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.

Wed, Jun 18 - Tue, Sep 23

SAN

San Diego Intl.

ORD

O'Hare Intl.

$175 Roundtrip, found 2 days ago

$175

Roundtrip

found 2 days ago

Select Frontier Airlines flight, departing Wed, Jun 18 from San Diego Intl. to O'Hare Intl., returning Tue, Sep 23, priced at $175 found 2 days ago

Wed, Jun 18 - Tue, Sep 23

SAN

San Diego Intl.

ORD

O'Hare Intl.

$175 Roundtrip, found 2 days ago

$175

Roundtrip

found 2 days ago

Select Spirit Airlines flight, departing Wed, Jun 18 from San Diego Intl. to O'Hare Intl., returning Tue, Sep 23, priced at $175 found 2 days ago

Wed, Jun 18 - Tue, Sep 23

SAN

San Diego Intl.

ORD

O'Hare Intl.

$191 Roundtrip, found 2 days ago

$191

Roundtrip

found 2 days ago

Select Spirit Airlines flight, departing Wed, Jun 18 from San Diego Intl. to O'Hare Intl., returning Tue, Sep 23, priced at $191 found 2 days ago

Wed, Jun 18 - Tue, Sep 23

SAN

San Diego Intl.

ORD

O'Hare Intl.

$204 Roundtrip, found 2 days ago

$204

Roundtrip

found 2 days ago

Select Spirit Airlines flight, departing Wed, Jun 18 from San Diego Intl. to O'Hare Intl., returning Tue, Sep 23, priced at $204 found 2 days ago

Wed, Jun 18 - Tue, Sep 23

SAN

San Diego Intl.

ORD

O'Hare Intl.

$220 Roundtrip, found 2 days ago

$220

Roundtrip

found 2 days ago

Select Spirit Airlines flight, departing Wed, Jun 18 from San Diego Intl. to O'Hare Intl., returning Tue, Sep 23, priced at $220 found 2 days ago

Wed, Jun 18 - Tue, Sep 23

SAN

San Diego Intl.

ORD

O'Hare Intl.

$240 Roundtrip, found 2 days ago

$240

Roundtrip

found 2 days ago

Select Spirit Airlines flight, departing Wed, Jun 18 from San Diego Intl. to O'Hare Intl., returning Tue, Sep 23, priced at $240 found 2 days ago

Wed, Jun 18 - Tue, Sep 23

SAN

San Diego Intl.

ORD

O'Hare Intl.

$249 Roundtrip, found 2 days ago

$249

Roundtrip

found 2 days ago

Select United flight, departing Wed, Jun 18 from San Diego Intl. to O'Hare Intl., returning Tue, Sep 23, priced at $249 found 2 days ago

Wed, Jun 18 - Tue, Sep 23

SAN

San Diego Intl.

ORD

O'Hare Intl.

$256 Roundtrip, found 2 days ago

$256

Roundtrip

found 2 days ago

Select Spirit Airlines flight, departing Wed, Jun 18 from San Diego Intl. to O'Hare Intl., returning Tue, Sep 23, priced at $256 found 2 days ago

Wed, Jun 18 - Tue, Sep 23

SAN

San Diego Intl.

ORD

O'Hare Intl.

$259 Roundtrip, found 2 days ago

$259

Roundtrip

found 2 days ago

Select American Airlines flight, departing Wed, Jun 18 from San Diego Intl. to O'Hare Intl., returning Tue, Sep 23, priced at $259 found 2 days ago

Wed, Jun 18 - Tue, Sep 23

SAN

San Diego Intl.

ORD

O'Hare Intl.

$276 Roundtrip, found 2 days ago

$276

Roundtrip

found 2 days ago

Select Spirit Airlines flight, departing Wed, Jun 18 from San Diego Intl. to O'Hare Intl., returning Tue, Sep 23, priced at $276 found 2 days ago

Wed, Jun 18 - Tue, Sep 23

SAN

San Diego Intl.

ORD

O'Hare Intl.

$279 Roundtrip, found 2 days ago

$279

Roundtrip

found 2 days ago

Select American Airlines flight, departing Wed, Jun 18 from San Diego Intl. to O'Hare Intl., returning Tue, Sep 23, priced at $279 found 2 days ago

Wed, Jun 18 - Tue, Sep 23

SAN

San Diego Intl.

ORD

O'Hare Intl.

$294 Roundtrip, found 2 days ago

$294

Roundtrip

found 2 days ago

Select American Airlines flight, departing Wed, Jun 18 from San Diego Intl. to O'Hare Intl., returning Tue, Sep 23, priced at $294 found 2 days ago

Wed, Jun 18 - Tue, Sep 23

SAN

San Diego Intl.

ORD

O'Hare Intl.

$295 Roundtrip, found 2 days ago

$295

Roundtrip

found 2 days ago

Select Spirit Airlines flight, departing Wed, Jun 18 from San Diego Intl. to O'Hare Intl., returning Tue, Sep 23, priced at $295 found 2 days ago

Wed, Jun 18 - Tue, Sep 23

SAN

San Diego Intl.

ORD

O'Hare Intl.

$299 Roundtrip, found 2 days ago

$299

Roundtrip

found 2 days ago

Select American Airlines flight, departing Wed, Jun 18 from San Diego Intl. to O'Hare Intl., returning Tue, Sep 23, priced at $299 found 2 days ago

Wed, Jun 18 - Tue, Sep 23

SAN

San Diego Intl.

ORD

O'Hare Intl.

$304 Roundtrip, found 2 days ago

$304

Roundtrip

found 2 days ago

Select American Airlines flight, departing Wed, Jun 18 from San Diego Intl. to O'Hare Intl., returning Tue, Sep 23, priced at $304 found 2 days ago

Wed, Jun 18 - Tue, Sep 23

SAN

San Diego Intl.

ORD

O'Hare Intl.

$307 Roundtrip, found 2 days ago

$307

Roundtrip

found 2 days ago

Select Delta flight, departing Wed, Jun 18 from San Diego Intl. to O'Hare Intl., returning Tue, Sep 23, priced at $307 found 2 days ago

Wed, Jun 18 - Tue, Sep 23

SAN

San Diego Intl.

ORD

O'Hare Intl.

$309 Roundtrip, found 2 days ago

$309

Roundtrip

found 2 days ago

Select Delta flight, departing Wed, Jun 18 from San Diego Intl. to O'Hare Intl., returning Tue, Sep 23, priced at $309 found 2 days ago

Wed, Jun 18 - Tue, Sep 23

SAN

San Diego Intl.

ORD

O'Hare Intl.

$311 Roundtrip, found 2 days ago

$311

Roundtrip

found 2 days ago

Select Spirit Airlines flight, departing Wed, Jun 18 from San Diego Intl. to O'Hare Intl., returning Tue, Sep 23, priced at $311 found 2 days ago

Wed, Jun 18 - Tue, Sep 23

SAN

San Diego Intl.

ORD

O'Hare Intl.

$314 Roundtrip, found 2 days ago

$314

Roundtrip

found 2 days ago

Select American Airlines flight, departing Wed, Jun 18 from San Diego Intl. to O'Hare Intl., returning Tue, Sep 23, priced at $314 found 2 days ago

Wed, Jun 18 - Tue, Sep 23

SAN

San Diego Intl.

ORD

O'Hare Intl.

$466 Roundtrip, found 2 days ago

$466

Roundtrip

found 2 days ago

Select Alaska Airlines flight, departing Wed, Jun 18 from San Diego Intl. to O'Hare Intl., returning Tue, Sep 23, priced at $466 found 2 days ago