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

Search hundreds of travel sites at once for deals on flights to San Francisco

Wed 12/13
Wed 12/20
Any month
Compare vs. KAYAK |

Good to Know

Average Price:
$352
(avg. price over the last 2 weeks)
Good Deal:
$258
or less (round trip)

When to Book Flights from Chicago Midway to San Francisco

Flight prices as travel date approaches
-1 day
-2 days

Top tips for Finding a Cheap Flight

Looking for a cheap flight? 25% of our users found flights on this route for $258 or less.
The cheapest flight from Chicago Midway to San Francisco was found 25 days before departure, on average.
Book at least 2 weeks before departure in order to get a below-average price.
Morning departure is around 11% cheaper than an evening flight, on average*.
*Average of the lowest prices shown in KAYAK’s search results for departures within the next 30 days

FAQs for Booking Chicago Midway to San Francisco Flights

How long does a flight from Chicago Midway to San Francisco take?
An average nonstop flight takes 4h 55m, covering a distance of 1851 miles.
How many flights are there between Chicago Midway and San Francisco?
There are 49 (nonstop) flights between Chicago Midway and San Francisco per week, averaging 7 per day.
Which airlines provide the cheapest flights from Chicago Midway to San Francisco?
In the past 3 days, the cheapest round-trip tickets were found on Multiple Airlines ($227), Southwest ($254) and Delta ($264).
Do I need a passport to fly between Chicago Midway and San Francisco?
No.
Which airlines fly most frequently between Chicago Midway and San Francisco?
Southwest (7 times daily) are the most frequent flyers on this route.
What’s the cheapest day of the week to fly Chicago Midway to San Francisco?
For Chicago Midway to San Francisco, Monday is the cheapest day to fly on average and Saturday is the most expensive. Flying from San Francisco back to Chicago Midway, the best deals are generally found on Wednesday, with Tuesday being the most expensive.

Book cheap flights from Chicago Midway to San Francisco (round-trip)

Airports
Origin
Chicago
$227
only
$227
Destination
San Francisco
$227
only
$227
Mon, Feb 5
MDW
SFO
8h 20m
Tue, Feb 6
SFO
MDW
10h 00m
Trip: 2 days
Overall 0.0 Poor
Based on 0 reviews
Thu, Jan 18
MDW
SFO
4h 55m
Tue, Jan 23
SFO
MDW
4h 15m
Trip: 6 days
2.6MediocreShow reviews
Overall 2.6 Mediocre
Based on 1 reviews
Boarding
8.8
Comfort
8.5
Crew
9.0
Entertainment
8.0
Food
7.9
FLL
MCI
Okay 5.5

Bossy lead flight attendant and the mid-cabin was very cold and not corrected even when a number of people asked.

LAS
BWI
Excellent 10.0

Plane was on time. Boarding was seamless. Crew was very polite and attentive. I even had two coffees with hazelnut creamer. I love southwest and how they continue to offer amenities at no additional fee!

DAL
AUS
Excellent 10.0

Southwest is always great. Best part is they are always on time

ISP
TPA
Good 7.6

I like that two checked in bags are included in the price. ISP is close to my home and easy to get in and out of. The airline is always on time, even when there is a late departure.

The seats have changed. They are narrower in width, the knee room is less, the staff while still professional is more serious, not as fun and friendly. Spicy snacks and peanuts are limited. Cookies go better with tea and coffee on the late night flights.

TPA
MKE
Good 7.3

Crew was great

Flight delayed slightly, not too bad, but it seemed to take a long time to get the plane boarded, which is unusual from my experience with Southwest

Wed, Jan 10
MDW
SFO
6h 45m
Wed, Jan 17
SFO
MDW
7h 24m
Trip: 8 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 14179 reviews
Overall
8.0
Boarding
8.1
Comfort
7.7
Crew
8.4
Entertainment
7.5
Food
7.3
MCO
YYZ
Excellent 8.3

On time as scheduled.

N/A

ATL
MEX
Excellent 8.6

Sandwich for dinner

FLL
ATL
Good 6.0

The plane was really cool. Some more advanced technologies than other Airline companies. Crew was good too.

Issue happened with my landing. Didn't make it in time to next gate. Delta did everything they could to blame me, insulted me on The phone and definitely provided the worst customer service

LAX
OAK
Mediocre 2.0

Due to the earthquakes, the film festival I was going to was cancelled. Ten days prior to the flight I called AeroMexico to cancel and they said there would be a cancellation penalty, which was fine. When I tried to redeem my credit, they said there was also an additional "No-show fee" even though I called to cancel 10 days prior, which left a total of $70 credit after all their penalties. I called and emailed to complain but they did nothing but pass me to someone else who was equally unhelpful. I will never fly AeroMexico for any reason in the future.

LHR
JFK
Good 7.0

Delays!

Sat, Jan 27
MDW
SFO
4h 55m
Mon, Jan 29
SFO
MDW
6h 25m
Trip: 3 days
Overall 0.0 Poor
Based on 0 reviews
Tue, Jan 16
MDW
SFO
7h 17m
Tue, Feb 6
SFO
MDW
6h 26m
Trip: 22 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 14179 reviews
Overall
8.0
Boarding
8.1
Comfort
7.7
Crew
8.4
Entertainment
7.5
Food
7.3
LAX
OAK
Mediocre 2.0

Due to the earthquakes, the film festival I was going to was cancelled. Ten days prior to the flight I called AeroMexico to cancel and they said there would be a cancellation penalty, which was fine. When I tried to redeem my credit, they said there was also an additional "No-show fee" even though I called to cancel 10 days prior, which left a total of $70 credit after all their penalties. I called and emailed to complain but they did nothing but pass me to someone else who was equally unhelpful. I will never fly AeroMexico for any reason in the future.

FLL
ATL
Good 6.0

The plane was really cool. Some more advanced technologies than other Airline companies. Crew was good too.

Issue happened with my landing. Didn't make it in time to next gate. Delta did everything they could to blame me, insulted me on The phone and definitely provided the worst customer service

SFO
DTW
Okay 4.0

Arrived.

Late, slow, de-icing in Detroit took nearly an hour!

LHR
JFK
Good 7.0

Delays!

SJC
LAX
Mediocre 2.0

They were very dishonest about everything. We need to be there in Australia on Monday morning for very important event but reached Australia Monday night 8PM. Virgin Australia contatcted out their flight from SJC to LAX through Delta and Delta cancelled flights becaue no-show of Pilot to operate the plan. What a Joke???? We asked them to put us through another carrier to LAX for connecting flight they refused.Very very BAD. It was a big miss for us.. never again Delta/Virgin Australia..............

Thu, Jan 18
MDW
SFO
4h 55m
Mon, Jan 22
SFO
MDW
4h 10m
Trip: 5 days
2.6MediocreShow reviews
Overall 2.6 Mediocre
Based on 1 reviews
Boarding
8.8
Comfort
8.5
Crew
9.0
Entertainment
8.0
Food
7.9
TPA
MKE
Good 7.3

Crew was great

Flight delayed slightly, not too bad, but it seemed to take a long time to get the plane boarded, which is unusual from my experience with Southwest

ISP
TPA
Good 7.6

I like that two checked in bags are included in the price. ISP is close to my home and easy to get in and out of. The airline is always on time, even when there is a late departure.

The seats have changed. They are narrower in width, the knee room is less, the staff while still professional is more serious, not as fun and friendly. Spicy snacks and peanuts are limited. Cookies go better with tea and coffee on the late night flights.

MSY
DAL
Excellent 10.0

Great!

N/a

DAL
MSY
Excellent 10.0

Great

BNA
CHS
Excellent 10.0

Prompt boarding and smooth flight

Wed, Jan 17
MDW
SFO
6h 57m
Wed, Feb 7
SFO
MDW
6h 46m
Trip: 22 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 14179 reviews
Overall
8.0
Boarding
8.1
Comfort
7.7
Crew
8.4
Entertainment
7.5
Food
7.3
MCO
YYZ
Excellent 8.3

On time as scheduled.

N/A

YYZ
YQB
Okay 5.0

They had to change tires before we lelt in Toronto. And we spent more than one hour on the tarmac.

SFO
DTW
Okay 4.0

Arrived.

Late, slow, de-icing in Detroit took nearly an hour!

LGA
DFW
Excellent 10.0

On time with no drama

LHR
JFK
Good 7.0

Delays!

Fri, Jan 19
MDW
SFO
5h 00m
Tue, Jan 23
SFO
MDW
4h 10m
Trip: 5 days
2.6MediocreShow reviews
Overall 2.6 Mediocre
Based on 1 reviews
Boarding
8.8
Comfort
8.5
Crew
9.0
Entertainment
8.0
Food
7.9
TPA
MKE
Good 7.3

Crew was great

Flight delayed slightly, not too bad, but it seemed to take a long time to get the plane boarded, which is unusual from my experience with Southwest

LAS
BWI
Excellent 10.0

Plane was on time. Boarding was seamless. Crew was very polite and attentive. I even had two coffees with hazelnut creamer. I love southwest and how they continue to offer amenities at no additional fee!

FLL
MCI
Okay 5.5

Bossy lead flight attendant and the mid-cabin was very cold and not corrected even when a number of people asked.

MSY
DAL
Excellent 10.0

Great!

N/a

RDU
MDW
Excellent 10.0

On time. Fun crew.

Sat, Jan 13
MDW
SFO
6h 30m
Wed, Jan 24
SFO
MDW
6h 25m
Trip: 12 days
Overall 0.0 Poor
Based on 0 reviews
Sat, Jan 20
MDW
SFO
9h 58m
Sat, Feb 10
SFO
MDW
6h 40m
Trip: 22 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 14179 reviews
Overall
8.0
Boarding
8.1
Comfort
7.7
Crew
8.4
Entertainment
7.5
Food
7.3
LAX
SJC
Okay 4.0

On time arrival

Small aircraft. Loud engine noise. Biased treatment for tickets booked on non Delta sites

MCO
YYZ
Excellent 8.3

On time as scheduled.

N/A

LGA
DFW
Excellent 10.0

On time with no drama

LHR
JFK
Good 7.0

Delays!

ATL
MEX
Excellent 8.6

Sandwich for dinner

Tue, Jan 23
MDW
SFO
7h 31m
Tue, Feb 13
SFO
MDW
7h 48m
Trip: 22 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 14179 reviews
Overall
8.0
Boarding
8.1
Comfort
7.7
Crew
8.4
Entertainment
7.5
Food
7.3
LAX
OAK
Mediocre 2.0

Due to the earthquakes, the film festival I was going to was cancelled. Ten days prior to the flight I called AeroMexico to cancel and they said there would be a cancellation penalty, which was fine. When I tried to redeem my credit, they said there was also an additional "No-show fee" even though I called to cancel 10 days prior, which left a total of $70 credit after all their penalties. I called and emailed to complain but they did nothing but pass me to someone else who was equally unhelpful. I will never fly AeroMexico for any reason in the future.

MCO
YYZ
Excellent 8.3

On time as scheduled.

N/A

LAX
SJC
Okay 4.0

On time arrival

Small aircraft. Loud engine noise. Biased treatment for tickets booked on non Delta sites

MEX
JFK
Mediocre 3.6

Nothing really.

Boarding process was horribly handled. Food was inadequate. Stewardess was saccharine. Bathroom door didn’t shut completely. I was told this wasn’t an international flight and therefore no free alcohol. Aero Mexico flight to Mexico City had much better food, free alcohol and more attentive service personnel. Also delays because of equipment problems.

LHR
JFK
Good 7.0

Delays!

Wed, Jan 24
MDW
SFO
7h 31m
Wed, Feb 14
SFO
MDW
7h 48m
Trip: 22 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 14179 reviews
Overall
8.0
Boarding
8.1
Comfort
7.7
Crew
8.4
Entertainment
7.5
Food
7.3
SFO
LAX
Excellent 10.0

Excellent service and upgraded snacks in economy

Nothing

FLL
ATL
Good 6.0

The plane was really cool. Some more advanced technologies than other Airline companies. Crew was good too.

Issue happened with my landing. Didn't make it in time to next gate. Delta did everything they could to blame me, insulted me on The phone and definitely provided the worst customer service

MCO
YYZ
Excellent 8.3

On time as scheduled.

N/A

LHR
JFK
Good 7.0

Delays!

YYZ
YQB
Okay 5.0

They had to change tires before we lelt in Toronto. And we spent more than one hour on the tarmac.

Sat, Jan 27
MDW
SFO
7h 00m
Sat, Feb 10
SFO
MDW
6h 45m
Trip: 15 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 14179 reviews
Overall
8.0
Boarding
8.1
Comfort
7.7
Crew
8.4
Entertainment
7.5
Food
7.3
YYZ
YQB
Okay 5.0

They had to change tires before we lelt in Toronto. And we spent more than one hour on the tarmac.

MEX
JFK
Mediocre 3.6

Nothing really.

Boarding process was horribly handled. Food was inadequate. Stewardess was saccharine. Bathroom door didn’t shut completely. I was told this wasn’t an international flight and therefore no free alcohol. Aero Mexico flight to Mexico City had much better food, free alcohol and more attentive service personnel. Also delays because of equipment problems.

MCO
YYZ
Excellent 8.3

On time as scheduled.

N/A

ATL
MEX
Excellent 8.6

Sandwich for dinner

FLL
ATL
Good 6.0

The plane was really cool. Some more advanced technologies than other Airline companies. Crew was good too.

Issue happened with my landing. Didn't make it in time to next gate. Delta did everything they could to blame me, insulted me on The phone and definitely provided the worst customer service

Tue, Jan 30
MDW
SFO
7h 17m
Tue, Feb 20
SFO
MDW
6h 12m
Trip: 22 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 14179 reviews
Overall
8.0
Boarding
8.1
Comfort
7.7
Crew
8.4
Entertainment
7.5
Food
7.3
ATL
MEX
Excellent 8.6

Sandwich for dinner

YYZ
YQB
Okay 5.0

They had to change tires before we lelt in Toronto. And we spent more than one hour on the tarmac.

LAX
SJC
Okay 4.0

On time arrival

Small aircraft. Loud engine noise. Biased treatment for tickets booked on non Delta sites

MCO
YYZ
Excellent 8.3

On time as scheduled.

N/A

SJC
LAX
Mediocre 2.0

They were very dishonest about everything. We need to be there in Australia on Monday morning for very important event but reached Australia Monday night 8PM. Virgin Australia contatcted out their flight from SJC to LAX through Delta and Delta cancelled flights becaue no-show of Pilot to operate the plan. What a Joke???? We asked them to put us through another carrier to LAX for connecting flight they refused.Very very BAD. It was a big miss for us.. never again Delta/Virgin Australia..............

Wed, Jan 31
MDW
SFO
6h 45m
Wed, Feb 14
SFO
MDW
7h 48m
Trip: 15 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 14179 reviews
Overall
8.0
Boarding
8.1
Comfort
7.7
Crew
8.4
Entertainment
7.5
Food
7.3
LGA
DFW
Excellent 10.0

On time with no drama

MEX
JFK
Mediocre 3.6

Nothing really.

Boarding process was horribly handled. Food was inadequate. Stewardess was saccharine. Bathroom door didn’t shut completely. I was told this wasn’t an international flight and therefore no free alcohol. Aero Mexico flight to Mexico City had much better food, free alcohol and more attentive service personnel. Also delays because of equipment problems.

FLL
ATL
Good 6.0

The plane was really cool. Some more advanced technologies than other Airline companies. Crew was good too.

Issue happened with my landing. Didn't make it in time to next gate. Delta did everything they could to blame me, insulted me on The phone and definitely provided the worst customer service

MCO
YYZ
Excellent 8.3

On time as scheduled.

N/A

LHR
JFK
Good 7.0

Delays!

Sat, Feb 3
MDW
SFO
7h 15m
Tue, Feb 6
SFO
MDW
6h 46m
Trip: 4 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 14179 reviews
Overall
8.0
Boarding
8.1
Comfort
7.7
Crew
8.4
Entertainment
7.5
Food
7.3
LAX
OAK
Mediocre 2.0

Due to the earthquakes, the film festival I was going to was cancelled. Ten days prior to the flight I called AeroMexico to cancel and they said there would be a cancellation penalty, which was fine. When I tried to redeem my credit, they said there was also an additional "No-show fee" even though I called to cancel 10 days prior, which left a total of $70 credit after all their penalties. I called and emailed to complain but they did nothing but pass me to someone else who was equally unhelpful. I will never fly AeroMexico for any reason in the future.

MCO
YYZ
Excellent 8.3

On time as scheduled.

N/A

SFO
LAX
Excellent 10.0

Excellent service and upgraded snacks in economy

Nothing

LGA
DFW
Excellent 10.0

On time with no drama

YYZ
YQB
Okay 5.0

They had to change tires before we lelt in Toronto. And we spent more than one hour on the tarmac.

Tue, Feb 6
MDW
SFO
7h 17m
Tue, Feb 27
SFO
MDW
6h 12m
Trip: 22 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 14179 reviews
Overall
8.0
Boarding
8.1
Comfort
7.7
Crew
8.4
Entertainment
7.5
Food
7.3
FLL
ATL
Good 6.0

The plane was really cool. Some more advanced technologies than other Airline companies. Crew was good too.

Issue happened with my landing. Didn't make it in time to next gate. Delta did everything they could to blame me, insulted me on The phone and definitely provided the worst customer service

SFO
DTW
Okay 4.0

Arrived.

Late, slow, de-icing in Detroit took nearly an hour!

SJC
LAX
Mediocre 2.0

They were very dishonest about everything. We need to be there in Australia on Monday morning for very important event but reached Australia Monday night 8PM. Virgin Australia contatcted out their flight from SJC to LAX through Delta and Delta cancelled flights becaue no-show of Pilot to operate the plan. What a Joke???? We asked them to put us through another carrier to LAX for connecting flight they refused.Very very BAD. It was a big miss for us.. never again Delta/Virgin Australia..............

LAX
SJC
Okay 4.0

On time arrival

Small aircraft. Loud engine noise. Biased treatment for tickets booked on non Delta sites

MEX
JFK
Mediocre 3.6

Nothing really.

Boarding process was horribly handled. Food was inadequate. Stewardess was saccharine. Bathroom door didn’t shut completely. I was told this wasn’t an international flight and therefore no free alcohol. Aero Mexico flight to Mexico City had much better food, free alcohol and more attentive service personnel. Also delays because of equipment problems.

Wed, Feb 7
MDW
SFO
7h 16m
Wed, Feb 14
SFO
MDW
7h 04m
Trip: 8 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 14179 reviews
Overall
8.0
Boarding
8.1
Comfort
7.7
Crew
8.4
Entertainment
7.5
Food
7.3
ATL
MEX
Excellent 8.6

Sandwich for dinner

LHR
JFK
Good 7.0

Delays!

LAX
SJC
Okay 4.0

On time arrival

Small aircraft. Loud engine noise. Biased treatment for tickets booked on non Delta sites

MEX
JFK
Mediocre 3.6

Nothing really.

Boarding process was horribly handled. Food was inadequate. Stewardess was saccharine. Bathroom door didn’t shut completely. I was told this wasn’t an international flight and therefore no free alcohol. Aero Mexico flight to Mexico City had much better food, free alcohol and more attentive service personnel. Also delays because of equipment problems.

FLL
ATL
Good 6.0

The plane was really cool. Some more advanced technologies than other Airline companies. Crew was good too.

Issue happened with my landing. Didn't make it in time to next gate. Delta did everything they could to blame me, insulted me on The phone and definitely provided the worst customer service

Sat, Feb 10
MDW
SFO
9h 58m
Sat, Mar 3
SFO
MDW
9h 32m
Trip: 22 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 14179 reviews
Overall
8.0
Boarding
8.1
Comfort
7.7
Crew
8.4
Entertainment
7.5
Food
7.3
ATL
MEX
Excellent 8.6

Sandwich for dinner

YYZ
YQB
Okay 5.0

They had to change tires before we lelt in Toronto. And we spent more than one hour on the tarmac.

LAX
OAK
Mediocre 2.0

Due to the earthquakes, the film festival I was going to was cancelled. Ten days prior to the flight I called AeroMexico to cancel and they said there would be a cancellation penalty, which was fine. When I tried to redeem my credit, they said there was also an additional "No-show fee" even though I called to cancel 10 days prior, which left a total of $70 credit after all their penalties. I called and emailed to complain but they did nothing but pass me to someone else who was equally unhelpful. I will never fly AeroMexico for any reason in the future.

SFO
LAX
Excellent 10.0

Excellent service and upgraded snacks in economy

Nothing

MCO
YYZ
Excellent 8.3

On time as scheduled.

N/A

Tue, Feb 13
MDW
SFO
8h 01m
Tue, Mar 6
SFO
MDW
9h 28m
Trip: 22 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 14179 reviews
Overall
8.0
Boarding
8.1
Comfort
7.7
Crew
8.4
Entertainment
7.5
Food
7.3
SFO
DTW
Okay 4.0

Arrived.

Late, slow, de-icing in Detroit took nearly an hour!

LHR
JFK
Good 7.0

Delays!

LGA
DFW
Excellent 10.0

On time with no drama

ATL
MEX
Excellent 8.6

Sandwich for dinner

YYZ
YQB
Okay 5.0

They had to change tires before we lelt in Toronto. And we spent more than one hour on the tarmac.

Show more results
*
Prices are per person and are for e–tickets and include all taxes & fees in USD.

We attempt to get accurate prices, however, prices are not guaranteed.

Here's why:

We’re not the seller.
At KAYAK we don’t set the prices, so it’s not possible for us to guarantee what other companies are selling.

We compile tonnes of data for you
Our service lets you quickly and easily compare results from hundreds of travel sites at once. In this sense, KAYAK is a search engine and we can't guarantee prices we find.

Why aren’t prices accurate 100% of the time?
Prices on airline seats, hotel rooms and car rentals can change frequently. Several people may also be trying to buy the same travel option simultaneously. As a result, you may find, on occasion, that certain prices are no longer available.

If you have more questions or if you have a bad price to report to us,
please send us an and someone from our team will get back to you promptly.

^
The fares displayed include all taxes and fees for economy class travel and were found by the provider in the last 72 hours. Seats are limited and may not be available on all flights and days. Fares are subject to change and may not be available on all flights or dates of travel. Some carriers charge additional fees for extra checked bags. Please check the carriers' sites.