Are there direct flights from Chicago to San Antonio?

Yes, direct flights are commonly available from Chicago to San Antonio. Historically, direct flights accounted for approximately 73.2% of all available options across the trailing 90 days. For flights that included stopovers, travelers typically encountered 2 stopovers. This indicates a strong prevalence of non-stop options for this route.

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 duration historically extends to 13 hours and 29 minutes. Travelers can expect a significantly shorter journey when opting for non-stop service on this route.

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 suggests that price drops are a common occurrence over the trailing 30 days. Travelers can typically expect to see opportunities for price reductions on this route.

Flights From Chicago

To San Antonio

Cheap Flights from Chicago to San Antonio

Browse current best options from Chicago. Become a member to unlock all deals and get alerts when new deals appear.

Deals from

Chicago

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

Prices updated 2 days ago

405 airlines compared

80%+ AI score for best value

Fares are subject to change and may not be available for all dates. (Data last updated Jul 26, 2026.)

Today’s best flight deals from Chicago to San Antonio

Explore current cheapest deals departing from Chicago to San Antonio

2026-10-14 – 2026-10-21
CHI - San Antonio
47% AI deal score
$257
$241
Round trip
2026-09-26 – 2026-09-28
CHI - San Antonio
49% AI deal score
$277
$243
Round trip
2026-10-03 – 2026-10-10
CHI - San Antonio
47% AI deal score
$257
$244
Round trip
2026-08-27 – 2026-08-31
CHI - San Antonio
67% AI deal score
$316
$247
Round trip
2026-08-29 – 2026-08-31
CHI - San Antonio
67% AI deal score
$312
$247
Round trip
2026-08-20 – 2026-08-22
CHI - San Antonio
67% AI deal score
$322
$247
Round trip
2026-09-19 – 2026-09-24
CHI - San Antonio
48% AI deal score
$270
$247
Round trip
2026-09-03 – 2026-09-10
CHI - San Antonio
47% AI deal score
$258
$247
Round trip
2026-09-05 – 2026-09-12
CHI - San Antonio
47% AI deal score
$258
$247
Round trip
2026-09-19 – 2026-09-21
CHI - San Antonio
49% AI deal score
$276
$247
Round trip

Chicago to San Antonio: Overview

Insights for flights from Chicago to San Antonio

For travelers looking for cheap flights from Chicago to San Antonio, almost all itineraries are non-stop, with 73.2% of recent fares being direct flights from Chicago to San Antonio. When connecting flights are necessary, they typically involve 2 stopovers. New deals for this route show up several times a week, suggesting a regular cadence for price changes.

When considering the cheapest time to fly from Chicago to San Antonio, you'll find that July is 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. These months offer the best value for this route.

A typical journey from Chicago to San Antonio takes about 2h 59m, including both direct and connecting itineraries. This duration reflects the overall travel time you can expect for this route. The distance between Chicago and San Antonio is 1677 kilometers, classifying it as a medium-haul flight.

Fares for flights from Chicago to San Antonio typically range from $153–$251, with a median of $184. Right now, fares to San Antonio are below the typical level, indicating a potentially favorable time to purchase. Currently, 3% of recent fares are classified as a good price for this route.

How much is a round trip from Chicago to San Antonio

Regular price: $212 - $295

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

Regular prices for flights from Chicago to San Antonio typically range from $212 to $295. The current lowest deal is $234 with Frontier Airlines for travel from Oct 10-Oct 13.

now $234

Low $212

High $295

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

United Airlines

Last-minute flights going from Chicago to San Antonio

Mon, Jul 27

⌛ Last-Minute

ORD - San Antonio

Chicago (ORD) - San Antonio (SAT)

Frontier Airlines

$443

$352

One-way

Tue, Jul 28

⌛ Last-Minute

ORD - San Antonio

Chicago (ORD) - San Antonio (SAT)

Frontier Airlines

$447

$341

One-way

Tue, Jul 28

⌛ Last-Minute

ORD - San Antonio

Chicago (ORD) - San Antonio (SAT)

Frontier Airlines

$442

$351

One-way

Sat, Aug 1

⌛ Last-Minute

ORD - San Antonio

Chicago (ORD) - San Antonio (SAT)

Frontier Airlines

$488

$325

One-way

Sat, Aug 1

⌛ Last-Minute

ORD - San Antonio

Chicago (ORD) - San Antonio (SAT)

Frontier Airlines

$438

$325

One-way

Sat, Aug 1

⌛ Last-Minute

ORD - San Antonio

Chicago (ORD) - San Antonio (SAT)

Frontier Airlines

$491

$341

One-way

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

4 nights

Aug 1 - Aug 5

$488 → $325

33%

2 nights

Aug 1 - Aug 3

$502 → $351

30%

3 nights

Aug 1 - Aug 4

$491 → $341

31%

13 nights

Dec 15 - Dec 28

$492 → $357

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 prices around $234.

📅 Best time to fly

Fly in December for the best prices.

Historically, December is the cheapest month to fly from Chicago to San Antonio, with a median price of $149.

⏱️ Flight duration

Direct flights take 2h 59m.

The typical direct flight from Chicago to San Antonio takes 2 hours and 59 minutes.

✈️ Airlines & availability

73.2% of recent flights are direct.

Most flights on this route are direct, with 73.2% of recent flights being nonstop.

🏆 Airline highlight

United Airlines offers direct flights.

United Airlines provides direct flight options from Chicago to San Antonio.

🎯 Booking tip

Deals appear regularly on this route.

Deals for flights from Chicago to San Antonio appear regularly, typically within a 30-day window.

Chicago main airports to depart from

O Hare International (ORD)

Cheapest

O'Hare International Airport is a major hub, offering many flight options from Chicago to San Antonio.

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

💸 Flights from ~$209

San Antonio main airports to arrive at

San Antonio International (SAT)

Cheapest

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

📍 ~12 km from San Antonio (reachable by car)

💸 Flights from ~$209

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, offering many options.

📍 ~120 km from San Antonio (reachable by car, but expect heavy traffic).

💸 Flights from ~$153

Business & First Class Flight Deals to San Antonio

78% AI deal score

$1,031

$707

Save $324

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 within this window was $254. In contrast, booking 7-13 days before departure typically resulted in a significantly higher average price of $562. Planning ahead can lead to substantial 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 above $251 were typically in the more expensive range. Comparing prices to these historical benchmarks can help you identify a favorable offer.

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 competitive prices, with a median of $153. Over the trailing 270 days, the annual median price for this route was $184. While June had a median price of $155, it was also identified as the most expensive month on 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: $212 - $295

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

Regular prices for flights from Chicago to San Antonio typically range from $212 to $295. The current lowest deal is $234 with Frontier Airlines for travel from Oct 10-Oct 13.

now $234

Low $212

High $295

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

United Airlines

Last-minute flights going from Chicago to San Antonio

Mon, Jul 27

⌛ Last-Minute

ORD - San Antonio

Chicago (ORD) - San Antonio (SAT)

Frontier Airlines

$443

$352

One-way

Tue, Jul 28

⌛ Last-Minute

ORD - San Antonio

Chicago (ORD) - San Antonio (SAT)

Frontier Airlines

$447

$341

One-way

Tue, Jul 28

⌛ Last-Minute

ORD - San Antonio

Chicago (ORD) - San Antonio (SAT)

Frontier Airlines

$442

$351

One-way

Sat, Aug 1

⌛ Last-Minute

ORD - San Antonio

Chicago (ORD) - San Antonio (SAT)

Frontier Airlines

$488

$325

One-way

Sat, Aug 1

⌛ Last-Minute

ORD - San Antonio

Chicago (ORD) - San Antonio (SAT)

Frontier Airlines

$438

$325

One-way

Sat, Aug 1

⌛ Last-Minute

ORD - San Antonio

Chicago (ORD) - San Antonio (SAT)

Frontier Airlines

$491

$341

One-way

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

4 nights

Aug 1 - Aug 5

$488 → $325

33%

2 nights

Aug 1 - Aug 3

$502 → $351

30%

3 nights

Aug 1 - Aug 4

$491 → $341

31%

13 nights

Dec 15 - Dec 28

$492 → $357

27%

Popular Airports to fly from Chicago to San Antonio