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Cheap flights from San Francisco to Chicago from $109

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 3/18. 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
6:35 pm - 12:10 am
MDW
-
SFO
7h 35m
2 stops
$232Southwest
Tue, Mar 24 - Mon, Mar 30
Southwest Logo
5:25 am - 11:35 am
SFO
-
MDW
4h 10mnonstop
Southwest Logo
10:00 am - 12:35 pm
MDW
-
SFO
4h 35mnonstop
$235Southwest
Tue, Apr 28 - Tue, May 5
Delta Logo
11:39 pm - 9:56 am
SFO
-
MDW
8h 17m
1 stop
Delta Logo
7:16 pm - 11:54 pm
MDW
-
SFO
6h 38m
1 stop
$237Delta
Mon, Apr 27 - Mon, May 4
Frontier Logo
8:05 am - 11:51 pm
SFO
-
MDW
13h 46m
1 stop
Frontier Logo
11:25 am - 12:28 am
MDW
-
SFO
15h 03m
2 stops
$239Frontier
Thu, Mar 5 - Wed, Mar 11
Southwest Logo
10:55 pm - 8:50 am
SFO
-
MDW
7h 55m
1 stop
Southwest Logo
9:25 pm - 12:05 am
MDW
-
SFO
4h 40mnonstop
$242Southwest
Tue, Mar 17 - Thu, Mar 19
Southwest Logo
5:10 am - 11:10 am
SFO
-
MDW
4h 00mnonstop
Southwest Logo
3:35 pm - 9:05 pm
MDW
-
SFO
7h 30m
1 stop
$245Southwest
Mon, Mar 9 - Tue, Mar 17
Southwest Logo
5:15 am - 11:25 am
SFO
-
MDW
4h 10mnonstop
Southwest Logo
5:30 pm - 9:55 pm
MDW
-
SFO
6h 25m
1 stop
$247Southwest
Mon, Apr 20 - Sat, Apr 25
Frontier Logo
6:00 am - 10:19 pm
SFO
-
MDW
14h 19m
2 stops
Frontier Logo
6:00 am - 4:54 pm
MDW
-
SFO
12h 54m
1 stop
$249Frontier
Tue, Apr 14 - Sat, Apr 18
Southwest Logo
11:25 pm - 5:40 am
SFO
-
MDW
4h 15mnonstop
Southwest Logo
5:15 pm - 10:05 pm
MDW
-
SFO
6h 50m
1 stop
$250Southwest
Tue, Apr 28 - Tue, May 5
Frontier Logo
6:29 pm - 12:35 pm
SFO
-
MDW
40h 06m
2 stops
Frontier Logo
3:29 pm - 10:31 pm
MDW
-
SFO
9h 02m
1 stop
$251Frontier
Sat, Apr 25 - Fri, May 1

Southwest flights from San Francisco to Chicago Midway Airport

Our best Southwest deals on San Francisco to Chicago Midway Airport flight tickets
Southwest
Apr 28
SFO5:25 amSan Francisco
4h 10m
MDW11:35 amChicago Midway
May 5
MDW10:00 amChicago Midway
4h 35m
SFO12:35 pmSan Francisco
$235
Southwest
Mar 9
SFO5:10 amSan Francisco
4h 00m
MDW11:10 amChicago Midway
Mar 17
MDW3:35 pmChicago Midway
7h 30m
1 stop
SFO9:05 pmSan Francisco
$245
Southwest
Apr 20
SFO5:15 amSan Francisco
4h 10m
MDW11:25 amChicago Midway
Apr 27
MDW5:15 pmChicago Midway
7h 50m
1 stop
SFO11:05 pmSan Francisco
$247

Delta flights from San Francisco to Chicago Midway Airport

Our best Delta deals on San Francisco to Chicago Midway Airport flight tickets
Delta
Apr 27
SFO11:39 pmSan Francisco
8h 17m
1 stop
MDW9:56 amChicago Midway
May 4
MDW7:16 pmChicago Midway
6h 38m
1 stop
SFO11:54 pmSan Francisco
$237
Delta
May 19
SFO8:30 amSan Francisco
10h 39m
1 stop
MDW9:09 pmChicago Midway
May 30
MDW9:22 amChicago Midway
6h 47m
1 stop
SFO2:09 pmSan Francisco
$284
Delta
Mar 30
SFO10:35 pmSan Francisco
9h 21m
1 stop
MDW9:56 amChicago Midway
Apr 4
MDW2:05 pmChicago Midway
9h 21m
1 stop
SFO9:26 pmSan Francisco
$294

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 February 19, 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

Tue 3/24

11:25 pm-5:30 am

Nonstop4h 05m

Chicago Midway

Mon 3/30

6:35 pm-12:10 am

2 stops7h 35m

$232

San FranciscoChicago

SFO - MDW

SFOMDW

San Francisco

Tue 4/28

5:25 am-11:35 am

Nonstop4h 10m

Chicago Midway

Tue 5/5

10:00 am-12:35 pm

Nonstop4h 35m

$235

San FranciscoChicago

SFO - MDW

SFOMDW

San Francisco

Mon 4/27

11:39 pm-9:56 am

1 stop8h 17m

Chicago Midway

Mon 5/4

7:16 pm-11:54 pm

1 stop6h 38m

$237

San FranciscoChicago

SFO - MDW

SFOMDW

San Francisco

Thu 3/5

8:05 am-11:51 pm

1 stop13h 46m

Chicago Midway

Wed 3/11

11:25 am-12:28 am

2 stops15h 03m

$239

San FranciscoChicago

SFO - MDW

SFOMDW

San Francisco

Tue 3/17

10:55 pm-8:50 am

1 stop7h 55m

Chicago Midway

Thu 3/19

9:25 pm-12:05 am

Nonstop4h 40m

$242

San FranciscoChicago

SFO - MDW

SFOMDW

San Francisco

Mon 3/9

5:10 am-11:10 am

Nonstop4h 00m

Chicago Midway

Tue 3/17

3:35 pm-9:05 pm

1 stop7h 30m

$245

San FranciscoChicago

SFO - MDW

SFOMDW

San Francisco

Mon 4/20

5:15 am-11:25 am

Nonstop4h 10m

Chicago Midway

Sat 4/25

5:30 pm-9:55 pm

1 stop6h 25m

$247

San FranciscoChicago

SFO - MDW

SFOMDW

San Francisco

Tue 4/14

6:00 am-10:19 pm

2 stops14h 19m

Chicago Midway

Sat 4/18

6:00 am-4:54 pm

1 stop12h 54m

$249

San FranciscoChicago

SFO - MDW

SFOMDW

San Francisco

Tue 4/28

11:25 pm-5:40 am

Nonstop4h 15m

Chicago Midway

Tue 5/5

5:15 pm-10:05 pm

1 stop6h 50m

$250

San FranciscoChicago

SFO - MDW

SFOMDW

San Francisco

Sat 4/25

6:29 pm-12:35 pm

2 stops40h 06m

Chicago Midway

Fri 5/1

3:29 pm-10:31 pm

1 stop9h 02m

$251

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 August is also very affordable. Most momondo users find prices during this month for around $289.

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 $376. 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 $488.

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 $588. 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 $364 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 $253 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 51% 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

$154

Fastest flight time

4h 00m

Direct flights

Every day
The best one-way flight to Chicago Midway Airport from San Francisco in the past 72 hours is $154. The best round-trip flight deal from San Francisco to Chicago Midway Airport found on momondo in the last 72 hours is $339.
The fastest flight from San Francisco to Chicago Midway Airport takes 4h 00m
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 4h 00m.

  • 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
9,325 reviews
Search United Airlines flights
FrontierPriceFrom $147Free CancellationRating
5.7
3,046 reviews
Search Frontier flights
SouthwestPriceFrom $228Free CancellationRating
8.0
4,295 reviews
Search Southwest flights
DeltaPriceFrom $241Free CancellationRating
7.9
8,215 reviews
Search Delta flights

  • Southwest Flights From San Francisco to Chicago Midway Airport

    Southwest flight deals from San Francisco to Chicago Midway Airport start from $228 round-trip. Over the 4 Southwest flights for this route in a normal week, average airfare is usually $390 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
Benton Harbor
Saint Joseph
Portage
Lansing
Valparaiso
Schererville
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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