Flights from Chicago to Bostonia

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.

Thu, Oct 16 - Tue, Oct 21

ORD

O'Hare Intl.

SAN

San Diego Intl.

$163 Roundtrip, found 2 days ago

$163

Roundtrip

found 2 days ago

Select Frontier Airlines flight, departing Thu, Oct 16 from O'Hare Intl. to San Diego Intl., returning Tue, Oct 21, priced at $163 found 2 days ago

Tue, Jul 22 - Fri, Jul 25

ORD

O'Hare Intl.

SAN

San Diego Intl.

$164 Roundtrip, found 3 days ago

$164

Roundtrip

found 3 days ago

Select Frontier Airlines flight, departing Tue, Jul 22 from O'Hare Intl. to San Diego Intl., returning Fri, Jul 25, priced at $164 found 3 days ago

Wed, Jul 23 - Fri, Jul 25

ORD

O'Hare Intl.

SAN

San Diego Intl.

$168 Roundtrip, found 3 days ago

$168

Roundtrip

found 3 days ago

Select Frontier Airlines flight, departing Wed, Jul 23 from O'Hare Intl. to San Diego Intl., returning Fri, Jul 25, priced at $168 found 3 days ago

Tue, Oct 14 - Sat, Oct 18

ORD

O'Hare Intl.

SAN

San Diego Intl.

$171 Roundtrip, found 2 days ago

$171

Roundtrip

found 2 days ago

Select Hawaiian Airlines flight, departing Tue, Oct 14 from O'Hare Intl. to San Diego Intl., returning Sat, Oct 18, priced at $171 found 2 days ago

Thu, Oct 16 - Tue, Oct 21

ORD

O'Hare Intl.

SAN

San Diego Intl.

$177 Roundtrip, found 2 days ago

$177

Roundtrip

found 2 days ago

Select Alaska Airlines flight, departing Thu, Oct 16 from O'Hare Intl. to San Diego Intl., returning Tue, Oct 21, priced at $177 found 2 days ago

Thu, Oct 16 - Tue, Oct 21

ORD

O'Hare Intl.

SAN

San Diego Intl.

$178 Roundtrip, found 2 days ago

$178

Roundtrip

found 2 days ago

Select Spirit Airlines flight, departing Thu, Oct 16 from O'Hare Intl. to San Diego Intl., returning Tue, Oct 21, priced at $178 found 2 days ago

Tue, Oct 14 - Thu, Oct 23

ORD

O'Hare Intl.

SAN

San Diego Intl.

$184 Roundtrip, found 2 days ago

$184

Roundtrip

found 2 days ago

Select Hawaiian Airlines flight, departing Tue, Oct 14 from O'Hare Intl. to San Diego Intl., returning Thu, Oct 23, priced at $184 found 2 days ago

Thu, Oct 16 - Tue, Oct 21

ORD

O'Hare Intl.

SAN

San Diego Intl.

$184 Roundtrip, found 2 days ago

$184

Roundtrip

found 2 days ago

Select Alaska Airlines flight, departing Thu, Oct 16 from O'Hare Intl. to San Diego Intl., returning Tue, Oct 21, priced at $184 found 2 days ago

Thu, Oct 16 - Tue, Oct 21

ORD

O'Hare Intl.

SAN

San Diego Intl.

$184 Roundtrip, found 2 days ago

$184

Roundtrip

found 2 days ago

Select American Airlines flight, departing Thu, Oct 16 from O'Hare Intl. to San Diego Intl., returning Tue, Oct 21, priced at $184 found 2 days ago

Thu, Oct 16 - Tue, Oct 21

ORD

O'Hare Intl.

SAN

San Diego Intl.

$184 Roundtrip, found 2 days ago

$184

Roundtrip

found 2 days ago

Select United flight, departing Thu, Oct 16 from O'Hare Intl. to San Diego Intl., returning Tue, Oct 21, priced at $184 found 2 days ago

Thu, Oct 16 - Tue, Oct 21

ORD

O'Hare Intl.

SAN

San Diego Intl.

$187 Roundtrip, found 2 days ago

$187

Roundtrip

found 2 days ago

Select United flight, departing Thu, Oct 16 from O'Hare Intl. to San Diego Intl., returning Tue, Oct 21, priced at $187 found 2 days ago

Tue, Jul 22 - Wed, Jul 30

ORD

O'Hare Intl.

SAN

San Diego Intl.

$191 Roundtrip, found 2 days ago

$191

Roundtrip

found 2 days ago

Select Spirit Airlines flight, departing Tue, Jul 22 from O'Hare Intl. to San Diego Intl., returning Wed, Jul 30, priced at $191 found 2 days ago

Thu, Oct 16 - Tue, Oct 21

ORD

O'Hare Intl.

SAN

San Diego Intl.

$193 Roundtrip, found 2 days ago

$193

Roundtrip

found 2 days ago

Select United flight, departing Thu, Oct 16 from O'Hare Intl. to San Diego Intl., returning Tue, Oct 21, priced at $193 found 2 days ago

Thu, Oct 16 - Tue, Oct 21

ORD

O'Hare Intl.

SAN

San Diego Intl.

$194 Roundtrip, found 2 days ago

$194

Roundtrip

found 2 days ago

Select United flight, departing Thu, Oct 16 from O'Hare Intl. to San Diego Intl., returning Tue, Oct 21, priced at $194 found 2 days ago

Mon, Oct 13 - Thu, Oct 23

ORD

O'Hare Intl.

SAN

San Diego Intl.

$197 Roundtrip, found 2 days ago

$197

Roundtrip

found 2 days ago

Select Hawaiian Airlines flight, departing Mon, Oct 13 from O'Hare Intl. to San Diego Intl., returning Thu, Oct 23, priced at $197 found 2 days ago

Sat, Jul 26 - Mon, Jul 28

ORD

O'Hare Intl.

SAN

San Diego Intl.

$198 Roundtrip, found 2 days ago

$198

Roundtrip

found 2 days ago

Select Spirit Airlines flight, departing Sat, Jul 26 from O'Hare Intl. to San Diego Intl., returning Mon, Jul 28, priced at $198 found 2 days ago

Thu, Jul 24 - Sat, Jul 26

ORD

O'Hare Intl.

SAN

San Diego Intl.

$199 Roundtrip, found 2 days ago

$199

Roundtrip

found 2 days ago

Select Frontier Airlines flight, departing Thu, Jul 24 from O'Hare Intl. to San Diego Intl., returning Sat, Jul 26, priced at $199 found 2 days ago

Thu, Oct 16 - Tue, Oct 21

ORD

O'Hare Intl.

SAN

San Diego Intl.

$348 Roundtrip, found 2 days ago

$348

Roundtrip

found 2 days ago

Select Delta flight, departing Thu, Oct 16 from O'Hare Intl. to San Diego Intl., returning Tue, Oct 21, priced at $348 found 2 days ago

Thu, Oct 16 - Tue, Oct 21

ORD

O'Hare Intl.

CLD

McClellan-Palomar

$404 Roundtrip, found 2 days ago

$404

Roundtrip

found 2 days ago

Select American Airlines flight, departing Thu, Oct 16 from O'Hare Intl. to McClellan-Palomar, returning Tue, Oct 21, priced at $404 found 2 days ago

Thu, Oct 16 - Tue, Oct 21

ORD

O'Hare Intl.

SAN

San Diego Intl.

$629 Roundtrip, found 2 days ago

$629

Roundtrip

found 2 days ago

Select JetBlue Airways flight, departing Thu, Oct 16 from O'Hare Intl. to San Diego Intl., returning Tue, Oct 21, priced at $629 found 2 days ago