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

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Good to Know

Low Season:
September
Best time to beat the crowds
4%
expected price decrease
High Season:
February
Most popular time to fly
32%
expected price increase
Average Price:
$314
(avg. price over the last 2 weeks)
Good Deal:
$226
or less (round trip)

When to Book Flights from San Antonio to Chicago

Average price per month
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 $226 or less.
The cheapest flight from San Antonio to Chicago was found 30 days before departure, on average.
Book at least 2 weeks before departure in order to get a below-average price.
High season is considered to be January, February and March. The cheapest month to fly is September.
Morning departure is around 13% more expensive 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 San Antonio to Chicago Flights

How long does a flight from San Antonio to Chicago take?
An average nonstop flight takes 2h 42m, covering a distance of 1046 miles.
How many flights are there between San Antonio and Chicago?
There are 256 (nonstop) flights between San Antonio and Chicago per week, averaging 38 per day.
Which airlines provide the cheapest flights from San Antonio to Chicago?
In the past 3 days, the cheapest round-trip tickets were found on Frontier ($182), Multiple Airlines ($221) and United ($229).
Do I need a passport to fly between San Antonio and Chicago?
No.
Which airlines fly most frequently between San Antonio and Chicago?
Air Canada (6 times daily), United (6 times daily), American Airlines (3 times daily) are the most frequent flyers on this route.
What’s the cheapest day of the week to fly San Antonio to Chicago?
For San Antonio to Chicago, Tuesday is the cheapest day to fly on average and Saturday is the most expensive. Flying from Chicago back to San Antonio, the best deals are generally found on Monday, with Thursday being the most expensive.

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

Airports
Origin
San Antonio
$182
only
$182
Destination
Chicago
$182
only
$182
Tue, Jan 23
SAT
ORD
15h 09m
Tue, Jan 30
ORD
SAT
11h 30m
Trip: 8 days
4.3OkayShow reviews
Overall 4.3 Okay
Based on 1 reviews
Overall
5.9
Boarding
6.4
Comfort
5.4
Crew
6.8
Entertainment
4.5
Food
4.7
ISP
TPA
Mediocre 2.3

In flight crew was cordial, warm, professional

Everything else was a sh*tshow: bad information, confused and angry employees, flight was 7-hours late

MCO
OMA
Excellent 8.0

Nice flight. No issues. Flight staff was great.

Front desk check in guy in Orlando was a bit shady. Asked that we pay for our check-in bags with cash and wanted 10$ cash to put our seats together. I did not give him cash and had to ask for a reciept for the checked bags. We were 4 hours early for check in.

MKE
PHX
Mediocre 3.0

Service was awful. Delayed for more than 8hrs without an explanation of what type of maintenance issues were happening. Never given a straight answer as to what was happening. Food vouchers were only offered after the airport restaurants had closed. Once the plane was finished the crew had timed out and we could not leave till the following afternoon. Ended up being put up in a hotel for the night and lost an entire day of our weekend get away. Poor contingency planning on frontiers part. There was no reason

DEN
RNO
Excellent 8.6

Easy flight with good price.

No one takes cash anymore! Have to pay for all snacks! Not alot of room for broad shoulders.

MIA
LGA
Mediocre 2.0

if you have a hard engagement that you have to make, i hate to say it, but use a bigger airline. These guys are not dependable nyc -> miami. Have had 2 flights cancelled and delayed over 6 hours in the last 6 months. Only one scheduled flight everyday. If you can risk it, fine, but otherwise not worth it.

Sun, Feb 11
SAT
ORD
2h 42m
Tue, Feb 13
ORD
SAT
11h 30m
Trip: 3 days
Overall 0.0 Poor
Based on 0 reviews
Tue, Feb 6
SAT
ORD
2h 49m
Wed, Feb 21
ORD
SAT
3h 16m
Trip: 16 days
6.9GoodShow reviews
Overall 6.9 Good
Based on 30 reviews
Overall
7.2
Boarding
7.4
Comfort
6.9
Crew
7.7
Entertainment
6.5
Food
6.4
SAT
ORD
Mediocre 2.0

I am TSA approved. I am Global Entry approved. The TSA pre- check did not appear on my boarding passes. I was body searched 3 times, had no privileges, my luggage opened and scrutinized.

SAT
ORD
Excellent 10.0

Wifi worked well. Seat was comfortable. Plenty of room.

SAT
ORD
Good 7.3

Flight on time.

Seats uncomfortable

SAT
ORD
Okay 4.0

Nothing

Flight attendees were very rude and the flight from Chicago to Louisville. The plane was delayed by an hour for maintenance, the plane was disgusting, very dirty and nasty.

SAT
ORD
Excellent 8.0

You have reached your limit on how tight you can pack the seats. I am 6ft. 1in. When I sit all the way back in the seat my knees still hit the seat in front of me.

Sat, Feb 10
SAT
ORD
2h 48m
Thu, Feb 22
ORD
SAT
2h 53m
Trip: 13 days
8.1ExcellentShow reviews
Overall 8.1 Excellent
Based on 5 reviews
Overall
7.3
Boarding
7.5
Comfort
7.1
Crew
7.8
Entertainment
6.7
Food
6.6
SAT
ORD
Excellent 8.0

Every thing. I am not rating it as excellent only for the 'Maxim' : "There is always scope for Improvement"

Nil. No complaints what so ever.

PHL
ORD
Mediocre 2.0

The baggage customer service said the crew will wait for us, but they never did. THANKS for NOTHING!

CDG
DFW
Good 6.3

The snacks and meals were decent, as far as plane food goes (although the “vegetables” with the chicken were pretty awful). Also the entertainment selection had a wide assortment of movies, but disappointing tv show selection.

The boarding process was a mess. Just a huddle of people, with no clear direction and no one enforcing lines or boarding groups. Also my husband and I weren’t seated together and when I tried to change it online, the entire flight showed as booked. However once on board there were clearly a number of empty seats.

LAX
AKL
Excellent 8.3

New plane, great crew on board.

seats were hard especially for a 13 1/2 hour flight.

GRU
LIM
Good 7.0

Entertainment, crew

Several flights were delayed and canceled on last minute.

Tue, Jan 30
SAT
ORD
15h 09m
Mon, Feb 5
ORD
SAT
21h 44m
Trip: 7 days
4.3OkayShow reviews
Overall 4.3 Okay
Based on 1 reviews
Overall
5.9
Boarding
6.4
Comfort
5.4
Crew
6.8
Entertainment
4.5
Food
4.7
MKE
PHX
Mediocre 3.0

Service was awful. Delayed for more than 8hrs without an explanation of what type of maintenance issues were happening. Never given a straight answer as to what was happening. Food vouchers were only offered after the airport restaurants had closed. Once the plane was finished the crew had timed out and we could not leave till the following afternoon. Ended up being put up in a hotel for the night and lost an entire day of our weekend get away. Poor contingency planning on frontiers part. There was no reason

RSW
PVD
Excellent 10.0

Basic, simple. No frills but economical

Seats did not recline.. So uncomfortable

LAX
DEN
Excellent 8.0

Time management

Service

ATL
TTN
Excellent 9.3

I was having a terrible migraine and one of the female on flight staff directed me to open seats where I could lay down. She also provided me with lots of water and a bag of ice!

ATL
LAS
Good 6.0

The crew was very friendly.

The seats were close together and not very comfortable. No entertainment, for example a movie for a 4 hour flight. You have to pay for everything. Only thing complimentary is water.

Thu, Feb 1
SAT
ORD
15h 09m
Sat, Feb 10
ORD
SAT
21h 44m
Trip: 10 days
4.3OkayShow reviews
Overall 4.3 Okay
Based on 1 reviews
Overall
5.9
Boarding
6.4
Comfort
5.4
Crew
6.8
Entertainment
4.5
Food
4.7
MIA
LGA
Mediocre 2.0

if you have a hard engagement that you have to make, i hate to say it, but use a bigger airline. These guys are not dependable nyc -> miami. Have had 2 flights cancelled and delayed over 6 hours in the last 6 months. Only one scheduled flight everyday. If you can risk it, fine, but otherwise not worth it.

RSW
PVD
Excellent 10.0

Basic, simple. No frills but economical

Seats did not recline.. So uncomfortable

MCO
OMA
Excellent 8.0

Nice flight. No issues. Flight staff was great.

Front desk check in guy in Orlando was a bit shady. Asked that we pay for our check-in bags with cash and wanted 10$ cash to put our seats together. I did not give him cash and had to ask for a reciept for the checked bags. We were 4 hours early for check in.

ATL
TTN
Excellent 9.3

I was having a terrible migraine and one of the female on flight staff directed me to open seats where I could lay down. She also provided me with lots of water and a bag of ice!

GRR
MCO
Excellent 10.0

Early departure. Non stop. Early arrival. Ease of travel.

Tue, Feb 6
SAT
ORD
15h 09m
Sun, Feb 18
ORD
SAT
11h 30m
Trip: 13 days
4.3OkayShow reviews
Overall 4.3 Okay
Based on 1 reviews
Overall
5.9
Boarding
6.4
Comfort
5.4
Crew
6.8
Entertainment
4.5
Food
4.7
DEN
RNO
Excellent 8.6

Easy flight with good price.

No one takes cash anymore! Have to pay for all snacks! Not alot of room for broad shoulders.

LAX
DEN
Excellent 8.0

Time management

Service

ATL
TTN
Excellent 9.3

I was having a terrible migraine and one of the female on flight staff directed me to open seats where I could lay down. She also provided me with lots of water and a bag of ice!

MIA
LGA
Mediocre 2.0

if you have a hard engagement that you have to make, i hate to say it, but use a bigger airline. These guys are not dependable nyc -> miami. Have had 2 flights cancelled and delayed over 6 hours in the last 6 months. Only one scheduled flight everyday. If you can risk it, fine, but otherwise not worth it.

ATL
LAS
Good 6.0

The crew was very friendly.

The seats were close together and not very comfortable. No entertainment, for example a movie for a 4 hour flight. You have to pay for everything. Only thing complimentary is water.

Wed, Feb 7
SAT
ORD
2h 53m
Wed, Feb 21
ORD
SAT
3h 16m
Trip: 15 days
6.9GoodShow reviews
Overall 6.9 Good
Based on 30 reviews
Overall
7.2
Boarding
7.4
Comfort
6.9
Crew
7.7
Entertainment
6.5
Food
6.4
SAT
ORD
Good 6.6

Crew took special care of my guitar -- much appreciated.

Small plane. Kept bumping my head when I got up.

SAT
ORD
Excellent 10.0

In flight snack

SAT
ORD
Okay 4.0

Nothing

Flight attendees were very rude and the flight from Chicago to Louisville. The plane was delayed by an hour for maintenance, the plane was disgusting, very dirty and nasty.

SAT
ORD
Good 7.2

The fact that it was actually on time and flight went according to plan.

Seats uncomfortable with very little room.

SAT
ORD
Mediocre 2.0

I am TSA approved. I am Global Entry approved. The TSA pre- check did not appear on my boarding passes. I was body searched 3 times, had no privileges, my luggage opened and scrutinized.

Wed, Feb 14
SAT
ORD
2h 48m
Thu, Feb 22
ORD
SAT
2h 53m
Trip: 9 days
8.1ExcellentShow reviews
Overall 8.1 Excellent
Based on 5 reviews
Overall
7.3
Boarding
7.5
Comfort
7.1
Crew
7.8
Entertainment
6.7
Food
6.6
CMH
DCA
Mediocre 2.0

Never knew flying domestically with a company named American would be so impossible. A true joke. Never had such difficulties traveling about. Super unsatisfiee and will not be traveling with them again. I urge everyone considering to purchase other airlines as well.

TPA
PHX
Excellent 9.3

We had a newer plane. I LOVED that the seatbelts had a little more room, and also that each seat had it down screen. I really enjoyed the new pre-flight video; it was entertaining and I appreciated that it allowed the crew to get ready, rather than demonstrate a seatbelt for us.

I am not sure how boarding groups work, but I will never understand why we don't board from the back of the plane to the front. People waiting and trying to load luggage or climb over others makes the pre-flight more stressful than it needs to be. (This is obviously not specific to you airline.)

PHL
ORD
Mediocre 2.0

The baggage customer service said the crew will wait for us, but they never did. THANKS for NOTHING!

SAT
ORD
Good 7.6

On time, staff at gate and on plane friendly and courteous.

No plug for electronics. Seats crowded with heavy person next to me.

DFW
MSY
Excellent 10.0

Travel time

No snacks on flight. The charging stations come in between legs space and very uncomfortable they got to be re adjusted. Make sure these are taken care in upcoming flights.

Mon, Feb 26
SAT
ORD
2h 47m
Tue, Mar 6
ORD
SAT
2h 53m
Trip: 9 days
Overall 0.0 Poor
Based on 0 reviews
Tue, Feb 13
SAT
ORD
15h 09m
Thu, Feb 22
ORD
SAT
11h 30m
Trip: 10 days
4.3OkayShow reviews
Overall 4.3 Okay
Based on 1 reviews
Overall
5.9
Boarding
6.4
Comfort
5.4
Crew
6.8
Entertainment
4.5
Food
4.7
ISP
TPA
Mediocre 2.3

In flight crew was cordial, warm, professional

Everything else was a sh*tshow: bad information, confused and angry employees, flight was 7-hours late

ATL
TTN
Excellent 9.3

I was having a terrible migraine and one of the female on flight staff directed me to open seats where I could lay down. She also provided me with lots of water and a bag of ice!

DEN
DCA
Excellent 8.0

Time management

Service

MCO
OMA
Excellent 8.0

Nice flight. No issues. Flight staff was great.

Front desk check in guy in Orlando was a bit shady. Asked that we pay for our check-in bags with cash and wanted 10$ cash to put our seats together. I did not give him cash and had to ask for a reciept for the checked bags. We were 4 hours early for check in.

RSW
PVD
Excellent 10.0

Basic, simple. No frills but economical

Seats did not recline.. So uncomfortable

Thu, Feb 8
SAT
ORD
2h 42m
Sat, Feb 17
ORD
SAT
3h 12m
Trip: 10 days
6.9GoodShow reviews
Overall 6.9 Good
Based on 30 reviews
Overall
7.2
Boarding
7.4
Comfort
6.9
Crew
7.7
Entertainment
6.5
Food
6.4
SAT
ORD
Okay 4.0

Dirty

SAT
ORD
Mediocre 2.0

Two hour delay.

SAT
ORD
Good 6.6

Crew took special care of my guitar -- much appreciated.

Small plane. Kept bumping my head when I got up.

SAT
ORD
Mediocre 2.0

3 hr delay.,..no real reason. :(

SAT
ORD
Mediocre 2.0

I am TSA approved. I am Global Entry approved. The TSA pre- check did not appear on my boarding passes. I was body searched 3 times, had no privileges, my luggage opened and scrutinized.

Tue, Feb 20
SAT
ORD
2h 53m
Mon, Feb 26
ORD
SAT
2h 53m
Trip: 7 days
8.1ExcellentShow reviews
Overall 8.1 Excellent
Based on 5 reviews
Overall
7.3
Boarding
7.5
Comfort
7.1
Crew
7.8
Entertainment
6.7
Food
6.6
GRU
LIM
Good 7.0

Entertainment, crew

Several flights were delayed and canceled on last minute.

SAT
ORD
Good 7.6

On time, staff at gate and on plane friendly and courteous.

No plug for electronics. Seats crowded with heavy person next to me.

CDG
DFW
Good 6.3

The snacks and meals were decent, as far as plane food goes (although the “vegetables” with the chicken were pretty awful). Also the entertainment selection had a wide assortment of movies, but disappointing tv show selection.

The boarding process was a mess. Just a huddle of people, with no clear direction and no one enforcing lines or boarding groups. Also my husband and I weren’t seated together and when I tried to change it online, the entire flight showed as booked. However once on board there were clearly a number of empty seats.

DFW
SFO
Good 6.0

The seats actually had individual screens, which was a very nice surprise. There’s a decent movie collection. alao the flight attendants were very nice and friendly.

The tv show selection is quite poor. Also, like the previous flight, my husband and I weren’t seated together (not even in the same row) and when I tried to change it online, the entire flight showed as booked. However once on board there were clearly a number of empty seats.

PHL
ORD
Mediocre 2.0

The baggage customer service said the crew will wait for us, but they never did. THANKS for NOTHING!

Tue, Feb 27
SAT
ORD
2h 53m
Tue, Mar 6
ORD
SAT
3h 12m
Trip: 8 days
Overall 0.0 Poor
Based on 0 reviews
Tue, Feb 20
SAT
ORD
15h 09m
Tue, Feb 27
ORD
SAT
11h 30m
Trip: 8 days
4.3OkayShow reviews
Overall 4.3 Okay
Based on 1 reviews
Overall
5.9
Boarding
6.4
Comfort
5.4
Crew
6.8
Entertainment
4.5
Food
4.7
MCO
OMA
Excellent 8.0

Nice flight. No issues. Flight staff was great.

Front desk check in guy in Orlando was a bit shady. Asked that we pay for our check-in bags with cash and wanted 10$ cash to put our seats together. I did not give him cash and had to ask for a reciept for the checked bags. We were 4 hours early for check in.

MKE
PHX
Mediocre 3.0

Service was awful. Delayed for more than 8hrs without an explanation of what type of maintenance issues were happening. Never given a straight answer as to what was happening. Food vouchers were only offered after the airport restaurants had closed. Once the plane was finished the crew had timed out and we could not leave till the following afternoon. Ended up being put up in a hotel for the night and lost an entire day of our weekend get away. Poor contingency planning on frontiers part. There was no reason

GRR
MCO
Excellent 10.0

Early departure. Non stop. Early arrival. Ease of travel.

LAX
DEN
Excellent 8.0

Time management

Service

OMA
MCO
Excellent 8.0

Nice flight. Arrived early.

4.99 for a can of coke???

Thu, Feb 15
SAT
ORD
2h 44m
Wed, Feb 21
ORD
SAT
3h 16m
Trip: 7 days
6.9GoodShow reviews
Overall 6.9 Good
Based on 30 reviews
Overall
7.2
Boarding
7.4
Comfort
6.9
Crew
7.7
Entertainment
6.5
Food
6.4
SAT
ORD
Good 7.3

Flight on time.

Seats uncomfortable

SAT
ORD
Mediocre 2.0

Two hour delay.

SAT
ORD
Good 7.2

The fact that it was actually on time and flight went according to plan.

Seats uncomfortable with very little room.

SAT
ORD
Mediocre 2.0

I am TSA approved. I am Global Entry approved. The TSA pre- check did not appear on my boarding passes. I was body searched 3 times, had no privileges, my luggage opened and scrutinized.

SAT
ORD
Okay 4.0

Dirty

Wed, Feb 21
SAT
ORD
2h 53m
Tue, Feb 27
ORD
SAT
2h 53m
Trip: 7 days
8.1ExcellentShow reviews
Overall 8.1 Excellent
Based on 5 reviews
Overall
7.3
Boarding
7.5
Comfort
7.1
Crew
7.8
Entertainment
6.7
Food
6.6
DFW
MSY
Excellent 10.0

Travel time

No snacks on flight. The charging stations come in between legs space and very uncomfortable they got to be re adjusted. Make sure these are taken care in upcoming flights.

GRU
LIM
Good 7.0

Entertainment, crew

Several flights were delayed and canceled on last minute.

ORD
MSP
Okay 5.6

The touch down at MSP. Was sitting over the wing and barely felt it.

Was told carry on needed to be checked because there wasn't any more overhead room for my 9X14X16. So then I had to dig through it at the gate to remove lithium batteries and it took an additional 20+ minutes at MSP to get to baggage claim/wait/claim bag. There was plenty of room in overhead storage for my bag.

PHL
ORD
Mediocre 2.0

The baggage customer service said the crew will wait for us, but they never did. THANKS for NOTHING!

TPA
PHX
Excellent 9.3

We had a newer plane. I LOVED that the seatbelts had a little more room, and also that each seat had it down screen. I really enjoyed the new pre-flight video; it was entertaining and I appreciated that it allowed the crew to get ready, rather than demonstrate a seatbelt for us.

I am not sure how boarding groups work, but I will never understand why we don't board from the back of the plane to the front. People waiting and trying to load luggage or climb over others makes the pre-flight more stressful than it needs to be. (This is obviously not specific to you airline.)

Wed, Feb 28
SAT
ORD
2h 47m
Tue, Mar 6
ORD
SAT
2h 53m
Trip: 7 days
Overall 0.0 Poor
Based on 0 reviews
Thu, Feb 22
SAT
ORD
15h 09m
Sat, Mar 3
ORD
SAT
21h 48m
Trip: 10 days
4.3OkayShow reviews
Overall 4.3 Okay
Based on 1 reviews
Overall
5.9
Boarding
6.4
Comfort
5.4
Crew
6.8
Entertainment
4.5
Food
4.7
LAX
DEN
Excellent 8.0

Time management

Service

MCO
OMA
Excellent 8.0

Nice flight. No issues. Flight staff was great.

Front desk check in guy in Orlando was a bit shady. Asked that we pay for our check-in bags with cash and wanted 10$ cash to put our seats together. I did not give him cash and had to ask for a reciept for the checked bags. We were 4 hours early for check in.

MKE
PHX
Mediocre 3.0

Service was awful. Delayed for more than 8hrs without an explanation of what type of maintenance issues were happening. Never given a straight answer as to what was happening. Food vouchers were only offered after the airport restaurants had closed. Once the plane was finished the crew had timed out and we could not leave till the following afternoon. Ended up being put up in a hotel for the night and lost an entire day of our weekend get away. Poor contingency planning on frontiers part. There was no reason

ATL
LAS
Good 6.0

The crew was very friendly.

The seats were close together and not very comfortable. No entertainment, for example a movie for a 4 hour flight. You have to pay for everything. Only thing complimentary is water.

ATL
TTN
Excellent 9.3

I was having a terrible migraine and one of the female on flight staff directed me to open seats where I could lay down. She also provided me with lots of water and a bag of ice!

Sat, Feb 17
SAT
ORD
2h 50m
Wed, Feb 21
ORD
SAT
3h 16m
Trip: 5 days
6.9GoodShow reviews
Overall 6.9 Good
Based on 30 reviews
Overall
7.2
Boarding
7.4
Comfort
6.9
Crew
7.7
Entertainment
6.5
Food
6.4
SAT
ORD
Mediocre 2.0

I am TSA approved. I am Global Entry approved. The TSA pre- check did not appear on my boarding passes. I was body searched 3 times, had no privileges, my luggage opened and scrutinized.

SAT
ORD
Okay 4.0

Dirty

SAT
ORD
Excellent 10.0

Wifi worked well. Seat was comfortable. Plenty of room.

SAT
ORD
Okay 4.0

Nothing

Flight attendees were very rude and the flight from Chicago to Louisville. The plane was delayed by an hour for maintenance, the plane was disgusting, very dirty and nasty.

SAT
ORD
Excellent 10.0

In flight snack

Show more results

San Antonio to Chicago Flight Information

Avg. Flight Duration 2h 56m
Flights Arrive in Chicago
Flights Depart from San Antonio
Flight Price $182
Distance 1046 miles
Airlines Frontier, United, American Airlines
*
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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.