35 pmOakland
$267
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Delta flights from San Francisco Bay Area to Chicago Midway Airport

Our best Delta deals on San Francisco Bay Area to Chicago Midway Airport flight tickets
Delta
Dec 3
OAK5:55 amOakland
10h 23m
2 stops
MDW6:18 pmChicago Midway
Dec 6
MDW1:14 pmChicago Midway
10h 46m
2 stops
OAK10:00 pmOakland
$285
Find similar
Delta
Dec 9
SFO2:00 pmSan Francisco
7h 47m
1 stop
MDW11:47 pmChicago Midway
Jan 18
MDW1:49 pmChicago Midway
11h 41m
2 stops
SFO11:30 pmSan Francisco
$294
Find similar
Delta
Nov 27
SFO12:30 pmSan Francisco
9h 10m
1 stop
MDW11:40 pmChicago Midway
Dec 6
MDW9:29 amChicago Midway
6h 54m
1 stop
SFO2:23 pmSan Francisco
$296
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momondo Fare Finder

 
Customize your flight search to find flights from San Francisco Bay Area to Chicago Midway Airport 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 Midway Airport that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

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 - MDW

OAKMDW

Oakland

Wed 1/7

11:10 am-5:15 pm

Nonstop4h 05m

Chicago Midway

Sat 1/10

8:25 am-3:05 pm

1 stop8h 40m

$265

OaklandChicago

OAK - MDW

OAKMDW

Oakland

Wed 1/7

11:10 am-5:15 pm

Nonstop4h 05m

Chicago Midway

Sat 1/10

7:40 pm-10:35 pm

Nonstop4h 55m

$267

OaklandChicago

OAK - MDW

OAKMDW

Oakland

Wed 1/7

8:30 pm-5:05 am

1 stop6h 35m

Chicago Midway

Sat 1/10

8:25 am-3:05 pm

1 stop8h 40m

$275

OaklandChicago

OAK - MDW

OAKMDW

Oakland

Sun 12/7

5:25 am-11:30 am

Nonstop4h 05m

Chicago Midway

Tue 12/9

3:10 pm-8:05 pm

1 stop6h 55m

$277

OaklandChicago

OAK - MDW

OAKMDW

Oakland

Wed 12/3

5:55 am-6:18 pm

2 stops10h 23m

Chicago Midway

Sat 12/6

1:14 pm-10:00 pm

2 stops10h 46m

$285

San FranciscoChicago

SFO - MDW

SFOMDW

San Francisco

Tue 12/9

2:00 pm-11:47 pm

1 stop7h 47m

Chicago Midway

Sun 1/18

1:49 pm-11:30 pm

2 stops11h 41m

$294

San FranciscoChicago

SFO - MDW

SFOMDW

San Francisco

Thu 11/27

7:15 am-4:39 pm

1 stop7h 24m

Chicago Midway

Sat 12/6

6:00 am-2:47 pm

1 stop10h 47m

$296

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

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 Midway Airport

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 Midway Airport?

The month of January is, on average, the cheapest month to fly to Chicago Midway Airport from San Francisco Bay Area, with most prices found around $207. If you are unable to visit Chicago Midway Airport during the month of January, then departing from San Francisco Bay Area during the month February is also very affordable. Most momondo users find prices during this month for around $242.

What is the cheapest day to depart on your flight to Chicago Midway Airport?

According to our data, Tuesday is the cheapest day to fly to Chicago Midway Airport from San Francisco Bay Area. The lowest ticket price found for a Tuesday departure recently was $395. Keep in mind that prices can always vary depending on your route and whether or not you are flying domestic or international. On the other hand, Sunday is the most expensive day to depart from San Francisco Bay Area because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $508.

What is the cheapest time of day to depart on your flight to Chicago Midway Airport?

Flying to Chicago Midway Airport from San Francisco Bay Area in the afternoon is the least expensive time of day to depart. momondo users have found prices as low as $330 when looking at flights departing in the afternoon. Try not to purchase tickets at noon because they tend to be around $586. Of course, these prices can vary depending on the time of year and what airport you fly to.

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

Fly from San Francisco to Chicago Midway for the best San Francisco Bay Area - Chicago Midway flight prices

How far in advance should I book a flight to Chicago Midway Airport?

You are more likely to see cheaper flights to Chicago Midway Airport from San Francisco Bay Area when booking weeks ahead of your departure date. In general, you can expect to find flights to Chicago Midway Airport for around $367 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Chicago Midway Airport from San Francisco Bay Area for as low as $239 on momondo.

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

There is only 1 cabin class available to choose from on San Francisco Bay Area to Chicago Midway 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 Midway Airport flights?

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

Cheap San Francisco Bay Area to Chicago Midway Airport flight deals and tips

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

Fastest flight time

4h 00m

Direct flights

Every day
The fastest flight from San Francisco Bay Area to Chicago Midway Airport takes 4h 00m
Direct flights go from San Francisco Bay Area to Chicago Midway Airport every day.
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  • When did momondo last update prices for flights from San Francisco Bay Area to Chicago Midway Airport?

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

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

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

    The minimum age a child must be to fly alone is five but airlines that offer an unaccompanied minor (UNMR) service will have their own age restrictions, including rules around flight length, timings, and stopovers. We always recommend checking with the individual airline you are booking with to travel from San Francisco Bay Area to Chicago Midway Airport.

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

    The required travel and health documents for your Chicago Midway Airport trip may vary depending on your itinerary and personal circumstances. As a general rule, you should carry multiple documents, including a national ID card or driver's license and a passport valid for six months after your intended arrival at Chicago Midway Airport. We recommend that you seek guidance from your airline or a reliable third party such as IATA.

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

Best airlines flying from San Francisco Bay Area to Chicago Midway Airport

Compare and see reviews for airlines that fly from San Francisco Bay Area to Chicago Midway Airport with momondo
Airline
Rating
Free Cancellation
Price
United AirlinesPriceFrom $133Free CancellationRating
7.4
9,013 reviews
Search United Airlines flights
FrontierPriceFrom $147Free CancellationRating
5.8
3,106 reviews
Search Frontier flights
American AirlinesPriceFrom $197Free CancellationRating
7.2
11,050 reviews
Search American Airlines flights
SouthwestPriceFrom $219Free CancellationRating
8.0
4,244 reviews
Search Southwest flights
DeltaPriceFrom $256Free CancellationRating
7.9
8,007 reviews
Search Delta 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?

To find the flight that best suits your needs, momondo gathers a range of flights from a large pool of different airlines and agents; you can then use our insights and filters to find and book the right flight to Chicago from San Francisco Bay Area.

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

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

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

Once you have performed a search for San Francisco Bay Area to Chicago flights, momondo helps you find the right one by offering useful filters to narrow down your flight selection. Flights can be filtered by multiple factors such as airline, airport and price; but also by other criteria like aircraft type and payment method.

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

Yes momondo offers price alerts on flights to Chicago from San Francisco Bay Area. 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.

An easier way to manage your Chicago Midway Airport trip

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