Find Cheap Flights from Chicago Midway to San Antonio (MDW - SAT)

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Good to Know

Average Price:
$383
(avg. price over the last 2 weeks)
Good Deal:
$277
or less (round trip)

When to Book Flights from Chicago Midway to San Antonio

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 $277 or less.
The cheapest flight from Chicago Midway to San Antonio was found 37 days before departure, on average.
Book at least 2 weeks before departure in order to get a below-average price.
Morning departure is around 4% 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 Antonio Flights

How long does a flight from Chicago Midway to San Antonio take?
An average nonstop flight takes 5h 19m, covering a distance of 1037 miles.
How many flights are there between Chicago Midway and San Antonio?
There are 34 (nonstop) flights between Chicago Midway and San Antonio per week, averaging 4 per day.
Which airlines provide the cheapest flights from Chicago Midway to San Antonio?
In the past 3 days, the cheapest round-trip tickets were found on Delta ($210)
Do I need a passport to fly between Chicago Midway and San Antonio?
No.
Which airlines fly most frequently between Chicago Midway and San Antonio?
Southwest (4 times daily) are the most frequent flyers on this route.
What’s the cheapest day of the week to fly Chicago Midway to San Antonio?
For Chicago Midway to San Antonio, Wednesday is the cheapest day to fly on average and Friday is the most expensive. Flying from San Antonio back to Chicago Midway, the best deals are generally found on Wednesday, with Thursday being the most expensive.

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

Airports
Origin
Chicago
$210
only
$210
Destination
San Antonio
$210
only
$210
Wed, Jan 10
MDW
SAT
5h 29m
Wed, Jan 17
SAT
MDW
5h 10m
Trip: 8 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 13713 reviews
Overall
8.0
Boarding
8.1
Comfort
7.7
Crew
8.4
Entertainment
7.5
Food
7.3
AMS
YYZ
Excellent 8.3

The flight attendant named Steven went so far beyond the call. He was attentive, he fixed our video system when no one else could and when he learned we were celebrating an anniversary he brought us a present. He was awesome!

LGA
MCO
Good 6.0

Staff not attentive to customer needs. I asked for a blanket and the stewardess never came back to me.

JFK
CUN
Excellent 9.0

Entertainment and crew were great- comfortable seats, got to watch a couple of movies with headphones provided by Delta; forgot mine so I assumed I would be miserable thru the whole 4 hour flight. so glad I was wrong! Would definitely take another flight with Delta... looking into the frequent flyer program as we speak

PTY
ATL
Excellent 9.6

Crew was kind, entertainment and food were good

Seats are really tight

PHL
JFK
Excellent 9.0

We were probably in the air for 30 mins; great short flight. Plane wasn’t filled so had plenty of space.

Wed, Feb 7
MDW
SAT
6h 50m
Wed, Feb 21
SAT
MDW
5h 41m
Trip: 15 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 13713 reviews
Overall
8.0
Boarding
8.1
Comfort
7.7
Crew
8.4
Entertainment
7.5
Food
7.3
JFK
ROC
Good 7.2

Flight crew was good, we arrived early on flight out and back! Feel like seats are tinier than ever, maybe it was just me. Food (water & pretzels) were OK, but nothing special (then again it was a short flight, so I didn't expect anything). Plane was small so we needed to gate check bags and the gate attendant came around and tagged everyone's bag for us, well before boarding which was hugely efficient - kudos to her on that!

Gate attendant's mic was broken (or she didn't know how to use) so she had to yell into the boarding area.

AMS
YYZ
Excellent 8.3

The flight attendant named Steven went so far beyond the call. He was attentive, he fixed our video system when no one else could and when he learned we were celebrating an anniversary he brought us a present. He was awesome!

SEA
SJC
Okay 5.6

No vegetarian options in first class.. and go go wouldn5 hook up. Flight was an hour late...but that was ok.

The pilot did a nice job of flying in and banking so we could see the view..

JFK
CUN
Excellent 9.0

Entertainment and crew were great- comfortable seats, got to watch a couple of movies with headphones provided by Delta; forgot mine so I assumed I would be miserable thru the whole 4 hour flight. so glad I was wrong! Would definitely take another flight with Delta... looking into the frequent flyer program as we speak

ATL
HPN
Good 7.3

It was on time

It was crowded and cramped.

Wed, Feb 21
MDW
SAT
7h 12m
Sat, Feb 24
SAT
MDW
7h 30m
Trip: 4 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 13713 reviews
Overall
8.0
Boarding
8.1
Comfort
7.7
Crew
8.4
Entertainment
7.5
Food
7.3
JFK
CUN
Excellent 9.0

Entertainment and crew were great- comfortable seats, got to watch a couple of movies with headphones provided by Delta; forgot mine so I assumed I would be miserable thru the whole 4 hour flight. so glad I was wrong! Would definitely take another flight with Delta... looking into the frequent flyer program as we speak

SAV
ATL
Good 7.0

The flight was on schedule

It was crowded and cramped.

ATL
HPN
Good 7.3

It was on time

It was crowded and cramped.

JFK
ROC
Good 7.2

Flight crew was good, we arrived early on flight out and back! Feel like seats are tinier than ever, maybe it was just me. Food (water & pretzels) were OK, but nothing special (then again it was a short flight, so I didn't expect anything). Plane was small so we needed to gate check bags and the gate attendant came around and tagged everyone's bag for us, well before boarding which was hugely efficient - kudos to her on that!

Gate attendant's mic was broken (or she didn't know how to use) so she had to yell into the boarding area.

LAX
HNL
Okay 5.0

The gentleman at the gate was super helpful and helped us check our bags at the gate.

Zero leg room. Zero arm room. The entertainment system did not function. No food for such a long flight unless you pay more then the food is actually worth.

Thu, Jan 11
MDW
SAT
5h 19m
Sat, Jan 13
SAT
MDW
7h 03m
Trip: 3 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 13713 reviews
Overall
8.0
Boarding
8.1
Comfort
7.7
Crew
8.4
Entertainment
7.5
Food
7.3
SAV
ATL
Good 7.0

The flight was on schedule

It was crowded and cramped.

PHL
JFK
Excellent 9.0

We were probably in the air for 30 mins; great short flight. Plane wasn’t filled so had plenty of space.

LAX
HNL
Okay 5.0

The gentleman at the gate was super helpful and helped us check our bags at the gate.

Zero leg room. Zero arm room. The entertainment system did not function. No food for such a long flight unless you pay more then the food is actually worth.

AMS
YYZ
Excellent 8.3

The flight attendant named Steven went so far beyond the call. He was attentive, he fixed our video system when no one else could and when he learned we were celebrating an anniversary he brought us a present. He was awesome!

PBI
ATL
Good 6.0

On time; safe flight

Service from boarding to landing was impersonal. No headphones etc. Etc.

Wed, Jan 17
MDW
SAT
5h 19m
Thu, Jan 25
SAT
MDW
8h 06m
Trip: 9 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 13713 reviews
Overall
8.0
Boarding
8.1
Comfort
7.7
Crew
8.4
Entertainment
7.5
Food
7.3
JFK
CUN
Excellent 9.0

Entertainment and crew were great- comfortable seats, got to watch a couple of movies with headphones provided by Delta; forgot mine so I assumed I would be miserable thru the whole 4 hour flight. so glad I was wrong! Would definitely take another flight with Delta... looking into the frequent flyer program as we speak

SEA
SJC
Okay 5.6

No vegetarian options in first class.. and go go wouldn5 hook up. Flight was an hour late...but that was ok.

The pilot did a nice job of flying in and banking so we could see the view..

LAX
HNL
Okay 5.0

The gentleman at the gate was super helpful and helped us check our bags at the gate.

Zero leg room. Zero arm room. The entertainment system did not function. No food for such a long flight unless you pay more then the food is actually worth.

LGA
MCO
Good 6.0

Staff not attentive to customer needs. I asked for a blanket and the stewardess never came back to me.

PBI
ATL
Good 6.0

On time; safe flight

Service from boarding to landing was impersonal. No headphones etc. Etc.

Tue, Feb 6
MDW
SAT
6h 46m
Mon, Feb 12
SAT
MDW
5h 27m
Trip: 7 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 13713 reviews
Overall
8.0
Boarding
8.1
Comfort
7.7
Crew
8.4
Entertainment
7.5
Food
7.3
PTY
ATL
Excellent 9.6

Crew was kind, entertainment and food were good

Seats are really tight

SEA
SJC
Okay 5.6

No vegetarian options in first class.. and go go wouldn5 hook up. Flight was an hour late...but that was ok.

The pilot did a nice job of flying in and banking so we could see the view..

JFK
CUN
Excellent 9.0

Entertainment and crew were great- comfortable seats, got to watch a couple of movies with headphones provided by Delta; forgot mine so I assumed I would be miserable thru the whole 4 hour flight. so glad I was wrong! Would definitely take another flight with Delta... looking into the frequent flyer program as we speak

LGA
MCO
Good 6.0

Staff not attentive to customer needs. I asked for a blanket and the stewardess never came back to me.

LAX
HNL
Okay 5.0

The gentleman at the gate was super helpful and helped us check our bags at the gate.

Zero leg room. Zero arm room. The entertainment system did not function. No food for such a long flight unless you pay more then the food is actually worth.

Thu, Dec 14
MDW
SAT
5h 45m
Mon, Dec 18
SAT
MDW
7h 37m
Trip: 5 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 13713 reviews
Overall
8.0
Boarding
8.1
Comfort
7.7
Crew
8.4
Entertainment
7.5
Food
7.3
LAX
HNL
Okay 5.0

The gentleman at the gate was super helpful and helped us check our bags at the gate.

Zero leg room. Zero arm room. The entertainment system did not function. No food for such a long flight unless you pay more then the food is actually worth.

SEA
SJC
Okay 5.6

No vegetarian options in first class.. and go go wouldn5 hook up. Flight was an hour late...but that was ok.

The pilot did a nice job of flying in and banking so we could see the view..

ATL
HPN
Good 7.3

It was on time

It was crowded and cramped.

JFK
CUN
Excellent 9.0

Entertainment and crew were great- comfortable seats, got to watch a couple of movies with headphones provided by Delta; forgot mine so I assumed I would be miserable thru the whole 4 hour flight. so glad I was wrong! Would definitely take another flight with Delta... looking into the frequent flyer program as we speak

SAV
ATL
Good 7.0

The flight was on schedule

It was crowded and cramped.

Wed, Mar 28
MDW
SAT
7h 25m
Wed, Apr 4
SAT
MDW
5h 59m
Trip: 8 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 13713 reviews
Overall
8.0
Boarding
8.1
Comfort
7.7
Crew
8.4
Entertainment
7.5
Food
7.3
SEA
SJC
Okay 5.6

No vegetarian options in first class.. and go go wouldn5 hook up. Flight was an hour late...but that was ok.

The pilot did a nice job of flying in and banking so we could see the view..

LAX
HNL
Okay 5.0

The gentleman at the gate was super helpful and helped us check our bags at the gate.

Zero leg room. Zero arm room. The entertainment system did not function. No food for such a long flight unless you pay more then the food is actually worth.

SAV
ATL
Good 7.0

The flight was on schedule

It was crowded and cramped.

ATL
HPN
Good 7.3

It was on time

It was crowded and cramped.

LGA
MCO
Good 6.0

Staff not attentive to customer needs. I asked for a blanket and the stewardess never came back to me.

Wed, Mar 14
MDW
SAT
7h 25m
Mon, Mar 19
SAT
MDW
8h 21m
Trip: 6 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 13713 reviews
Overall
8.0
Boarding
8.1
Comfort
7.7
Crew
8.4
Entertainment
7.5
Food
7.3
SAV
ATL
Good 7.0

The flight was on schedule

It was crowded and cramped.

PTY
ATL
Excellent 9.6

Crew was kind, entertainment and food were good

Seats are really tight

AMS
YYZ
Excellent 8.3

The flight attendant named Steven went so far beyond the call. He was attentive, he fixed our video system when no one else could and when he learned we were celebrating an anniversary he brought us a present. He was awesome!

SEA
SJC
Okay 5.6

No vegetarian options in first class.. and go go wouldn5 hook up. Flight was an hour late...but that was ok.

The pilot did a nice job of flying in and banking so we could see the view..

JFK
DTW
Excellent 10.0

I got off the flight at out side,but i forgot to carried my small bag .and then the Crew returned me the bag very soon.they were very kind,thank you very much.

Fri, Dec 1
MDW
SAT
5h 51m
Sun, Dec 3
SAT
MDW
6h 49m
Trip: 3 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 13713 reviews
Overall
8.0
Boarding
8.1
Comfort
7.7
Crew
8.4
Entertainment
7.5
Food
7.3
JFK
ROC
Good 7.2

Flight crew was good, we arrived early on flight out and back! Feel like seats are tinier than ever, maybe it was just me. Food (water & pretzels) were OK, but nothing special (then again it was a short flight, so I didn't expect anything). Plane was small so we needed to gate check bags and the gate attendant came around and tagged everyone's bag for us, well before boarding which was hugely efficient - kudos to her on that!

Gate attendant's mic was broken (or she didn't know how to use) so she had to yell into the boarding area.

JFK
CUN
Excellent 9.0

Entertainment and crew were great- comfortable seats, got to watch a couple of movies with headphones provided by Delta; forgot mine so I assumed I would be miserable thru the whole 4 hour flight. so glad I was wrong! Would definitely take another flight with Delta... looking into the frequent flyer program as we speak

JFK
DTW
Excellent 10.0

I got off the flight at out side,but i forgot to carried my small bag .and then the Crew returned me the bag very soon.they were very kind,thank you very much.

PHL
JFK
Excellent 9.0

We were probably in the air for 30 mins; great short flight. Plane wasn’t filled so had plenty of space.

PBI
ATL
Good 6.0

On time; safe flight

Service from boarding to landing was impersonal. No headphones etc. Etc.

Wed, Nov 29
MDW
SAT
5h 51m
Sun, Dec 3
SAT
MDW
5h 24m
Trip: 5 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 13713 reviews
Overall
8.0
Boarding
8.1
Comfort
7.7
Crew
8.4
Entertainment
7.5
Food
7.3
SAV
ATL
Good 7.0

The flight was on schedule

It was crowded and cramped.

JFK
CUN
Excellent 9.0

Entertainment and crew were great- comfortable seats, got to watch a couple of movies with headphones provided by Delta; forgot mine so I assumed I would be miserable thru the whole 4 hour flight. so glad I was wrong! Would definitely take another flight with Delta... looking into the frequent flyer program as we speak

LGA
MCO
Good 6.0

Staff not attentive to customer needs. I asked for a blanket and the stewardess never came back to me.

JFK
DTW
Excellent 10.0

I got off the flight at out side,but i forgot to carried my small bag .and then the Crew returned me the bag very soon.they were very kind,thank you very much.

PBI
ATL
Good 6.0

On time; safe flight

Service from boarding to landing was impersonal. No headphones etc. Etc.

Fri, Dec 22
MDW
SAT
7h 13m
Sat, Jan 6
SAT
MDW
7h 03m
Trip: 16 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 13713 reviews
Overall
8.0
Boarding
8.1
Comfort
7.7
Crew
8.4
Entertainment
7.5
Food
7.3
JFK
DTW
Excellent 10.0

I got off the flight at out side,but i forgot to carried my small bag .and then the Crew returned me the bag very soon.they were very kind,thank you very much.

LGA
MCO
Good 6.0

Staff not attentive to customer needs. I asked for a blanket and the stewardess never came back to me.

AMS
YYZ
Excellent 8.3

The flight attendant named Steven went so far beyond the call. He was attentive, he fixed our video system when no one else could and when he learned we were celebrating an anniversary he brought us a present. He was awesome!

JFK
CUN
Excellent 9.0

Entertainment and crew were great- comfortable seats, got to watch a couple of movies with headphones provided by Delta; forgot mine so I assumed I would be miserable thru the whole 4 hour flight. so glad I was wrong! Would definitely take another flight with Delta... looking into the frequent flyer program as we speak

LAX
HNL
Okay 5.0

The gentleman at the gate was super helpful and helped us check our bags at the gate.

Zero leg room. Zero arm room. The entertainment system did not function. No food for such a long flight unless you pay more then the food is actually worth.

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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.