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Cheap flights from San Francisco to Chicago Midway Airport from $95

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 11/16. 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

Cheap round-trip flights

These are some of the best round-trip flight deals from San Francisco to Chicago that have been recently found on momondo from popular airlines, departing in the coming months.

Cheap one-way flights

Flying one-way? These are some of the best deals recently discovered on momondo for flights from San Francisco to Chicago.

Cheap last minute flights

Planning a quick getaway from San Francisco to Chicago? These are the last-minute flight deals available now.

Cheap direct flights

If you prefer a non-stop journey, check out our latest direct flight deals to Chicago, so you can enjoy a seamless trip without layovers.

Cheap bus & train deals from San Francisco to Chicago

Find recent round-trip train or bus tickets from San Francisco to Chicago.

All round-trip flight deals to Chicago

The cheapest plane tickets to Chicago found on KAYAK recently.
10:51 pm - 11:05 amSFO-MDW
10h 14m1 stop
6:13 pm - 11:27 pmMDW-SFO
7h 14m1 stop
$208Frontier
Find Deal
Sat, Nov 16 - Mon, Nov 18
8:53 pm - 10:21 amSFO-MDW
11h 28m1 stop
9:40 pm - 7:10 amMDW-SFO
11h 30m1 stop
$210Frontier
Find Deal
Sat, Nov 16 - Sat, Nov 23
10:14 am - 10:25 pmSFO-MDW
10h 11m1 stop
6:13 pm - 11:27 pmMDW-SFO
7h 14m1 stop
$214Frontier
Find Deal
Fri, Nov 15 - Mon, Nov 18
10:19 pm - 9:54 pmSFO-MDW
21h 35m1 stop
6:13 pm - 11:27 pmMDW-SFO
7h 14m1 stop
$215Frontier
Find Deal
Thu, Nov 14 - Mon, Nov 18
5:40 am - 5:02 pmSFO-MDW
9h 22m1 stop
6:49 pm - 12:49 amMDW-SFO
8h 00m1 stop
$256Delta
Find Deal
Tue, Nov 26 - Wed, Nov 27
9:25 am - 3:35 pmSFO-MDW
4h 10mnonstop
4:50 pm - 7:30 pmMDW-SFO
4h 40mnonstop
$258Southwest
Find Deal
Sat, Dec 7 - Tue, Dec 10
5:40 am - 5:02 pmSFO-MDW
9h 22m1 stop
4:58 pm - 11:23 pmMDW-SFO
8h 25m1 stop
$266Delta
Find Deal
Tue, Nov 26 - Fri, Dec 6
6:15 am - 12:25 pmSFO-MDW
4h 10mnonstop
1:45 pm - 9:15 pmMDW-SFO
9h 30m2 stops
$272Southwest
Find Deal
Thu, Feb 20 - Mon, Feb 24
12:25 am - 8:50 amSFO-MDW
6h 25m1 stop
1:26 pm - 9:00 pmMDW-SFO
9h 34m1 stop
$276Delta
Find Deal
Sun, Dec 8 - Mon, Jan 13
9:10 am - 3:20 pmSFO-MDW
4h 10mnonstop
4:45 pm - 7:40 pmMDW-SFO
4h 55mnonstop
$278Southwest
Find Deal
Fri, Dec 13 - Sun, Jan 12
8:53 pm - 10:21 amSFO-MDW
11h 28m1 stop
$95Frontier
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Sat, Nov 16
11:47 pm - 1:24 pmSFO-MDW
11h 37m1 stop
$97Frontier
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Sun, Jan 5
8:15 am - 2:25 pmSFO-MDW
4h 10mnonstop
$109Southwest
Find Deal
Wed, Dec 11
6:10 am - 12:20 pmSFO-MDW
4h 10mnonstop
$125Southwest
Find Deal
Sat, Feb 15
5:40 am - 4:10 pmSFO-MDW
8h 30m1 stop
$128Delta
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Wed, Dec 25
12:25 am - 8:50 amSFO-MDW
6h 25m1 stop
$138Delta
Find Deal
Sun, Dec 8
9:53 am - 3:01 pmSFO-MDW
27h 08m3 stops
Wed, Nov 27
1:55 pm - 10:36 amSFO-MDW
18h 41m3 stops
$356WestJet
Find Deal
Fri, Jan 10
1:55 pm - 10:36 amSFO-MDW
18h 41m3 stops
$364WestJet
Find Deal
Fri, Jan 31
6:15 pm - 5:51 pmSFO-MDW
21h 36m3 stops
Wed, Dec 18
6:00 am - 12:04 pmSFO-MDW
28h 04m1 stop
7:00 am - 12:34 amMDW-SFO
19h 34m1 stop
$247Frontier
Find Deal
Thu, Nov 7 - Tue, Nov 26
10:14 am - 10:25 pmSFO-MDW
10h 11m1 stop
6:13 pm - 11:27 pmMDW-SFO
7h 14m1 stop
$254Frontier
Find Deal
Fri, Nov 8 - Mon, Nov 18
10:51 pm - 11:05 amSFO-MDW
10h 14m1 stop
9:40 pm - 7:10 amMDW-SFO
11h 30m1 stop
$258Frontier
Find Deal
Sat, Nov 9 - Sat, Nov 23
10:19 pm - 9:54 pmSFO-MDW
21h 35m1 stop
11:33 am - 8:44 pmMDW-SFO
11h 11m1 stop
$301Frontier
Find Deal
Thu, Nov 7 - Tue, Nov 12
5:05 am - 3:40 pmSFO-MDW
8h 35m2 stops
5:00 pm - 12:35 amMDW-SFO
9h 35m1 stop
$508Southwest
Find Deal
Sat, Nov 9 - Sat, Nov 23
8:15 am - 2:25 pmSFO-MDW
4h 10mnonstop
11:05 am - 1:50 pmMDW-SFO
4h 45mnonstop
$521Southwest
Find Deal
Wed, Nov 6 - Fri, Nov 8
10:20 am - 8:05 pmSFO-MDW
7h 45m1 stop
11:05 am - 1:50 pmMDW-SFO
4h 45mnonstop
$530Southwest
Find Deal
Wed, Nov 6 - Fri, Nov 8
10:58 pm - 8:55 amSFO-MDW
7h 57m1 stop
9:24 am - 3:59 pmMDW-SFO
8h 35m1 stop
$618Delta
Find Deal
Wed, Nov 6 - Sat, Nov 9
10:58 pm - 8:55 amSFO-MDW
7h 57m1 stop
9:31 am - 2:54 pmMDW-SFO
7h 23m1 stop
$698Delta
Find Deal
Tue, Nov 5 - Tue, Nov 12
10:58 pm - 8:55 amSFO-MDW
7h 57m1 stop
9:24 am - 2:33 pmMDW-SFO
7h 09m1 stop
$757Delta
Find Deal
Thu, Nov 7 - Sun, Nov 10
8:15 am - 2:25 pmSFO-MDW
4h 10mnonstop
8:40 am - 11:25 amMDW-SFO
4h 45mnonstop
$238Southwest
Find Deal
Wed, Dec 11 - Sat, Dec 14
8:15 am - 2:25 pmSFO-MDW
4h 10mnonstop
4:50 pm - 7:30 pmMDW-SFO
4h 40mnonstop
$258Southwest
Find Deal
Wed, Dec 4 - Wed, Dec 11
9:10 am - 3:20 pmSFO-MDW
4h 10mnonstop
4:50 pm - 7:30 pmMDW-SFO
4h 40mnonstop
$278Southwest
Find Deal
Fri, Dec 13 - Mon, Dec 16
8:15 am - 2:25 pmSFO-MDW
4h 10mnonstop
4:50 pm - 7:30 pmMDW-SFO
4h 40mnonstop
$303Southwest
Find Deal
Thu, Dec 5 - Mon, Dec 9
8:15 am - 2:25 pmSFO-MDW
4h 10mnonstop
4:50 pm - 7:30 pmMDW-SFO
4h 40mnonstop
$342Southwest
Find Deal
Tue, Dec 3 - Tue, Dec 10
10:20 am - 4:30 pmSFO-MDW
4h 10mnonstop
11:20 am - 1:55 pmMDW-SFO
4h 35mnonstop
$368Southwest
Find Deal
Thu, Apr 10 - Tue, Apr 15
6:00 am - 12:10 pmSFO-MDW
4h 10mnonstop
11:05 am - 1:50 pmMDW-SFO
4h 45mnonstop
$383Southwest
Find Deal
Wed, Nov 27 - Sun, Dec 15
9:10 am - 3:20 pmSFO-MDW
4h 10mnonstop
4:50 pm - 7:30 pmMDW-SFO
4h 40mnonstop
$399Southwest
Find Deal
Mon, Nov 25 - Mon, Dec 9
6:10 am - 12:20 pmSFO-MDW
4h 10mnonstop
11:20 am - 1:55 pmMDW-SFO
4h 35mnonstop
$407Southwest
Find Deal
Fri, Apr 4 - Tue, Apr 8
12:40 pm - 6:45 pmSFO-MDW
4h 05mnonstop
7:05 pm - 9:45 pmMDW-SFO
4h 40mnonstop
$428Southwest
Find Deal
Sat, Mar 22 - Sun, Mar 30

Delta flights from San Francisco to Chicago Midway Airport

Our best Delta deals on San Francisco to Chicago Midway Airport flight tickets
Delta
Nov 26
SFO5:40 amSan Francisco
9h 22m
1 stop
MDW5:02 pmChicago Midway
Nov 27
MDW6:49 pmChicago Midway
8h 00m
1 stop
SFO12:49 amSan Francisco
Delta
Nov 26
SFO5:40 amSan Francisco
9h 22m
1 stop
MDW5:02 pmChicago Midway
Dec 6
MDW4:58 pmChicago Midway
8h 25m
1 stop
SFO11:23 pmSan Francisco
Delta
Dec 8
SFO12:25 amSan Francisco
6h 25m
1 stop
MDW8:50 amChicago Midway
Jan 13
MDW1:26 pmChicago Midway
9h 34m
1 stop
SFO9:00 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
Nov 16
SFO10:51 pmSan Francisco
10h 14m
1 stop
MDW11:05 amChicago Midway
Nov 18
MDW6:13 pmChicago Midway
7h 14m
1 stop
SFO11:27 pmSan Francisco
Frontier
Nov 16
SFO8:53 pmSan Francisco
11h 28m
1 stop
MDW10:21 amChicago Midway
Nov 23
MDW9:40 pmChicago Midway
11h 30m
1 stop
SFO7:10 amSan Francisco
Frontier
Nov 15
SFO10:14 amSan Francisco
10h 11m
1 stop
MDW10:25 pmChicago Midway
Nov 18
MDW6:13 pmChicago Midway
7h 14m
1 stop
SFO11:27 pmSan Francisco

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 from San Francisco to Chicago Midway Airport?

September. The cheapest time of year to fly to Chicago Midway Airport from San Francisco is September. Most expensive is October

What is the cheapest day to depart San Francisco for Chicago Midway Airport?

Saturday. The cheapest day of the week is typically Saturday. The most expensive is typically Monday

When is the cheapest time to fly from San Francisco to Chicago Midway Airport?

In the afternoon. San Francisco to Chicago Midway Airport flights are approximately 32% more expensive at noon than in the afternoon

What is the cheapest airline that flies to Chicago Midway Airport from San Francisco?

Frontier. Frontier, Alaska Airlines, and United Airlines are the most popular carriers operating from San Francisco to Chicago Midway Airport

How far in advance should you book San Francisco to Chicago Midway Airport flights?

43 days before. The cheapest time to buy a flight from San Francisco to Chicago Midway Airport is approximately 43 days to departure

How many flights depart from San Francisco to Chicago Midway Airport on average per week?

As of November 2024, 6 flights take off from San Francisco and land in Chicago Midway Airport each week. The most common flight departure day for this route is Sunday, with 17% of weekly flights taking off on this day.

Can stopping save me money on San Francisco to Chicago Midway Airport flights?

You could potentially save up to 43% 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 2024, prices for San Francisco to Chicago Midway Airport flights are approximately 67% 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

$95

Fastest flight time

4h 05m

Direct flights

Every day
The best one-way flight to Chicago Midway Airport from San Francisco in the past 72 hours is $95. The best round-trip flight deal from San Francisco to Chicago Midway Airport found on momondo in the last 72 hours is $208.
The fastest flight from San Francisco to Chicago Midway Airport takes 4h 05m
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 $71Free CancellationRating
6.1
3,573 reviews
Search Frontier flights
Alaska AirlinesPriceFrom $168Free CancellationRating
8.0
9,423 reviews
Search Alaska Airlines flights
United AirlinesPriceFrom $185Free CancellationRating
7.4
9,226 reviews
Search United Airlines flights
SouthwestPriceFrom $210Free CancellationRating
8.1
5,089 reviews
Search Southwest flights
DeltaPriceFrom $236Free CancellationRating
8.0
8,829 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 $210 round-trip. Over the 6 Southwest flights for this route in a normal week, average airfare is usually $385 round-trip - but some users have found much cheaper deals with momondo.


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

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