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Cheap flights from San Francisco to Chicago Midway Airport from $61

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 Midway Airport departing on 4/27. 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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0 bags

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Find the cheapest flights from San Francisco to Chicago

Cheap round-trip flights

KAYAK's recommended round-trip deals from the most popular airlines that fly from San Francisco to Chicago.
Southwest Logo
7:20 am - 4:50 pmSFO-MDW
7h 30m1 stop
Southwest Logo
6:10 pm - 11:50 pmMDW-SFO
7h 40m1 stop
$198Southwest
Find Deal
Sat, May 24 - Fri, May 30
Southwest Logo
6:35 pm - 5:20 amSFO-MDW
8h 45m1 stop
Southwest Logo
11:25 am - 1:55 pmMDW-SFO
4h 30mnonstop
$207Southwest
Find Deal
Tue, Apr 22 - Wed, Apr 23
Southwest Logo
3:45 pm - 11:55 pmSFO-MDW
6h 10m1 stop
Southwest Logo
5:25 pm - 11:30 pmMDW-SFO
8h 05m1 stop
$212Southwest
Find Deal
Tue, May 20 - Wed, Jun 11
Frontier Logo
11:38 pm - 10:05 amSFO-MDW
8h 27m1 stop
Frontier Logo
4:47 pm - 11:08 pmMDW-SFO
8h 21m1 stop
$236Frontier
Find Deal
Thu, Apr 24 - Fri, Apr 25
Frontier Logo
6:20 am - 7:08 pmSFO-MDW
10h 48m1 stop
Frontier Logo
10:48 am - 10:22 pmMDW-SFO
13h 34m1 stop
$238Frontier
Find Deal
Thu, May 1 - Sat, May 10
Frontier Logo
12:11 am - 3:34 pmSFO-MDW
13h 23m1 stop
Frontier Logo
8:00 am - 1:19 pmMDW-SFO
31h 19m1 stop
$240Frontier
Find Deal
Thu, Apr 24 - Sun, Apr 27
Frontier Logo
8:32 pm - 5:20 amSFO-MDW
6h 48m1 stop
Frontier Logo
8:01 pm - 12:33 amMDW-SFO
6h 32m1 stop
$245Frontier
Find Deal
Sun, Apr 20 - Fri, Apr 25
Delta Logo
6:30 am - 2:22 pmSFO-MDW
5h 52m1 stop
Delta Logo
1:08 pm - 6:56 pmMDW-SFO
7h 48m1 stop
$257Delta
Find Deal
Sun, Apr 20 - Wed, May 7
Delta Logo
12:49 am - 8:43 amSFO-MDW
5h 54m1 stop
Delta Logo
10:39 am - 6:50 pmMDW-SFO
10h 11m1 stop
$267Delta
Find Deal
Mon, Jun 16 - Wed, Jun 18
Delta Logo
12:40 am - 8:36 amSFO-MDW
5h 56m1 stop
Delta Logo
10:35 am - 6:52 pmMDW-SFO
10h 17m1 stop
$277Delta
Find Deal
Fri, Jul 18 - Sat, Jul 26

Southwest flights from San Francisco to Chicago Midway Airport

Our best Southwest deals on San Francisco to Chicago Midway Airport flight tickets
Southwest
May 24
SFO7:20 amSan Francisco
7h 30m
1 stop
MDW4:50 pmChicago Midway
May 30
MDW6:10 pmChicago Midway
7h 40m
1 stop
SFO11:50 pmSan Francisco
Southwest
Apr 22
SFO6:35 pmSan Francisco
8h 45m
1 stop
MDW5:20 amChicago Midway
Apr 23
MDW11:25 amChicago Midway
4h 30m
SFO1:55 pmSan Francisco
Southwest
May 20
SFO3:45 pmSan Francisco
6h 10m
1 stop
MDW11:55 pmChicago Midway
Jun 11
MDW5:25 pmChicago Midway
8h 05m
1 stop
SFO11:30 pmSan Francisco

Frontier flights from San Francisco to Chicago Midway Airport

Our best Frontier deals on San Francisco to Chicago Midway Airport flight tickets
Frontier
Apr 24
SFO11:38 pmSan Francisco
8h 27m
1 stop
MDW10:05 amChicago Midway
Apr 25
MDW4:47 pmChicago Midway
8h 21m
1 stop
SFO11:08 pmSan Francisco
Frontier
May 1
SFO6:20 amSan Francisco
10h 48m
1 stop
MDW7:08 pmChicago Midway
May 10
MDW10:48 amChicago Midway
13h 34m
1 stop
SFO10:22 pmSan Francisco
Frontier
Apr 24
SFO12:11 amSan Francisco
13h 23m
1 stop
MDW3:34 pmChicago Midway
Apr 27
MDW8:00 amChicago Midway
31h 19m
1 stop
SFO1:19 pmSan Francisco

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 September is, on average, the cheapest month to fly to Chicago Midway Airport from San Francisco, with most prices found around $184. If you are unable to visit Chicago Midway Airport during the month of September, then departing from San Francisco during the month January is also very affordable. Most momondo users find prices during this month for around $207.

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 $225. 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 $416.

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 $178 when looking at flights departing in the afternoon. Try not to purchase tickets at noon because they tend to be around $486. 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 19 weeks ahead of your departure date. In general, you can expect to find flights to Chicago Midway Airport for around $284 when searching 19 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 $135 on momondo.

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

There are 1 cabin classes 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.

How have San Francisco to Chicago Midway Airport flight prices changed over time?

As of April 2025, prices for San Francisco to Chicago Midway Airport flights are approximately 14% cheaper 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

$61

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 $61. The best round-trip flight deal from San Francisco to Chicago Midway Airport found on momondo in the last 72 hours is $198.
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.

  • 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
FrontierPriceFrom $65Free CancellationRating
5.9
3,277 reviews
Search Frontier flights
Alaska AirlinesPriceFrom $115Free CancellationRating
8.0
9,823 reviews
Search Alaska Airlines flights
United AirlinesPriceFrom $185Free CancellationRating
7.4
8,615 reviews
Search United Airlines flights
SouthwestPriceFrom $208Free CancellationRating
8.0
4,275 reviews
Search Southwest flights
DeltaPriceFrom $236Free CancellationRating
8.0
7,899 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 $208 round-trip. Over the 8 Southwest flights for this route in a normal week, average airfare is usually $398 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
Portage
Lansing
Saint Joseph
Schererville
Valparaiso
Munster
Crown Point
Monticello
Chesterton
Griffith
Porter
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.


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