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Cheap flights from San Francisco to Chicago from $124

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 2/3. 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 - 5:30 am
SFO
-
MDW
4h 05mnonstop
Southwest Logo
4:05 pm - 10:35 pm
MDW
-
SFO
8h 30m2 stops
$252Southwest
Fri, Mar 13 - Mon, Mar 16
Delta Logo
8:05 pm - 8:52 am
SFO
-
MDW
10h 47m2 stops
Delta Logo
12:45 pm - 7:56 pm
MDW
-
SFO
9h 11m1 stop
$253Delta
Mon, Jan 26 - Thu, Feb 12
Delta Logo
10:54 pm - 8:52 am
SFO
-
MDW
7h 58m1 stop
Delta Logo
9:53 am - 5:49 pm
MDW
-
SFO
9h 56m2 stops
$254Delta
Sun, Feb 1 - Wed, Feb 4
Delta Logo
1:10 pm - 8:47 am
SFO
-
MDW
17h 37m2 stops
Delta Logo
1:10 pm - 11:59 pm
MDW
-
SFO
12h 49m2 stops
$255Delta
Thu, Apr 16 - Tue, Apr 28
Southwest Logo
2:00 pm - 9:50 pm
SFO
-
MDW
5h 50m1 stop
Southwest Logo
8:05 am - 2:40 pm
MDW
-
SFO
8h 35m1 stop
$256Southwest
Mon, Feb 2 - Thu, Feb 5
Frontier Logo
6:15 am - 9:12 pm
SFO
-
MDW
12h 57m2 stops
Frontier Logo
6:00 am - 9:39 pm
MDW
-
SFO
17h 39m1 stop
$257Frontier
Thu, Feb 12 - Sun, Feb 15
Frontier Logo
6:15 am - 10:19 pm
SFO
-
MDW
14h 04m2 stops
Frontier Logo
7:30 am - 5:54 pm
MDW
-
SFO
12h 24m1 stop
$258Frontier
Mon, Jan 26 - Sun, Feb 8
Southwest Logo
5:55 am - 11:55 am
SFO
-
MDW
4h 00mnonstop
Southwest Logo
8:15 am - 11:15 am
MDW
-
SFO
5h 00mnonstop
$259Southwest
Thu, Feb 12 - Sat, Feb 14
Southwest Logo
5:55 am - 4:40 pm
SFO
-
MDW
8h 45m2 stops
Southwest Logo
5:10 pm - 10:05 pm
MDW
-
SFO
6h 55m1 stop
$260Southwest
Wed, Mar 11 - Wed, Mar 18
Southwest Logo
5:55 am - 4:40 pm
SFO
-
MDW
8h 45m2 stops
Southwest Logo
7:40 pm - 12:10 am
MDW
-
SFO
6h 30m1 stop
$261Southwest
Wed, Apr 1 - Sun, Apr 5

Southwest flights from San Francisco to Chicago Midway Airport

Our best Southwest deals on San Francisco to Chicago Midway Airport flight tickets
Southwest
Mar 13
SFO11:25 pmSan Francisco
4h 05m
MDW5:30 amChicago Midway
Mar 16
MDW4:05 pmChicago Midway
8h 30m
2 stops
SFO10:35 pmSan Francisco
$252
Southwest
Feb 2
SFO2:00 pmSan Francisco
5h 50m
1 stop
MDW9:50 pmChicago Midway
Feb 5
MDW8:05 amChicago Midway
8h 35m
1 stop
SFO2:40 pmSan Francisco
$256
Southwest
Feb 12
SFO5:55 amSan Francisco
4h 00m
MDW11:55 amChicago Midway
Feb 14
MDW8:15 amChicago Midway
5h 00m
SFO11:15 amSan Francisco
$259

Frontier flights from San Francisco to Chicago Midway Airport

Our best Frontier deals on San Francisco to Chicago Midway Airport flight tickets
Frontier
Jan 13
SFO11:20 pmSan Francisco
9h 11m
1 stop
MDW10:31 amChicago Midway
Jan 15
MDW6:10 amChicago Midway
9h 14m
1 stop
SFO1:24 pmSan Francisco
$252
Frontier
Jan 13
SFO11:20 pmSan Francisco
9h 11m
1 stop
MDW10:31 amChicago Midway
Jan 16
MDW6:10 amChicago Midway
9h 14m
1 stop
SFO1:24 pmSan Francisco
$256
Frontier
Feb 12
SFO6:15 amSan Francisco
12h 57m
2 stops
MDW9:12 pmChicago Midway
Feb 15
MDW6:00 amChicago Midway
17h 39m
1 stop
SFO9:39 pmSan Francisco
$257

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 January 8, 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

San FranciscoChicago

SFO - MDW

SFOMDW

San Francisco

Fri 3/13

11:25 pm-5:30 am

Nonstop4h 05m

Chicago Midway

Mon 3/16

4:05 pm-10:35 pm

2 stops8h 30m

$252

San FranciscoChicago

SFO - MDW

SFOMDW

San Francisco

Mon 1/26

8:05 pm-8:52 am

2 stops10h 47m

Chicago Midway

Thu 2/12

12:45 pm-7:56 pm

1 stop9h 11m

$253

San FranciscoChicago

SFO - MDW

SFOMDW

San Francisco

Sun 2/1

10:54 pm-8:52 am

1 stop7h 58m

Chicago Midway

Wed 2/4

9:53 am-5:49 pm

2 stops9h 56m

$254

San FranciscoChicago

SFO - MDW

SFOMDW

San Francisco

Thu 4/16

1:10 pm-8:47 am

2 stops17h 37m

Chicago Midway

Tue 4/28

1:10 pm-11:59 pm

2 stops12h 49m

$255

San FranciscoChicago

SFO - MDW

SFOMDW

San Francisco

Mon 2/2

2:00 pm-9:50 pm

1 stop5h 50m

Chicago Midway

Thu 2/5

8:05 am-2:40 pm

1 stop8h 35m

$256

San FranciscoChicago

SFO - MDW

SFOMDW

San Francisco

Thu 2/12

6:15 am-9:12 pm

2 stops12h 57m

Chicago Midway

Sun 2/15

6:00 am-9:39 pm

1 stop17h 39m

$257

San FranciscoChicago

SFO - MDW

SFOMDW

San Francisco

Mon 1/26

6:15 am-10:19 pm

2 stops14h 04m

Chicago Midway

Sun 2/8

7:30 am-5:54 pm

1 stop12h 24m

$258

San FranciscoChicago

SFO - MDW

SFOMDW

San Francisco

Thu 2/12

5:55 am-11:55 am

Nonstop4h 00m

Chicago Midway

Sat 2/14

8:15 am-11:15 am

Nonstop5h 00m

$259

San FranciscoChicago

SFO - MDW

SFOMDW

San Francisco

Wed 3/11

5:55 am-4:40 pm

2 stops8h 45m

Chicago Midway

Wed 3/18

5:10 pm-10:05 pm

1 stop6h 55m

$260

San FranciscoChicago

SFO - MDW

SFOMDW

San Francisco

Wed 4/1

5:55 am-4:40 pm

2 stops8h 45m

Chicago Midway

Sun 4/5

7:40 pm-12:10 am

1 stop6h 30m

$261

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 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 February is also very affordable. Most momondo users find prices during this month for around $271.

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

According to our data, Tuesday is the cheapest day to fly to Chicago Midway Airport from San Francisco. The lowest ticket price found for a Tuesday departure recently was $370. 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 $492.

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 $586. 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 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 $357 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 $238 on momondo.

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

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

You could potentially save up to 46% on your flight if you consider stops on a San Francisco to Chicago Midway Airport flight.

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

$242

Fastest flight time

3h 55m

Direct flights

Every day
The best one-way flight to Chicago Midway Airport from San Francisco in the past 72 hours is $242. The best round-trip flight deal from San Francisco to Chicago Midway Airport found on momondo in the last 72 hours is $374.
The fastest flight from San Francisco to Chicago Midway Airport takes 3h 55m
Direct flights go from San Francisco to Chicago Midway Airport every day.
Search flight deals

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

    A flight from San Francisco to Chicago Midway will travel around 1847.1 mi. In terms of flight time, this usually takes a little over 3h 55m.

  • 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
9,139 reviews
Search United Airlines flights
FrontierPriceFrom $155Free CancellationRating
5.7
3,062 reviews
Search Frontier flights
American AirlinesPriceFrom $197Free CancellationRating
7.2
11,095 reviews
Search American Airlines flights
SouthwestPriceFrom $217Free CancellationRating
8.0
4,250 reviews
Search Southwest flights
DeltaPriceFrom $256Free CancellationRating
7.9
8,025 reviews
Search Delta flights

Traveling to a place near Chicago?

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