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Cheap flights from San Francisco to Chicago from $165

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 8/22. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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.
Frontier Logo
11:00 pm - 11:07 am
SFO
-
MDW
10h 07m
1 stop
Frontier Logo
12:11 pm - 7:18 pm
MDW
-
SFO
9h 07m
1 stop
$318Frontier
Sat, Jul 25 - Tue, Jul 28
Frontier Logo
10:10 pm - 11:07 am
SFO
-
MDW
10h 57m
1 stop
Frontier Logo
6:05 am - 7:18 pm
MDW
-
SFO
15h 13m
1 stop
$319Frontier
Tue, Jul 14 - Sat, Jul 18
Frontier Logo
10:10 pm - 11:07 am
SFO
-
MDW
10h 57m
1 stop
Frontier Logo
12:11 pm - 7:18 pm
MDW
-
SFO
9h 07m
1 stop
$320Frontier
Tue, Jul 21 - Sat, Jul 25
Frontier Logo
11:00 pm - 11:07 am
SFO
-
MDW
10h 07m
1 stop
Frontier Logo
12:11 pm - 7:18 pm
MDW
-
SFO
9h 07m
1 stop
$321Frontier
Fri, Jul 24 - Tue, Jul 28
Delta Logo
12:40 am - 8:49 am
SFO
-
MDW
6h 09m
1 stop
Delta Logo
5:25 pm - 12:15 am
MDW
-
SFO
8h 50m
1 stop
$322Delta
Wed, Nov 18 - Thu, Dec 3
Multiple Airlines Logo
11:00 pm - 11:07 am
SFO
-
MDW
10h 07m
1 stop
Multiple Airlines Logo
8:11 pm - 5:07 pm
MDW
-
SFO
22h 56m
2 stops
$323Multiple Airlines
Mon, Jul 13 - Thu, Jul 16
Multiple Airlines Logo
10:10 pm - 9:51 am
SFO
-
MDW
9h 41m
1 stop
Multiple Airlines Logo
8:20 pm - 5:07 pm
MDW
-
SFO
22h 47m
2 stops
$324Multiple Airlines
Tue, Aug 4 - Sun, Aug 9
Delta Logo
9:30 am - 8:48 am
SFO
-
MDW
21h 18m
2 stops
Delta Logo
7:13 pm - 11:53 pm
MDW
-
SFO
6h 40m
1 stop
$325Delta
Tue, Sep 29 - Wed, Sep 30
Frontier Logo
12:29 am - 3:50 pm
SFO
-
MDW
13h 21m
1 stop
Frontier Logo
6:05 am - 7:18 pm
MDW
-
SFO
15h 13m
1 stop
$326Frontier
Tue, Jul 7 - Thu, Jul 16
Frontier Logo
10:01 am - 8:31 pm
SFO
-
MDW
8h 30m
1 stop
Frontier Logo
11:50 am - 7:03 pm
MDW
-
SFO
9h 13m
1 stop
$327Frontier
Sun, Aug 23 - Sun, Aug 30

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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
Jul 17
SFO11:40 pmSan Francisco
4h 15m
MDW5:55 amChicago Midway
Jul 22
MDW9:30 pmChicago Midway
4h 45m
SFO12:15 amSan Francisco
$322
Southwest
Aug 19
SFO11:40 pmSan Francisco
4h 10m
MDW5:50 amChicago Midway
Aug 25
MDW10:25 amChicago Midway
4h 30m
SFO12:55 pmSan Francisco
$329
Southwest
Aug 19
SFO6:50 amSan Francisco
6h 15m
1 stop
MDW3:05 pmChicago Midway
Aug 23
MDW10:10 amChicago Midway
4h 35m
SFO12:45 pmSan Francisco
$332

Frontier flights from San Francisco to Chicago Midway Airport

Our best Frontier deals on San Francisco to Chicago Midway Airport flight tickets
Frontier
Jul 25
SFO11:00 pmSan Francisco
10h 07m
1 stop
MDW11:07 amChicago Midway
Jul 30
MDW12:11 pmChicago Midway
9h 07m
1 stop
SFO7:18 pmSan Francisco
$318
Frontier
Jul 14
SFO10:10 pmSan Francisco
10h 57m
1 stop
MDW11:07 amChicago Midway
Jul 18
MDW6:05 amChicago Midway
15h 13m
1 stop
SFO7:18 pmSan Francisco
$319
Frontier
Jul 21
SFO10:10 pmSan Francisco
10h 57m
1 stop
MDW11:07 amChicago Midway
Jul 25
MDW12:11 pmChicago Midway
9h 07m
1 stop
SFO7:18 pmSan Francisco
$320

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 June 27, 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 - MDW

SFOMDW

San Francisco

Sat 7/25

11:00 pm-11:07 am

1 stop10h 07m

Chicago Midway

Tue 7/28

12:11 pm-7:18 pm

1 stop9h 07m

$318

San FranciscoChicago

SFO - MDW

SFOMDW

San Francisco

Tue 7/14

10:10 pm-11:07 am

1 stop10h 57m

Chicago Midway

Sat 7/18

6:05 am-7:18 pm

1 stop15h 13m

$319

San FranciscoChicago

SFO - MDW

SFOMDW

San Francisco

Tue 7/21

10:10 pm-11:07 am

1 stop10h 57m

Chicago Midway

Sat 7/25

12:11 pm-7:18 pm

1 stop9h 07m

$320

San FranciscoChicago

SFO - MDW

SFOMDW

San Francisco

Fri 7/24

11:00 pm-11:07 am

1 stop10h 07m

Chicago Midway

Tue 7/28

12:11 pm-7:18 pm

1 stop9h 07m

$321
Quickest round-trip

San FranciscoChicago

SFO - MDW

SFOMDW

San Francisco

Wed 11/18

12:40 am-8:49 am

1 stop6h 09m

Chicago Midway

Thu 12/3

5:25 pm-12:15 am

1 stop8h 50m

$322

San FranciscoChicago

SFO - MDW

SFOMDW

San Francisco

Mon 7/13

11:00 pm-11:07 am

1 stop10h 07m

Chicago Midway

Thu 7/16

8:11 pm-5:07 pm

2 stops22h 56m

$323

San FranciscoChicago

SFO - MDW

SFOMDW

San Francisco

Tue 8/4

10:10 pm-9:51 am

1 stop9h 41m

Chicago Midway

Sun 8/9

8:20 pm-5:07 pm

2 stops22h 47m

$324

San FranciscoChicago

SFO - MDW

SFOMDW

San Francisco

Tue 9/29

9:30 am-8:48 am

2 stops21h 18m

Chicago Midway

Wed 9/30

7:13 pm-11:53 pm

1 stop6h 40m

$325

San FranciscoChicago

SFO - MDW

SFOMDW

San Francisco

Tue 7/7

12:29 am-3:50 pm

1 stop13h 21m

Chicago Midway

Thu 7/16

6:05 am-7:18 pm

1 stop15h 13m

$326

San FranciscoChicago

SFO - MDW

SFOMDW

San Francisco

Sun 8/23

10:01 am-8:31 pm

1 stop8h 30m

Chicago Midway

Sun 8/30

11:50 am-7:03 pm

1 stop9h 13m

$327

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?

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 August is also very affordable. Most momondo users find prices during this month for around $307.

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 $426. 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 $503.

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 $464. 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 $392 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

$223

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 $223. The best round-trip flight deal from San Francisco to Chicago Midway Airport found on momondo in the last 72 hours is $403.
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 $147Free CancellationRating
5.6
2,861 reviews
Search Frontier flights
United AirlinesPriceFrom $207Free CancellationRating
7.4
9,896 reviews
Search United Airlines flights
DeltaPriceFrom $225Free CancellationRating
7.8
8,451 reviews
Search Delta flights
SouthwestPriceFrom $252Free CancellationRating
7.9
4,246 reviews
Search Southwest flights

  • Southwest Flights From San Francisco to Chicago Midway Airport

    Southwest flight deals from San Francisco to Chicago Midway Airport start from $252 round-trip. Over the 11 Southwest flights for this route in a normal week, average airfare is usually $426 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
Saint Joseph
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

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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