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Cheap flights from Chicago Midway Airport to San Francisco Bay Area from $100

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 1/8. 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 Chicago Midway Airport to San Francisco Bay Area

Cheap round-trip flights

Enter your travel dates to find the best prices.
Frontier Logo
6:10 am - 1:24 pmMDW-SFO
9h 14m1 stop
Frontier Logo
11:20 pm - 12:05 pmSFO-MDW
10h 45m1 stop
$262Frontier
Find Deal
Sat, Jan 17 - Mon, Jan 19
Frontier Logo
3:01 pm - 9:01 pmMDW-SFO
8h 00m1 stop
Frontier Logo
6:24 am - 9:50 pmSFO-MDW
13h 26m1 stop
$263Frontier
Find Deal
Sun, Dec 21 - Sun, Dec 28
Frontier Logo
3:01 pm - 9:01 pmMDW-SFO
8h 00m1 stop
Frontier Logo
8:58 am - 2:05 pmSFO-MDW
27h 07m1 stop
$264Frontier
Find Deal
Sun, Jan 4 - Thu, Jan 8
Southwest Logo
8:15 am - 11:15 amMDW-SFO
5h 00mnonstop
Southwest Logo
7:05 am - 5:20 pmSFO-MDW
8h 15m1 stop
$265Southwest
Find Deal
Sat, Jan 10 - Sat, Jan 17
Southwest Logo
8:15 am - 11:15 amMDW-SFO
5h 00mnonstop
Southwest Logo
6:25 am - 12:25 pmSFO-MDW
4h 00mnonstop
$267Southwest
Find Deal
Sat, Jan 17 - Mon, Jan 19
Southwest Logo
4:05 pm - 6:40 pmMDW-OAK
4h 35mnonstop
Southwest Logo
5:55 am - 12:00 pmOAK-MDW
4h 05mnonstop
$267Southwest
Find Deal
Thu, Dec 11 - Sat, Jan 24
Southwest Logo
8:15 am - 11:00 amMDW-SFO
4h 45mnonstop
Southwest Logo
6:25 am - 12:25 pmSFO-MDW
4h 00mnonstop
$269Southwest
Find Deal
Tue, Dec 16 - Sun, Jan 11
Delta Logo
4:29 pm - 12:20 amMDW-SFO
9h 51m1 stop
Delta Logo
11:46 am - 10:07 pmSFO-MDW
8h 21m1 stop
$274Delta
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Sat, Dec 13 - Wed, Jan 7
Delta Logo
10:49 am - 10:12 pmMDW-SJC
13h 23m2 stops
Delta Logo
7:15 am - 11:47 pmSJC-MDW
14h 32m2 stops
$314Delta
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Tue, Dec 9 - Thu, Dec 11
Delta Logo
6:45 am - 5:40 pmMDW-SJC
12h 55m2 stops
Delta Logo
7:45 am - 10:07 pmSJC-MDW
12h 22m2 stops
$354Delta
Find Deal
Sat, Jan 10 - Sat, Jan 17

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
Jan 17
MDW6:10 amChicago Midway
9h 14m
1 stop
SFO1:24 pmSan Francisco
Jan 19
SFO11:20 pmSan Francisco
10h 45m
1 stop
MDW12:05 pmChicago Midway
$262
Find similar
Frontier
Dec 21
MDW3:01 pmChicago Midway
8h 00m
1 stop
SFO9:01 pmSan Francisco
Dec 28
SFO6:24 amSan Francisco
13h 26m
1 stop
MDW9:50 pmChicago Midway
$263
Find similar
Frontier
Jan 4
MDW3:01 pmChicago Midway
8h 00m
1 stop
SFO9:01 pmSan Francisco
Jan 8
SFO8:58 amSan Francisco
27h 07m
1 stop
MDW2:05 pmChicago Midway
$264
Find similar

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
Jan 10
MDW8:15 amChicago Midway
5h 00m
SFO11:15 amSan Francisco
Jan 17
SFO7:05 amSan Francisco
8h 15m
1 stop
MDW5:20 pmChicago Midway
$265
Find similar
Southwest
Jan 17
MDW8:15 amChicago Midway
5h 00m
SFO11:15 amSan Francisco
Jan 19
SFO6:25 amSan Francisco
4h 00m
MDW12:25 pmChicago Midway
$267
Find similar
Southwest
Dec 16
MDW8:15 amChicago Midway
4h 45m
SFO11:00 amSan Francisco
Jan 11
SFO6:25 amSan Francisco
4h 00m
MDW12:25 pmChicago Midway
$269
Find similar

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 November 17, 2025.
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 1/17

6:10 am-1:24 pm

1 stop9h 14m

San Francisco

Mon 1/19

11:20 pm-12:05 pm

1 stop10h 45m

$262

ChicagoSan Francisco

MDW - SFO

MDWSFO

Chicago Midway

Sun 12/21

3:01 pm-9:01 pm

1 stop8h 00m

San Francisco

Sun 12/28

6:24 am-9:50 pm

1 stop13h 26m

$263

ChicagoSan Francisco

MDW - SFO

MDWSFO

Chicago Midway

Sun 1/4

3:01 pm-9:01 pm

1 stop8h 00m

San Francisco

Thu 1/8

8:58 am-2:05 pm

1 stop27h 07m

$264

ChicagoSan Francisco

MDW - SFO

MDWSFO

Chicago Midway

Sat 1/10

8:15 am-11:15 am

Nonstop5h 00m

San Francisco

Sat 1/17

7:05 am-5:20 pm

1 stop8h 15m

$265

ChicagoSan Francisco

MDW - SFO

MDWSFO

Chicago Midway

Sat 1/17

8:15 am-11:15 am

Nonstop5h 00m

San Francisco

Mon 1/19

6:25 am-12:25 pm

Nonstop4h 00m

$267

ChicagoOakland

MDW - OAK

MDWOAK

Chicago Midway

Thu 12/11

4:05 pm-6:40 pm

Nonstop4h 35m

Oakland

Sat 1/24

5:55 am-12:00 pm

Nonstop4h 05m

$267

ChicagoSan Francisco

MDW - SFO

MDWSFO

Chicago Midway

Tue 12/16

8:15 am-11:00 am

Nonstop4h 45m

San Francisco

Sun 1/11

6:25 am-12:25 pm

Nonstop4h 00m

$269

ChicagoSan Francisco

MDW - SFO

MDWSFO

Chicago Midway

Sat 12/13

4:29 pm-12:20 am

1 stop9h 51m

San Francisco

Wed 1/7

11:46 am-10:07 pm

1 stop8h 21m

$274

ChicagoSan Jose

MDW - SJC

MDWSJC

Chicago Midway

Tue 12/9

10:49 am-10:12 pm

2 stops13h 23m

San Jose

Thu 12/11

7:15 am-11:47 pm

2 stops14h 32m

$314

ChicagoSan Jose

MDW - SJC

MDWSJC

Chicago Midway

Sat 1/10

6:45 am-5:40 pm

2 stops12h 55m

San Jose

Sat 1/17

7:45 am-10:07 pm

2 stops12h 22m

$354

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 February is also cheap. Prices for this month can be found on momondo for an average of $332.

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 Thursday. momondo users have found tickets for Thursday departures for as low as $321. 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 $487.

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 morning. Flights from Chicago Midway Airport to San Francisco Bay Area during this time can be as low as $356. In contrast, the most expensive time of day to depart to San Francisco Bay Area is at noon when prices are around $465.

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

3 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 3 airports near San Francisco Bay Area: Oakland (OAK), San Francisco (SFO), San Jose (SJC)
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  • 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
5.8
3,106 reviews
Search Frontier flights
United AirlinesPriceFrom $217Free CancellationRating
7.4
9,014 reviews
Search United Airlines flights
SouthwestPriceFrom $227Free CancellationRating
8.0
4,244 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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