Flights from Chicago to Pearsall

Cheapest flights from Chicago

These prices were available within the past 7 days. Prices quoted are per person, round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Tue, Oct 21 - Wed, Oct 22

ORD

O'Hare Intl.

SAT

San Antonio Intl.

$217 Roundtrip, found 5 hours ago

$217

Roundtrip

found 5 hours ago

Select Delta flight, departing Tue, Oct 21 from O'Hare Intl. to San Antonio Intl., returning Wed, Oct 22, priced at $217 found 5 hours ago

Sat, Oct 25 - Sat, Oct 25

ORD

O'Hare Intl.

SAT

San Antonio Intl.

$218 Roundtrip, found 3 days ago

$218

Roundtrip

found 3 days ago

Select Frontier Airlines flight, departing Sat, Oct 25 from O'Hare Intl. to San Antonio Intl., returning Sat, Oct 25, priced at $218 found 3 days ago

Mon, Oct 20 - Thu, Oct 23

ORD

O'Hare Intl.

SAT

San Antonio Intl.

$229 Roundtrip, found 5 hours ago

$229

Roundtrip

found 5 hours ago

Select Spirit Airlines flight, departing Mon, Oct 20 from O'Hare Intl. to San Antonio Intl., returning Thu, Oct 23, priced at $229 found 5 hours ago

Sun, Oct 19 - Mon, Oct 20

ORD

O'Hare Intl.

SAT

San Antonio Intl.

$229 Roundtrip, found 5 hours ago

$229

Roundtrip

found 5 hours ago

Select Spirit Airlines flight, departing Sun, Oct 19 from O'Hare Intl. to San Antonio Intl., returning Mon, Oct 20, priced at $229 found 5 hours ago

Tue, Oct 21 - Tue, Oct 28

ORD

O'Hare Intl.

SAT

San Antonio Intl.

$235 Roundtrip, found 2 days ago

$235

Roundtrip

found 2 days ago

Select United flight, departing Tue, Oct 21 from O'Hare Intl. to San Antonio Intl., returning Tue, Oct 28, priced at $235 found 2 days ago

Tue, Oct 21 - Tue, Oct 28

ORD

O'Hare Intl.

SAT

San Antonio Intl.

$235 Roundtrip, found 2 days ago

$235

Roundtrip

found 2 days ago

Select American Airlines flight, departing Tue, Oct 21 from O'Hare Intl. to San Antonio Intl., returning Tue, Oct 28, priced at $235 found 2 days ago

Sat, Oct 18 - Fri, Oct 24

ORD

O'Hare Intl.

SAT

San Antonio Intl.

$236 Roundtrip, found 5 hours ago

$236

Roundtrip

found 5 hours ago

Select American Airlines flight, departing Sat, Oct 18 from O'Hare Intl. to San Antonio Intl., returning Fri, Oct 24, priced at $236 found 5 hours ago

Fri, Oct 17 - Sat, Oct 25

ORD

O'Hare Intl.

SAT

San Antonio Intl.

$238 Roundtrip, found 5 hours ago

$238

Roundtrip

found 5 hours ago

Select Frontier Airlines flight, departing Fri, Oct 17 from O'Hare Intl. to San Antonio Intl., returning Sat, Oct 25, priced at $238 found 5 hours ago

Tue, Oct 21 - Tue, Oct 28

ORD

O'Hare Intl.

SAT

San Antonio Intl.

$241 Roundtrip, found 2 days ago

$241

Roundtrip

found 2 days ago

Select American Airlines flight, departing Tue, Oct 21 from O'Hare Intl. to San Antonio Intl., returning Tue, Oct 28, priced at $241 found 2 days ago

Mon, Oct 20 - Mon, Oct 20

ORD

O'Hare Intl.

SAT

San Antonio Intl.

$243 Roundtrip, found 5 hours ago

$243

Roundtrip

found 5 hours ago

Select Frontier Airlines flight, departing Mon, Oct 20 from O'Hare Intl. to San Antonio Intl., returning Mon, Oct 20, priced at $243 found 5 hours ago

Mon, Oct 20 - Thu, Oct 23

ORD

O'Hare Intl.

SAT

San Antonio Intl.

$243 Roundtrip, found 5 hours ago

$243

Roundtrip

found 5 hours ago

Select Frontier Airlines flight, departing Mon, Oct 20 from O'Hare Intl. to San Antonio Intl., returning Thu, Oct 23, priced at $243 found 5 hours ago

Tue, Oct 21 - Tue, Oct 28

ORD

O'Hare Intl.

SAT

San Antonio Intl.

$245 Roundtrip, found 2 days ago

$245

Roundtrip

found 2 days ago

Select United flight, departing Tue, Oct 21 from O'Hare Intl. to San Antonio Intl., returning Tue, Oct 28, priced at $245 found 2 days ago

Tue, Oct 21 - Tue, Oct 28

ORD

O'Hare Intl.

SAT

San Antonio Intl.

$246 Roundtrip, found 2 days ago

$246

Roundtrip

found 2 days ago

Select Spirit Airlines flight, departing Tue, Oct 21 from O'Hare Intl. to San Antonio Intl., returning Tue, Oct 28, priced at $246 found 2 days ago

Tue, Oct 21 - Tue, Oct 28

ORD

O'Hare Intl.

SAT

San Antonio Intl.

$247 Roundtrip, found 2 days ago

$247

Roundtrip

found 2 days ago

Select American Airlines flight, departing Tue, Oct 21 from O'Hare Intl. to San Antonio Intl., returning Tue, Oct 28, priced at $247 found 2 days ago

Fri, Oct 17 - Mon, Oct 20

ORD

O'Hare Intl.

SAT

San Antonio Intl.

$248 Roundtrip, found 5 hours ago

$248

Roundtrip

found 5 hours ago

Select Frontier Airlines flight, departing Fri, Oct 17 from O'Hare Intl. to San Antonio Intl., returning Mon, Oct 20, priced at $248 found 5 hours ago

Mon, Oct 20 - Thu, Oct 23

ORD

O'Hare Intl.

SAT

San Antonio Intl.

$253 Roundtrip, found 5 hours ago

$253

Roundtrip

found 5 hours ago

Select Spirit Airlines flight, departing Mon, Oct 20 from O'Hare Intl. to San Antonio Intl., returning Thu, Oct 23, priced at $253 found 5 hours ago

Mon, Oct 20 - Mon, Oct 20

ORD

O'Hare Intl.

SAT

San Antonio Intl.

$253 Roundtrip, found 6 days ago

$253

Roundtrip

found 6 days ago

Select Spirit Airlines flight, departing Mon, Oct 20 from O'Hare Intl. to San Antonio Intl., returning Mon, Oct 20, priced at $253 found 6 days ago

Tue, Oct 21 - Tue, Oct 28

ORD

O'Hare Intl.

SAT

San Antonio Intl.

$255 Roundtrip, found 2 days ago

$255

Roundtrip

found 2 days ago

Select Delta flight, departing Tue, Oct 21 from O'Hare Intl. to San Antonio Intl., returning Tue, Oct 28, priced at $255 found 2 days ago

Tue, Oct 21 - Tue, Oct 28

ORD

O'Hare Intl.

SAT

San Antonio Intl.

$256 Roundtrip, found 2 days ago

$256

Roundtrip

found 2 days ago

Select United flight, departing Tue, Oct 21 from O'Hare Intl. to San Antonio Intl., returning Tue, Oct 28, priced at $256 found 2 days ago

Sat, Oct 18 - Tue, Oct 21

ORD

O'Hare Intl.

SAT

San Antonio Intl.

$257 Roundtrip, found 5 days ago

$257

Roundtrip

found 5 days ago

Select United flight, departing Sat, Oct 18 from O'Hare Intl. to San Antonio Intl., returning Tue, Oct 21, priced at $257 found 5 days ago