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 have been direct. For connecting flights, the median number of stopovers observed across the trailing 90 days was 2. Travelers prioritizing direct routes may find fewer options compared to those willing to make connections.

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

A direct flight from San Antonio to Chicago typically has a duration of 3 hours and 0 minutes. For flights with one stop, the median travel time extends to approximately 8 hours and 16 minutes. This difference highlights the convenience of direct options for travelers. The total distance covered on this route is 1668 kilometers.

How often do San Antonio to Chicago flight prices drop?

Flight prices for the San Antonio to Chicago route are classified as experiencing frequent drops. This indicates that travelers historically have regular opportunities to find reduced fares. Price fluctuations are a common characteristic of this route, offering potential savings for those monitoring prices.

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

462 airlines compared

80%+ AI score for best value

Fares are subject to change and may not be available for all dates. (Data last updated Sep 15, 2026.)

Today’s best flight deals from San Antonio to Chicago

Explore current cheapest deals departing from San Antonio to Chicago

2026-10-21 – 2026-10-28
SAT - Chicago
48% AI deal score
$241
$222
Round trip
2026-11-03 – 2026-11-18
SAT - Chicago
65% AI deal score
$262
$224
Round trip
2026-11-06 – 2026-11-10
SAT - Chicago
73% AI deal score
$319
$226
Round trip
2026-10-20 – 2026-10-28
SAT - Chicago
45% AI deal score
$228
$235
Round trip
2026-10-20 – 2026-11-18
SAT - Chicago
43% AI deal score
$201
$235
Round trip
2026-10-20 – 2026-11-04
SAT - Chicago
44% AI deal score
$205
$235
Round trip
2026-10-13 – 2026-10-28
SAT - Chicago
44% AI deal score
$206
$235
Round trip
2026-10-13 – 2026-11-04
SAT - Chicago
44% AI deal score
$202
$235
Round trip
2026-10-13 – 2026-10-20
SAT - Chicago
46% AI deal score
$241
$235
Round trip
2026-10-13 – 2026-10-21
SAT - Chicago
45% AI deal score
$229
$235
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 flights, the typical number of connections is 2. This means you'll usually find options that include at least one stop on your journey.

When is the cheapest time to fly from San Antonio to Chicago? The data indicates that January is the most affordable month, with a median fare of $229. Following closely, March offers a median fare of $273, and April presents a median of $308. These months generally provide more budget-friendly options for your trip.

A typical journey from San Antonio to Chicago takes about 3h 0m, including connections. This median duration accounts for both direct and connecting itineraries. For non-stop flights, the median travel time is also 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. This distance typically involves a flight duration that falls within the medium-haul category, often requiring a few hours in the air.

How much is a round trip from San Antonio to Chicago

Regular price: $171 - $320

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 $171 and $320. The current lowest deal is $224 with Frontier Airlines, for travel from Oct 26-Nov 17.

now $224

Low $171

High $320

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

Mon, Sep 14

⌛ Last-Minute

SAT - Chicago

San Antonio (SAT) - Chicago (ORD)

Frontier Airlines

$426

$349

One-way

Mon, Sep 14

⌛ Last-Minute

SAT - Chicago

San Antonio (SAT) - Chicago (ORD)

Frontier Airlines

$485

$380

One-way

Tue, Sep 15

⌛ Last-Minute

SAT - Chicago

San Antonio (SAT) - Chicago (ORD)

Frontier Airlines

$476

$350

One-way

Tue, Sep 15

⌛ Last-Minute

SAT - Chicago

San Antonio (SAT) - Chicago (ORD)

Frontier Airlines

$487

$380

One-way

Tue, Sep 15

⌛ Last-Minute

SAT - Chicago

San Antonio (SAT) - Chicago (ORD)

Frontier Airlines

$485

$380

One-way

Wed, Sep 16

⌛ Last-Minute

SAT - Chicago

San Antonio (SAT) - Chicago (ORD)

Frontier Airlines

$410

$344

One-way

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

3 nights

Sep 17 - Sep 20

$461 → $327

29%

4 nights

Sep 15 - Sep 19

$476 → $350

27%

1 night

Sep 16 - Sep 17

$468 → $359

23%

1 night

Sep 15 - Sep 16

$487 → $380

22%

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 for this route.

📅 Best time to fly

January offers the lowest median prices.

Historically, January, March, and April show the lowest median prices for this route.

⏱️ Flight duration

Direct flights take 3h 0m.

Direct flights typically take 3h 0m, while connecting flights average 22h 48m.

✈️ Airlines & availability

Connecting flights are dominant.

Only 14% of recent flights from San Antonio to Chicago are direct.

🏆 Airline highlight

Frontier Airlines offers a recent deal.

A recent deal with Frontier Airlines was found for $224.

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

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

💸 Flights from ~$365

Chicago main airports to arrive at

O Hare International (ORD)

Cheapest

O'Hare International Airport is a major hub, offering extensive connections for your trip to Chicago.

📍 ~25 km from Chicago (reachable by car, train, or bus).

💸 Flights from ~$242

Airports nearby Chicago used as alternative

General Mitchell International (MKE)

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

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

💸 Flights from ~$277

Business & First Class Flight Deals to Chicago

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

Elite

Best Elite deals to Chicago

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

From SAT

Elite

Oct 30

Chicago, United States

83% AI deal score

$1,413

$727

Save $686

United Airlines

Business Class

From SAT

Elite

Dec 22

Chicago, United States

81% AI deal score

$1,434

$828

Save $606

United Airlines

Business Class

From SAT

Elite

Sep 23

Chicago, United States

78% AI deal score

$1,652

$945

Save $707

From SAT

Elite

Dec 15

Chicago, United States

77% AI deal score

$936

$688

Save $248

United Airlines

Business Class

From SAT

Elite

Sep 22

Chicago, United States

77% AI deal score

$1,556

$982

Save $574

From SAT

Elite

Sep 15

Chicago, United States

77% AI deal score

$1,725

$985

Save $740

From SAT

Elite

Sep 22

Chicago, United States

77% AI deal score

$1,625

$985

Save $640

From SAT

Elite

Sep 14

Chicago, United States

77% AI deal score

$1,755

$1,001

Save $754

From SAT

Elite

Sep 15

Chicago, United States

77% AI deal score

$1,755

$1,013

Save $742

From SAT

Elite

Dec 24

Chicago, United States

76% AI deal score

$925

$708

Save $217

United Airlines

Business Class

From SAT

Elite

Oct 20

Chicago, United States

75% AI deal score

$1,248

$897

Save $351

From SAT

Elite

Sep 17

Chicago, United States

75% AI deal score

$1,661

$1,029

Save $632

Frequently Asked Questions About Flights to Chicago

Historically, the optimal booking window for flights from San Antonio to Chicago is typically 7-13 days prior to departure. During this period, the average price observed was around $470. Booking too far in advance, such as 60+ days out, or too close to departure, like 0-6 days before, often results in higher average prices, reaching approximately $625 and $618 respectively. Therefore, travelers generally find better value by planning their purchase within this specific timeframe.

Across the trailing quarter, a flight from San Antonio to Chicago is considered a good deal when priced at or below $390. The median price for this route over the same period was $549. Prices can vary, with 75% of fares historically observed at $819 or less. Aiming for a fare under $390 typically represents a significant saving on this route.

Historically, the cheapest months to fly from San Antonio to Chicago include January, with a median price of $229, and March, with a median of $273. April also shows favorable pricing, with a median of $308. These months typically offer prices significantly lower than the annual median of $549 for this route. Travelers looking for the most economical options should consider these periods.

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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

How much is a round trip from San Antonio to Chicago

Regular price: $171 - $320

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 $171 and $320. The current lowest deal is $224 with Frontier Airlines, for travel from Oct 26-Nov 17.

now $224

Low $171

High $320

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

Mon, Sep 14

⌛ Last-Minute

SAT - Chicago

San Antonio (SAT) - Chicago (ORD)

Frontier Airlines

$426

$349

One-way

Mon, Sep 14

⌛ Last-Minute

SAT - Chicago

San Antonio (SAT) - Chicago (ORD)

Frontier Airlines

$485

$380

One-way

Tue, Sep 15

⌛ Last-Minute

SAT - Chicago

San Antonio (SAT) - Chicago (ORD)

Frontier Airlines

$476

$350

One-way

Tue, Sep 15

⌛ Last-Minute

SAT - Chicago

San Antonio (SAT) - Chicago (ORD)

Frontier Airlines

$487

$380

One-way

Tue, Sep 15

⌛ Last-Minute

SAT - Chicago

San Antonio (SAT) - Chicago (ORD)

Frontier Airlines

$485

$380

One-way

Wed, Sep 16

⌛ Last-Minute

SAT - Chicago

San Antonio (SAT) - Chicago (ORD)

Frontier Airlines

$410

$344

One-way

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

3 nights

Sep 17 - Sep 20

$461 → $327

29%

4 nights

Sep 15 - Sep 19

$476 → $350

27%

1 night

Sep 16 - Sep 17

$468 → $359

23%

1 night

Sep 15 - Sep 16

$487 → $380

22%

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 for this route.

📅 Best time to fly

January offers the lowest median prices.

Historically, January, March, and April show the lowest median prices for this route.

⏱️ Flight duration

Direct flights take 3h 0m.

Direct flights typically take 3h 0m, while connecting flights average 22h 48m.

✈️ Airlines & availability

Connecting flights are dominant.

Only 14% of recent flights from San Antonio to Chicago are direct.

🏆 Airline highlight

Frontier Airlines offers a recent deal.

A recent deal with Frontier Airlines was found for $224.

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

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

💸 Flights from ~$365

Chicago main airports to arrive at

O Hare International (ORD)

Cheapest

O'Hare International Airport is a major hub, offering extensive connections for your trip to Chicago.

📍 ~25 km from Chicago (reachable by car, train, or bus).

💸 Flights from ~$242

Airports nearby Chicago used as alternative

General Mitchell International (MKE)

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

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

💸 Flights from ~$277

Business & First Class Flight Deals to Chicago

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

Elite

Best Elite deals to Chicago

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

From SAT

Elite

Oct 30

Chicago, United States

83% AI deal score

$1,413

$727

Save $686

United Airlines

Business Class

From SAT

Elite

Dec 22

Chicago, United States

81% AI deal score

$1,434

$828

Save $606

United Airlines

Business Class

From SAT

Elite

Sep 23

Chicago, United States

78% AI deal score

$1,652

$945

Save $707

From SAT

Elite

Dec 15

Chicago, United States

77% AI deal score

$936

$688

Save $248

United Airlines

Business Class

From SAT

Elite

Sep 22

Chicago, United States

77% AI deal score

$1,556

$982

Save $574

From SAT

Elite

Sep 15

Chicago, United States

77% AI deal score

$1,725

$985

Save $740

From SAT

Elite

Sep 22

Chicago, United States

77% AI deal score

$1,625

$985

Save $640

From SAT

Elite

Sep 14

Chicago, United States

77% AI deal score

$1,755

$1,001

Save $754

From SAT

Elite

Sep 15

Chicago, United States

77% AI deal score

$1,755

$1,013

Save $742

From SAT

Elite

Dec 24

Chicago, United States

76% AI deal score

$925

$708

Save $217

United Airlines

Business Class

From SAT

Elite

Oct 20

Chicago, United States

75% AI deal score

$1,248

$897

Save $351

From SAT

Elite

Sep 17

Chicago, United States

75% AI deal score

$1,661

$1,029

Save $632

Frequently Asked Questions About Flights to Chicago

Cheap Flights from San Antonio to Chicago

Today’s best flight deals from San Antonio to Chicago

San Antonio to Chicago: Overview

Insights for flights from San Antonio to Chicago

How much is a round trip from San Antonio to Chicago

The cheapest time to fly from San Antonio to Chicago

Direct flights from San Antonio to Chicago

Last-minute flights going from San Antonio to Chicago

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

Popular Airports to fly from San Antonio to Chicago

San Antonio - Chicago route insights

Recent fares are above the typical level.

January offers the lowest median prices.

Direct flights take 3h 0m.

Connecting flights are dominant.

Frontier Airlines offers a recent deal.

Deals appear frequently.

San Antonio main airports to depart from

Chicago main airports to arrive at

Airports nearby Chicago used as alternative

Business & First Class Flight Deals to Chicago

Best Elite deals to Chicago

Oct 30

Dec 22

Sep 23

Dec 15

Sep 22

Sep 15

Sep 22

Sep 14

Sep 15

Dec 24

Oct 20

Sep 17

Frequently Asked Questions About Flights to Chicago

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

What's a cheap fare from San Antonio to Chicago?

When is the cheapest time of year to fly from San Antonio to Chicago?

Can I fly direct from San Antonio to Chicago?

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

How often do San Antonio to Chicago flight prices drop?

Related routes

More routes from San Antonio

Flights to Chicago from other cities

San Antonio to Chicago: Overview

Insights for flights from San Antonio to Chicago

How much is a round trip from San Antonio to Chicago

The cheapest time to fly from San Antonio to Chicago

Direct flights from San Antonio to Chicago

Last-minute flights going from San Antonio to Chicago

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

Popular Airports to fly from San Antonio to Chicago

San Antonio - Chicago route insights

Recent fares are above the typical level.

January offers the lowest median prices.

Direct flights take 3h 0m.

Connecting flights are dominant.

Frontier Airlines offers a recent deal.

Deals appear frequently.

San Antonio main airports to depart from

Chicago main airports to arrive at

Airports nearby Chicago used as alternative

Business & First Class Flight Deals to Chicago

Best Elite deals to Chicago

Oct 30

Dec 22

Sep 23

Dec 15

Sep 22

Sep 15

Sep 22

Sep 14

Sep 15

Dec 24

Oct 20

Sep 17

Frequently Asked Questions About Flights to Chicago

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

What's a cheap fare from San Antonio to Chicago?

When is the cheapest time of year to fly from San Antonio to Chicago?