$128+ Flights from Chicago to San Antonio

One-way flight from Chicago (CHI) to San Antonio

Highest demand for flights based on searches. 5% potential increase in price ($24 potential increase over avg. RT price).

Cheapest flight prices on average. 1% potential price decrease ($4 potential savings vs. average RT price).

Average for round-trip flights in June 2025

Price to beat on a round-trip flight from Chicago (CHI) to San Antonio.

Price to beat on a one-way flight from Chicago (CHI) to San Antonio.

Find flight deals from Chicago to San Antonio

Cheapest flights from Chicago to San Antonio
Explore the most affordable flight options available from Chicago to San Antonio. Find the lowest fares from popular airlines and budget airlines, with prices last updated on June 30, 2025.

Tue 7/157:00 amORD - SAT

1 stop11h 02mMultiple Airlines

Tue 7/227:52 pmSAT - ORD

1 stop10h 11mMultiple Airlines

Deal found 6/29

$181

Tue 7/297:08 amORD - SAT

1 stop11h 28mSpirit Airlines

Sun 8/105:38 pmSAT - ORD

1 stop27h 52mSpirit Airlines

Deal found 6/28

$182

Thu 9/45:04 pmMDW - SAT

1 stop23h 26mFrontier

Mon 9/85:35 pmSAT - MDW

1 stop5h 45mFrontier

Deal found 6/29

$191

Mon 7/285:01 amORD - SAT

1 stop11h 51mFrontier

Mon 8/45:38 pmSAT - ORD

1 stop6h 44mFrontier

Deal found 6/30

$205

Wed 9/32:55 pmORD - SAT

Nonstop2h 54mAmerican Airlines

Mon 9/87:00 amSAT - ORD

Nonstop2h 53mAmerican Airlines

Deal found 6/28

$235

Sat 8/29:45 pmMDW - SAT

Nonstop2h 40mSouthwest

Mon 8/46:30 pmSAT - MDW

Nonstop2h 40mSouthwest

Deal found 6/28

$235

Thu 8/149:31 amMDW - SAT

1 stop6h 10mDelta

Thu 8/215:15 amSAT - MDW

1 stop6h 33mDelta

Deal found 6/30

$255

Best flights from Chicago to San Antonio
Discover carefully curated flight deals from Chicago to San Antonio that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated June 30, 2025.

Tue 7/157:00 amORD - SAT

1 stop11h 02mMultiple Airlines

Tue 7/227:52 pmSAT - ORD

1 stop10h 11mMultiple Airlines

Deal found 6/29

$181

Tue 7/297:08 amORD - SAT

1 stop11h 28mSpirit Airlines

Sun 8/105:38 pmSAT - ORD

1 stop27h 52mSpirit Airlines

Deal found 6/28

$182

Thu 9/45:04 pmMDW - SAT

1 stop23h 26mFrontier

Mon 9/85:35 pmSAT - MDW

1 stop5h 45mFrontier

Deal found 6/29

$191

Wed 9/32:55 pmORD - SAT

Nonstop2h 54mAmerican Airlines

Mon 9/87:00 amSAT - ORD

Nonstop2h 53mAmerican Airlines

Deal found 6/28

$235

Sat 8/29:45 pmMDW - SAT

Nonstop2h 40mSouthwest

Mon 8/46:30 pmSAT - MDW

Nonstop2h 40mSouthwest

Deal found 6/28

$235

Thu 8/1412:43 pmMDW - SAT

1 stop6h 47mDelta

Thu 8/2111:27 amSAT - MDW

1 stop7h 10mDelta

Deal found 6/30

$255

Mon 7/285:01 amORD - SAT

1 stop11h 51mFrontier

Mon 8/45:38 pmSAT - ORD

1 stop6h 44mFrontier

Deal found 6/30

$205

Last-minute flights from Chicago to San Antonio
Discover last-minute flight deals from Chicago to San Antonio. Data last updated June 30, 2025 and is based on user searches.

Sat 7/53:52 pmORD - SAT

1 stop7h 19mAmerican Airlines

Sun 7/131:25 pmSAT - ORD

Nonstop2h 59mAmerican Airlines

Deal found 6/28

$439

Sat 7/510:26 amMDW - SAT

1 stop6h 38mDelta

Sun 7/66:30 amSAT - MDW

1 stop5h 29mDelta

Deal found 6/30

$771

Mon 7/76:20 amMDW - SAT

1 stop10h 32mFrontier

Mon 7/145:38 pmSAT - MDW

1 stop17h 02mFrontier

Deal found 6/30

$352

Tue 7/87:00 amORD - SAT

1 stop11h 02mMultiple Airlines

Sat 7/127:52 pmSAT - ORD

1 stop10h 11mMultiple Airlines

Deal found 6/29

$233

Tue 7/87:00 amORD - SAT

1 stop11h 02mFrontier

Fri 8/155:38 pmSAT - ORD

1 stop6h 44mFrontier

Deal found 6/28

$269

Tue 7/87:27 amORD - SAT

1 stop6h 35mSpirit Airlines

Thu 8/212:50 pmSAT - ORD

1 stop14h 00mSpirit Airlines

Deal found 6/28

$307

Tue 7/88:30 amMDW - SAT

Nonstop2h 50mSouthwest

Thu 8/215:50 amSAT - MDW

Nonstop2h 35mSouthwest

Deal found 6/28

$473

Tue 7/157:00 amORD - SAT

1 stop11h 02mMultiple Airlines

Tue 7/227:52 pmSAT - ORD

1 stop10h 11mMultiple Airlines

Deal found 6/29

$181

Thu 7/242:55 pmMDW - SAT

1 stop25h 57mFrontier

Sun 7/278:14 pmSAT - MDW

1 stop15h 27mFrontier

Deal found 6/29

$273

Fri 7/2510:31 amMDW - SAT

2 stops12h 11mMultiple Airlines

Sun 7/277:10 amSAT - MDW

2 stops26h 31mMultiple Airlines

Deal found 6/29

$382

Mon 7/285:01 amORD - SAT

1 stop11h 51mFrontier

Mon 8/45:38 pmSAT - ORD

1 stop6h 44mFrontier

Deal found 6/30

$205

Tue 7/297:08 amORD - SAT

1 stop11h 28mSpirit Airlines

Sun 8/105:38 pmSAT - ORD

1 stop27h 52mSpirit Airlines

Deal found 6/28

$182

One-way flights from Chicago to San Antonio
Search for one-way flight options from Chicago to San Antonio. Find affordable one-way fares based on user searches. Data last updated June 30, 2025.

Wed 7/306:00 amMDW - SAT

1 stop5h 19mDelta

Deal found 6/30

$128

Thu 7/177:08 amORD - SAT

1 stop11h 28mSpirit Airlines

Deal found 6/30

$130

Wed 8/61:50 pmORD - SAT

2 stops9h 15mSouthwest

Deal found 6/29

$133

Mon 9/83:30 pmMDW - SAT

2 stops6h 25mSouthwest

Deal found 6/29

$133

Sun 7/275:40 amORD - SAT

1 stop13h 33mFrontier

Deal found 6/28

$135

Sun 9/215:04 pmMDW - SAT

1 stop23h 26mFrontier

Deal found 6/30

$135

Wed 7/305:40 pmORD - SAT

2 stops22h 53mMultiple Airlines

Deal found 6/29

$137

Thu 7/312:42 pmORD - SAT

Nonstop2h 56mAmerican Airlines

Deal found 6/28

$143

Fri 7/43:40 pmORD - SAT

1 stop6h 15mDelta

Deal found 6/27

$153

Sun 8/37:40 pmORD - SAT

Nonstop2h 58mUnited Airlines

Deal found 6/29

$163

Fri 8/81:11 pmMDW - SAT

2 stops9h 31mMultiple Airlines

Deal found 6/28

$166

Cheapflights Fare Finder

Use the filters below to find and compare flights from Chicago to San Antonio that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

ChicagoSan Antonio

ORD - SAT

ORDSAT

Chicago O'Hare Intl

Tue 7/15

7:00 am-6:02 pm

1 stop11h 02m

San Antonio

Tue 7/22

7:52 pm-6:03 am

1 stop10h 11m

$181

ChicagoSan Antonio

ORD - SAT

ORDSAT

Chicago O'Hare Intl

Tue 7/29

7:08 am-6:36 pm

1 stop11h 28m

San Antonio

Sun 8/10

5:38 pm-9:30 pm

1 stop27h 52m

$182

ChicagoSan Antonio

MDW - SAT

MDWSAT

Chicago Midway

Thu 9/4

5:04 pm-4:30 pm

1 stop23h 26m

San Antonio

Mon 9/8

5:35 pm-11:20 pm

1 stop5h 45m

$191

ChicagoSan Antonio

ORD - SAT

ORDSAT

Chicago O'Hare Intl

Mon 7/28

5:01 am-4:52 pm

1 stop11h 51m

San Antonio

Mon 8/4

5:38 pm-12:22 am

1 stop6h 44m

$205

ChicagoSan Antonio

ORD - SAT

ORDSAT

Chicago O'Hare Intl

Wed 9/3

2:55 pm-5:49 pm

Nonstop2h 54m

San Antonio

Mon 9/8

7:00 am-9:53 am

Nonstop2h 53m

$235

ChicagoSan Antonio

MDW - SAT

MDWSAT

Chicago Midway

Sat 8/2

9:45 pm-12:25 am

Nonstop2h 40m

San Antonio

Mon 8/4

6:30 pm-9:10 pm

Nonstop2h 40m

$235

ChicagoSan Antonio

MDW - SAT

MDWSAT

Chicago Midway

Thu 8/14

12:43 pm-7:30 pm

1 stop6h 47m

San Antonio

Thu 8/21

11:27 am-6:37 pm

1 stop7h 10m

$255

ChicagoSan Antonio

ORD - SAT

ORDSAT

Chicago O'Hare Intl

Sat 9/20

6:00 am-7:22 pm

2 stops13h 22m

$128

ChicagoSan Antonio

MDW - SAT

MDWSAT

Chicago Midway

Wed 7/30

6:00 am-11:19 am

1 stop5h 19m

$128

ChicagoSan Antonio

ORD - SAT

ORDSAT

Chicago O'Hare Intl

Wed 9/17

1:30 pm-10:00 pm

2 stops8h 30m

$133

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/30

Showing 1-10 of 18 results

The best insider tips for Chicago to San Antonio flights

Cheapflights partnered with top experts to bring you the best recommendations for your Chicago to San Antonio trip

Airports

ORD

Expect long walks between terminals at ORD; plan extra time for navigating this busy airport.

MDW

Use the 'L' train for a quick, cost-effective way to reach MDW from downtown Chicago in under 30 minutes.

SAT

For a quick ride to downtown San Antonio, use rideshare services from SAT, taking about 15 minutes.

Our travel experts

Ramsey Qubein

Expert on ORD, MDW and SAT

Best time to book a flight from Chicago to San Antonio

Have a flexible travel schedule? Discover the best time to fly to San Antonio from Chicago with our price prediction graph.

Estimated round-trip price

Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from Chicago to San Antonio

How far ahead should I book a flight from Chicago to San Antonio?

Booking 71 days in advance of your planned departure date is, on average, the best time to get cheap flights from Chicago to San Antonio. The general trend is that the closer you book to the departure date, the more expensive your flight will be.

What is the cheapest month to book a flight from Chicago to San Antonio?

Currently, August is the cheapest month in which you can book a flight from Chicago to San Antonio (average of $295). Flying from Chicago to San Antonio in March is currently the most expensive (average of $376). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

What is the cheapest time of day to fly from CHI to SAT?

It’s typically best to fly out from Chicago to San Antonio at noon. Doing so could potentially save you 10% on the flight price compared to flying in the morning, which is usually more expensive.

What is the cheapest day to fly from Chicago to San Antonio?

Travelers seeking maximum savings on their Chicago to San Antonio flight should consider departing on Wednesday afternoons when fares are most often at their lowest. Sunday afternoons flights should be avoided if possible as fares are typically the most expensive at this time.

Weekly flight availability from Chicago to San Antonio

The most flights from CHI to SAT are scheduled on a Monday (33 on average). You will have fewer flight options on Wednesday, which is when the least amount of flights are scheduled (3 on average).

How much does it cost to fly round-trip from Chicago to San Antonio?

Reviews of airlines servicing San Antonio

Read reviews from past customers who have flown Southwest, Delta, and United Airlines from Chicago to San Antonio. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.

8.0

Very good

Reviews

1 / 20

8.0

Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.

8.0

Very good

8.0

Very good

Reviews

1 / 20

8.0

Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.

Delta

8.0

Very good

7,973 reviews

8.0

Very good

Reviews

1 / 20

8.0

Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.

United Airlines

7.4

Good

8,852 reviews

8.0

Very good

Reviews

1 / 20

8.0

Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.

American Airlines

7.2

Good

10,000 reviews

8.0

Very good

Reviews

1 / 20

8.0

Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.

Spirit Airlines

6.3

Okay

8,094 reviews

8.0

Very good