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, approximately 14% of flights on this route have been direct. For connecting flights, the median number of stopovers observed was 2. Travelers prioritizing a direct journey should be aware of this historical distribution.

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

A direct flight from San Antonio to Chicago typically takes about 3 hours and 0 minutes. For flights with one stop, the median travel time extends to approximately 8 hours and 16 minutes. The distance covered on this route is 1668 kilometers. Travelers should factor in these durations when planning their journey.

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 indicates that travelers may often find opportunities for more affordable fares. Keeping an eye on price trends can be beneficial for securing a good deal on this 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 1 day ago

451 airlines compared

80%+ AI score for best value

Fares are subject to change and may not be available for all dates. (Data last updated Aug 18, 2026.)

Today’s best flight deals from San Antonio to Chicago

Explore current cheapest deals departing from San Antonio to Chicago

2026-09-10 – 2026-09-14
SAT - Chicago
76% AI deal score
$273
$173
Round trip
2026-09-22 – 2026-09-26
SAT - Chicago
76% AI deal score
$269
$173
Round trip
2026-09-12 – 2026-09-16
SAT - Chicago
76% AI deal score
$272
$178
Round trip
2026-09-19 – 2026-09-21
SAT - Chicago
75% AI deal score
$270
$178
Round trip
2026-09-05 – 2026-09-09
SAT - Chicago
76% AI deal score
$277
$178
Round trip
2026-09-16 – 2026-09-22
SAT - Chicago
75% AI deal score
$257
$178
Round trip
2026-09-09 – 2026-09-16
SAT - Chicago
75% AI deal score
$257
$178
Round trip
2026-10-22 – 2026-10-26
SAT - Chicago
74% AI deal score
$256
$178
Round trip
2026-10-14 – 2026-10-19
SAT - Chicago
73% AI deal score
$252
$188
Round trip
2026-09-05 – 2026-09-08
SAT - Chicago
75% AI deal score
$278
$189
Round trip

San Antonio to Chicago: Overview

Insights for flights from San Antonio to Chicago

Only 14% of recent fares from San Antonio to Chicago are non-stop, indicating that most itineraries connect at least once. When connections are involved, the typical number of stopovers is 2. This means you will likely encounter at least one layover on your journey, and often two, when searching for flights on this route.

For travelers looking for cheap flights from San Antonio to Chicago, fares typically range from $390–$819, with a median price of $549. Right now, current fares are significantly above the typical level, and 0% of recent fares were classified as a good price, suggesting higher prices at present.

The cheapest time to fly from San Antonio to Chicago is typically in January, with a median fare of $229. Other affordable months include March, where the median fare is $273, and April, with a median fare of $308. These months offer the lowest median prices for this route.

A typical journey from San Antonio to Chicago takes about 3h 0m including connections. While direct flights from San Antonio to Chicago also have a median flight time of 3h 0m, connecting itineraries can extend the total travel time significantly. Given that most itineraries involve connections, this 3-hour duration represents the overall median for the route.

How much is a round trip from San Antonio to Chicago

Regular price: $217 - $302

Prices are currently below the regular range.

The regular price range for flights from San Antonio to Chicago is typically between $217 and $302. The current lowest deal is $173 with Frontier Airlines for travel from Sep 10-Sep 14.

now $173

Low $217

High $302

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

American Airlines

Last-minute flights going from San Antonio to Chicago

Tue, Aug 18

⌛ Last-Minute

SAT - Chicago

San Antonio (SAT) - Chicago (ORD)

Frontier Airlines

$430

$347

One-way

Wed, Aug 19

⌛ Last-Minute

SAT - Chicago

San Antonio (SAT) - Chicago (ORD)

Frontier Airlines

$454

$346

One-way

Wed, Aug 19

⌛ Last-Minute

SAT - Chicago

San Antonio (SAT) - Chicago (ORD)

Frontier Airlines

$414

$347

One-way

Wed, Aug 19

⌛ Last-Minute

SAT - Chicago

San Antonio (SAT) - Chicago (ORD)

Frontier Airlines

$525

$352

One-way

Thu, Aug 20

⌛ Last-Minute

SAT - Chicago

San Antonio (SAT) - Chicago (ORD)

Frontier Airlines

$414

$346

One-way

Fri, Aug 21

⌛ Last-Minute

SAT - Chicago

San Antonio (SAT) - Chicago (ORD)

Frontier Airlines

$525

$340

One-way

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

2 nights

Aug 19 - Aug 21

$546 → $352

36%

1 night

Aug 22 - Aug 23

$532 → $340

36%

2 nights

Aug 21 - Aug 23

$525 → $340

35%

4 nights

Aug 21 - Aug 25

$510 → $346

32%

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 from San Antonio to Chicago are above the typical level at $173.

📅 Best time to fly

January is historically the cheapest month to fly.

Historically, January is the cheapest month to fly from San Antonio to Chicago, with a median price of $229.

⏱️ Flight duration

Direct flights take 3h 0m.

Direct flights from San Antonio to Chicago typically take 3h 0m, while connecting flights average 22h 48m.

✈️ Airlines & availability

14% of recent flights are direct.

14% of recent flights from San Antonio to Chicago are direct, with connecting flights having 2 stopovers.

🏆 Airline highlight

Frontier Airlines offers a recent deal for $173.

Frontier Airlines recently offered a deal from San Antonio to Chicago for $173.

🎯 Booking tip

Deals appear frequently on this route.

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

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 from San Antonio.

📍 ~25 km from Chicago city center (reachable by car, train, and bus).

💸 Flights from ~$240

Airports nearby Chicago used as alternative

General Mitchell International (MKE)

General Mitchell International Airport is a major international airport with significant carrier presence and direct flight options.

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

💸 Flights from ~$334

Business & First Class Flight Deals to Chicago

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San Antonio to Chicago: Overview

Insights for flights from San Antonio to Chicago

How much is a round trip from San Antonio to Chicago

Regular price: $217 - $302

Prices are currently below the regular range.

The regular price range for flights from San Antonio to Chicago is typically between $217 and $302. The current lowest deal is $173 with Frontier Airlines for travel from Sep 10-Sep 14.

now $173

Low $217

High $302

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

American Airlines

Last-minute flights going from San Antonio to Chicago

Tue, Aug 18

⌛ Last-Minute

SAT - Chicago

San Antonio (SAT) - Chicago (ORD)

Frontier Airlines

$430

$347

One-way

Wed, Aug 19

⌛ Last-Minute

SAT - Chicago

San Antonio (SAT) - Chicago (ORD)

Frontier Airlines

$454

$346

One-way

Wed, Aug 19

⌛ Last-Minute

SAT - Chicago

San Antonio (SAT) - Chicago (ORD)

Frontier Airlines

$414

$347

One-way

Wed, Aug 19

⌛ Last-Minute

SAT - Chicago

San Antonio (SAT) - Chicago (ORD)

Frontier Airlines

$525

$352

One-way

Thu, Aug 20

⌛ Last-Minute

SAT - Chicago

San Antonio (SAT) - Chicago (ORD)

Frontier Airlines

$414

$346

One-way

Fri, Aug 21

⌛ Last-Minute

SAT - Chicago

San Antonio (SAT) - Chicago (ORD)

Frontier Airlines

$525

$340

One-way

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

2 nights

Aug 19 - Aug 21

$546 → $352

36%

1 night

Aug 22 - Aug 23

$532 → $340

36%

2 nights

Aug 21 - Aug 23

$525 → $340

35%

4 nights

Aug 21 - Aug 25

$510 → $346

32%

Popular Airports to fly from San Antonio to Chicago