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Cheap flights from San Francisco to Chicago from $136

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 9/23. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult
1 adult, Economy, 0 bags

Discover deals from 900+ travel sites with momondo.

Find the cheapest flights from San Francisco to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
Delta Logo
12:05 am - 8:48 amSFO  San Francisco-MDW Chicago Midway
6h 43m1 stop Minneapolis St Paul
Delta Logo
5:15 pm - 11:56 pmMDW  Chicago Midway-SFO San Francisco
8h 41m1 stop Atlanta Hartsfield-Jackson
$277Delta
Wed, Sep 30 - Wed, Oct 7
Delta Logo
10:59 pm - 9:07 amSFO  San Francisco-MDW Chicago Midway
8h 08m1 stop Detroit Metropolitan Wayne County
Delta Logo
1:27 pm - 6:17 pmMDW  Chicago Midway-SFO San Francisco
6h 50m1 stop Detroit Metropolitan Wayne County
$277Delta
Wed, Sep 30 - Tue, Oct 6
Southwest Logo
10:40 am - 9:10 pmSFO  San Francisco-MDW Chicago Midway
8h 30m1 stop Phoenix Sky Harbor Intl
Southwest Logo
6:15 am - 10:55 amMDW  Chicago Midway-SFO San Francisco
6h 40m1 stop San Diego
$277Southwest
Wed, Sep 16 - Mon, Sep 21
Southwest Logo
6:35 am - 4:05 pmSFO  San Francisco-MDW Chicago Midway
7h 30m2 stops Denver Intl Des Moines
Southwest Logo
5:00 pm - 10:50 pmMDW  Chicago Midway-SFO San Francisco
7h 50m2 stops Kansas City Denver Intl
$277Southwest
Wed, Sep 9 - Fri, Sep 11
Southwest Logo
11:15 am - 10:50 pmSFO  San Francisco-MDW Chicago Midway
9h 35m2 stops San Diego Denver Intl
Southwest Logo
1:45 pm - 7:35 pmMDW  Chicago Midway-SFO San Francisco
7h 50m2 stops Omaha Eppley Airfield San Diego
$277Southwest
Tue, Sep 1 - Sat, Sep 5
Delta Logo
10:59 pm - 9:07 amSFO  San Francisco-MDW Chicago Midway
8h 08m1 stop Detroit Metropolitan Wayne County
Delta Logo
5:31 pm - 11:58 pmMDW  Chicago Midway-SFO San Francisco
8h 27m1 stop Minneapolis St Paul
$277Delta
Wed, Sep 30 - Wed, Oct 7
Delta Logo
9:55 pm - 9:49 amSFO  San Francisco-MDW Chicago Midway
9h 54m1 stop Atlanta Hartsfield-Jackson
Delta Logo
2:00 pm - 8:32 pmMDW  Chicago Midway-SFO San Francisco
8h 32m1 stop Minneapolis St Paul
$277Delta
Tue, Sep 22 - Mon, Sep 28
Frontier Logo
11:58 pm - 11:59 amSFO  San Francisco-MDW Chicago Midway
10h 01m1 stop Dallas/Fort Worth
Frontier Logo
6:40 am - 6:20 pmMDW  Chicago Midway-SFO San Francisco
13h 40m1 stop Atlanta Hartsfield-Jackson
$278Frontier
Sun, Oct 4 - Sun, Oct 11
Frontier Logo
10:48 pm - 10:58 amSFO  San Francisco-MDW Chicago Midway
10h 10m1 stop Atlanta Hartsfield-Jackson
Frontier Logo
6:40 am - 6:20 pmMDW  Chicago Midway-SFO San Francisco
13h 40m1 stop Atlanta Hartsfield-Jackson
$280Frontier
Mon, Oct 12 - Mon, Oct 19
Frontier Logo
10:48 pm - 10:58 amSFO  San Francisco-MDW Chicago Midway
10h 10m1 stop Atlanta Hartsfield-Jackson
Frontier Logo
6:40 am - 6:20 pmMDW  Chicago Midway-SFO San Francisco
13h 40m1 stop Atlanta Hartsfield-Jackson
$280Frontier
Tue, Oct 13 - Thu, Oct 22

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Frontier flights from San Francisco to Chicago Midway Airport

Our best Frontier deals on San Francisco to Chicago Midway Airport flight tickets
Frontier
Oct 4
SFO11:58 pmSan Francisco
10h 01m
1 stop
MDW11:59 amChicago Midway
Oct 11
MDW6:40 amChicago Midway
13h 40m
1 stop
SFO6:20 pmSan Francisco
$278
Frontier
Aug 27
SFO10:01 amSan Francisco
8h 30m
1 stop
MDW8:31 pmChicago Midway
Sep 3
MDW11:50 amChicago Midway
9h 36m
1 stop
SFO7:26 pmSan Francisco
$280
Frontier
Oct 2
SFO11:58 pmSan Francisco
10h 01m
1 stop
MDW11:59 amChicago Midway
Oct 5
MDW12:54 pmChicago Midway
11h 34m
1 stop
SFO10:28 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
Aug 27
SFO10:05 amSan Francisco
8h 00m
1 stop
MDW8:05 pmChicago Midway
Aug 29
MDW1:45 pmChicago Midway
7h 50m
2 stops
SFO7:35 pmSan Francisco
$282
Southwest
Sep 2
SFO10:30 amSan Francisco
4h 10m
MDW4:40 pmChicago Midway
Sep 5
MDW6:00 pmChicago Midway
4h 35m
SFO8:35 pmSan Francisco
$287
Southwest
Sep 26
SFO3:25 pmSan Francisco
11h 05m
1 stop
MDW4:30 amChicago Midway
Sep 29
MDW3:10 pmChicago Midway
8h 00m
2 stops
SFO9:10 pmSan Francisco
$288

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 August 7, 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 San Francisco - MDW Chicago Midway

SFOMDW

San Francisco

Wed 9/30

12:05 am-8:48 am

1 stop6h 43m

Chicago Midway

Wed 10/7

5:15 pm-11:56 pm

1 stop8h 41m

$277
Quickest round-trip

San FranciscoChicago

SFO San Francisco - MDW Chicago Midway

SFOMDW

San Francisco

Wed 9/30

10:59 pm-9:07 am

1 stop8h 08m

Chicago Midway

Tue 10/6

1:27 pm-6:17 pm

1 stop6h 50m

$277

San FranciscoChicago

SFO San Francisco - MDW Chicago Midway

SFOMDW

San Francisco

Wed 9/16

10:40 am-9:10 pm

1 stop8h 30m

Chicago Midway

Mon 9/21

6:15 am-10:55 am

1 stop6h 40m

$277

San FranciscoChicago

SFO San Francisco - MDW Chicago Midway

SFOMDW

San Francisco

Wed 9/9

6:35 am-4:05 pm

2 stops7h 30m

Chicago Midway

Fri 9/11

5:00 pm-10:50 pm

2 stops7h 50m

$277

San FranciscoChicago

SFO San Francisco - MDW Chicago Midway

SFOMDW

San Francisco

Tue 9/1

11:15 am-10:50 pm

2 stops9h 35m

Chicago Midway

Sat 9/5

1:45 pm-7:35 pm

2 stops7h 50m

$277

San FranciscoChicago

SFO San Francisco - MDW Chicago Midway

SFOMDW

San Francisco

Wed 9/30

10:59 pm-9:07 am

1 stop8h 08m

Chicago Midway

Wed 10/7

5:31 pm-11:58 pm

1 stop8h 27m

$277

San FranciscoChicago

SFO San Francisco - MDW Chicago Midway

SFOMDW

San Francisco

Tue 9/22

9:55 pm-9:49 am

1 stop9h 54m

Chicago Midway

Mon 9/28

2:00 pm-8:32 pm

1 stop8h 32m

$277

San FranciscoChicago

SFO San Francisco - MDW Chicago Midway

SFOMDW

San Francisco

Sun 10/4

11:58 pm-11:59 am

1 stop10h 01m

Chicago Midway

Sun 10/11

6:40 am-6:20 pm

1 stop13h 40m

$278

San FranciscoChicago

SFO San Francisco - MDW Chicago Midway

SFOMDW

San Francisco

Mon 10/12

10:48 pm-10:58 am

1 stop10h 10m

Chicago Midway

Mon 10/19

6:40 am-6:20 pm

1 stop13h 40m

$280

San FranciscoChicago

SFO San Francisco - MDW Chicago Midway

SFOMDW

San Francisco

Tue 10/13

10:48 pm-10:58 am

1 stop10h 10m

Chicago Midway

Thu 10/22

6:40 am-6:20 pm

1 stop13h 40m

$280

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?

Prices are currently low for flights on this route.

Typical prices usually range from $279 to $468.
The lowest price recently found on this route was $277.

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 $266. If you are unable to visit Chicago Midway Airport during the month of January, then departing from San Francisco during the month April is also very affordable. Most momondo users find prices during this month for around $343.

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 $428. 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 $511.

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 evening is the least expensive time of day to depart. momondo users have found prices as low as $445 when looking at flights departing in the evening. Try not to purchase tickets in the morning because they tend to be around $473. 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 $407 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 $292 on momondo.

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

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

No. A direct flight is the cheapest option for a flight between San Francisco to Chicago Midway Airport.

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 00m

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 $354.
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

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 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
DeltaPriceFrom $205Free CancellationRating
7.8
8,499 reviews
Search Delta flights
FrontierPriceFrom $213Free CancellationRating
5.6
2,722 reviews
Search Frontier flights
JetBluePriceFrom $224Free CancellationRating
7.1
3,025 reviews
Search JetBlue flights
SouthwestPriceFrom $266Free CancellationRating
8.0
4,216 reviews
Search Southwest flights
United AirlinesPriceFrom $359Free CancellationRating
7.4
10,080 reviews
Search United Airlines flights

  • Southwest Flights From San Francisco to Chicago Midway Airport

    Southwest flight deals from San Francisco to Chicago Midway Airport start from $266 round-trip. Over the 12 Southwest flights for this route in a normal week, average airfare is usually $432 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
Portage
Benton Harbor
Lansing
Saint Joseph
Valparaiso
Schererville
Munster
Chesterton
Monticello
Crown Point
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

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.
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