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Cheap flights from Chicago Midway Airport to San Francisco Bay Area from $89

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 5/7. 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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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.
Southwest Logo
10:00 am - 12:35 pm
MDW
-
SFO
4h 35mnonstop
Southwest Logo
5:25 am - 11:35 am
SFO
-
MDW
4h 10mnonstop
$224Southwest
Sat, Apr 25 - Wed, Apr 29
Frontier Logo
2:15 pm - 5:34 pm
MDW
-
SFO
29h 19m
1 stop
Frontier Logo
9:58 am - 2:34 pm
SFO
-
MDW
26h 36m
2 stops
$225Frontier
Tue, Apr 14 - Thu, Apr 16
Frontier Logo
6:30 am - 5:34 pm
MDW
-
SFO
13h 04m
1 stop
Frontier Logo
6:00 am - 10:14 pm
SFO
-
MDW
14h 14m
2 stops
$226Frontier
Wed, Apr 15 - Sat, Apr 18
Southwest Logo
5:10 am - 11:50 am
MDW
-
SFO
8h 40m
1 stop
Southwest Logo
5:40 am - 5:15 pm
SFO
-
MDW
9h 35m
2 stops
$227Southwest
Sat, Apr 18 - Sat, Apr 25
Frontier Logo
6:30 am - 5:34 pm
MDW
-
SFO
13h 04m
1 stop
Frontier Logo
7:00 am - 10:14 pm
SFO
-
MDW
13h 14m
2 stops
$228Frontier
Wed, Apr 15 - Wed, Apr 22
Southwest Logo
9:00 pm - 11:35 pm
MDW
-
SFO
4h 35mnonstop
Southwest Logo
5:25 am - 11:35 am
SFO
-
MDW
4h 10mnonstop
$230Southwest
Wed, Apr 8 - Tue, Apr 14
Frontier Logo
6:00 am - 5:34 pm
MDW
-
SFO
13h 34m
1 stop
Frontier Logo
11:16 pm - 12:35 pm
SFO
-
MDW
11h 19m
1 stop
$231Frontier
Sat, Apr 18 - Sun, Apr 26
Delta Logo
1:59 pm - 8:38 pm
MDW
-
SJC
8h 39m
1 stop
Delta Logo
10:55 pm - 8:43 am
SJC
-
MDW
7h 48m
1 stop
$329Delta
Mon, May 11 - Tue, May 19
Delta Logo
6:23 am - 5:15 pm
MDW
-
SJC
12h 52m
2 stops
Delta Logo
10:55 pm - 8:43 am
SJC
-
MDW
7h 48m
1 stop
$334Delta
Mon, May 11 - Tue, May 19
Delta Logo
6:23 am - 3:27 pm
MDW
-
SJC
11h 04m
2 stops
Delta Logo
7:00 am - 9:09 pm
SJC
-
MDW
12h 09m
2 stops
$339Delta
Mon, May 11 - Tue, May 19

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
Apr 14
MDW2:15 pmChicago Midway
29h 19m
1 stop
SFO5:34 pmSan Francisco
Apr 16
SFO9:58 amSan Francisco
26h 36m
2 stops
MDW2:34 pmChicago Midway
$225
Frontier
Apr 15
MDW6:30 amChicago Midway
13h 04m
1 stop
SFO5:34 pmSan Francisco
Apr 18
SFO6:00 amSan Francisco
14h 14m
2 stops
MDW10:14 pmChicago Midway
$226
Frontier
Apr 15
MDW6:30 amChicago Midway
13h 04m
1 stop
SFO5:34 pmSan Francisco
Apr 22
SFO7:00 amSan Francisco
13h 14m
2 stops
MDW10:14 pmChicago Midway
$228

Delta flights from Chicago Midway Airport to San Francisco Bay Area

Our best Delta deals on Chicago Midway Airport to San Francisco Bay Area flight tickets
Delta
May 9
MDW1:59 pmChicago Midway
8h 38m
1 stop
SFO8:37 pmSan Francisco
May 12
SFO11:59 pmSan Francisco
6h 44m
1 stop
MDW8:43 amChicago Midway
$237
Delta
May 4
MDW7:16 pmChicago Midway
6h 38m
1 stop
SFO11:54 pmSan Francisco
May 9
SFO6:00 amSan Francisco
8h 12m
1 stop
MDW4:12 pmChicago Midway
$251
Delta
Mar 24
MDW1:10 pmChicago Midway
7h 57m
1 stop
SFO7:07 pmSan Francisco
Mar 31
SFO10:40 pmSan Francisco
8h 13m
1 stop
MDW8:53 amChicago 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 March 3, 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

ChicagoSan Francisco

MDW - SFO

MDWSFO

Chicago Midway

Sat 4/25

10:00 am-12:35 pm

Nonstop4h 35m

San Francisco

Wed 4/29

5:25 am-11:35 am

Nonstop4h 10m

$224

ChicagoSan Francisco

MDW - SFO

MDWSFO

Chicago Midway

Tue 4/14

2:15 pm-5:34 pm

1 stop29h 19m

San Francisco

Thu 4/16

9:58 am-2:34 pm

2 stops26h 36m

$225

ChicagoSan Francisco

MDW - SFO

MDWSFO

Chicago Midway

Wed 4/15

6:30 am-5:34 pm

1 stop13h 04m

San Francisco

Sat 4/18

6:00 am-10:14 pm

2 stops14h 14m

$226

ChicagoSan Francisco

MDW - SFO

MDWSFO

Chicago Midway

Sat 4/18

5:10 am-11:50 am

1 stop8h 40m

San Francisco

Sat 4/25

5:40 am-5:15 pm

2 stops9h 35m

$227

ChicagoSan Francisco

MDW - SFO

MDWSFO

Chicago Midway

Wed 4/15

6:30 am-5:34 pm

1 stop13h 04m

San Francisco

Wed 4/22

7:00 am-10:14 pm

2 stops13h 14m

$228

ChicagoSan Francisco

MDW - SFO

MDWSFO

Chicago Midway

Wed 4/8

9:00 pm-11:35 pm

Nonstop4h 35m

San Francisco

Tue 4/14

5:25 am-11:35 am

Nonstop4h 10m

$230

ChicagoSan Francisco

MDW - SFO

MDWSFO

Chicago Midway

Sat 4/18

6:00 am-5:34 pm

1 stop13h 34m

San Francisco

Sun 4/26

11:16 pm-12:35 pm

1 stop11h 19m

$231

ChicagoSan Jose

MDW - SJC

MDWSJC

Chicago Midway

Mon 5/11

1:59 pm-8:38 pm

1 stop8h 39m

San Jose

Tue 5/19

10:55 pm-8:43 am

1 stop7h 48m

$329

ChicagoSan Jose

MDW - SJC

MDWSJC

Chicago Midway

Mon 5/11

6:23 am-5:15 pm

2 stops12h 52m

San Jose

Tue 5/19

10:55 pm-8:43 am

1 stop7h 48m

$334

ChicagoSan Jose

MDW - SJC

MDWSJC

Chicago Midway

Mon 5/11

6:23 am-3:27 pm

2 stops11h 04m

San Jose

Tue 5/19

7:00 am-9:09 pm

2 stops12h 09m

$339

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 $286. If you aren’t able to travel to San Francisco Bay Area during the month of October, then flying in April is also cheap. Prices for this month can be found on momondo for an average of $326.

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 $394.

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 $298. In contrast, the most expensive time of day to depart to San Francisco Bay Area is in the afternoon when prices are around $508.

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

Fly from Chicago Midway to San Francisco 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 30m

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 30m
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

  • 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
FrontierPriceFrom $90Free CancellationRating
5.7
3,041 reviews
Search Frontier flights
United AirlinesPriceFrom $217Free CancellationRating
7.4
9,378 reviews
Search United Airlines flights
SouthwestPriceFrom $217Free CancellationRating
8.0
4,301 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.

An easier way to manage your San Francisco Bay Area trip

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