Latest deals
Insights
When to book
FAQs
Reviews
Price Alerts

Cheap flights from San Francisco to Chicago Midway Airport from $48

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 2/25. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult
0 bags

Deals available from 900+ travel sites.

Save money when you book flights with momondo
Big names and deals
Big names and deals
Search 100s of travel sites to compare prices.
Filter for what you want
Filter for what you want
Free Wi-Fi? Stopover? Instantly customize your results.
Trusted and free
Trusted and free
We’re completely free to use - no hidden charges or fees.
Price Alerts
Price Alerts
Not ready to book? to track prices.

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 from San Francisco to Chicago

The cheapest plane tickets from San Francisco to Chicago found on KAYAK recently.
2:53 pm - 12:17 amSFO-MDW
7h 24m1 stop
7:05 am - 12:43 amMDW-SFO
19h 38m1 stop
$112Frontier
Find Deal
mié., feb. 19 - mié., feb. 26
6:00 am - 12:17 amSFO-MDW
16h 17m1 stop
7:05 am - 1:33 pmMDW-SFO
8h 28m1 stop
$117Frontier
Find Deal
sáb., mar. 1 - mié., mar. 5
6:00 am - 12:17 amSFO-MDW
16h 17m1 stop
7:05 am - 1:33 pmMDW-SFO
8h 28m1 stop
$123Frontier
Find Deal
sáb., mar. 1 - mié., mar. 5
6:00 am - 12:17 amSFO-MDW
16h 17m1 stop
7:05 am - 12:43 amMDW-SFO
19h 38m1 stop
$124Frontier
Find Deal
sáb., mar. 1 - mié., mar. 5
6:15 am - 12:25 pmSFO-MDW
4h 10mnonstop
6:20 pm - 9:00 pmMDW-SFO
4h 40mnonstop
$217Southwest
Find Deal
lun., mar. 3 - jue., mar. 6
6:15 am - 12:25 pmSFO-MDW
4h 10mnonstop
6:20 am - 12:30 pmMDW-SFO
8h 10m1 stop
$228Southwest
Find Deal
lun., feb. 10 - mié., feb. 12
6:15 am - 12:25 pmSFO-MDW
4h 10mnonstop
4:45 pm - 7:40 pmMDW-SFO
4h 55mnonstop
$237Southwest
Find Deal
jue., feb. 20 - lun., feb. 24
12:40 am - 9:35 amSFO-MDW
6h 55m1 stop
5:05 pm - 11:19 pmMDW-SFO
8h 14m1 stop
$257Delta
Find Deal
jue., feb. 13 - dom., feb. 16
10:45 pm - 8:51 amSFO-MDW
8h 06m1 stop
5:05 pm - 11:19 pmMDW-SFO
8h 14m1 stop
$288Delta
Find Deal
vie., feb. 14 - dom., feb. 16
12:40 am - 9:35 amSFO-MDW
6h 55m1 stop
12:44 pm - 8:17 pmMDW-SFO
9h 33m1 stop
$318Delta
Find Deal
lun., feb. 17 - mar., feb. 25
7:46 pm - 12:17 amSFO-MDW
26h 31m1 stop
$48Frontier
Find Deal
mar., feb. 25
6:00 am - 12:17 amSFO-MDW
16h 17m1 stop
$49Frontier
Find Deal
mié., mar. 5
2:53 pm - 12:17 amSFO-MDW
7h 24m1 stop
$57Frontier
Find Deal
mié., feb. 12
2:53 pm - 12:17 amSFO-MDW
7h 24m1 stop
$58Frontier
Find Deal
mié., feb. 12
6:10 am - 12:20 pmSFO-MDW
4h 10mnonstop
$90Southwest
Find Deal
sáb., feb. 22
7:08 pm - 10:09 amSFO-MDW
13h 01m1 stop
jue., abr. 17
6:10 am - 12:20 pmSFO-MDW
4h 10mnonstop
$99Southwest
Find Deal
sáb., mar. 1
7:08 pm - 10:09 amSFO-MDW
13h 01m1 stop
dom., abr. 20
10:45 pm - 8:51 amSFO-MDW
8h 06m1 stop
$129Delta
Find Deal
jue., feb. 20
12:30 am - 9:45 amSFO-MDW
7h 15m1 stop
$159Delta
Find Deal
lun., mar. 24
9:10 pm - 12:17 amSFO-MDW
25h 07m1 stop
7:15 am - 12:09 amMDW-SFO
18h 54m1 stop
$245Frontier
Find Deal
dom., ene. 26 - dom., feb. 2
9:26 am - 12:54 amSFO-MDW
13h 28m1 stop
8:15 am - 11:59 pmMDW-SFO
17h 44m1 stop
$253Frontier
Find Deal
vie., ene. 24 - mar., feb. 4
9:26 am - 12:54 amSFO-MDW
13h 28m1 stop
7:15 am - 12:47 pmMDW-SFO
7h 32m1 stop
$266Frontier
Find Deal
vie., ene. 24 - jue., feb. 6
9:26 am - 12:54 amSFO-MDW
13h 28m1 stop
8:15 am - 12:09 amMDW-SFO
17h 54m1 stop
$273Frontier
Find Deal
vie., ene. 24 - mié., feb. 5
6:10 am - 12:20 pmSFO-MDW
4h 10mnonstop
4:45 pm - 7:40 pmMDW-SFO
4h 55mnonstop
$502Southwest
Find Deal
dom., ene. 26 - dom., feb. 2
7:15 am - 4:45 pmSFO-MDW
7h 30m1 stop
4:45 pm - 7:40 pmMDW-SFO
4h 55mnonstop
$512Southwest
Find Deal
dom., ene. 26 - dom., feb. 2
6:35 am - 4:50 pmSFO-MDW
8h 15m1 stop
4:45 pm - 7:40 pmMDW-SFO
4h 55mnonstop
$518Southwest
Find Deal
vie., ene. 24 - jue., feb. 6
12:40 am - 9:39 amSFO-MDW
6h 59m1 stop
2:08 pm - 7:12 pmMDW-SFO
7h 04m1 stop
$522Delta
Find Deal
dom., ene. 26 - mar., feb. 4
12:40 am - 9:39 amSFO-MDW
6h 59m1 stop
1:26 pm - 8:57 pmMDW-SFO
9h 31m1 stop
$528Delta
Find Deal
jue., ene. 23 - jue., feb. 6
12:40 am - 9:39 amSFO-MDW
6h 59m1 stop
10:57 am - 6:22 pmMDW-SFO
9h 25m1 stop
$627Delta
Find Deal
dom., ene. 26 - vie., ene. 31
6:15 am - 12:25 pmSFO-MDW
4h 10mnonstop
6:20 pm - 9:00 pmMDW-SFO
4h 40mnonstop
$217Southwest
Find Deal
lun., mar. 3 - jue., mar. 6
6:15 am - 12:25 pmSFO-MDW
4h 10mnonstop
4:45 pm - 7:40 pmMDW-SFO
4h 55mnonstop
$237Southwest
Find Deal
jue., feb. 20 - lun., feb. 24
7:00 am - 1:05 pmSFO-MDW
4h 05mnonstop
11:20 am - 1:55 pmMDW-SFO
4h 35mnonstop
$247Southwest
Find Deal
mié., abr. 2 - mié., abr. 9
10:20 am - 4:30 pmSFO-MDW
4h 10mnonstop
9:30 am - 12:25 pmMDW-SFO
4h 55mnonstop
$257Southwest
Find Deal
jue., feb. 27 - dom., mar. 2
6:10 am - 12:20 pmSFO-MDW
4h 10mnonstop
9:30 am - 12:25 pmMDW-SFO
4h 55mnonstop
$273Southwest
Find Deal
sáb., feb. 22 - dom., feb. 23
6:15 am - 12:25 pmSFO-MDW
4h 10mnonstop
4:45 pm - 7:40 pmMDW-SFO
4h 55mnonstop
$277Southwest
Find Deal
lun., feb. 10 - mar., feb. 18
10:20 am - 4:30 pmSFO-MDW
4h 10mnonstop
9:30 am - 12:25 pmMDW-SFO
4h 55mnonstop
$292Southwest
Find Deal
vie., feb. 21 - dom., feb. 23
10:20 am - 4:30 pmSFO-MDW
4h 10mnonstop
11:05 am - 1:55 pmMDW-SFO
4h 50mnonstop
$302Southwest
Find Deal
jue., feb. 13 - sáb., feb. 22
6:15 am - 12:25 pmSFO-MDW
4h 10mnonstop
9:30 am - 12:25 pmMDW-SFO
4h 55mnonstop
$307Southwest
Find Deal
jue., feb. 20 - dom., feb. 23
6:10 am - 12:20 pmSFO-MDW
4h 10mnonstop
11:05 am - 1:55 pmMDW-SFO
4h 50mnonstop
$312Southwest
Find Deal
sáb., feb. 22 - sáb., mar. 1

Delta flights from San Francisco to Chicago Midway Airport

Our best Delta deals on San Francisco to Chicago Midway Airport flight tickets
Delta
Feb 13
SFO12:40 amSan Francisco
6h 55m
1 stop
MDW9:35 amChicago Midway
Feb 16
MDW5:05 pmChicago Midway
8h 14m
1 stop
SFO11:19 pmSan Francisco
Delta
Feb 14
SFO10:45 pmSan Francisco
8h 06m
1 stop
MDW8:51 amChicago Midway
Feb 16
MDW5:05 pmChicago Midway
8h 14m
1 stop
SFO11:19 pmSan Francisco
Delta
Feb 17
SFO12:40 amSan Francisco
6h 55m
1 stop
MDW9:35 amChicago Midway
Feb 25
MDW12:44 pmChicago Midway
9h 33m
1 stop
SFO8:17 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
Feb 19
SFO2:53 pmSan Francisco
7h 24m
1 stop
MDW12:17 amChicago Midway
Feb 26
MDW7:05 amChicago Midway
19h 38m
1 stop
SFO12:43 amSan Francisco
Frontier
Mar 1
SFO6:00 amSan Francisco
16h 17m
1 stop
MDW12:17 amChicago Midway
Mar 5
MDW7:05 amChicago Midway
8h 28m
1 stop
SFO1:33 pmSan Francisco
Frontier
Mar 1
SFO6:00 amSan Francisco
16h 17m
1 stop
MDW12:17 amChicago Midway
Mar 5
MDW7:05 amChicago Midway
8h 28m
1 stop
SFO1:33 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 $169. 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, 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 $201. 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 $278.

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?

You are more likely to see cheaper flights to Chicago Midway Airport from San Francisco when booking 12 weeks ahead of your departure date. In general, you can expect to find flights to Chicago Midway Airport for around $285 when searching 12 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 $161 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 January 2025, prices for San Francisco to Chicago Midway Airport flights are approximately 18% 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

$48

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 $48. The best round-trip flight deal from San Francisco to Chicago Midway Airport found on momondo in the last 72 hours is $112.
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 $77Free CancellationRating
6.0
3,443 reviews
Search Frontier flights
Alaska AirlinesPriceFrom $168Free CancellationRating
8.0
9,706 reviews
Search Alaska Airlines flights
United AirlinesPriceFrom $185Free CancellationRating
7.4
8,984 reviews
Search United Airlines flights
SouthwestPriceFrom $219Free CancellationRating
8.1
4,662 reviews
Search Southwest flights
DeltaPriceFrom $236Free CancellationRating
8.0
8,521 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 4 Southwest flights for this route in a normal week, average airfare is usually $432 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
Hammond
New Buffalo
Portage
Benton Harbor
Lansing
Saint Joseph
Valparaiso
Munster
Crown Point
Schererville
Monticello
Chesterton
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.

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.
1 adult
From?
To?
dom. 1/26
dom. 2/2
Email me momondo's favorite deals

Find better results for your trip to Chicago