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Cheap flights from San Francisco to Chicago from $124

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.
Southwest Logo
9:20 am - 8:00 pmSFO  San Francisco-MDW Chicago Midway
8h 40m2 stops Denver Intl Houston Hobby
Southwest Logo
6:05 am - 11:25 amMDW  Chicago Midway-SFO San Francisco
7h 20m1 stop Las Vegas Harry Reid Intl
$256Southwest
Sat, Oct 24 - Tue, Oct 27
Southwest Logo
7:20 am - 7:35 pmSFO  San Francisco-MDW Chicago Midway
10h 15m1 stop Austin Bergstrom
Southwest Logo
12:15 pm - 8:20 pmMDW  Chicago Midway-SFO San Francisco
10h 05m1 stop Austin Bergstrom
$256Southwest
Sat, Oct 17 - Tue, Oct 20
Southwest Logo
1:30 pm - 10:25 pmSFO  San Francisco-MDW Chicago Midway
6h 55m1 stop Las Vegas Harry Reid Intl
Southwest Logo
10:15 am - 7:20 pmMDW  Chicago Midway-SFO San Francisco
11h 05m2 stops Oklahoma City Will Rogers World Denver Intl
$256Southwest
Wed, Nov 4 - Tue, Nov 10
Frontier Logo
11:52 pm - 11:25 amSFO  San Francisco-MDW Chicago Midway
9h 33m1 stop Dallas/Fort Worth
Frontier Logo
12:20 pm - 10:29 pmMDW  Chicago Midway-SFO San Francisco
12h 09m1 stop Dallas/Fort Worth
$257Frontier
Wed, Nov 4 - Mon, Nov 9
Frontier Logo
11:52 pm - 11:22 amSFO  San Francisco-MDW Chicago Midway
9h 30m1 stop Dallas/Fort Worth
Frontier Logo
12:20 pm - 10:29 pmMDW  Chicago Midway-SFO San Francisco
12h 09m1 stop Dallas/Fort Worth
$257Frontier
Tue, Oct 27 - Mon, Nov 2
Frontier Logo
11:52 pm - 11:25 amSFO  San Francisco-MDW Chicago Midway
9h 33m1 stop Dallas/Fort Worth
Frontier Logo
12:20 pm - 10:29 pmMDW  Chicago Midway-SFO San Francisco
12h 09m1 stop Dallas/Fort Worth
$258Frontier
Wed, Oct 28 - Mon, Nov 2
Delta Logo
10:59 pm - 10:24 amSFO  San Francisco-MDW Chicago Midway
9h 25m1 stop Atlanta Hartsfield-Jackson
Delta Logo
5:29 pm - 11:57 pmMDW  Chicago Midway-SFO San Francisco
8h 28m1 stop Minneapolis St Paul
$267Delta
Tue, Nov 10 - Mon, Nov 16
Delta Logo
11:39 pm - 8:50 amSFO  San Francisco-MDW Chicago Midway
7h 11m1 stop Minneapolis St Paul
Delta Logo
9:30 am - 2:26 pmMDW  Chicago Midway-SFO San Francisco
6h 56m1 stop Detroit Metropolitan Wayne County
$267Delta
Mon, Nov 16 - Wed, Nov 18
Multiple Airlines Logo
11:59 pm - 12:17 pmSFO  San Francisco-MDW Chicago Midway
10h 18m1 stop Dallas/Fort Worth
Multiple Airlines Logo
1:26 pm - 2:25 pmMDW  Chicago Midway-SFO San Francisco
26h 59m2 stops Knoxville McGhee Tyson Las Vegas Harry Reid Intl
$506Multiple Airlines
Sun, Oct 11 - Mon, Oct 19
Multiple Airlines Logo
11:52 pm - 5:47 pmSFO  San Francisco-MDW Chicago Midway
15h 55m3 stops Dallas/Fort Worth Greenville Mid-Delta Atlanta Hartsfield-Jackson
Multiple Airlines Logo
6:42 pm - 4:02 pmMDW  Chicago Midway-SFO San Francisco
23h 20m3 stops Atlanta Hartsfield-Jackson Houston George Bush Intcntl Phoenix Sky Harbor Intl
$633Multiple Airlines
Fri, Nov 6 - Sun, Nov 8

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Southwest flights from San Francisco to Chicago Midway Airport

Our best Southwest deals on San Francisco to Chicago Midway Airport flight tickets
Southwest
Oct 17
SFO7:20 amSan Francisco
10h 15m
1 stop
MDW7:35 pmChicago Midway
Oct 20
MDW12:15 pmChicago Midway
10h 05m
1 stop
SFO8:20 pmSan Francisco
$256
Southwest
Oct 13
SFO4:50 pmSan Francisco
9h 40m
1 stop
MDW4:30 amChicago Midway
Oct 14
MDW6:25 amChicago Midway
8h 20m
1 stop
SFO12:45 pmSan Francisco
$257
Southwest
Oct 15
SFO2:40 pmSan Francisco
8h 00m
1 stop
MDW12:40 amChicago Midway
Oct 20
MDW8:55 pmChicago Midway
4h 45m
SFO11:40 pmSan Francisco
$258

Frontier flights from San Francisco to Chicago Midway Airport

Our best Frontier deals on San Francisco to Chicago Midway Airport flight tickets
Frontier
Nov 4
SFO7:25 pmSan Francisco
14h 00m
2 stops
MDW11:25 amChicago Midway
Nov 10
MDW12:27 pmChicago Midway
31h 52m
2 stops
SFO6:19 pmSan Francisco
$259
Frontier
Oct 16
SFO11:59 pmSan Francisco
12h 36m
1 stop
MDW2:35 pmChicago Midway
Oct 20
MDW6:21 amChicago Midway
13h 34m
1 stop
SFO5:55 pmSan Francisco
$260
Frontier
Nov 6
SFO9:14 amSan Francisco
12h 33m
2 stops
MDW11:47 pmChicago Midway
Nov 10
MDW12:27 pmChicago Midway
12h 02m
1 stop
SFO10:29 pmSan Francisco
$266

momondo Fare Finder

 
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

Sat 10/24

9:20 am-8:00 pm

2 stops8h 40m

Chicago Midway

Tue 10/27

6:05 am-11:25 am

1 stop7h 20m

$256

San FranciscoChicago

SFO San Francisco - MDW Chicago Midway

SFOMDW

San Francisco

Sat 10/17

7:20 am-7:35 pm

1 stop10h 15m

Chicago Midway

Tue 10/20

12:15 pm-8:20 pm

1 stop10h 05m

$256

San FranciscoChicago

SFO San Francisco - MDW Chicago Midway

SFOMDW

San Francisco

Wed 11/4

1:30 pm-10:25 pm

1 stop6h 55m

Chicago Midway

Tue 11/10

10:15 am-7:20 pm

2 stops11h 05m

$256

San FranciscoChicago

SFO San Francisco - MDW Chicago Midway

SFOMDW

San Francisco

Wed 11/4

11:52 pm-11:25 am

1 stop9h 33m

Chicago Midway

Mon 11/9

12:20 pm-10:29 pm

1 stop12h 09m

$257

San FranciscoChicago

SFO San Francisco - MDW Chicago Midway

SFOMDW

San Francisco

Tue 10/27

11:52 pm-11:22 am

1 stop9h 30m

Chicago Midway

Mon 11/2

12:20 pm-10:29 pm

1 stop12h 09m

$257

San FranciscoChicago

SFO San Francisco - MDW Chicago Midway

SFOMDW

San Francisco

Wed 10/28

11:52 pm-11:25 am

1 stop9h 33m

Chicago Midway

Mon 11/2

12:20 pm-10:29 pm

1 stop12h 09m

$258

San FranciscoChicago

SFO San Francisco - MDW Chicago Midway

SFOMDW

San Francisco

Tue 11/10

10:59 pm-10:24 am

1 stop9h 25m

Chicago Midway

Mon 11/16

5:29 pm-11:57 pm

1 stop8h 28m

$267
Quickest round-trip

San FranciscoChicago

SFO San Francisco - MDW Chicago Midway

SFOMDW

San Francisco

Mon 11/16

11:39 pm-8:50 am

1 stop7h 11m

Chicago Midway

Wed 11/18

9:30 am-2:26 pm

1 stop6h 56m

$267

San FranciscoChicago

SFO San Francisco - MDW Chicago Midway

SFOMDW

San Francisco

Sun 10/11

11:59 pm-12:17 pm

1 stop10h 18m

Chicago Midway

Mon 10/19

1:26 pm-2:25 pm

2 stops26h 59m

$506

San FranciscoChicago

SFO San Francisco - MDW Chicago Midway

SFOMDW

San Francisco

Fri 11/6

11:52 pm-5:47 pm

3 stops15h 55m

Chicago Midway

Sun 11/8

6:42 pm-4:02 pm

3 stops23h 20m

$633

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 $345 to $561.
The lowest price recently found on this route was $256.

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 $332.

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 $427. 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 $444 when looking at flights departing in the evening. Try not to purchase tickets in the morning because they tend to be around $478. 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 $416 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 $296 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?

You could potentially save up to 24% 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

$124

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 $124. The best round-trip flight deal from San Francisco to Chicago Midway Airport found on momondo in the last 72 hours is $256.
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
FrontierPriceFrom $190Free CancellationRating
5.6
2,599 reviews
Search Frontier flights
DeltaPriceFrom $205Free CancellationRating
7.8
8,581 reviews
Search Delta flights
JetBluePriceFrom $224Free CancellationRating
7.1
3,035 reviews
Search JetBlue flights
SouthwestPriceFrom $266Free CancellationRating
8.0
4,190 reviews
Search Southwest flights
United AirlinesPriceFrom $359Free CancellationRating
7.4
10,214 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 9 Southwest flights for this route in a normal week, average airfare is usually $435 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
Porter
Crown Point
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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