FlightsFrom 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 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 San Antonio to Chicago

Explore current cheapest deals departing from San Antonio to Chicago

August 18 - August 26

Cheapest

SAT - Chicago

$254

$212

Round trip

August 19 - August 25

Cheapest
Best

SAT - Chicago

$264

$212

Round trip

July 22 - July 29

SAT - Chicago

$257

$230

Round trip

July 8 - July 14

SAT - Chicago

$268

$231

Round trip

July 15 - July 21

SAT - Chicago

$263

$231

Round trip

July 15 - July 22

SAT - Chicago

$263

$231

Round trip

July 7 - July 14

Earliest

SAT - Chicago

$268

$232

Round trip

August 4 - August 25

SAT - Chicago

$144

$234

Round trip

August 19 - August 25

SAT - Chicago

$175

$234

Round trip

August 12 - August 15

SAT - Chicago

$275

$234

Round trip

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

Route Intelligence — 486,190 Searches this Week

Insights for flights from San Antonio to Chicago

Most itineraries for flights from San Antonio to Chicago connect at least once, with only 19.4% of recent fares being non-stop. For those connecting itineraries, the typical number of stopovers is 2.
A typical journey from San Antonio to Chicago takes about 19h 31m, including connections. This duration accounts for the majority of itineraries that involve at least one stopover.
When is the cheapest time to fly from San Antonio to Chicago? The most affordable month to fly is typically January, with a median fare of $229. Other budget-friendly options include March, where the median fare is $273, and April, with a median fare of $308.
Fares for flights from San Antonio to Chicago are typically $361–$674, with a median of $455. Right now, current fares are above the typical level. New deals appear almost daily for this route, but currently, 0% of recent fares are classified as a good price.
The distance between San Antonio and Chicago is 1668 km, classifying this as a medium-haul route.

How much is a round trip from San Antonio to Chicago

Regular price: $208 - $290

Prices are currently within the regular range.

The regular price range for flights from San Antonio to Chicago is $208 to $290. The current lowest deal is $212 with Frontier Airlines, for travel from Aug 18 to Aug 26.

now $212

Low $208

High $290

The cheapest time to fly from San Antonio to Chicago

Flights from San Antonio to Chicago are cheapest in January, with a median price of $229. The most expensive month to fly is February, with a median price of $692. Prices are generally lower from January to December.

January

Cheapest

Flights from $229

February

Most Expensive

Flights from $692

Jan
Feb
Mar
Apr
May
Jun
Jul
Aug
Sep
Oct
Nov
Dec

Direct flights from San Antonio to Chicago

Airline logo

Southwest Airlines

Airline logo

United Airlines

Last-minute flights going from San Antonio to Chicago

Tue, Jun 16

⌛ Last-Minute

SAT - Chicago

Frontier Airlines

San Antonio (SAT) - Chicago (ORD)

Frontier Airlines

$432

$352

One-way

Tue, Jun 16

⌛ Last-Minute

SAT - Chicago

Frontier Airlines

San Antonio (SAT) - Chicago (ORD)

Frontier Airlines

$429

$391

One-way

Wed, Jun 17

⌛ Last-Minute

SAT - Chicago

Frontier Airlines

San Antonio (SAT) - Chicago (ORD)

Frontier Airlines

$432

$391

One-way

Thu, Jun 18

⌛ Last-Minute

SAT - Chicago

Frontier Airlines

San Antonio (SAT) - Chicago (ORD)

Frontier Airlines

$387

$342

One-way

Thu, Jun 18

⌛ Last-Minute

SAT - Chicago

Frontier Airlines

San Antonio (SAT) - Chicago (ORD)

Frontier Airlines

$427

$390

One-way

Thu, Jun 18

⌛ Last-Minute

SAT - Chicago

Frontier Airlines

San Antonio (SAT) - Chicago (ORD)

Frontier Airlines

$434

$391

One-way

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

3 nights

Nov 12 - Nov 15

$384  →  $270

30%

1 night

Jun 20 - Jun 21

$436  →  $342

22%

2 nights

Jun 19 - Jun 21

$434  →  $342

21%

3 nights

Jun 20 - Jun 23

$430  →  $342

20%

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, with a median price of $455.

📅 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

Connecting flights typically take 19h 31m.

Flights from San Antonio to Chicago typically take 19h 31m, with most flights having 2 stopovers.

✈️ Airlines & availability

Connecting flights are dominant on this route.

Only 19.4% of recent deals are for direct flights, making connecting flights dominant.

🏆 Airline highlight

Frontier Airlines offers a recent deal for $212.

A recent deal from Frontier Airlines to Chicago O Hare International Airport was found for $212.

🎯 Booking tip

Deals appear frequently, with over 1 deal per day.

Historically, deals for this route appear frequently, with more than 1 deal per day.

San Antonio main airports to depart from

San Antonio International (SAT)

Cheapest

San Antonio International offers the cheapest flights to Chicago, making it a good value departure option.

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

💸 Flights from ~$212

Chicago main airports to arrive at

O Hare International (ORD)

Cheapest

O'Hare International Airport is a good option for flights from San Antonio to Chicago.

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

💸 Flights from ~$212

Chicago Midway International (MDW)

Chicago Midway International Airport is another choice for your trip from San Antonio to Chicago.

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

💸 Flights from ~$234

Chicago Rockford International (RFD)

Chicago Rockford International Airport serves the Chicago area for flights from San Antonio.

📍 ~110 km from Chicago city center (reachable by car)

💸 Flights from ~$393

Airports nearby Chicago used as alternative

General Mitchell International (MKE)

General Mitchell International offers excellent proximity to Chicago with high-frequency flight options and direct rail access.

📍 ~135 km from Chicago (reachable by rail; travel time can be affected by heavy traffic).

💸 Flights from ~$286

South Bend International (SBN)

South Bend International is geographically the closest alternative to Chicago, with direct commuter rail connections.

📍 ~125 km from Chicago (reachable by rail).

💸 Flights from ~$298

Gerald R. Ford International (GRR)

Gerald R. Ford International is a major regional hub, a good alternative for travelers on Chicago's eastern side.

📍 ~205 km from Chicago (requires a significant drive).

💸 Flights from ~$269

Dane County Regional (MSN)

Cheapest

Dane County Regional is a reliable regional airport, less congested than Chicago or Milwaukee airports.

📍 ~200 km from Chicago.

💸 Flights from ~$231

Fort Wayne International (FWA)

Fort Wayne International offers stable regional service, an alternative for southeastern Chicago suburbs.

📍 ~240 km from Chicago (significant distance).

💸 Flights from ~$294

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

Sep 03

Chicago, United States

84% AI deal score

$1,358

$671

Save $687

From SAT

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Sep 17

Chicago, United States

84% AI deal score

$1,371

$675

Save $696

From SAT

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Jul 06

Chicago, United States

81% AI deal score

$1,698

$887

Save $811

From SAT

Elite

Aug 01

Chicago, United States

79% AI deal score

$1,085

$742

Save $343

From SAT

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Aug 01

Chicago, United States

79% AI deal score

$1,070

$742

Save $328

From SAT

Elite

Aug 26

Chicago, United States

78% AI deal score

$1,004

$715

Save $289

From SAT

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Aug 01

Chicago, United States

78% AI deal score

$1,032

$750

Save $282

From SAT

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Jul 21

Chicago, United States

78% AI deal score

$1,365

$812

Save $553

From SAT

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Jul 06

Chicago, United States

77% AI deal score

$3,640

$2,056

Save $1,584

From SAT

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Aug 05

Chicago, United States

77% AI deal score

$923

$707

Save $216

From SAT

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Aug 04

Chicago, United States

77% AI deal score

$930

$715

Save $215

From SAT

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Oct 11

Chicago, United States

77% AI deal score

$1,291

$858

Save $433

From SAT

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Jun 30

Chicago, United States

76% AI deal score

$866

$711

Save $155

From SAT

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Sep 10

Chicago, United States

76% AI deal score

$1,309

$826

Save $483

From SAT

Elite

Jul 08

Chicago, United States

72% AI deal score

$3,320

$1,946

Save $1,374

From SAT

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Jul 21

Chicago, United States

72% AI deal score

$3,187

$1,952

Save $1,235

From SAT

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Jul 21

Chicago, United States

72% AI deal score

$3,317

$1,952

Save $1,365

From SAT

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Jul 21

Chicago, United States

72% AI deal score

$3,571

$2,026

Save $1,545

From SAT

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Jul 06

Chicago, United States

72% AI deal score

$3,222

$2,030

Save $1,192

From SAT

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Jul 13

Chicago, United States

72% AI deal score

$3,324

$2,030

Save $1,294

From SAT

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Nov 23

Chicago, United States

72% AI deal score

$967

$750

Save $217

From SAT

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Aug 05

Chicago, United States

71% AI deal score

$2,803

$1,951

Save $852

From SAT

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Jul 08

Chicago, United States

71% AI deal score

$3,226

$1,952

Save $1,274

From SAT

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Aug 06

Chicago, United States

71% AI deal score

$2,805

$1,952

Save $853

From SAT

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Aug 10

Chicago, United States

71% AI deal score

$2,816

$1,982

Save $834

From SAT

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Oct 23

Chicago, United States

71% AI deal score

$2,900

$2,001

Save $899

From SAT

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Oct 22

Chicago, United States

71% AI deal score

$2,905

$2,030

Save $875

From SAT

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Oct 23

Chicago, United States

71% AI deal score

$2,964

$2,057

Save $907

From SAT

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Jul 13

Chicago, United States

71% AI deal score

$3,197

$2,121

Save $1,076

From SAT

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Jul 01

Chicago, United States

71% AI deal score

$3,275

$2,193

Save $1,082

From SAT

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Jul 01

Chicago, United States

71% AI deal score

$3,426

$2,271

Save $1,155

From SAT

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Sep 22

Chicago, United States

71% AI deal score

$872

$715

Save $157

From SAT

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Jul 28

Chicago, United States

71% AI deal score

$879

$742

Save $137

From SAT

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Jul 22

Chicago, United States

71% AI deal score

$896

$742

Save $154

From SAT

Elite

Jul 21

Chicago, United States

71% AI deal score

$899

$742

Save $157

From SAT

Elite

Oct 13

Chicago, United States

71% AI deal score

$881

$659

Save $222

From SAT

Elite

Aug 31

Chicago, United States

71% AI deal score

$941

$667

Save $274

From SAT

Elite

Aug 06

Chicago, United States

71% AI deal score

$942

$675

Save $267

From SAT

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Aug 08

Chicago, United States

71% AI deal score

$915

$675

Save $240

From SAT

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Aug 01

Chicago, United States

71% AI deal score

$946

$694

Save $252

From SAT

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Oct 13

Chicago, United States

71% AI deal score

$919

$694

Save $225

From SAT

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Aug 12

Chicago, United States

70% AI deal score

$2,822

$1,956

Save $866

From SAT

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Oct 03

Chicago, United States

70% AI deal score

$2,776

$2,000

Save $776

From SAT

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Oct 03

Chicago, United States

70% AI deal score

$2,776

$2,056

Save $720

From SAT

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Oct 22

Chicago, United States

70% AI deal score

$2,900

$2,086

Save $814

From SAT

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Jun 26

Chicago, United States

70% AI deal score

$3,349

$2,381

Save $968

From SAT

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Sep 24

Chicago, United States

70% AI deal score

$885

$742

Save $143

From SAT

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Jul 24

Chicago, United States

70% AI deal score

$880

$762

Save $118

From SAT

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Sep 25

Chicago, United States

70% AI deal score

$908

$770

Save $138

From SAT

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Oct 29

Chicago, United States

70% AI deal score

$931

$788

Save $143

From SAT

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Jul 08

Chicago, United States

70% AI deal score

$940

$811

Save $129

From SAT

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Jul 06

Chicago, United States

70% AI deal score

$951

$817

Save $134

From SAT

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Jul 15

Chicago, United States

70% AI deal score

$749

$659

Save $90

From SAT

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Jun 27

Chicago, United States

69% AI deal score

$3,199

$2,607

Save $592

From SAT

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Jun 26

Chicago, United States

69% AI deal score

$3,221

$2,660

Save $561

From SAT

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Jul 07

Chicago, United States

69% AI deal score

$923

$811

Save $112

From SAT

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Jul 14

Chicago, United States

69% AI deal score

$730

$659

Save $71

From SAT

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Jul 15

Chicago, United States

69% AI deal score

$730

$659

Save $71

From SAT

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Jul 08

Chicago, United States

69% AI deal score

$728

$659

Save $69

From SAT

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Jul 15

Chicago, United States

69% AI deal score

$749

$667

Save $82

From SAT

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Jul 14

Chicago, United States

68% AI deal score

$804

$742

Save $62

From SAT

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Jul 30

Chicago, United States

68% AI deal score

$894

$815

Save $79

From SAT

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Jun 20

Chicago, United States

68% AI deal score

$926

$846

Save $80

From SAT

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Jul 22

Chicago, United States

68% AI deal score

$730

$665

Save $65

From SAT

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Jul 16

Chicago, United States

67% AI deal score

$820

$777

Save $43

From SAT

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Oct 11

Chicago, United States

67% AI deal score

$850

$788

Save $62

From SAT

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Jul 04

Chicago, United States

67% AI deal score

$873

$815

Save $58

From SAT

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Jul 15

Chicago, United States

67% AI deal score

$893

$848

Save $45

From SAT

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Jul 11

Chicago, United States

67% AI deal score

$909

$848

Save $61

From SAT

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Nov 25

Chicago, United States

67% AI deal score

$1,489

$1,188

Save $301

From SAT

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Jul 22

Chicago, United States

67% AI deal score

$736

$694

Save $42

From SAT

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Jul 22

Chicago, United States

67% AI deal score

$743

$694

Save $49

From SAT

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Jul 15

Chicago, United States

67% AI deal score

$736

$694

Save $42

From SAT

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Jul 28

Chicago, United States

67% AI deal score

$731

$694

Save $37

From SAT

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Jul 21

Chicago, United States

67% AI deal score

$729

$694

Save $35

From SAT

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Nov 21

Chicago, United States

67% AI deal score

$817

$767

Save $50

From SAT

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Jun 26

Chicago, United States

66% AI deal score

$3,559

$3,388

Save $171

From SAT

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Nov 13

Chicago, United States

66% AI deal score

$814

$787

Save $27

From SAT

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Jul 19

Chicago, United States

49% AI deal score

$1,632

$1,498

Save $134

From SAT

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Jul 21

Chicago, United States

49% AI deal score

$743

$694

Save $49

From SAT

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Jul 15

Chicago, United States

48% AI deal score

$1,652

$1,526

Save $126

From SAT

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Jul 25

Chicago, United States

46% AI deal score

$1,648

$1,630

Save $18

From SAT

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Nov 07

Chicago, United States

45% AI deal score

$1,349

From SAT

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Dec 04

Chicago, United States

44% AI deal score

$1,253

From SAT

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Dec 03

Chicago, United States

43% AI deal score

$1,349

From SAT

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Jul 13

Chicago, United States

40% AI deal score

$1,595

From SAT

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Jul 16

Chicago, United States

39% AI deal score

$1,595

From SAT

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Jul 29

Chicago, United States

38% AI deal score

$1,701

From SAT

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Jul 16

Chicago, United States

38% AI deal score

$2,031

From SAT

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Jun 18

Chicago, United States

38% AI deal score

$2,462

From SAT

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Jul 16

Chicago, United States

37% AI deal score

$1,796

From SAT

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Aug 29

Chicago, United States

37% AI deal score

$1,887

From SAT

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Aug 15

Chicago, United States

37% AI deal score

$1,926

From SAT

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Aug 17

Chicago, United States

37% AI deal score

$1,937

From SAT

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Jul 14

Chicago, United States

37% AI deal score

$2,021

From SAT

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Jul 06

Chicago, United States

37% AI deal score

$2,183

From SAT

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Dec 30

Chicago, United States

37% AI deal score

$2,183

From SAT

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Jun 27

Chicago, United States

36% AI deal score

$2,183

From SAT

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Jul 01

Chicago, United States

36% AI deal score

$2,249

From SAT

Elite

Jul 17

Chicago, United States

36% AI deal score

$2,404

Frequently Asked Questions About Flights to Chicago

Historically, the best time to book flights from San Antonio to Chicago is typically 7-13 days before departure. During this booking window, the average price for a flight is around $470. Booking too early, such as 60+ days out, tends to result in higher prices, averaging $625. Similarly, booking within 0-6 days of departure also sees elevated prices, with an average of $618.

Across the trailing quarter, a good price for a flight from San Antonio to Chicago is considered to be $361 or less. The median price for this route over the same period was $455. Prices can go higher, with 75% of fares being $674 or less.

Historically, the cheapest months to fly from San Antonio to Chicago are January, March, and April. In January, the median price was $229, while March saw a median of $273, and April had a median of $308. These prices are significantly lower than the annual median price of $455 for this route.