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Cheap flights from San Francisco to Chicago from $127

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 1/22. 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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Cheap round-trip flights

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Southwest Logo
6:10 am - 12:15 pmSFO-MDW
4h 05mnonstop
Southwest Logo
8:20 am - 3:05 pmMDW-SFO
8h 45m1 stop
$283Southwest
Find Deal
Wed, Dec 10 - Wed, Dec 17
Southwest Logo
5:10 am - 11:10 amSFO-MDW
4h 00mnonstop
Southwest Logo
3:05 pm - 12:10 amMDW-SFO
11h 05m2 stops
$284Southwest
Find Deal
Sun, Mar 8 - Sat, Mar 14
Frontier Logo
8:43 am - 10:12 pmSFO-MDW
11h 29m2 stops
Frontier Logo
7:24 pm - 5:34 pmMDW-SFO
24h 10m1 stop
$285Frontier
Find Deal
Thu, Dec 11 - Sun, Dec 14
Delta Logo
12:40 am - 9:08 amSFO-MDW
6h 28m1 stop
Delta Logo
1:49 pm - 11:30 pmMDW-SFO
11h 41m2 stops
$286Delta
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Wed, Jan 21 - Mon, Jan 26
Frontier Logo
6:05 am - 2:05 pmSFO-MDW
6h 00m1 stop
Frontier Logo
6:10 am - 1:24 pmMDW-SFO
9h 14m1 stop
$287Frontier
Find Deal
Fri, Jan 9 - Fri, Jan 16
Frontier Logo
6:05 am - 2:05 pmSFO-MDW
6h 00m1 stop
Frontier Logo
6:10 am - 1:24 pmMDW-SFO
9h 14m1 stop
$288Frontier
Find Deal
Fri, Jan 9 - Fri, Jan 16
Southwest Logo
5:55 am - 11:55 amSFO-MDW
4h 00mnonstop
Southwest Logo
5:20 am - 9:55 amMDW-SFO
6h 35m1 stop
$289Southwest
Find Deal
Thu, Feb 12 - Mon, Feb 16
Frontier Logo
11:55 am - 7:54 pmSFO-MDW
5h 59m1 stop
Frontier Logo
6:10 am - 1:24 pmMDW-SFO
9h 14m1 stop
$291Frontier
Find Deal
Fri, Jan 16 - Mon, Jan 19
Delta Logo
12:40 am - 9:08 amSFO-MDW
6h 28m1 stop
Delta Logo
1:49 pm - 11:28 pmMDW-SFO
11h 39m2 stops
$292Delta
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Wed, Jan 7 - Mon, Jan 12
Southwest Logo
6:10 am - 12:15 pmSFO-MDW
4h 05mnonstop
Southwest Logo
8:15 am - 11:00 amMDW-SFO
4h 45mnonstop
$294Southwest
Find Deal
Wed, Dec 10 - Wed, Dec 17

Southwest flights from San Francisco to Chicago Midway Airport

Our best Southwest deals on San Francisco to Chicago Midway Airport flight tickets
Southwest
Dec 10
SFO6:10 amSan Francisco
4h 05m
MDW12:15 pmChicago Midway
Dec 17
MDW8:20 amChicago Midway
8h 45m
1 stop
SFO3:05 pmSan Francisco
$283
Find similar
Southwest
Mar 8
SFO5:10 amSan Francisco
4h 00m
MDW11:10 amChicago Midway
Mar 14
MDW3:05 pmChicago Midway
11h 05m
2 stops
SFO12:10 amSan Francisco
$284
Find similar
Southwest
Feb 12
SFO5:55 amSan Francisco
4h 00m
MDW11:55 amChicago Midway
Feb 22
MDW6:10 amChicago Midway
8h 30m
1 stop
SFO12:40 pmSan Francisco
$289
Find similar

Delta flights from San Francisco to Chicago Midway Airport

Our best Delta deals on San Francisco to Chicago Midway Airport flight tickets
Delta
Jan 21
SFO12:40 amSan Francisco
6h 28m
1 stop
MDW9:08 amChicago Midway
Jan 26
MDW1:49 pmChicago Midway
11h 41m
2 stops
SFO11:30 pmSan Francisco
$286
Find similar
Delta
Dec 30
SFO12:10 amSan Francisco
8h 56m
1 stop
MDW11:06 amChicago Midway
Jan 6
MDW6:14 pmChicago Midway
7h 11m
1 stop
SFO11:25 pmSan Francisco
$288
Find similar
Delta
Jan 7
SFO12:40 amSan Francisco
6h 28m
1 stop
MDW9:08 amChicago Midway
Jan 12
MDW1:49 pmChicago Midway
11h 39m
2 stops
SFO11:28 pmSan Francisco
$292
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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 November 26, 2025.
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

Wed 12/10

6:10 am-12:15 pm

Nonstop4h 05m

Chicago Midway

Wed 12/17

8:20 am-3:05 pm

1 stop8h 45m

$283

San FranciscoChicago

SFO - MDW

SFOMDW

San Francisco

Sun 3/8

5:10 am-11:10 am

Nonstop4h 00m

Chicago Midway

Sat 3/14

3:05 pm-12:10 am

2 stops11h 05m

$284

San FranciscoChicago

SFO - MDW

SFOMDW

San Francisco

Thu 12/11

8:43 am-10:12 pm

2 stops11h 29m

Chicago Midway

Sun 12/14

7:24 pm-5:34 pm

1 stop24h 10m

$285

San FranciscoChicago

SFO - MDW

SFOMDW

San Francisco

Wed 1/21

12:40 am-9:08 am

1 stop6h 28m

Chicago Midway

Mon 1/26

1:49 pm-11:30 pm

2 stops11h 41m

$286

San FranciscoChicago

SFO - MDW

SFOMDW

San Francisco

Fri 1/9

6:05 am-2:05 pm

1 stop6h 00m

Chicago Midway

Fri 1/16

6:10 am-1:24 pm

1 stop9h 14m

$287

San FranciscoChicago

SFO - MDW

SFOMDW

San Francisco

Fri 1/9

6:05 am-2:05 pm

1 stop6h 00m

Chicago Midway

Fri 1/16

6:10 am-1:24 pm

1 stop9h 14m

$288

San FranciscoChicago

SFO - MDW

SFOMDW

San Francisco

Thu 2/12

5:55 am-11:55 am

Nonstop4h 00m

Chicago Midway

Mon 2/16

5:20 am-9:55 am

1 stop6h 35m

$289

San FranciscoChicago

SFO - MDW

SFOMDW

San Francisco

Fri 1/16

11:55 am-7:54 pm

1 stop5h 59m

Chicago Midway

Mon 1/19

6:10 am-1:24 pm

1 stop9h 14m

$291

San FranciscoChicago

SFO - MDW

SFOMDW

San Francisco

Wed 1/7

12:40 am-9:08 am

1 stop6h 28m

Chicago Midway

Mon 1/12

1:49 pm-11:28 pm

2 stops11h 39m

$292

San FranciscoChicago

SFO - MDW

SFOMDW

San Francisco

Wed 12/10

6:10 am-12:15 pm

Nonstop4h 05m

Chicago Midway

Wed 12/17

8:15 am-11:00 am

Nonstop4h 45m

$294

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 $202. 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 $242.

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 $395. 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 $508.

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 $366 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 $239 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 19% 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?

As of November 2025, prices for San Francisco to Chicago Midway Airport flights are approximately 251% more expensive when compared to flights at the same time last year.

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

$168

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 $168. The best round-trip flight deal from San Francisco to Chicago Midway Airport found on momondo in the last 72 hours is $342.
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
9,046 reviews
Search United Airlines flights
FrontierPriceFrom $147Free CancellationRating
5.8
3,099 reviews
Search Frontier flights
American AirlinesPriceFrom $197Free CancellationRating
7.2
11,038 reviews
Search American Airlines flights
SouthwestPriceFrom $217Free CancellationRating
8.0
4,254 reviews
Search Southwest flights
DeltaPriceFrom $256Free CancellationRating
7.9
7,999 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 $217 round-trip. Over the 5 Southwest flights for this route in a normal week, average airfare is usually $399 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
Schererville
Valparaiso
Crown Point
Munster
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

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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