Are there direct flights from Chicago to San Antonio?

Yes, direct flights are commonly available from Chicago to San Antonio. Historically, direct flights have accounted for approximately 73.2% of all flights on this route. For flights with stopovers, travelers typically encountered a median of 2 stopovers. This indicates a strong preference and availability for non-stop options.

How long does it take to fly from Chicago to San Antonio?

A direct flight from Chicago to San Antonio typically takes 2 hours and 59 minutes, covering a distance of 1677 kilometers. For flights with one stop, the median travel time historically extends to 13 hours and 29 minutes. Travelers can expect a significantly shorter journey when opting for non-stop service.

How often do Chicago to San Antonio flight prices drop?

Historically, flight prices for the Chicago to San Antonio route have shown regular fluctuations. This pattern suggests that price drops are a consistent occurrence across the trailing 30 days. Travelers monitoring this route can often find opportunities to secure better fares due to these regular price adjustments.

Flights From Chicago

To San Antonio

Cheap Flights from Chicago to San Antonio

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Deals from

Chicago

RatePunk searches hundreds of travel sites at once for deals on flights to San Antonio

Prices updated 1 day ago

461 airlines compared

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Fares are subject to change and may not be available for all dates. (Data last updated Sep 14, 2026.)

Today’s best flight deals from Chicago to San Antonio

Explore current cheapest deals departing from Chicago to San Antonio

2026-10-07 – 2026-10-09
CHI - San Antonio
66% AI deal score
$268
$220
Round trip
2026-10-07 – 2026-10-14
CHI - San Antonio
49% AI deal score
$251
$222
Round trip
2026-10-20 – 2026-11-03
CHI - San Antonio
44% AI deal score
$221
$235
Round trip
2026-10-21 – 2026-11-03
CHI - San Antonio
44% AI deal score
$221
$235
Round trip
2026-10-31 – 2026-11-03
CHI - San Antonio
49% AI deal score
$265
$236
Round trip
2026-10-21 – 2026-10-27
CHI - San Antonio
47% AI deal score
$251
$236
Round trip
2026-11-14 – 2026-11-17
CHI - San Antonio
49% AI deal score
$262
$237
Round trip
2026-11-04 – 2026-11-17
CHI - San Antonio
44% AI deal score
$220
$237
Round trip
2026-10-20 – 2026-11-17
CHI - San Antonio
43% AI deal score
$211
$237
Round trip
2026-10-21 – 2026-11-17
CHI - San Antonio
43% AI deal score
$211
$237
Round trip

Chicago to San Antonio: Overview

Insights for flights from Chicago to San Antonio

Most itineraries for flights from Chicago to San Antonio are non-stop, accounting for 73.2% of recent fares. For the remaining itineraries that include connections, travelers typically encounter 2 stopovers. This strong direct-flight presence means you can often find convenient options for your journey.

When considering cheap flights from Chicago to San Antonio, fares are typically $153–$251, with a median of $184. Right now, current fares are significantly below the typical level, making it a potentially opportune time to book. Currently, 3% of recent fares are classified as a good price, indicating that deals are present but may require some flexibility to secure.

The cheapest time to fly from Chicago to San Antonio is during the summer months. July stands out as the most affordable month, with a median fare of $149. Following closely are August, with a median fare of $153, and June, where the median fare is $155. New deals for this route show up several times a week, offering regular opportunities to find competitive prices.

A typical journey from Chicago to San Antonio takes approximately 2h 59m, which includes both direct and connecting itineraries. This duration reflects the overall travel time you can expect, especially given that most flights on this route are non-stop. The total distance covered on this route is 1677 kilometers, classifying it as a medium-haul flight.

How much is a round trip from Chicago to San Antonio

Regular price: $177 - $294

Prices for flights from Chicago to San Antonio are currently within the regular range.

The regular price range for flights from Chicago to San Antonio is between $177 and $294. The current lowest deal is $221 with Frontier Airlines for travel from Oct 28-Nov 17.

now $221

Low $177

High $294

The cheapest time to fly from Chicago to San Antonio

The cheapest month to fly from Chicago to San Antonio is December, with a median price of $149. The most expensive month is September, with a median price of $595. Prices are generally lower from January to December.

December

Cheapest

Flights from $149

September

Most Expensive

Flights from $595

Jan

Feb

Mar

Apr

May

Jun

Jul

Aug

Sep

Oct

Nov

Dec

Direct flights from Chicago to San Antonio

Southwest Airlines

Last-minute flights going from Chicago to San Antonio

Tue, Sep 15

⌛ Last-Minute

ORD - San Antonio

Chicago (ORD) - San Antonio (SAT)

Frontier Airlines

$487

$367

One-way

Tue, Sep 15

⌛ Last-Minute

ORD - San Antonio

Chicago (ORD) - San Antonio (SAT)

Frontier Airlines

$401

$370

One-way

Wed, Sep 16

⌛ Last-Minute

ORD - San Antonio

Chicago (ORD) - San Antonio (SAT)

Frontier Airlines

$499

$380

One-way

Thu, Sep 17

⌛ Last-Minute

ORD - San Antonio

Chicago (ORD) - San Antonio (SAT)

Frontier Airlines

$470

$384

One-way

Thu, Sep 17

⌛ Last-Minute

ORD - San Antonio

Chicago (ORD) - San Antonio (SAT)

Frontier Airlines

$477

$413

One-way

Thu, Sep 17

⌛ Last-Minute

ORD - San Antonio

Chicago (ORD) - San Antonio (SAT)

Frontier Airlines

$467

$415

One-way

Biggest price drops on these dates for flights from Chicago to San Antonio

2 nights

Dec 14 - Dec 16

$452 → $257

43%

2 nights

Dec 10 - Dec 12

$448 → $267

40%

4 nights

Dec 7 - Dec 11

$446 → $292

34%

2 nights

Sep 17 - Sep 19

$477 → $347

27%

Popular Airports to fly from Chicago to San Antonio

Chicago - San Antonio route insights

💸 Price insights

Recent fares are below the typical level.

Recent fares from Chicago to San Antonio are below the typical level, with a median of $184.

📅 Best time to fly

July, August, and June offer the lowest median prices.

Historically, July ($149), August ($153), and June ($155) have offered the lowest median prices.

⏱️ Flight duration

Direct flights average 2h 59m.

Direct flights from Chicago to San Antonio typically take 2h 59m, while connecting flights average 19h 57m.

✈️ Airlines & availability

73.2% of recent flights are direct.

Historically, 73.2% of flights on this route have been direct, indicating strong availability.

🏆 Airline highlight

Southwest Airlines offers direct flights.

Southwest Airlines provides direct flights from Chicago to San Antonio.

🎯 Booking tip

Deals appear regularly on this route.

Deals on flights from Chicago to San Antonio appear regularly, offering frequent savings opportunities.

Chicago main airports to depart from

O Hare International (ORD)

Cheapest

Depart from O Hare International for flights to San Antonio, with fares from $220.

📍 ~25 km from Chicago city center (reachable by car or train).

💸 Flights from ~$220

San Antonio main airports to arrive at

San Antonio International (SAT)

Cheapest

San Antonio International Airport is a convenient arrival choice for flights from Chicago to San Antonio.

📍 ~12 km from city center (reachable by car)

💸 Flights from ~$223

Airports nearby San Antonio used as alternative

Austin–Bergstrom International (AUS)

Cheapest

Austin–Bergstrom International is a major international hub with an extensive flight network, useful for San Antonio.

📍 ~120 km from San Antonio (reachable by car, but heavy traffic on I-35 can increase travel time).

💸 Flights from ~$205

Business & First Class Flight Deals to San Antonio

Discover luxury on the budget with premium cabin class on flights from Chicago to San Antonio.

Elite

Best Elite deals to San Antonio

Exclusive daily First Class, Business Class, and Premium Economy flight deals, refreshed every 24 hours.

From ORD

Elite

Nov 13

San Antonio, United States

83% AI deal score

$1,597

$857

Save $740

United Airlines

Business Class

From ORD

Elite

Feb 25

San Antonio, United States

80% AI deal score

$1,298

$837

Save $461

United Airlines

Business Class

From ORD

Elite

Nov 16

San Antonio, United States

79% AI deal score

$1,231

$833

Save $398

United Airlines

Business Class

From ORD

Elite

Oct 24

San Antonio, United States

70% AI deal score

$1,027

$827

Save $200

United Airlines

Business Class

From ORD

Elite

Dec 16

San Antonio, United States

70% AI deal score

$1,002

$827

Save $175

United Airlines

Business Class

From ORD

Elite

Dec 18

San Antonio, United States

70% AI deal score

$1,062

$843

Save $219

United Airlines

Business Class

From ORD

Elite

Dec 18

San Antonio, United States

70% AI deal score

$1,054

$847

Save $207

United Airlines

Business Class

From ORD

Elite

Nov 21

San Antonio, United States

69% AI deal score

$977

$827

Save $150

United Airlines

Business Class

From ORD

Elite

Nov 13

San Antonio, United States

69% AI deal score

$968

$843

Save $125

United Airlines

Business Class

From ORD

Elite

Oct 16

San Antonio, United States

69% AI deal score

$978

$847

Save $131

United Airlines

Business Class

From ORD

Elite

Oct 21

San Antonio, United States

69% AI deal score

$996

$865

Save $131

United Airlines

Business Class

From ORD

Elite

Nov 18

San Antonio, United States

69% AI deal score

$1,023

$865

Save $158

United Airlines

Business Class

Frequently Asked Questions About Flights to San Antonio

Historically, the best deals for flights from Chicago to San Antonio are found when booking 60+ days in advance. During the trailing 90 days, the average price for flights booked in this window was $254. In comparison, booking 7-13 days out typically resulted in an average price of $562. Planning ahead can lead to significant savings on this route.

Across the trailing quarter, a good deal for a flight from Chicago to San Antonio was considered to be $153 or less. The median price for this route over the same period was $184. Prices at or below the $153 threshold represent a strong value for travelers.

Historically, July has been one of the best months to fly from Chicago to San Antonio, with a median price of $149. August also offered favorable pricing, with a median of $153. The annual median price for this route across the trailing 270 days was $184, indicating that certain months offer notable savings compared to the yearly average.

Related routes

More routes from Chicago

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Flights to San Antonio from other cities

Flights from Charlotte to San Antonio Flights from Dallas to San Antonio Flights from Denver to San Antonio Flights from Des Moines to San Antonio Flights from Detroit to San Antonio Flights from El Paso to San Antonio Flights from Hong Kong to San Antonio Flights from Houston to San Antonio Flights from Indianapolis to San Antonio Flights from Istanbul to San Antonio Flights from Las Vegas to San Antonio Flights from Sioux Falls to San Antonio

Chicago to San Antonio: Overview

Insights for flights from Chicago to San Antonio

How much is a round trip from Chicago to San Antonio

Regular price: $177 - $294

Prices for flights from Chicago to San Antonio are currently within the regular range.

The regular price range for flights from Chicago to San Antonio is between $177 and $294. The current lowest deal is $221 with Frontier Airlines for travel from Oct 28-Nov 17.

now $221

Low $177

High $294

The cheapest time to fly from Chicago to San Antonio

December

Cheapest

Flights from $149

September

Most Expensive

Flights from $595

Jan

Feb

Mar

Apr

May

Jun

Jul

Aug

Sep

Oct

Nov

Dec

Direct flights from Chicago to San Antonio

Southwest Airlines

Last-minute flights going from Chicago to San Antonio

Tue, Sep 15

⌛ Last-Minute

ORD - San Antonio

Chicago (ORD) - San Antonio (SAT)

Frontier Airlines

$487

$367

One-way

Tue, Sep 15

⌛ Last-Minute

ORD - San Antonio

Chicago (ORD) - San Antonio (SAT)

Frontier Airlines

$401

$370

One-way

Wed, Sep 16

⌛ Last-Minute

ORD - San Antonio

Chicago (ORD) - San Antonio (SAT)

Frontier Airlines

$499

$380

One-way

Thu, Sep 17

⌛ Last-Minute

ORD - San Antonio

Chicago (ORD) - San Antonio (SAT)

Frontier Airlines

$470

$384

One-way

Thu, Sep 17

⌛ Last-Minute

ORD - San Antonio

Chicago (ORD) - San Antonio (SAT)

Frontier Airlines

$477

$413

One-way

Thu, Sep 17

⌛ Last-Minute

ORD - San Antonio

Chicago (ORD) - San Antonio (SAT)

Frontier Airlines

$467

$415

One-way

Biggest price drops on these dates for flights from Chicago to San Antonio

2 nights

Dec 14 - Dec 16

$452 → $257

43%

2 nights

Dec 10 - Dec 12

$448 → $267

40%

4 nights

Dec 7 - Dec 11

$446 → $292

34%

2 nights

Sep 17 - Sep 19

$477 → $347

27%

Popular Airports to fly from Chicago to San Antonio

Chicago - San Antonio route insights

💸 Price insights

Recent fares are below the typical level.

Recent fares from Chicago to San Antonio are below the typical level, with a median of $184.

📅 Best time to fly

July, August, and June offer the lowest median prices.

Historically, July ($149), August ($153), and June ($155) have offered the lowest median prices.

⏱️ Flight duration

Direct flights average 2h 59m.

Direct flights from Chicago to San Antonio typically take 2h 59m, while connecting flights average 19h 57m.

✈️ Airlines & availability

73.2% of recent flights are direct.

Historically, 73.2% of flights on this route have been direct, indicating strong availability.

🏆 Airline highlight

Southwest Airlines offers direct flights.

Southwest Airlines provides direct flights from Chicago to San Antonio.

🎯 Booking tip

Deals appear regularly on this route.

Deals on flights from Chicago to San Antonio appear regularly, offering frequent savings opportunities.

Chicago main airports to depart from

O Hare International (ORD)

Cheapest

Depart from O Hare International for flights to San Antonio, with fares from $220.

📍 ~25 km from Chicago city center (reachable by car or train).

💸 Flights from ~$220

San Antonio main airports to arrive at

San Antonio International (SAT)

Cheapest

San Antonio International Airport is a convenient arrival choice for flights from Chicago to San Antonio.

📍 ~12 km from city center (reachable by car)

💸 Flights from ~$223

Airports nearby San Antonio used as alternative

Austin–Bergstrom International (AUS)

Cheapest

Austin–Bergstrom International is a major international hub with an extensive flight network, useful for San Antonio.

San Antonio, United States

69% AI deal score

$1,023

$865

Save $158

United Airlines

Business Class

Frequently Asked Questions About Flights to San Antonio

Cheap Flights from Chicago to San Antonio

Today’s best flight deals from Chicago to San Antonio

Chicago to San Antonio: Overview

Insights for flights from Chicago to San Antonio

How much is a round trip from Chicago to San Antonio

The cheapest time to fly from Chicago to San Antonio

Direct flights from Chicago to San Antonio

Last-minute flights going from Chicago to San Antonio

Biggest price drops on these dates for flights from Chicago to San Antonio

Popular Airports to fly from Chicago to San Antonio

Chicago - San Antonio route insights

Recent fares are below the typical level.

July, August, and June offer the lowest median prices.

Direct flights average 2h 59m.

73.2% of recent flights are direct.

Southwest Airlines offers direct flights.

Deals appear regularly on this route.

Chicago main airports to depart from

San Antonio main airports to arrive at

Airports nearby San Antonio used as alternative

Business & First Class Flight Deals to San Antonio

Best Elite deals to San Antonio

Nov 13

Feb 25

Nov 16

Oct 24

Dec 16

Dec 18

Dec 18

Nov 21

Nov 13

Oct 16

Oct 21

Nov 18

Frequently Asked Questions About Flights to San Antonio

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

How do I know if a Chicago to San Antonio flight is a good deal?

What's the best month to fly from Chicago to San Antonio?

Are there direct flights from Chicago to San Antonio?

How long does it take to fly from Chicago to San Antonio?

How often do Chicago to San Antonio flight prices drop?

Related routes

More routes from Chicago

Flights to San Antonio from other cities

Chicago to San Antonio: Overview

Insights for flights from Chicago to San Antonio

How much is a round trip from Chicago to San Antonio

The cheapest time to fly from Chicago to San Antonio

Direct flights from Chicago to San Antonio

Last-minute flights going from Chicago to San Antonio

Biggest price drops on these dates for flights from Chicago to San Antonio

Popular Airports to fly from Chicago to San Antonio

Chicago - San Antonio route insights

Recent fares are below the typical level.

July, August, and June offer the lowest median prices.

Direct flights average 2h 59m.

73.2% of recent flights are direct.

Southwest Airlines offers direct flights.

Deals appear regularly on this route.

Chicago main airports to depart from

San Antonio main airports to arrive at

Airports nearby San Antonio used as alternative

Business & First Class Flight Deals to San Antonio

Best Elite deals to San Antonio

Nov 13

Feb 25

Nov 16

Oct 24

Dec 16

Dec 18

Dec 18

Nov 21

Nov 13

Oct 16

Oct 21

Nov 18

Frequently Asked Questions About Flights to San Antonio

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

How do I know if a Chicago to San Antonio flight is a good deal?

What's the best month to fly from Chicago to San Antonio?