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Cheap flights from Chicago Midway Airport to San Francisco Bay Area from $119

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Chicago Midway Airport to San Francisco Bay Area departing on 5/5. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult
0 bags

Find the cheapest flights from Chicago Midway Airport to San Francisco Bay Area

Cheap round-trip flights

Enter your travel dates to find the best prices.
Delta Logo
7:16 pm - 11:53 pm
MDW
-
SFO
6h 37m
1 stop
Delta Logo
10:59 pm - 10:07 am
SFO
-
MDW
9h 08m
1 stop
$243Delta
Fri, Jun 19 - Tue, Jun 23
Delta Logo
7:16 pm - 11:54 pm
MDW
-
SFO
6h 38m
1 stop
Delta Logo
10:55 pm - 8:47 am
SFO
-
MDW
7h 52m
1 stop
$245Delta
Fri, May 1 - Tue, May 5
Delta Logo
7:06 pm - 11:46 pm
MDW
-
SFO
6h 40m
1 stop
Delta Logo
11:56 pm - 9:08 am
SFO
-
MDW
7h 12m
1 stop
$246Delta
Thu, Jul 9 - Fri, Jul 17
Southwest Logo
9:00 pm - 11:35 pm
MDW
-
SFO
4h 35mnonstop
Southwest Logo
3:35 pm - 12:05 am
SFO
-
MDW
6h 30m
1 stop
$247Southwest
Tue, Jun 2 - Tue, Jun 9
Southwest Logo
4:30 pm - 8:45 pm
MDW
-
OAK
6h 15m
1 stop
Southwest Logo
11:55 pm - 6:00 am
OAK
-
MDW
4h 05mnonstop
$247Southwest
Wed, May 20 - Tue, May 26
Frontier Logo
6:00 am - 7:34 pm
MDW
-
SFO
15h 34m
1 stop
Frontier Logo
10:15 pm - 11:12 am
SFO
-
MDW
10h 57m
1 stop
$250Frontier
Thu, May 28 - Mon, Jun 8
Southwest Logo
9:45 pm - 12:20 am
MDW
-
SFO
4h 35mnonstop
Southwest Logo
5:25 am - 11:35 am
SFO
-
MDW
4h 10mnonstop
$251Southwest
Thu, May 7 - Wed, May 13
Southwest Logo
9:50 pm - 12:25 am
MDW
-
OAK
4h 35mnonstop
Southwest Logo
5:50 am - 11:55 am
OAK
-
MDW
4h 05mnonstop
$251Southwest
Thu, May 28 - Tue, Jun 2
Frontier Logo
6:00 am - 5:34 pm
MDW
-
SFO
13h 34m
1 stop
Frontier Logo
11:26 pm - 2:12 pm
SFO
-
MDW
12h 46m
1 stop
$252Frontier
Fri, May 1 - Mon, May 4
Frontier Logo
3:07 pm - 11:04 pm
MDW
-
SFO
9h 57m
1 stop
Frontier Logo
11:59 pm - 2:12 pm
SFO
-
MDW
12h 13m
1 stop
$253Frontier
Thu, May 7 - Wed, May 13

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Frontier flights from Chicago Midway Airport to San Francisco Bay Area

Our best Frontier deals on Chicago Midway Airport to San Francisco Bay Area flight tickets
Frontier
May 28
MDW6:00 amChicago Midway
15h 34m
1 stop
SFO7:34 pmSan Francisco
Jun 8
SFO10:15 pmSan Francisco
10h 57m
1 stop
MDW11:12 amChicago Midway
$250
Frontier
Apr 22
MDW6:15 amChicago Midway
13h 19m
1 stop
SFO5:34 pmSan Francisco
Apr 25
SFO10:38 pmSan Francisco
9h 20m
1 stop
MDW9:58 amChicago Midway
$251
Frontier
May 1
MDW6:00 amChicago Midway
13h 34m
1 stop
SFO5:34 pmSan Francisco
May 4
SFO11:26 pmSan Francisco
12h 46m
1 stop
MDW2:12 pmChicago Midway
$252

Southwest flights from Chicago Midway Airport to San Francisco Bay Area

Our best Southwest deals on Chicago Midway Airport to San Francisco Bay Area flight tickets
Southwest
Jun 2
MDW9:00 pmChicago Midway
4h 35m
SFO11:35 pmSan Francisco
Jun 9
SFO3:35 pmSan Francisco
6h 30m
1 stop
MDW12:05 amChicago Midway
$247
Southwest
May 7
MDW9:45 pmChicago Midway
4h 35m
SFO12:20 amSan Francisco
May 13
SFO5:25 amSan Francisco
4h 10m
MDW11:35 amChicago Midway
$251
Southwest
May 13
MDW7:55 amChicago Midway
6h 35m
1 stop
OAK12:30 pmOakland
May 19
OAK8:15 amOakland
6h 45m
1 stop
MDW5:00 pmChicago Midway
$257

momondo Fare Finder

 
Customize your flight search to find flights from Chicago Midway Airport to San Francisco Bay Area 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 18, 2026.
Use the filters below to find and compare flights from Chicago Midway Airport to San Francisco Bay Area that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

ChicagoSan Francisco

MDW - SFO

MDWSFO

Chicago Midway

Fri 6/19

7:16 pm-11:53 pm

1 stop6h 37m

San Francisco

Tue 6/23

10:59 pm-10:07 am

1 stop9h 08m

$243

ChicagoSan Francisco

MDW - SFO

MDWSFO

Chicago Midway

Fri 5/1

7:16 pm-11:54 pm

1 stop6h 38m

San Francisco

Tue 5/5

10:55 pm-8:47 am

1 stop7h 52m

$245

ChicagoSan Francisco

MDW - SFO

MDWSFO

Chicago Midway

Thu 7/9

7:06 pm-11:46 pm

1 stop6h 40m

San Francisco

Fri 7/17

11:56 pm-9:08 am

1 stop7h 12m

$246

ChicagoSan Francisco

MDW - SFO

MDWSFO

Chicago Midway

Tue 6/2

9:00 pm-11:35 pm

Nonstop4h 35m

San Francisco

Tue 6/9

3:35 pm-12:05 am

1 stop6h 30m

$247

ChicagoOakland

MDW - OAK

MDWOAK

Chicago Midway

Wed 5/20

4:30 pm-8:45 pm

1 stop6h 15m

Oakland

Tue 5/26

11:55 pm-6:00 am

Nonstop4h 05m

$247

ChicagoSan Francisco

MDW - SFO

MDWSFO

Chicago Midway

Thu 5/28

6:00 am-7:34 pm

1 stop15h 34m

San Francisco

Mon 6/8

10:15 pm-11:12 am

1 stop10h 57m

$250

ChicagoSan Francisco

MDW - SFO

MDWSFO

Chicago Midway

Thu 5/7

9:45 pm-12:20 am

Nonstop4h 35m

San Francisco

Wed 5/13

5:25 am-11:35 am

Nonstop4h 10m

$251
Quickest round-trip

ChicagoOakland

MDW - OAK

MDWOAK

Chicago Midway

Thu 5/28

9:50 pm-12:25 am

Nonstop4h 35m

Oakland

Tue 6/2

5:50 am-11:55 am

Nonstop4h 05m

$251

ChicagoSan Francisco

MDW - SFO

MDWSFO

Chicago Midway

Fri 5/1

6:00 am-5:34 pm

1 stop13h 34m

San Francisco

Mon 5/4

11:26 pm-2:12 pm

1 stop12h 46m

$252

ChicagoSan Francisco

MDW - SFO

MDWSFO

Chicago Midway

Thu 5/7

3:07 pm-11:04 pm

1 stop9h 57m

San Francisco

Wed 5/13

11:59 pm-2:12 pm

1 stop12h 13m

$253

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 San Francisco Bay Area from

How to get the cheapest flight ticket from Chicago Midway Airport to San Francisco Bay Area

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 San Francisco Bay Area?

In general, October is the cheapest month to fly from Chicago Midway Airport to San Francisco Bay Area. Due to it being the ‘off-season’ during this time, you can expect flight prices to be around $297. If you aren’t able to travel to San Francisco Bay Area during the month of October, then flying in May is also cheap. Prices for this month can be found on momondo for an average of $301.

What is the cheapest day to depart on your flight to San Francisco Bay Area?

On average, the least expensive day to fly to San Francisco Bay Area from Chicago Midway Airport is on a Wednesday. momondo users have found tickets for Wednesday departures for as low as $298. However, this price may fluctuate depending on the airline, the season, and holidays. On the other hand, Monday is the most expensive day to depart from Chicago Midway Airport because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $408.

What is the cheapest time of day to depart on your flight to San Francisco Bay Area?

Our most recent data shows that the best time of day to fly to San Francisco Bay Area is in the evening. Flights from Chicago Midway Airport to San Francisco Bay Area during this time can be as low as $335. In contrast, the most expensive time of day to depart to San Francisco Bay Area is at noon when prices are around $442.

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

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

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

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

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

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

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

Fastest flight time

4h 25m

Direct flights

Every day

Airports in San Francisco Bay Area

6 airports
The fastest flight from Chicago Midway Airport to San Francisco Bay Area takes 4h 25m
Direct flights go from Chicago Midway Airport to San Francisco Bay Area every day.
There are 6 airports in San Francisco Bay Area. From Chicago Midway Airport there are direct flights to Oakland (OAK), San Jose (SJC), San Francisco (SFO).
Search flight deals

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

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

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

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

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

    The minimum age for a child to fly alone is five, but airlines that offer an unaccompanied minor (UNMR) service may have their own age limitations. Flight duration, scheduling, and layovers are among the considerations that may influence age limits. We recommend that you double-check with the airline you are booking with for travel from Chicago Midway Airport to San Francisco Bay Area.

  • What documentation or ID do you need to fly to San Francisco Bay Area?

    The required travel and health documents for your San Francisco Bay Area 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 San Francisco Bay Area. 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 Chicago Midway Airport to San Francisco Bay Area?

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

Compare and see reviews for airlines that fly from Chicago Midway Airport to San Francisco Bay Area with momondo
Airline
Rating
Free Cancellation
Price
SouthwestPriceFrom $231Free CancellationRating
8.0
4,330 reviews
Search Southwest flights

Why use momondo?

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

momondo compares prices from hundreds of airlines and agents so you can find and book the best deal on flights from Chicago to San Francisco Bay Area. Millions of users trust and use momondo every year so you are in good hands.

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

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

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

momondo helps you find the best flight between Chicago and San Francisco Bay Area by providing filters to narrow your choice of flights to those matching your criteria. You can select flights based on numerous factors such as price, departure and landing times, airport and airline.

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

Price alerts on flights to San Francisco Bay Area from Chicago are quick and easy to set up on momondo. Simply perform a search and select the price alert feature. It is as simple as that.

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