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Cheap flights from San Francisco to Chicago from $133

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 to Chicago departing on 5/20. 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 to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
Southwest Logo
11:25 pm - 5:40 am
SFO
-
MDW
4h 15mnonstop
Southwest Logo
9:00 pm - 11:35 pm
MDW
-
SFO
4h 35mnonstop
$274Southwest
Mon, May 18 - Wed, May 27
Southwest Logo
11:25 pm - 5:40 am
SFO
-
MDW
4h 15mnonstop
Southwest Logo
12:50 pm - 9:25 pm
MDW
-
SFO
10h 35m
2 stops
$275Southwest
Tue, May 26 - Tue, Jun 2
Southwest Logo
7:40 pm - 4:35 am
SFO
-
MDW
6h 55m
1 stop
Southwest Logo
12:50 pm - 9:25 pm
MDW
-
SFO
10h 35m
2 stops
$276Southwest
Wed, May 27 - Wed, Jun 3
Frontier Logo
11:59 pm - 2:12 pm
SFO
-
MDW
12h 13m
1 stop
Frontier Logo
3:07 pm - 11:04 pm
MDW
-
SFO
9h 57m
1 stop
$277Frontier
Mon, May 18 - Sun, May 24
Frontier Logo
10:10 pm - 11:09 am
SFO
-
MDW
10h 59m
1 stop
Frontier Logo
3:07 pm - 11:04 pm
MDW
-
SFO
9h 57m
1 stop
$280Frontier
Tue, Jun 2 - Thu, Jun 4
Frontier Logo
10:15 pm - 11:09 am
SFO
-
MDW
10h 54m
1 stop
Frontier Logo
3:07 pm - 11:04 pm
MDW
-
SFO
9h 57m
1 stop
$281Frontier
Wed, May 13 - Tue, May 19
Southwest Logo
11:25 pm - 5:40 am
SFO
-
MDW
4h 15mnonstop
Southwest Logo
10:00 am - 12:35 pm
MDW
-
SFO
4h 35mnonstop
$282Southwest
Tue, May 26 - Tue, Jun 2
Frontier Logo
10:15 pm - 11:09 am
SFO
-
MDW
10h 54m
1 stop
Frontier Logo
3:07 pm - 11:04 pm
MDW
-
SFO
9h 57m
1 stop
$283Frontier
Tue, May 12 - Wed, May 13
Southwest Logo
5:15 am - 11:25 am
SFO
-
MDW
4h 10mnonstop
Southwest Logo
6:10 pm - 8:45 pm
MDW
-
SFO
4h 35mnonstop
$284Southwest
Mon, May 18 - Sat, May 23
Southwest Logo
1:15 pm - 11:55 pm
SFO
-
MDW
8h 40m
1 stop
Southwest Logo
5:25 pm - 10:25 pm
MDW
-
SFO
7h 00m
1 stop
$285Southwest
Thu, May 28 - Mon, Jun 1

Frontier flights from San Francisco to Chicago Midway Airport

Our best Frontier deals on San Francisco to Chicago Midway Airport flight tickets
Frontier
May 18
SFO11:59 pmSan Francisco
12h 13m
1 stop
MDW2:12 pmChicago Midway
May 24
MDW3:07 pmChicago Midway
9h 57m
1 stop
SFO11:04 pmSan Francisco
$277
Frontier
Jun 2
SFO10:10 pmSan Francisco
10h 59m
1 stop
MDW11:09 amChicago Midway
Jun 4
MDW3:07 pmChicago Midway
9h 57m
1 stop
SFO11:04 pmSan Francisco
$280
Frontier
May 13
SFO10:15 pmSan Francisco
10h 54m
1 stop
MDW11:09 amChicago Midway
May 19
MDW3:07 pmChicago Midway
9h 57m
1 stop
SFO11:04 pmSan Francisco
$281

Southwest flights from San Francisco to Chicago Midway Airport

Our best Southwest deals on San Francisco to Chicago Midway Airport flight tickets
Southwest
May 18
SFO11:25 pmSan Francisco
4h 15m
MDW5:40 amChicago Midway
May 27
MDW9:00 pmChicago Midway
4h 35m
SFO11:35 pmSan Francisco
$274
Southwest
May 26
SFO11:25 pmSan Francisco
4h 15m
MDW5:40 amChicago Midway
Jun 2
MDW12:50 pmChicago Midway
10h 35m
2 stops
SFO9:25 pmSan Francisco
$275
Southwest
May 27
SFO7:40 pmSan Francisco
6h 55m
1 stop
MDW4:35 amChicago Midway
Jun 3
MDW12:50 pmChicago Midway
10h 35m
2 stops
SFO9:25 pmSan Francisco
$276

momondo Fare Finder

 
Customize your flight search to find flights from San Francisco 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 30, 2026.
Use the filters below to find and compare flights from San Francisco to Chicago Midway Airport that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

San FranciscoChicago

SFO - MDW

SFOMDW

San Francisco

Mon 5/18

11:25 pm-5:40 am

Nonstop4h 15m

Chicago Midway

Wed 5/27

9:00 pm-11:35 pm

Nonstop4h 35m

$274

San FranciscoChicago

SFO - MDW

SFOMDW

San Francisco

Tue 5/26

11:25 pm-5:40 am

Nonstop4h 15m

Chicago Midway

Tue 6/2

12:50 pm-9:25 pm

2 stops10h 35m

$275

San FranciscoChicago

SFO - MDW

SFOMDW

San Francisco

Wed 5/27

7:40 pm-4:35 am

1 stop6h 55m

Chicago Midway

Wed 6/3

12:50 pm-9:25 pm

2 stops10h 35m

$276

San FranciscoChicago

SFO - MDW

SFOMDW

San Francisco

Mon 5/18

11:59 pm-2:12 pm

1 stop12h 13m

Chicago Midway

Sun 5/24

3:07 pm-11:04 pm

1 stop9h 57m

$277

San FranciscoChicago

SFO - MDW

SFOMDW

San Francisco

Tue 6/2

10:10 pm-11:09 am

1 stop10h 59m

Chicago Midway

Thu 6/4

3:07 pm-11:04 pm

1 stop9h 57m

$280

San FranciscoChicago

SFO - MDW

SFOMDW

San Francisco

Wed 5/13

10:15 pm-11:09 am

1 stop10h 54m

Chicago Midway

Tue 5/19

3:07 pm-11:04 pm

1 stop9h 57m

$281

San FranciscoChicago

SFO - MDW

SFOMDW

San Francisco

Tue 5/26

11:25 pm-5:40 am

Nonstop4h 15m

Chicago Midway

Tue 6/2

10:00 am-12:35 pm

Nonstop4h 35m

$282

San FranciscoChicago

SFO - MDW

SFOMDW

San Francisco

Tue 5/12

10:15 pm-11:09 am

1 stop10h 54m

Chicago Midway

Wed 5/13

3:07 pm-11:04 pm

1 stop9h 57m

$283
Quickest round-trip

San FranciscoChicago

SFO - MDW

SFOMDW

San Francisco

Mon 5/18

5:15 am-11:25 am

Nonstop4h 10m

Chicago Midway

Sat 5/23

6:10 pm-8:45 pm

Nonstop4h 35m

$284

San FranciscoChicago

SFO - MDW

SFOMDW

San Francisco

Thu 5/28

1:15 pm-11:55 pm

1 stop8h 40m

Chicago Midway

Mon 6/1

5:25 pm-10:25 pm

1 stop7h 00m

$285

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 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 typical price of a round-trip flight between San Francisco and Chicago Midway Airport?

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, 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 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. The lowest ticket price found for a Wednesday departure recently was $379. 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 because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $497.

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

Flying to Chicago Midway Airport from San Francisco 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 $638. Of course, these prices can vary depending on the time of year and what airport you fly to.

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

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

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

You are more likely to see cheaper flights to Chicago Midway Airport from San Francisco when booking weeks ahead of your departure date. In general, you can expect to find flights to Chicago Midway Airport for around $368 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 for as low as $276 on momondo.

How have San Francisco to Chicago Midway Airport flight prices changed over time?

When to book flights from San Francisco to Chicago Midway Airport

Are you open to changing your travel dates? Check out the ideal times to fly from San Francisco to Chicago Midway Airport according to our flight data. Find out which month and days have the cheapest flights.
Estimated round-trip price

Cheap San Francisco to Chicago Midway Airport (SFO to MDW) flight deals and tips

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

Best Price Found

$208

Fastest flight time

4h 05m

Direct flights

Every day
The best one-way flight to Chicago Midway Airport from San Francisco in the past 72 hours is $208. The best round-trip flight deal from San Francisco to Chicago Midway Airport found on momondo in the last 72 hours is $395.
The fastest flight from San Francisco to Chicago Midway Airport takes 4h 05m
Direct flights go from San Francisco to Chicago Midway Airport every day.
Search flight deals

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

  • How far is San Francisco to Chicago Midway by plane?

    A flight from San Francisco to Chicago Midway will travel around 1846.8 mi. In terms of flight time, this usually takes a little over 4h 05m.

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

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

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

  • How old do you have to be to fly from San Francisco Airport 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 Airport to Chicago Midway Airport.

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

    The travel and health documents required for your trip to Chicago Midway Airport can vary based on your itinerary and personal situation. As a rule, consider having multiple documents such as a national ID card or driver’s license, and a passport valid for six-months after you plan to arrive at Chicago Midway Airport. We always recommend checking with your airline or a trusted third party such as IATA to get advice.

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

  • What is the most popular airline from San Francisco to Chicago Midway Airport?

Best airlines flying from San Francisco to Chicago Midway Airport

Compare and see reviews for airlines that fly from San Francisco to Chicago Midway Airport with momondo
Airline
Rating
Free Cancellation
Price
United AirlinesPriceFrom $133Free CancellationRating
7.4
9,677 reviews
Search United Airlines flights
FrontierPriceFrom $147Free CancellationRating
5.6
2,969 reviews
Search Frontier flights
DeltaPriceFrom $225Free CancellationRating
7.9
8,463 reviews
Search Delta flights
SouthwestPriceFrom $250Free CancellationRating
8.0
4,314 reviews
Search Southwest flights

  • Southwest Flights From San Francisco to Chicago Midway Airport

    Southwest flight deals from San Francisco to Chicago Midway Airport start from $250 round-trip. Over the 12 Southwest flights for this route in a normal week, average airfare is usually $429 round-trip - but some users have found much cheaper deals with momondo.

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
Monticello
Chesterton
Porter
Griffith
Saint John

Why use momondo?

Why should I use momondo to find a flight deal from San Francisco 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.

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

Flights from San Francisco to Chicago with flexible booking policies can be found by using the search form above and then selecting our dedicated flexible booking filter, which will highlight only the flights where this policy is applied.

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

momondo offers useful filters to help you find the right flight. Choose specific flight times, airports or even what payment method you prefer. We have numerous options to help you book your ideal flight from San Francisco to Chicago.

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

Price alerts on flights to Chicago from San Francisco 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 Chicago Midway Airport trip

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