To San Antonio

Cheap Flights from Chicago to San Antonio

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

Prices updated 24 days ago

486,190 searches this week

171 airlines compared

80%+ AI score for best value

Fares are subject to change and may not be available for all dates. (Data last updated May 29, 2026.)

Today’s best flight deals from Chicago to San Antonio

Explore current cheapest deals departing from Chicago to San Antonio

Round trip

Sort by: Cheapest

August 4 - August 11

Cheapest

Best

ORD - San Antonio

$287

$210

Round trip

August 11 - August 25

ORD - San Antonio

$260

$211

Round trip

August 4 - August 8

ORD - San Antonio

$307

$229

Round trip

September 3 - September 8

ORD - San Antonio

$274

$229

Round trip

September 5 - September 8

ORD - San Antonio

$278

$229

Round trip

July 7 - July 8

Best

Earliest

ORD - San Antonio

$309

$230

Round trip

July 21 - July 25

ORD - San Antonio

$296

$239

Round trip

August 6 - August 11

ORD - San Antonio

$299

$240

Round trip

August 4 - August 9

ORD - San Antonio

$298

$240

Round trip

September 6 - September 8

ORD - San Antonio

$281

$240

Round trip

Unlock all 500+ flight deals to San Antonio and get alerts when great deals appear

Route Intelligence — 486,190 Searches this Week

Insights for flights from Chicago to San Antonio

For cheap flights from Chicago to San Antonio, a meaningful share are non-stop, while the rest connect once. Specifically, 50.2% of recent fares are for direct flights from Chicago to San Antonio. When itineraries do include connections, they typically involve 4 stopovers, which can significantly extend travel time.

Right now, fares to San Antonio from Chicago are typically $155–$760, with a median of $238. Current fares are below the typical level for this route. Only 4% of recent fares were classified as a good price, indicating that finding exceptional deals might require flexibility or advance planning. New deals show up several times a week, so monitoring prices can be beneficial.

When is the cheapest time to fly from Chicago to San Antonio? The data indicates that the cheapest months to fly are July, with a median fare of $149, followed by August at $153, and June at $155. These months offer more favorable pricing compared to the overall median for the route.

How long is the flight from Chicago to San Antonio? A typical journey from Chicago to San Antonio takes about 6h 1m, including connections. This duration accounts for both direct flights and those with stopovers, reflecting the overall travel experience on this medium-haul route. The total distance covered is 1677 km, classifying it as a medium-haul journey.

How much is a round trip from Chicago to San Antonio

Regular price: $228 - $330

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

The regular price range for flights from Chicago to San Antonio is between $228 and $330. The current lowest deal is $210 with Frontier Airlines for travel from August 4 to August 11.

now $210

Low $228

High $330

The cheapest time to fly from Chicago to San Antonio

The cheapest month to fly from Chicago to San Antonio is July, with a median price of $149. The most expensive month is April, with a median price of $768. Prices are generally lower from January to December.

July

Cheapest

Flights from $149

April

Most Expensive

Flights from $768

Jan

Feb

Mar

Apr

May

Jun

Jul

Aug

Sep

Oct

Nov

Dec

Direct flights from Chicago to San Antonio

American Airlines

Last-minute flights going from Chicago to San Antonio

Thu, Jun 18

⌛ Last-Minute

ORD - San Antonio

Chicago (ORD) - San Antonio (SAT)

Frontier Airlines

$442

$342

One-way

Fri, Jun 19

⌛ Last-Minute

ORD - San Antonio

Chicago (ORD) - San Antonio (SAT)

Frontier Airlines

$439

$342

One-way

Fri, Jun 19

⌛ Last-Minute

ORD - San Antonio

Chicago (ORD) - San Antonio (SAT)

Frontier Airlines

$443

$368

One-way

Sat, Jun 20

⌛ Last-Minute

ORD - San Antonio

Chicago (ORD) - San Antonio (SAT)

Frontier Airlines

$444

$348

One-way

Wed, Jul 1

⌛ Last-Minute

ORD - San Antonio

Chicago (ORD) - San Antonio (SAT)

Frontier Airlines

$304

$271

One-way

Wed, Jul 1

⌛ Last-Minute

ORD - San Antonio

Chicago (ORD) - San Antonio (SAT)

Frontier Airlines

$304

$271

One-way

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

3 nights

Jun 18 - Jun 21

$442 → $342

23%

3 nights

Jun 19 - Jun 22

$439 → $342

22%

1 night

Jun 20 - Jun 21

$444 → $348

22%

1 night

Jul 7 - Jul 8

$309 → $230

26%

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 at $210.

📅 Best time to fly

July is historically the cheapest month to fly

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

⏱️ Flight duration

Average flight time is 6h 1m

The typical flight duration from Chicago to San Antonio is 6 hours and 1 minute.

✈️ Airlines & availability

50.2% of deals are for direct flights

Historically, 50.2% of flight deals from Chicago to San Antonio are for direct flights.

🏆 Airline highlight

American Airlines offers direct flights

American Airlines is an airline that has historically offered direct flights on this route.

🎯 Booking tip

Deals appear regularly

Deals for flights from Chicago to San Antonio appear regularly, about 0.37 times per day.

Chicago main airports to depart from

O Hare International (ORD)

Cheapest

O'Hare International Airport is a major hub for flights from Chicago to San Antonio.

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

💸 Flights from ~$210

Chicago Midway International (MDW)

Chicago Midway International Airport offers another convenient option for flights to San Antonio.

📍 ~15 km from Chicago city center (reachable by car or train)

💸 Flights from ~$258

Chicago Rockford International (RFD)

Chicago Rockford International Airport provides an alternative departure point for your trip to San Antonio.

📍 ~120 km from Chicago city center (reachable by car)

💸 Flights from ~$366

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.

📍 ~15 km from city center (reachable by car)

💸 Flights from ~$210

Airports nearby San Antonio used as alternative

Austin–Bergstrom International (AUS)

Cheapest

Consider Austin–Bergstrom International for significantly more direct flight options to the San Antonio area.

📍 ~120 km from San Antonio (reachable by car)

💸 Flights from ~$169

Corpus Christi International (CRP)

Corpus Christi International provides additional options for travelers heading toward the Gulf Coast.

📍 ~170 km from San Antonio (reachable by car)

💸 Flights from ~$332

Laredo International (LRD)

Laredo International offers reliable domestic service within the US with a straightforward drive south.

📍 ~230 km from San Antonio (reachable by car)

💸 Flights from ~$251

Killeen–Fort Hood Regional (GRK)

Killeen–Fort Hood Regional is an alternative for travelers on the north side of San Antonio.

📍 ~120 km from San Antonio (reachable by car)

💸 Flights from ~$281

Victoria Regional (VCT)

Victoria Regional is geographically closer than some other regional options, but has extremely limited service.

📍 ~160 km from San Antonio (reachable by car)

💸 Flights from ~$246

Business & First Class Flight Deals to San Antonio

San Antonio, United States

39% AI deal score

$1,957

From ORD

Elite

Jun 20

San Antonio, United States

39% AI deal score

$13,925

Frequently Asked Questions About Flights to San Antonio

Historically, booking flights from Chicago to San Antonio 60 or more days in advance has typically yielded the lowest prices, with an average price of $254. For comparison, booking 14-27 days out saw an average price of $496, while booking 7-13 days before departure resulted in an average price of $562. Planning ahead by at least two months generally offers the most significant savings for this route.

Across the trailing quarter, a flight from Chicago to San Antonio is considered a good deal if it is priced at or below $155. The median price for this route historically has been $238. Prices can vary, with 75% of deals observed being $760 or less. Travelers aiming for the best value should target prices around the $155 mark.

Historically, July has been the cheapest month to fly from Chicago to San Antonio, with a median price of $149. August also offers good value, with a median price of $153. June is another favorable month, showing a median price of $155. These months are typically less expensive than the annual median price of $238 for this route.

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