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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 1/14. 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
3:18 pm - 11:48 amSFO-MDW
18h 30m1 stop
12:57 pm - 8:50 pmMDW-SFO
9h 53m1 stop
$136Frontier
Find Deal
Wed, Dec 4 - Wed, Dec 11
3:18 pm - 11:48 amSFO-MDW
18h 30m1 stop
7:15 am - 12:50 pmMDW-SFO
7h 35m1 stop
$138Frontier
Find Deal
Wed, Dec 4 - Mon, Dec 16
9:10 pm - 12:13 amSFO-MDW
25h 03m1 stop
7:15 am - 12:50 pmMDW-SFO
7h 35m1 stop
$139Frontier
Find Deal
Mon, Dec 9 - Mon, Dec 16
6:05 am - 3:40 pmSFO-MDW
7h 35m1 stop
11:05 am - 1:55 pmMDW-SFO
4h 50mnonstop
$237Southwest
Find Deal
Wed, Feb 19 - Sat, Feb 22
6:05 am - 5:05 pmSFO-MDW
9h 00m2 stops
11:05 am - 1:55 pmMDW-SFO
4h 50mnonstop
$242Southwest
Find Deal
Wed, Feb 19 - Sat, Feb 22
12:09 pm - 10:20 pmSFO-MDW
8h 11m1 stop
5:05 pm - 11:22 pmMDW-SFO
8h 17m1 stop
$256Delta
Find Deal
Thu, Jan 23 - Sat, Feb 1
10:45 pm - 8:54 amSFO-MDW
8h 09m1 stop
5:05 pm - 11:22 pmMDW-SFO
8h 17m1 stop
$257Delta
Find Deal
Sat, Jan 11 - Sat, Jan 18
12:40 am - 10:36 amSFO-MDW
7h 56m1 stop
5:05 pm - 11:22 pmMDW-SFO
8h 17m1 stop
$262Delta
Find Deal
Fri, Feb 21 - Sat, Mar 1
3:00 pm - 11:05 pmSFO-MDW
6h 05m1 stop
6:20 am - 12:30 pmMDW-SFO
8h 10m1 stop
$272Southwest
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Mon, Mar 3 - Wed, Mar 5
6:55 am - 12:13 amSFO-MDW
15h 18m1 stop
$61Frontier
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Tue, Jan 14
11:33 am - 8:12 pmSFO-MDW
6h 39m1 stop
$63Frontier
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Mon, Jan 27
6:10 am - 12:20 pmSFO-MDW
4h 10mnonstop
$99Southwest
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Sat, Feb 22
6:10 am - 12:20 pmSFO-MDW
4h 10mnonstop
$119Southwest
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Sun, Jan 12
12:09 pm - 10:20 pmSFO-MDW
8h 11m1 stop
$128Delta
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Thu, Jan 23
12:40 am - 8:51 amSFO-MDW
6h 11m1 stop
$138Delta
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Thu, Nov 28
7:38 am - 9:49 amSFO-MDW
24h 11m2 stops
Sat, Dec 28
8:09 pm - 11:41 amSFO-MDW
13h 32m1 stop
Mon, Nov 25
1:55 pm - 10:36 amSFO-MDW
18h 41m3 stops
$357WestJet
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Fri, Jan 17
1:55 pm - 10:36 amSFO-MDW
18h 41m3 stops
$358WestJet
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Fri, Jan 10
9:42 am - 1:12 amSFO-MDW
13h 30m1 stop
12:05 pm - 9:50 pmMDW-SFO
11h 45m1 stop
$318Frontier
Find Deal
Sat, Nov 23 - Thu, Nov 28
10:41 pm - 11:10 amSFO-MDW
10h 29m1 stop
12:05 pm - 9:50 pmMDW-SFO
11h 45m1 stop
$322Frontier
Find Deal
Sun, Nov 24 - Thu, Nov 28
10:41 pm - 11:10 amSFO-MDW
10h 29m1 stop
12:05 pm - 9:50 pmMDW-SFO
11h 45m1 stop
$324Frontier
Find Deal
Sun, Nov 24 - Thu, Nov 28
9:09 pm - 8:42 pmSFO-MDW
21h 33m1 stop
12:05 pm - 9:50 pmMDW-SFO
11h 45m1 stop
$334Frontier
Find Deal
Sun, Nov 24 - Thu, Nov 28
12:40 am - 8:51 amSFO-MDW
6h 11m1 stop
9:31 am - 2:54 pmMDW-SFO
7h 23m1 stop
$452Delta
Find Deal
Sat, Nov 23 - Thu, Nov 28
12:40 am - 8:51 amSFO-MDW
6h 11m1 stop
6:00 am - 12:40 pmMDW-SFO
8h 40m1 stop
$458Delta
Find Deal
Mon, Nov 25 - Thu, Dec 5
12:40 am - 8:51 amSFO-MDW
6h 11m1 stop
9:31 am - 2:54 pmMDW-SFO
7h 23m1 stop
$497Delta
Find Deal
Sat, Nov 23 - Thu, Nov 28
5:20 am - 3:05 pmSFO-MDW
7h 45m2 stops
6:10 am - 12:15 pmMDW-SFO
8h 05m1 stop
$533Southwest
Find Deal
Sun, Nov 24 - Thu, Nov 28
6:20 am - 5:00 pmSFO-MDW
8h 40m2 stops
4:35 pm - 8:45 pmMDW-SFO
6h 10m1 stop
$563Southwest
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Thu, Nov 21 - Tue, Nov 26
5:20 am - 3:05 pmSFO-MDW
7h 45m2 stops
9:55 am - 5:25 pmMDW-SFO
9h 30m2 stops
$568Southwest
Find Deal
Sun, Nov 24 - Thu, Nov 28
6:10 am - 12:20 pmSFO-MDW
4h 10mnonstop
11:05 am - 1:55 pmMDW-SFO
4h 50mnonstop
$198Southwest
Find Deal
Sat, Feb 22 - Sat, Mar 1
10:20 am - 4:30 pmSFO-MDW
4h 10mnonstop
11:05 am - 1:55 pmMDW-SFO
4h 50mnonstop
$228Southwest
Find Deal
Thu, Feb 13 - Sat, Mar 1
6:15 am - 12:25 pmSFO-MDW
4h 10mnonstop
6:20 pm - 9:00 pmMDW-SFO
4h 40mnonstop
$264Southwest
Find Deal
Mon, Mar 3 - Thu, Mar 6
10:20 am - 4:30 pmSFO-MDW
4h 10mnonstop
9:30 am - 12:25 pmMDW-SFO
4h 55mnonstop
$278Southwest
Find Deal
Thu, Feb 13 - Sun, Mar 2
8:15 am - 2:25 pmSFO-MDW
4h 10mnonstop
8:40 am - 11:25 amMDW-SFO
4h 45mnonstop
$328Southwest
Find Deal
Wed, Dec 11 - Sat, Dec 14
10:20 am - 4:30 pmSFO-MDW
4h 10mnonstop
9:30 am - 12:25 pmMDW-SFO
4h 55mnonstop
$333Southwest
Find Deal
Fri, Feb 14 - Sun, Mar 2
6:10 am - 12:20 pmSFO-MDW
4h 10mnonstop
7:05 pm - 9:45 pmMDW-SFO
4h 40mnonstop
$349Southwest
Find Deal
Thu, Mar 6 - Sun, Mar 9
7:00 am - 1:05 pmSFO-MDW
4h 05mnonstop
6:20 pm - 9:00 pmMDW-SFO
4h 40mnonstop
$374Southwest
Find Deal
Tue, Apr 1 - Fri, Apr 4
9:25 am - 3:35 pmSFO-MDW
4h 10mnonstop
4:50 pm - 7:30 pmMDW-SFO
4h 40mnonstop
$386Southwest
Find Deal
Sat, Dec 7 - Tue, Dec 10
9:10 am - 3:20 pmSFO-MDW
4h 10mnonstop
4:50 pm - 7:30 pmMDW-SFO
4h 40mnonstop
$398Southwest
Find Deal
Fri, Dec 13 - Tue, Dec 17

Delta flights from San Francisco to Chicago Midway Airport

Our best Delta deals on San Francisco to Chicago Midway Airport flight tickets
Delta
Jan 23
SFO12:09 pmSan Francisco
8h 11m
1 stop
MDW10:20 pmChicago Midway
Feb 1
MDW5:05 pmChicago Midway
8h 17m
1 stop
SFO11:22 pmSan Francisco
Delta
Jan 11
SFO10:45 pmSan Francisco
8h 09m
1 stop
MDW8:54 amChicago Midway
Jan 18
MDW5:05 pmChicago Midway
8h 17m
1 stop
SFO11:22 pmSan Francisco
Delta
Feb 21
SFO12:40 amSan Francisco
7h 56m
1 stop
MDW10:36 amChicago Midway
Mar 1
MDW5:05 pmChicago Midway
8h 17m
1 stop
SFO11:22 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
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
Dec 4
SFO3:18 pmSan Francisco
18h 30m
1 stop
MDW11:48 amChicago Midway
Dec 11
MDW12:57 pmChicago Midway
9h 53m
1 stop
SFO8:50 pmSan Francisco
Frontier
Dec 4
SFO3:18 pmSan Francisco
18h 30m
1 stop
MDW11:48 amChicago Midway
Dec 16
MDW7:15 amChicago Midway
7h 35m
1 stop
SFO12:50 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 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 November

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 Thursday

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 42% more expensive at noon than in the afternoon

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

25 days before. The cheapest time to buy a flight from San Francisco to Chicago Midway Airport is approximately 25 days to departure

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

You could potentially save up to 38% 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

$61

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 $61. 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
3,539 reviews
Search Frontier flights
Alaska AirlinesPriceFrom $115Free CancellationRating
8.0
9,458 reviews
Search Alaska Airlines flights
United AirlinesPriceFrom $185Free CancellationRating
7.4
9,172 reviews
Search United Airlines flights
SouthwestPriceFrom $210Free CancellationRating
8.1
5,015 reviews
Search Southwest flights
DeltaPriceFrom $236Free CancellationRating
8.0
8,758 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 4 Southwest flights for this route in a normal week, average airfare is usually $401 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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