Can I fly direct from San Antonio to Chicago?

Direct flights from San Antonio to Chicago are available, though they represent a smaller portion of the total routes. Historically, about 14% of flights on this route were direct in the trailing 90 days. For flights with connections, travelers typically encountered 2 stopovers. This indicates that while direct options exist, connecting flights are more common.

What's the flight time from San Antonio to Chicago?

The typical direct flight from San Antonio to Chicago has a median duration of 3 hours and 0 minutes, covering a distance of 1668 kilometers. For flights with one stop, the median travel time increases significantly to 8 hours and 16 minutes. Travelers should account for these differences when planning their journeys. The presence of stopovers can more than double the total travel time.

How often do San Antonio to Chicago flight prices drop?

Historically, flight prices for the San Antonio to Chicago route have shown frequent drops. This suggests that opportunities for finding deals arise regularly. Travelers monitoring this route over a 30-day period can often find favorable price changes. The frequent classification indicates that price fluctuations are a common occurrence for this particular route.

Flights From San Antonio

To Chicago

Cheap Flights from San Antonio to Chicago

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

Deals from

San Antonio

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

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 San Antonio to Chicago

Explore current cheapest deals departing from San Antonio to Chicago

2026-10-01 – 2026-10-17
SAT - Chicago
43% AI deal score
$214
$243
Round trip
2026-08-19 – 2026-08-25
SAT - Chicago
48% AI deal score
$269
$247
Round trip
2026-08-19 – 2026-08-24
SAT - Chicago
49% AI deal score
$278
$247
Round trip
2026-08-24 – 2026-08-31
SAT - Chicago
48% AI deal score
$266
$247
Round trip
2026-08-19 – 2026-08-22
SAT - Chicago
50% AI deal score
$286
$247
Round trip
2026-09-28 – 2026-09-30
SAT - Chicago
48% AI deal score
$272
$247
Round trip
2026-09-17 – 2026-09-28
SAT - Chicago
43% AI deal score
$226
$247
Round trip
2026-10-03 – 2026-10-05
SAT - Chicago
46% AI deal score
$256
$247
Round trip
2026-11-03 – 2026-11-07
SAT - Chicago
68% AI deal score
$338
$247
Round trip
2026-11-10 – 2026-11-14
SAT - Chicago
73% AI deal score
$357
$247
Round trip

San Antonio to Chicago: Overview

Insights for flights from San Antonio to Chicago

Most itineraries for flights from San Antonio to Chicago connect at least once, with only 14% of recent fares being non-stop. For connecting itineraries, the typical number of stopovers is 2.

Right now, fares for flights from San Antonio to Chicago are typically $390–$819, with a median of $549. Current fares are above the typical level, and 0% of recent fares were classified as a good price. New deals appear almost daily, suggesting frequent price fluctuations.

When looking for cheap flights from San Antonio to Chicago, the cheapest months to fly are typically January, with a median fare of $229, followed by March at $273, and April at $308.

A typical journey from San Antonio to Chicago takes about 3h 0m. This median duration includes both direct and connecting itineraries. For non-stop flights, the median time is 3h 0m, while connecting flights have a significantly longer median duration of 22h 48m.

The distance between San Antonio and Chicago is 1668 kilometers, classifying this as a medium-haul route.

How much is a round trip from San Antonio to Chicago

Regular price: $196 - $290

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

The regular price range for flights from San Antonio to Chicago is typically between $196 and $290. The current lowest deal is $285 with Frontier Airlines, for travel from Sep 14-Sep 23.

now $285

Low $196

High $290

The cheapest time to fly from San Antonio to Chicago

The cheapest month to fly from San Antonio to Chicago is December, with a median price of $323. The most expensive month is July, with a median price of $714. Prices are generally lower from April to December.

December

Cheapest

Flights from $323

July

Most Expensive

Flights from $714

Jan

Feb

Apr

May

Jun

Jul

Aug

Sep

Oct

Nov

Dec

Direct flights from San Antonio to Chicago

United Airlines

Last-minute flights going from San Antonio to Chicago

Wed, Aug 12

⌛ Last-Minute

SAT - Chicago

San Antonio (SAT) - Chicago (ORD)

$296

$327

One-way

Thu, Aug 13

⌛ Last-Minute

SAT - Chicago

San Antonio (SAT) - Chicago (MDW)

$195

$297

One-way

Thu, Aug 13

⌛ Last-Minute

SAT - Chicago

San Antonio (SAT) - Chicago (MDW)

$306

$317

One-way

Sat, Aug 15

⌛ Last-Minute

SAT - Chicago

San Antonio (SAT) - Chicago (ORD)

$180

$297

One-way

Sat, Aug 15

⌛ Last-Minute

SAT - Chicago

San Antonio (SAT) - Chicago (ORD)

$292

$327

One-way

Sat, Aug 15

⌛ Last-Minute

SAT - Chicago

San Antonio (SAT) - Chicago (ORD)

$292

$327

One-way

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

3 nights

Nov 12 - Nov 15

$366 → $292

20%

4 nights

Nov 12 - Nov 16

$366 → $296

19%

5 nights

Nov 10 - Nov 15

$359 → $292

19%

4 nights

Dec 17 - Dec 21

$375 → $317

15%

Popular Airports to fly from San Antonio to Chicago

San Antonio - Chicago route insights

💸 Price insights

Recent fares are above the typical level

Recent fares for San Antonio to Chicago are above the typical level of $549.

📅 Best time to fly

Fly in December for the best prices

Historically, December offers the lowest median price at $323 for this route.

⏱️ Flight duration

Direct flights take 3h 0m

The median flight duration is 3h 0m nonstop, or 22h 48m with connections.

✈️ Airlines & availability

Connecting flights are dominant

Only 14% of recent flights are direct, with connecting flights typically having 2 stopovers.

🏆 Airline highlight

United Airlines offers direct flights

United Airlines is one of the carriers offering direct flights on the San Antonio to Chicago route.

🎯 Booking tip

Deals appear frequently

Deals for flights from San Antonio to Chicago appear frequently, typically within 30 days.

San Antonio main airports to depart from

San Antonio International (SAT)

Cheapest

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

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

💸 Flights from ~$231

Chicago main airports to arrive at

O Hare International (ORD)

Cheapest

O'Hare International Airport is a major hub for flights to Chicago, offering many connections.

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

💸 Flights from ~$210

Airports nearby Chicago used as alternative

General Mitchell International (MKE)

General Mitchell International offers significant carrier presence and direct flight options for Chicago travelers.

📍 ~135 km from Chicago (reachable by train or car)

💸 Flights from ~$275

Business & First Class Flight Deals to Chicago

78% AI deal score

$986

$707

Save $279

Frequently Asked Questions About Flights to Chicago

Historically, booking flights from San Antonio to Chicago 7-13 days in advance has yielded the lowest average prices. During the trailing 90 days, the average price for this booking window was $470. In contrast, booking 0-6 days out typically saw prices around $618, while booking 60+ days in advance averaged $625. This suggests that last-minute deals can be found, but planning slightly ahead within this specific window is often more economical.

Across the trailing quarter, a flight from San Antonio to Chicago for $390 or less was considered a good price. The median price for this route over the same 90-day period was $549. Prices typically ranged up to $819 for the higher end of fares. Travelers aiming for a budget-friendly trip should target fares around the $390 mark.

Historically, January has been the cheapest month to fly from San Antonio to Chicago, with a median price of $229. March and April also offered relatively lower median prices at $273 and $308, respectively. The annual median price for this route across a 270-day window was $549. Travelers seeking the most economical options should consider these months for their journeys.

Related routes

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Flights to Chicago from other cities

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San Antonio to Chicago: Overview

Insights for flights from San Antonio to Chicago

Most itineraries for flights from San Antonio to Chicago connect at least once, with only 14% of recent fares being non-stop. For connecting itineraries, the typical number of stopovers is 2.

The distance between San Antonio and Chicago is 1668 kilometers, classifying this as a medium-haul route.

How much is a round trip from San Antonio to Chicago

Regular price: $196 - $290

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

The regular price range for flights from San Antonio to Chicago is typically between $196 and $290. The current lowest deal is $285 with Frontier Airlines, for travel from Sep 14-Sep 23.

now $285

Low $196

High $290

The cheapest time to fly from San Antonio to Chicago

December

Cheapest

Flights from $323

July

Most Expensive

Flights from $714

Jan

Feb

Apr

May

Jun

Jul

Aug

Sep

Oct

Nov

Dec

Direct flights from San Antonio to Chicago

United Airlines

Last-minute flights going from San Antonio to Chicago

Wed, Aug 12

⌛ Last-Minute

SAT - Chicago

San Antonio (SAT) - Chicago (ORD)

$296

$327

One-way

Thu, Aug 13

⌛ Last-Minute

SAT - Chicago

San Antonio (SAT) - Chicago (MDW)

$195

$297

One-way

Thu, Aug 13

⌛ Last-Minute

SAT - Chicago

San Antonio (SAT) - Chicago (MDW)

$306

$317

One-way

Sat, Aug 15

⌛ Last-Minute

SAT - Chicago

San Antonio (SAT) - Chicago (ORD)

$180

$297

One-way

Sat, Aug 15

⌛ Last-Minute

SAT - Chicago

San Antonio (SAT) - Chicago (ORD)

$292

$327

One-way

Sat, Aug 15

⌛ Last-Minute

SAT - Chicago

San Antonio (SAT) - Chicago (ORD)

$292

$327

One-way

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

3 nights

Nov 12 - Nov 15

$366 → $292

20%

4 nights

Nov 12 - Nov 16

$366 → $296

19%

5 nights

Nov 10 - Nov 15

$359 → $292

19%

4 nights

Dec 17 - Dec 21

$375 → $317

15%

Popular Airports to fly from San Antonio to Chicago