Flights from San Diego to Chicago

Cheapest flights from San Diego

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.

Sat, Jul 12 - Mon, Jul 21

SAN

San Diego Intl.

ORD

O'Hare Intl.

$204 Roundtrip, found 5 days ago

$204

Roundtrip

found 5 days ago

Select Frontier Airlines flight, departing Sat, Jul 12 from San Diego Intl. to O'Hare Intl., returning Mon, Jul 21, priced at $204 found 5 days ago

Sat, Jul 12 - Mon, Jul 21

SAN

San Diego Intl.

ORD

O'Hare Intl.

$205 Roundtrip, found 5 days ago

$205

Roundtrip

found 5 days ago

Select Spirit Airlines flight, departing Sat, Jul 12 from San Diego Intl. to O'Hare Intl., returning Mon, Jul 21, priced at $205 found 5 days ago

Wed, Jul 9 - Tue, Jul 22

SAN

San Diego Intl.

ORD

O'Hare Intl.

$206 Roundtrip, found 5 days ago

$206

Roundtrip

found 5 days ago

Select Frontier Airlines flight, departing Wed, Jul 9 from San Diego Intl. to O'Hare Intl., returning Tue, Jul 22, priced at $206 found 5 days ago

Wed, Jul 9 - Wed, Jul 23

SAN

San Diego Intl.

ORD

O'Hare Intl.

$207 Roundtrip, found 5 days ago

$207

Roundtrip

found 5 days ago

Select Frontier Airlines flight, departing Wed, Jul 9 from San Diego Intl. to O'Hare Intl., returning Wed, Jul 23, priced at $207 found 5 days ago

Sat, Jul 12 - Mon, Jul 21

SAN

San Diego Intl.

ORD

O'Hare Intl.

$209 Roundtrip, found 5 days ago

$209

Roundtrip

found 5 days ago

Select Frontier Airlines flight, departing Sat, Jul 12 from San Diego Intl. to O'Hare Intl., returning Mon, Jul 21, priced at $209 found 5 days ago

Wed, Jul 9 - Sat, Jul 19

SAN

San Diego Intl.

ORD

O'Hare Intl.

$212 Roundtrip, found 5 days ago

$212

Roundtrip

found 5 days ago

Select Frontier Airlines flight, departing Wed, Jul 9 from San Diego Intl. to O'Hare Intl., returning Sat, Jul 19, priced at $212 found 5 days ago

Mon, Jul 14 - Sat, Jul 19

SAN

San Diego Intl.

ORD

O'Hare Intl.

$213 Roundtrip, found 5 days ago

$213

Roundtrip

found 5 days ago

Select Spirit Airlines flight, departing Mon, Jul 14 from San Diego Intl. to O'Hare Intl., returning Sat, Jul 19, priced at $213 found 5 days ago

Sat, Jul 12 - Mon, Jul 21

SAN

San Diego Intl.

ORD

O'Hare Intl.

$214 Roundtrip, found 5 days ago

$214

Roundtrip

found 5 days ago

Select United flight, departing Sat, Jul 12 from San Diego Intl. to O'Hare Intl., returning Mon, Jul 21, priced at $214 found 5 days ago

Sat, Jul 12 - Mon, Jul 21

SAN

San Diego Intl.

ORD

O'Hare Intl.

$217 Roundtrip, found 5 days ago

$217

Roundtrip

found 5 days ago

Select Spirit Airlines flight, departing Sat, Jul 12 from San Diego Intl. to O'Hare Intl., returning Mon, Jul 21, priced at $217 found 5 days ago

Sat, Jul 12 - Mon, Jul 21

SAN

San Diego Intl.

ORD

O'Hare Intl.

$219 Roundtrip, found 5 days ago

$219

Roundtrip

found 5 days ago

Select Spirit Airlines flight, departing Sat, Jul 12 from San Diego Intl. to O'Hare Intl., returning Mon, Jul 21, priced at $219 found 5 days ago

Wed, Jul 9 - Fri, Jul 18

SAN

San Diego Intl.

ORD

O'Hare Intl.

$222 Roundtrip, found 5 days ago

$222

Roundtrip

found 5 days ago

Select Frontier Airlines flight, departing Wed, Jul 9 from San Diego Intl. to O'Hare Intl., returning Fri, Jul 18, priced at $222 found 5 days ago

Wed, Jul 9 - Sun, Jul 20

SAN

San Diego Intl.

ORD

O'Hare Intl.

$227 Roundtrip, found 5 days ago

$227

Roundtrip

found 5 days ago

Select Frontier Airlines flight, departing Wed, Jul 9 from San Diego Intl. to O'Hare Intl., returning Sun, Jul 20, priced at $227 found 5 days ago

Sat, Jul 12 - Mon, Jul 21

SAN

San Diego Intl.

ORD

O'Hare Intl.

$235 Roundtrip, found 5 days ago

$235

Roundtrip

found 5 days ago

Select American Airlines flight, departing Sat, Jul 12 from San Diego Intl. to O'Hare Intl., returning Mon, Jul 21, priced at $235 found 5 days ago

Sat, Jul 12 - Mon, Jul 21

SAN

San Diego Intl.

ORD

O'Hare Intl.

$237 Roundtrip, found 5 days ago

$237

Roundtrip

found 5 days ago

Select United flight, departing Sat, Jul 12 from San Diego Intl. to O'Hare Intl., returning Mon, Jul 21, priced at $237 found 5 days ago

Thu, Jul 10 - Fri, Jul 18

SAN

San Diego Intl.

ORD

O'Hare Intl.

$238 Roundtrip, found 5 days ago

$238

Roundtrip

found 5 days ago

Select Frontier Airlines flight, departing Thu, Jul 10 from San Diego Intl. to O'Hare Intl., returning Fri, Jul 18, priced at $238 found 5 days ago

Sat, Jul 12 - Mon, Jul 21

SAN

San Diego Intl.

ORD

O'Hare Intl.

$240 Roundtrip, found 5 days ago

$240

Roundtrip

found 5 days ago

Select Frontier Airlines flight, departing Sat, Jul 12 from San Diego Intl. to O'Hare Intl., returning Mon, Jul 21, priced at $240 found 5 days ago

Sat, Jul 12 - Mon, Jul 21

SAN

San Diego Intl.

ORD

O'Hare Intl.

$243 Roundtrip, found 5 days ago

$243

Roundtrip

found 5 days ago

Select Alaska Airlines flight, departing Sat, Jul 12 from San Diego Intl. to O'Hare Intl., returning Mon, Jul 21, priced at $243 found 5 days ago

Thu, Jul 10 - Sun, Jul 20

SAN

San Diego Intl.

ORD

O'Hare Intl.

$243 Roundtrip, found 5 days ago

$243

Roundtrip

found 5 days ago

Select Frontier Airlines flight, departing Thu, Jul 10 from San Diego Intl. to O'Hare Intl., returning Sun, Jul 20, priced at $243 found 5 days ago

Sat, Jul 12 - Mon, Jul 21

SAN

San Diego Intl.

ORD

O'Hare Intl.

$279 Roundtrip, found 5 days ago

$279

Roundtrip

found 5 days ago

Select Alaska Airlines flight, departing Sat, Jul 12 from San Diego Intl. to O'Hare Intl., returning Mon, Jul 21, priced at $279 found 5 days ago

Sat, Jul 12 - Mon, Jul 21

CLD

McClellan-Palomar

ORD

O'Hare Intl.

$321 Roundtrip, found 5 days ago

$321

Roundtrip

found 5 days ago

Select American Airlines flight, departing Sat, Jul 12 from McClellan-Palomar to O'Hare Intl., returning Mon, Jul 21, priced at $321 found 5 days ago