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Cheap flights from San Francisco to Chicago from $100

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 9/4. 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 (SFO-MDW)

Cheap round-trip flights

Logo
5:45 am - 8:52 pmSFO-MDW
13h 07m1 stop
Logo
7:03 pm - 9:21 pmMDW-SFO
28h 18m1 stop
$203
Find Deal
Fri, Sep 26 - Mon, Sep 29
Frontier Logo
6:34 am - 12:24 amSFO-MDW
15h 50m1 stop
Frontier Logo
6:24 pm - 12:14 amMDW-SFO
7h 50m1 stop
$209Frontier
Find Deal
Fri, Oct 10 - Fri, Oct 17
Frontier Logo
3:25 pm - 12:36 amSFO-MDW
7h 11m1 stop
Frontier Logo
6:24 pm - 12:14 amMDW-SFO
7h 50m1 stop
$210Frontier
Find Deal
Thu, Oct 16 - Mon, Oct 20
Frontier Logo
6:29 am - 3:53 pmSFO-MDW
7h 24m1 stop
Frontier Logo
12:11 pm - 12:14 amMDW-SFO
14h 03m1 stop
$212Frontier
Find Deal
Mon, Oct 6 - Fri, Oct 24
Frontier Logo
11:57 pm - 10:28 amSFO-MDW
8h 31m1 stop
Frontier Logo
7:15 am - 11:02 pmMDW-SFO
17h 47m1 stop
$214Frontier
Find Deal
Fri, Oct 3 - Mon, Oct 6
Frontier Logo
11:57 pm - 1:11 pmSFO-MDW
11h 14m1 stop
Frontier Logo
6:24 pm - 2:22 pmMDW-SFO
21h 58m1 stop
$218Frontier
Find Deal
Sun, Oct 5 - Sun, Oct 26
Southwest Logo
6:15 am - 12:20 pmSFO-MDW
4h 05mnonstop
Southwest Logo
8:15 am - 11:00 amMDW-SFO
4h 45mnonstop
$245Southwest
Find Deal
Thu, Nov 27 - Wed, Dec 3
Southwest Logo
12:35 pm - 8:25 pmSFO-MDW
5h 50m1 stop
Southwest Logo
5:30 am - 9:50 amMDW-SFO
6h 20m1 stop
$251Southwest
Find Deal
Sat, Nov 8 - Wed, Nov 12
Delta Logo
12:45 am - 8:53 amSFO-MDW
6h 08m1 stop
Delta Logo
1:08 pm - 5:47 pmMDW-SFO
6h 39m1 stop
$257Delta
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Fri, Sep 26 - Sat, Oct 4
Delta Logo
10:50 pm - 9:40 amSFO-MDW
8h 50m1 stop
Delta Logo
1:08 pm - 5:47 pmMDW-SFO
6h 39m1 stop
$276Delta
Find Deal
Mon, Sep 22 - Wed, Sep 24

Frontier flights from San Francisco to Chicago Midway Airport

Our best Frontier deals on San Francisco to Chicago Midway Airport flight tickets
Frontier
Oct 10
SFO6:34 amSan Francisco
15h 50m
1 stop
MDW12:24 amChicago Midway
Oct 17
MDW6:24 pmChicago Midway
7h 50m
1 stop
SFO12:14 amSan Francisco
$209
Find similar
Frontier
Oct 16
SFO3:25 pmSan Francisco
7h 11m
1 stop
MDW12:36 amChicago Midway
Oct 20
MDW6:24 pmChicago Midway
7h 50m
1 stop
SFO12:14 amSan Francisco
$210
Find similar
Frontier
Oct 6
SFO6:29 amSan Francisco
7h 24m
1 stop
MDW3:53 pmChicago Midway
Oct 24
MDW12:11 pmChicago Midway
14h 03m
1 stop
SFO12:14 amSan Francisco
$212
Find similar

Southwest flights from San Francisco to Chicago Midway Airport

Our best Southwest deals on San Francisco to Chicago Midway Airport flight tickets
Southwest
Sep 3
SFO9:05 pmSan Francisco
9h 55m
1 stop
MDW9:00 amChicago Midway
Sep 5
MDW11:10 amChicago Midway
4h 35m
SFO1:45 pmSan Francisco
$229
Find similar
Southwest
Sep 3
SFO1:45 pmSan Francisco
6h 10m
1 stop
MDW9:55 pmChicago Midway
Sep 5
MDW5:25 amChicago Midway
6h 00m
1 stop
SFO9:25 amSan Francisco
$239
Find similar
Southwest
Nov 27
SFO6:15 amSan Francisco
4h 05m
MDW12:20 pmChicago Midway
Dec 3
MDW8:15 amChicago Midway
4h 45m
SFO11:00 amSan Francisco
$245
Find similar

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 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

Fri 9/26

5:45 am-8:52 pm

1 stop13h 07m

Chicago Midway

Mon 9/29

7:03 pm-9:21 pm

1 stop28h 18m

$203

San FranciscoChicago

SFO - MDW

SFOMDW

San Francisco

Fri 10/10

6:34 am-12:24 am

1 stop15h 50m

Chicago Midway

Fri 10/17

6:24 pm-12:14 am

1 stop7h 50m

$209

San FranciscoChicago

SFO - MDW

SFOMDW

San Francisco

Thu 10/16

3:25 pm-12:36 am

1 stop7h 11m

Chicago Midway

Mon 10/20

6:24 pm-12:14 am

1 stop7h 50m

$210

San FranciscoChicago

SFO - MDW

SFOMDW

San Francisco

Mon 10/6

6:29 am-3:53 pm

1 stop7h 24m

Chicago Midway

Fri 10/24

12:11 pm-12:14 am

1 stop14h 03m

$212

San FranciscoChicago

SFO - MDW

SFOMDW

San Francisco

Fri 10/3

11:57 pm-10:28 am

1 stop8h 31m

Chicago Midway

Mon 10/6

7:15 am-11:02 pm

1 stop17h 47m

$214

San FranciscoChicago

SFO - MDW

SFOMDW

San Francisco

Sun 10/5

11:57 pm-1:11 pm

1 stop11h 14m

Chicago Midway

Sun 10/26

6:24 pm-2:22 pm

1 stop21h 58m

$218

San FranciscoChicago

SFO - MDW

SFOMDW

San Francisco

Thu 11/27

6:15 am-12:20 pm

Nonstop4h 05m

Chicago Midway

Wed 12/3

8:15 am-11:00 am

Nonstop4h 45m

$245

San FranciscoChicago

SFO - MDW

SFOMDW

San Francisco

Sat 11/8

12:35 pm-8:25 pm

1 stop5h 50m

Chicago Midway

Wed 11/12

5:30 am-9:50 am

1 stop6h 20m

$251

San FranciscoChicago

SFO - MDW

SFOMDW

San Francisco

Fri 9/26

12:45 am-8:53 am

1 stop6h 08m

Chicago Midway

Sat 10/4

1:08 pm-5:47 pm

1 stop6h 39m

$257

San FranciscoChicago

SFO - MDW

SFOMDW

San Francisco

Mon 9/22

10:50 pm-9:40 am

1 stop8h 50m

Chicago Midway

Wed 9/24

1:08 pm-5:47 pm

1 stop6h 39m

$276

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 $207. 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 $247.

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 $396. 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 $492.

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 $284 when looking at flights departing in the evening. Try not to purchase tickets at noon because they tend to be around $535. 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 $342 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 $208 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 6% 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 August 2025, prices for San Francisco to Chicago Midway Airport flights are approximately 49% 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

$198

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 $198. The best round-trip flight deal from San Francisco to Chicago Midway Airport found on momondo in the last 72 hours is $307.
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 05m.

  • 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
8,943 reviews
Search United Airlines flights
FrontierPriceFrom $138Free CancellationRating
5.8
3,200 reviews
Search Frontier flights
American AirlinesPriceFrom $197Free CancellationRating
7.2
10,000 reviews
Search American Airlines flights
Alaska AirlinesPriceFrom $197Free CancellationRating
8.0
10,000 reviews
Search Alaska Airlines flights
SouthwestPriceFrom $212Free CancellationRating
8.0
4,242 reviews
Search Southwest flights
DeltaPriceFrom $256Free CancellationRating
7.9
7,979 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 $212 round-trip. Over the 8 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
Lansing
Portage
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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