$74 Cheap Flights from San Francisco (SFO) to Chicago (MDW)

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Cheap Flights from San Francisco to Chicago (SFO-MDW)

Prices were available within the past 7 days and start at $74 for one-way flights and $143 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Frontier Airlines
Sat, Oct 26 - Sat, Oct 26
SFO
San Francisco
MDW
Chicago
$143 Roundtrip, found 11 hours ago
$143
Roundtrip
found 11 hours ago
Select Frontier Airlines flight, departing Sat, Oct 26 from San Francisco to Chicago, returning Sat, Oct 26, priced at $143 found 11 hours ago
Frontier Airlines
Sat, Sep 21 - Wed, Sep 25
SFO
San Francisco
MDW
Chicago
$148 Roundtrip, just found
$148
Roundtrip
just found
Select Frontier Airlines flight, departing Sat, Sep 21 from San Francisco to Chicago, returning Wed, Sep 25, priced at $148 just found
Frontier Airlines
Sat, Nov 9 - Mon, Nov 11
SFO
San Francisco
MDW
Chicago
$152 Roundtrip, found 6 days ago
$152
Roundtrip
found 6 days ago
Select Frontier Airlines flight, departing Sat, Nov 9 from San Francisco to Chicago, returning Mon, Nov 11, priced at $152 found 6 days ago
Frontier Airlines
Sat, Aug 3 - Sat, Aug 17
SFO
San Francisco
MDW
Chicago
$155 Roundtrip, found 6 days ago
$155
Roundtrip
found 6 days ago
Select Frontier Airlines flight, departing Sat, Aug 3 from San Francisco to Chicago, returning Sat, Aug 17, priced at $155 found 6 days ago
Frontier Airlines
Wed, Sep 4 - Wed, Sep 4
SFO
San Francisco
MDW
Chicago
$162 Roundtrip, found 1 day ago
$162
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Wed, Sep 4 from San Francisco to Chicago, returning Wed, Sep 4, priced at $162 found 1 day ago
Frontier Airlines
Wed, Sep 4 - Sat, Sep 7
SFO
San Francisco
MDW
Chicago
$168 Roundtrip, found 1 hour ago
$168
Roundtrip
found 1 hour ago
Select Frontier Airlines flight, departing Wed, Sep 4 from San Francisco to Chicago, returning Sat, Sep 7, priced at $168 found 1 hour ago
Frontier Airlines
Sat, Aug 31 - Sat, Sep 7
SFO
San Francisco
MDW
Chicago
$168 Roundtrip, found 3 hours ago
$168
Roundtrip
found 3 hours ago
Select Frontier Airlines flight, departing Sat, Aug 31 from San Francisco to Chicago, returning Sat, Sep 7, priced at $168 found 3 hours ago
Frontier Airlines
Fri, Sep 6 - Sat, Sep 14
SFO
San Francisco
MDW
Chicago
$169 Roundtrip, found 6 hours ago
$169
Roundtrip
found 6 hours ago
Select Frontier Airlines flight, departing Fri, Sep 6 from San Francisco to Chicago, returning Sat, Sep 14, priced at $169 found 6 hours ago
Frontier Airlines
Sat, Jun 1 - Sat, Jun 1
SFO
San Francisco
MDW
Chicago
$171 Roundtrip, found 6 days ago
$171
Roundtrip
found 6 days ago
Select Frontier Airlines flight, departing Sat, Jun 1 from San Francisco to Chicago, returning Sat, Jun 1, priced at $171 found 6 days ago
Frontier Airlines
Wed, Aug 7 - Sat, Aug 17
SFO
San Francisco
MDW
Chicago
$175 Roundtrip, found 5 hours ago
$175
Roundtrip
found 5 hours ago
Select Frontier Airlines flight, departing Wed, Aug 7 from San Francisco to Chicago, returning Sat, Aug 17, priced at $175 found 5 hours ago
Flights from San Francisco (SFO) to Chicago (MDW)
Origin airport
San Francisco Intl.
Destination airport
Midway Intl.
Airlines serving
Delta, Frontier Airlines
Roundtrip price
$142
Distance
1851 mi

San Francisco to Chicago Flights

Whether you’re looking for a grand adventure or just want to get away for a last-minute break, flights from San Francisco to Chicago offer the perfect respite. Not only does exploring Chicago provide the chance to make some magical memories, dip into delectable dishes, and tour the local landmarks, but the cheap airfare means you won’t bust your budget. So no matter whether your ideal itinerary involves flying one way, non-stop, or round trip, you’re bound to find flights that match your schedule on Expedia, and at prices that won’t shock your wallet.

Bagging a cheap flight from San Francisco to Chicago may mean more dollars to spend on for one-of-a-kind souvenirs when you arrive, but it doesn’t mean you have to skimp on your travel experience, as Expedia offers a sizzling selection of cheap airlines that’ll put you in your happy place on their planes, whether that’s getting lost in a hair-raising airport thriller, dreaming on the passing landscape over a glass of bubbly, or jotting down your vacation bucket list at 38,000 feet. There’s also bound to be plenty of opportunities to snap a few photos of the high life that will make your friends green with envy. After all, enjoying the journey is part of the fun.

With so many affordable flights and so many wonderful adventures awaiting you, there’s no reason to put off booking a fantastic flight from to today. So don’t leave it to the last minute to make your dream trip a reality: pack your bags with your go-to travel accessories, put together your list of must-see attractions and can’t-miss activities, and get ready to broaden your horizons – with Expedia, the wonders of Chicago are only a plane trip away. Book your travel arrangements with us today!

If you would like to book flights to Chicago more flexibly many prefer to purchase one-way tickets with options to take different airlines. A one way ticket to Chicago is $74 now!

Frequently asked questions

How much is a one-way flight from SFO to MDW?
Get set to grab a bargain, because San Francisco flights to Chicago start from $88. This is based on the cheapest price found on Expedia for this route departing within the next three months. This airfare is for an Frontier Airlines flight, jetting off from San Francisco Airport on June 1 2024 and arriving at Midway Airport. The price of this flight was last updated on May 23 2024 and has not changed since.
How long does it take to fly from San Francisco Airport to Chicago Airport?
Book your trip with Frontier Airlines and you’ll be cruising the skies for about 4 hours and 3 minutes. This sought-after airline operates a direct flight that leaves at 12:46PM from San Francisco Intl. Airport (SFO) and reaches MDW at 6:49PM. Expedia has some of the best deals around, so find out what’s available on this route today.
Is it cheaper to buy a plane ticket from San Francisco Intl. Airport (SFO) to Midway Intl. Airport (MDW) last minute?
When it’s time to book your flights, it’s always better to be prepared. While you may be able to find a deal on a SFO to MDW flight at the last minute, fares usually don’t get cheaper as the departure date nears. Based on flight pricing and demand studies in 2022, we have found that the sweet spot to lock in a domestic flight is between 28 – 35 days in advance. For international travel it’s three to four months.
What is the cheapest airline flying from San Francisco Airport to Midway Airport in the next 90 days?
With tickets starting at $88 for a flight from San Francisco to Chicago, Frontier Airlines is the cheapest airline found on Expedia. This price is based on airfares found on Expedia with a departure date within the next 90 days and was updated on May 23 2024 and has not changed since. The flight takes off from San Francisco Airport on June 1 2024 and touches down at Chicago Airport.
What's the cheapest price for a flight from San Francisco Airport to Midway Airport next month?
Lock in a one-way flight from San Francisco to Chicago for just $88. This is the cheapest ticket for this route with a departure date in the next month. It’s an Frontier Airlines flight setting off from SFO on June 1 2024 and landing at Chicago Airport. The airfare was correct as of May 23 2024 and has not changed since. It was found after looking at all available flights on Expedia within the next 30 days.
Can I find cheap nonstop flights from SFO to MDW in the next three months?
Your next adventure doesn’t have to cost a small fortune. We’ve uncovered a roundtrip nonstop flight from San Francisco to Chicago in the next 90 days for $162. This price was found after searching all available flights on Expedia with a departure date within the next three months and was updated on May 23 2024. The flight via Frontier Airlines heads out of San Francisco Intl. Airport (SFO) on June 1 2024 and arrives at Chicago Airport. It has a return date of June 5 2024.You can easily track down nonstop cheap flights from SFO to Midway Intl. Airport (MDW) by using our filters. Start by searching for your journey, then press on “Nonstop” under “Filter by” on the left-hand side of the page. Your results will appear with the cheapest airfare first. If you don’t have to travel on a specific day, take advantage of our handy “Flexible dates” feature. This lets you compare ticket prices for nearby dates and grab the best possible deal.
What airports do you fly into for Chicago from San Francisco?
With Midway Intl. Airport (MDW), O’Hare Intl. Airport (ORD) and Lewis University Airport (LOT) to pick from, traveling from San Francisco to Chicago is a piece of cake. The city’s major gateway, Midway Intl. Airport (MDW), is approximately 9 mi southwest of the center. Apart from ticket costs, consider factors like bus or train options from the airport and the distance to your hotel before making your decision. Get your Chicago vacation off to a terrific start by exploring Wrigley Field and Millennium Park.
What are the most popular departure times for flights from San Francisco Airport to Midway Intl. Airport (MDW)?
For Frontier Airlines flights jetting out from San Francisco Airport to Chicago Airport, the most popular period is between 12:00 PM - 1:00 PM. If you want to avoid those frustrating delays, book the earliest flight. This way you can escape the heavy air traffic that accumulates in the afternoon and evening.
Can I change the date of my flight from San Francisco Intl. Airport (SFO) to MDW?
We know plans can get upended, so Expedia is here to help make things as easy as possible. To start, access your San Francisco Airport to MDW itinerary through the Expedia Trips portal and read the fare rules and restrictions about change fees or other charges. If you booked in the last 24 hours, some airlines will let you cancel without charge and organize new flights. If you bought your ticket more than 24 hours ago, connect with us through our Customer Service portal to find out what your options are.
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