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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 5/18. 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.
Southwest Logo
11:55 pm - 6:00 am
OAK
-
MDW
4h 05mnonstop
Southwest Logo
8:50 pm - 11:25 pm
MDW
-
OAK
4h 35mnonstop
$237Southwest
Wed, May 27 - Wed, Jun 3
Southwest Logo
5:50 am - 11:55 am
OAK
-
MDW
4h 05mnonstop
Southwest Logo
4:00 pm - 9:45 pm
MDW
-
OAK
7h 45m
1 stop
$247Southwest
Wed, May 27 - Wed, Jun 3
Southwest Logo
11:55 pm - 6:00 am
OAK
-
MDW
4h 05mnonstop
Southwest Logo
8:50 pm - 11:25 pm
MDW
-
OAK
4h 35mnonstop
$251Southwest
Sat, May 9 - Wed, May 13
Southwest Logo
10:45 am - 7:55 pm
OAK
-
MDW
7h 10m
2 stops
Southwest Logo
8:50 pm - 11:25 pm
MDW
-
OAK
4h 35mnonstop
$252Southwest
Wed, May 6 - Tue, May 12
Frontier Logo
5:25 pm - 2:12 pm
SFO
-
MDW
18h 47m
2 stops
Frontier Logo
3:07 pm - 11:04 pm
MDW
-
SFO
9h 57m
1 stop
$269Frontier
Thu, May 28 - Tue, Jun 2
Frontier Logo
10:15 pm - 11:04 am
SFO
-
MDW
10h 49m
1 stop
Frontier Logo
12:04 pm - 7:26 pm
MDW
-
SFO
9h 22m
1 stop
$270Frontier
Fri, Jun 5 - Fri, Jun 12
Delta Logo
12:15 am - 8:42 am
SFO
-
MDW
6h 27m
1 stop
Delta Logo
5:15 pm - 11:24 pm
MDW
-
SFO
8h 09m
1 stop
$271Delta
Wed, May 20 - Wed, Jun 3
Frontier Logo
11:52 pm - 2:07 pm
SFO
-
MDW
12h 15m
1 stop
Frontier Logo
3:02 pm - 10:57 pm
MDW
-
SFO
9h 55m
1 stop
$272Frontier
Sun, Aug 23 - Mon, Aug 31
Delta Logo
11:32 pm - 9:14 am
SFO
-
MDW
7h 42m
1 stop
Delta Logo
7:16 pm - 11:53 pm
MDW
-
SFO
6h 37m
1 stop
$273Delta
Wed, Jun 10 - Mon, Jun 15
Delta Logo
8:50 pm - 8:42 am
SJC
-
MDW
9h 52m
2 stops
Delta Logo
1:59 pm - 8:38 pm
MDW
-
SJC
8h 39m
1 stop
$276Delta
Thu, May 28 - Wed, Jun 3

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
May 27
OAK11:55 pmOakland
4h 05m
MDW6:00 amChicago Midway
Jun 3
MDW8:50 pmChicago Midway
4h 35m
OAK11:25 pmOakland
$237
Southwest
May 27
OAK5:50 amOakland
4h 05m
MDW11:55 amChicago Midway
Jun 3
MDW4:00 pmChicago Midway
7h 45m
1 stop
OAK9:45 pmOakland
$247
Southwest
May 9
OAK11:55 pmOakland
4h 05m
MDW6:00 amChicago Midway
May 13
MDW8:50 pmChicago Midway
4h 35m
OAK11:25 pmOakland
$251

Frontier flights from San Francisco Bay Area to Chicago Midway Airport

Our best Frontier deals on San Francisco Bay Area to Chicago Midway Airport flight tickets
Frontier
May 28
SFO5:25 pmSan Francisco
18h 47m
2 stops
MDW2:12 pmChicago Midway
Jun 2
MDW3:07 pmChicago Midway
9h 57m
1 stop
SFO11:04 pmSan Francisco
$269
Frontier
Jun 5
SFO10:15 pmSan Francisco
10h 49m
1 stop
MDW11:04 amChicago Midway
Jun 12
MDW12:04 pmChicago Midway
9h 22m
1 stop
SFO7:26 pmSan Francisco
$270
Frontier
Jun 5
SFO11:59 pmSan Francisco
12h 13m
1 stop
MDW2:12 pmChicago Midway
Jun 11
MDW12:27 pmChicago Midway
8h 59m
1 stop
SFO7:26 pmSan Francisco
$272

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 April 19, 2026.
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

Cheapest round-trip
Quickest round-trip

OaklandChicago

OAK - MDW

OAKMDW

Oakland

Wed 5/27

11:55 pm-6:00 am

Nonstop4h 05m

Chicago Midway

Wed 6/3

8:50 pm-11:25 pm

Nonstop4h 35m

$237

OaklandChicago

OAK - MDW

OAKMDW

Oakland

Wed 5/27

5:50 am-11:55 am

Nonstop4h 05m

Chicago Midway

Wed 6/3

4:00 pm-9:45 pm

1 stop7h 45m

$247

OaklandChicago

OAK - MDW

OAKMDW

Oakland

Sat 5/9

11:55 pm-6:00 am

Nonstop4h 05m

Chicago Midway

Wed 5/13

8:50 pm-11:25 pm

Nonstop4h 35m

$251

OaklandChicago

OAK - MDW

OAKMDW

Oakland

Wed 5/6

10:45 am-7:55 pm

2 stops7h 10m

Chicago Midway

Tue 5/12

8:50 pm-11:25 pm

Nonstop4h 35m

$252

San FranciscoChicago

SFO - MDW

SFOMDW

San Francisco

Thu 5/28

5:25 pm-2:12 pm

2 stops18h 47m

Chicago Midway

Tue 6/2

3:07 pm-11:04 pm

1 stop9h 57m

$269

San FranciscoChicago

SFO - MDW

SFOMDW

San Francisco

Fri 6/5

10:15 pm-11:04 am

1 stop10h 49m

Chicago Midway

Fri 6/12

12:04 pm-7:26 pm

1 stop9h 22m

$270

San FranciscoChicago

SFO - MDW

SFOMDW

San Francisco

Wed 5/20

12:15 am-8:42 am

1 stop6h 27m

Chicago Midway

Wed 6/3

5:15 pm-11:24 pm

1 stop8h 09m

$271

San FranciscoChicago

SFO - MDW

SFOMDW

San Francisco

Sun 8/23

11:52 pm-2:07 pm

1 stop12h 15m

Chicago Midway

Mon 8/31

3:02 pm-10:57 pm

1 stop9h 55m

$272

San FranciscoChicago

SFO - MDW

SFOMDW

San Francisco

Wed 6/10

11:32 pm-9:14 am

1 stop7h 42m

Chicago Midway

Mon 6/15

7:16 pm-11:53 pm

1 stop6h 37m

$273

San JoseChicago

SJC - MDW

SJCMDW

San Jose

Thu 5/28

8:50 pm-8:42 am

2 stops9h 52m

Chicago Midway

Wed 6/3

1:59 pm-8:38 pm

1 stop8h 39m

$276

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 $225. If you are unable to visit Chicago Midway Airport during the month of January, then departing from San Francisco Bay Area during the month August is also very affordable. Most momondo users find prices during this month for around $292.

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

According to our data, Wednesday is the cheapest day to fly to Chicago Midway Airport from San Francisco Bay Area. The lowest ticket price found for a Wednesday departure recently was $374. 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 $500.

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 $631. 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 Jose 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 $369 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 $276 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.
Search flight deals

Frequently asked questions about flying from San Francisco Bay Area to Chicago Midway Airport

  • 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
9,604 reviews
Search United Airlines flights
FrontierPriceFrom $147Free CancellationRating
5.7
2,985 reviews
Search Frontier flights
DeltaPriceFrom $241Free CancellationRating
7.9
8,422 reviews
Search Delta flights
SouthwestPriceFrom $250Free CancellationRating
8.0
4,327 reviews
Search Southwest flights

Traveling to a place near Chicago?

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

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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