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Cheap flights from San Francisco to Chicago Midway Airport from $62

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 2/5. 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.
10:29 pm - 11:48 amSFO-MDW
11h 19m1 stop
7:15 am - 12:46 pmMDW-SFO
7h 31m1 stop
$128Frontier
Find Deal
Thu, Jan 9 - Mon, Jan 13
10:29 pm - 11:48 amSFO-MDW
11h 19m1 stop
8:15 am - 12:11 amMDW-SFO
17h 56m1 stop
$129Frontier
Find Deal
Thu, Jan 9 - Wed, Jan 15
6:55 am - 12:13 amSFO-MDW
15h 18m1 stop
8:15 am - 12:09 amMDW-SFO
17h 54m1 stop
$136Frontier
Find Deal
Tue, Jan 14 - Tue, Jan 21
10:29 pm - 11:48 amSFO-MDW
11h 19m1 stop
8:15 am - 12:11 amMDW-SFO
17h 56m1 stop
$137Frontier
Find Deal
Thu, Jan 9 - Tue, Jan 14
8:10 am - 12:13 amSFO-MDW
14h 03m2 stops
8:15 am - 6:00 pmMDW-SFO
11h 45m2 stops
Thu, Jan 9 - Wed, Jan 15
2:39 pm - 11:44 amSFO-MDW
19h 05m1 stop
7:30 am - 9:21 pmMDW-SFO
15h 51m2 stops
Sat, Jan 18 - Sat, Jan 25
10:45 pm - 8:54 amSFO-MDW
8h 09m1 stop
5:05 pm - 11:22 pmMDW-SFO
8h 17m1 stop
$252Delta
Find Deal
Sun, Jan 12 - Sun, Jan 19
12:40 am - 10:42 amSFO-MDW
8h 02m1 stop
10:19 am - 6:06 pmMDW-SFO
9h 47m1 stop
$256Delta
Find Deal
Fri, Feb 21 - Wed, Feb 26
6:10 am - 12:20 pmSFO-MDW
4h 10mnonstop
11:05 am - 5:40 pmMDW-SFO
8h 35m1 stop
$257Southwest
Find Deal
Sat, Feb 15 - Wed, Feb 19
6:15 am - 12:25 pmSFO-MDW
4h 10mnonstop
4:45 pm - 7:40 pmMDW-SFO
4h 55mnonstop
$258Southwest
Find Deal
Thu, Feb 6 - Mon, Feb 10
6:55 am - 12:17 amSFO-MDW
15h 22m1 stop
$62Frontier
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Wed, Feb 5
6:55 am - 12:13 amSFO-MDW
15h 18m1 stop
$63Frontier
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Tue, Jan 14
12:59 am - 12:11 pmSFO-MDW
9h 12m1 stop
$64Frontier
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Tue, Feb 25
10:29 pm - 11:44 amSFO-MDW
11h 15m1 stop
$69Frontier
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Sat, Jan 25
6:15 am - 12:25 pmSFO-MDW
4h 10mnonstop
$87Southwest
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Fri, Feb 7
6:10 am - 12:20 pmSFO-MDW
4h 10mnonstop
$99Southwest
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Sat, Feb 15
7:08 pm - 10:09 amSFO-MDW
13h 01m1 stop
Thu, Apr 17
7:08 pm - 10:09 amSFO-MDW
13h 01m1 stop
Thu, Apr 17
12:40 am - 9:39 amSFO-MDW
6h 59m1 stop
$128Delta
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Mon, Jan 20
6:15 am - 5:18 pmSFO-MDW
9h 03m1 stop
$134Delta
Find Deal
Sat, Apr 12
2:34 pm - 7:32 pmSFO-MDW
26h 58m1 stop
8:15 am - 12:09 amMDW-SFO
17h 54m1 stop
$431Frontier
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Thu, Dec 19 - Wed, Jan 22
6:00 am - 7:32 pmSFO-MDW
11h 32m1 stop
10:04 pm - 12:11 amMDW-SFO
28h 07m1 stop
$481Frontier
Find Deal
Fri, Dec 20 - Mon, Jan 6
8:05 pm - 5:33 amSFO-MDW
7h 28m1 stop
8:41 pm - 7:52 amMDW-SFO
13h 11m1 stop
$530Frontier
Find Deal
Mon, Dec 23 - Mon, Dec 30
5:30 pm - 1:40 amSFO-MDW
6h 10m1 stop
11:30 am - 4:55 pmMDW-SFO
7h 25m1 stop
$598Southwest
Find Deal
Sun, Dec 22 - Wed, Dec 25
6:00 am - 9:09 pmSFO-MDW
13h 09m1 stop
10:27 pm - 2:57 pmMDW-SFO
18h 30m1 stop
$601Frontier
Find Deal
Mon, Dec 23 - Wed, Jan 1
3:00 pm - 11:20 pmSFO-MDW
6h 20m1 stop
1:00 pm - 7:15 pmMDW-SFO
8h 15m1 stop
$603Southwest
Find Deal
Thu, Dec 19 - Wed, Dec 25
12:45 pm - 10:45 pmSFO-MDW
8h 00m1 stop
10:00 am - 4:55 pmMDW-SFO
8h 55m2 stops
$613Southwest
Find Deal
Thu, Dec 19 - Wed, Dec 25
5:40 am - 4:24 pmSFO-MDW
8h 44m1 stop
9:30 am - 2:48 pmMDW-SFO
7h 18m1 stop
$628Delta
Find Deal
Mon, Dec 23 - Wed, Dec 25
10:59 pm - 8:50 amSFO-MDW
7h 51m1 stop
11:48 am - 9:14 pmMDW-SFO
11h 26m1 stop
$631Delta
Find Deal
Mon, Dec 23 - Wed, Dec 25
5:40 am - 4:24 pmSFO-MDW
8h 44m1 stop
9:30 am - 2:48 pmMDW-SFO
7h 18m1 stop
$683Delta
Find Deal
Thu, Dec 19 - Wed, Dec 25
6:10 am - 12:20 pmSFO-MDW
4h 10mnonstop
11:05 am - 1:55 pmMDW-SFO
4h 50mnonstop
$198Southwest
Find Deal
Sat, Feb 15 - Sat, Feb 22
6:10 am - 12:20 pmSFO-MDW
4h 10mnonstop
6:20 pm - 9:00 pmMDW-SFO
4h 40mnonstop
$218Southwest
Find Deal
Thu, Mar 13 - Mon, Mar 17
10:20 am - 4:30 pmSFO-MDW
4h 10mnonstop
9:30 am - 12:25 pmMDW-SFO
4h 55mnonstop
$238Southwest
Find Deal
Thu, Feb 13 - Mon, Feb 17
6:15 am - 12:25 pmSFO-MDW
4h 10mnonstop
4:45 pm - 7:40 pmMDW-SFO
4h 55mnonstop
$258Southwest
Find Deal
Thu, Feb 6 - Mon, Feb 10
6:10 am - 12:20 pmSFO-MDW
4h 10mnonstop
12:35 pm - 3:20 pmMDW-SFO
4h 45mnonstop
$270Southwest
Find Deal
Thu, Mar 20 - Wed, Apr 2
6:15 am - 12:25 pmSFO-MDW
4h 10mnonstop
9:05 am - 12:00 pmMDW-SFO
4h 55mnonstop
$271Southwest
Find Deal
Fri, Jan 17 - Sat, Jan 18
6:10 am - 12:20 pmSFO-MDW
4h 10mnonstop
9:05 am - 12:00 pmMDW-SFO
4h 55mnonstop
$278Southwest
Find Deal
Sun, Jan 12 - Sat, Jan 18
6:10 am - 12:20 pmSFO-MDW
4h 10mnonstop
4:45 pm - 7:40 pmMDW-SFO
4h 55mnonstop
$292Southwest
Find Deal
Sun, Jan 12 - Fri, Jan 17
6:15 am - 12:25 pmSFO-MDW
4h 10mnonstop
9:05 am - 12:00 pmMDW-SFO
4h 55mnonstop
$300Southwest
Find Deal
Thu, Jan 16 - Sat, Jan 18
6:10 am - 12:20 pmSFO-MDW
4h 10mnonstop
9:30 am - 12:25 pmMDW-SFO
4h 55mnonstop
$303Southwest
Find Deal
Sat, Feb 15 - Mon, Feb 17

Frontier flights from San Francisco to Chicago Midway Airport

Our best Frontier deals on San Francisco to Chicago Midway Airport flight tickets
Frontier
Jan 9
SFO10:29 pmSan Francisco
11h 19m
1 stop
MDW11:48 amChicago Midway
Jan 13
MDW7:15 amChicago Midway
7h 31m
1 stop
SFO12:46 pmSan Francisco
Frontier
Jan 9
SFO10:29 pmSan Francisco
11h 19m
1 stop
MDW11:48 amChicago Midway
Jan 15
MDW8:15 amChicago Midway
17h 56m
1 stop
SFO12:11 amSan Francisco
Frontier
Jan 14
SFO6:55 amSan Francisco
15h 18m
1 stop
MDW12:13 amChicago Midway
Jan 21
MDW8:15 amChicago Midway
17h 54m
1 stop
SFO12:09 amSan Francisco

Delta flights from San Francisco to Chicago Midway Airport

Our best Delta deals on San Francisco to Chicago Midway Airport flight tickets
Delta
Jan 12
SFO10:45 pmSan Francisco
8h 09m
1 stop
MDW8:54 amChicago Midway
Jan 19
MDW5:05 pmChicago Midway
8h 17m
1 stop
SFO11:22 pmSan Francisco
Delta
Feb 21
SFO12:40 amSan Francisco
8h 02m
1 stop
MDW10:42 amChicago Midway
Feb 26
MDW10:19 amChicago Midway
9h 47m
1 stop
SFO6:06 pmSan Francisco
Delta
Jan 1
SFO5:40 amSan Francisco
8h 30m
1 stop
MDW4:10 pmChicago Midway
Jan 24
MDW6:59 pmChicago Midway
6h 55m
1 stop
SFO11:54 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 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 September is, on average, the cheapest month to fly to Chicago Midway Airport from San Francisco, with most prices found around $167. If you are unable to visit Chicago Midway Airport during the month of September, then departing from San Francisco during the month April is also very affordable. Most momondo users find prices during this month for around $212.

What is the cheapest day to depart on your flight to Chicago Midway Airport?

According to our data, Saturday is the cheapest day to fly to Chicago Midway Airport from San Francisco. The lowest ticket price found for a Saturday departure recently was $232. 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 $343.

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 $217 when looking at flights departing in the afternoon. Try not to purchase tickets at noon because they tend to be around $368. 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?

We recommend purchasing flights from San Francisco to Chicago Midway Airport 25 days ahead of your departure date because this is when momondo users tend to see the best flight rates. On average, our users have found flights to Chicago Midway Airport for $271. In the past 72 hours, momondo users found flights from San Francisco to Chicago Midway Airport for as low as $78.

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.

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

You could potentially save up to 37% 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 December 2024, prices for San Francisco to Chicago Midway Airport flights are approximately 28% 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

$62

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 $62. The best round-trip flight deal from San Francisco to Chicago Midway Airport found on momondo in the last 72 hours is $128.
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 $83Free CancellationRating
6.1
3,479 reviews
Search Frontier flights
Alaska AirlinesPriceFrom $115Free CancellationRating
8.0
9,552 reviews
Search Alaska Airlines flights
United AirlinesPriceFrom $185Free CancellationRating
7.4
9,059 reviews
Search United Airlines flights
SouthwestPriceFrom $219Free CancellationRating
8.1
4,848 reviews
Search Southwest flights
DeltaPriceFrom $236Free CancellationRating
8.0
8,604 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 $219 round-trip. Over the 3 Southwest flights for this route in a normal week, average airfare is usually $435 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.


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