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 - Wed, Jul 30

SAN

San Diego Intl.

ORD

O'Hare Intl.

$167 Roundtrip, found 3 days ago

$167

Roundtrip

found 3 days ago

Select Spirit Airlines flight, departing Sat, Jul 12 from San Diego Intl. to O'Hare Intl., returning Wed, Jul 30, priced at $167 found 3 days ago

Thu, Jul 10 - Wed, Jul 30

SAN

San Diego Intl.

ORD

O'Hare Intl.

$174 Roundtrip, found 3 days ago

$174

Roundtrip

found 3 days ago

Select Spirit Airlines flight, departing Thu, Jul 10 from San Diego Intl. to O'Hare Intl., returning Wed, Jul 30, priced at $174 found 3 days ago

Sat, Jul 12 - Sat, Aug 2

SAN

San Diego Intl.

ORD

O'Hare Intl.

$186 Roundtrip, found 3 days ago

$186

Roundtrip

found 3 days ago

Select Spirit Airlines flight, departing Sat, Jul 12 from San Diego Intl. to O'Hare Intl., returning Sat, Aug 2, priced at $186 found 3 days ago

Thu, Jul 10 - Sat, Aug 2

SAN

San Diego Intl.

ORD

O'Hare Intl.

$193 Roundtrip, found 3 days ago

$193

Roundtrip

found 3 days ago

Select Spirit Airlines flight, departing Thu, Jul 10 from San Diego Intl. to O'Hare Intl., returning Sat, Aug 2, priced at $193 found 3 days ago

Tue, Jul 8 - Thu, Jul 31

SAN

San Diego Intl.

ORD

O'Hare Intl.

$223 Roundtrip, found 3 days ago

$223

Roundtrip

found 3 days ago

Select Frontier Airlines flight, departing Tue, Jul 8 from San Diego Intl. to O'Hare Intl., returning Thu, Jul 31, priced at $223 found 3 days ago

Sat, Jul 12 - Thu, Jul 31

SAN

San Diego Intl.

ORD

O'Hare Intl.

$228 Roundtrip, found 3 days ago

$228

Roundtrip

found 3 days ago

Select Frontier Airlines flight, departing Sat, Jul 12 from San Diego Intl. to O'Hare Intl., returning Thu, Jul 31, priced at $228 found 3 days ago

Sat, Jul 12 - Mon, Aug 4

SAN

San Diego Intl.

ORD

O'Hare Intl.

$232 Roundtrip, found 3 days ago

$232

Roundtrip

found 3 days ago

Select Spirit Airlines flight, departing Sat, Jul 12 from San Diego Intl. to O'Hare Intl., returning Mon, Aug 4, priced at $232 found 3 days ago

Mon, Jul 7 - Thu, Jul 31

SAN

San Diego Intl.

ORD

O'Hare Intl.

$238 Roundtrip, found 3 days ago

$238

Roundtrip

found 3 days ago

Select Frontier Airlines flight, departing Mon, Jul 7 from San Diego Intl. to O'Hare Intl., returning Thu, Jul 31, priced at $238 found 3 days ago

Thu, Jul 10 - Mon, Aug 4

SAN

San Diego Intl.

ORD

O'Hare Intl.

$239 Roundtrip, found 3 days ago

$239

Roundtrip

found 3 days ago

Select Spirit Airlines flight, departing Thu, Jul 10 from San Diego Intl. to O'Hare Intl., returning Mon, Aug 4, priced at $239 found 3 days ago

Sat, Jul 12 - Sun, Aug 3

SAN

San Diego Intl.

ORD

O'Hare Intl.

$242 Roundtrip, found 3 days ago

$242

Roundtrip

found 3 days ago

Select Spirit Airlines flight, departing Sat, Jul 12 from San Diego Intl. to O'Hare Intl., returning Sun, Aug 3, priced at $242 found 3 days ago

Sat, Jul 5 - Sat, Aug 2

SAN

San Diego Intl.

ORD

O'Hare Intl.

$243 Roundtrip, found 3 days ago

$243

Roundtrip

found 3 days ago

Select Frontier Airlines flight, departing Sat, Jul 5 from San Diego Intl. to O'Hare Intl., returning Sat, Aug 2, priced at $243 found 3 days ago

Thu, Jul 10 - Sun, Aug 3

SAN

San Diego Intl.

ORD

O'Hare Intl.

$249 Roundtrip, found 3 days ago

$249

Roundtrip

found 3 days ago

Select Spirit Airlines flight, departing Thu, Jul 10 from San Diego Intl. to O'Hare Intl., returning Sun, Aug 3, priced at $249 found 3 days ago

Fri, Jul 4 - Mon, Jul 28

SAN

San Diego Intl.

ORD

O'Hare Intl.

$253 Roundtrip, found 3 days ago

$253

Roundtrip

found 3 days ago

Select Frontier Airlines flight, departing Fri, Jul 4 from San Diego Intl. to O'Hare Intl., returning Mon, Jul 28, priced at $253 found 3 days ago

Sun, Jul 6 - Wed, Jul 30

SAN

San Diego Intl.

ORD

O'Hare Intl.

$268 Roundtrip, found 3 days ago

$268

Roundtrip

found 3 days ago

Select Spirit Airlines flight, departing Sun, Jul 6 from San Diego Intl. to O'Hare Intl., returning Wed, Jul 30, priced at $268 found 3 days ago

Sun, Jul 6 - Sat, Aug 2

SAN

San Diego Intl.

ORD

O'Hare Intl.

$287 Roundtrip, found 3 days ago

$287

Roundtrip

found 3 days ago

Select Spirit Airlines flight, departing Sun, Jul 6 from San Diego Intl. to O'Hare Intl., returning Sat, Aug 2, priced at $287 found 3 days ago

Sat, Jul 5 - Sun, Aug 3

SAN

San Diego Intl.

ORD

O'Hare Intl.

$294 Roundtrip, found 3 days ago

$294

Roundtrip

found 3 days ago

Select Frontier Airlines flight, departing Sat, Jul 5 from San Diego Intl. to O'Hare Intl., returning Sun, Aug 3, priced at $294 found 3 days ago

Sun, Jul 6 - Thu, Jul 31

SAN

San Diego Intl.

ORD

O'Hare Intl.

$304 Roundtrip, found 3 days ago

$304

Roundtrip

found 3 days ago

Select Frontier Airlines flight, departing Sun, Jul 6 from San Diego Intl. to O'Hare Intl., returning Thu, Jul 31, priced at $304 found 3 days ago

Sun, Jul 6 - Mon, Aug 4

SAN

San Diego Intl.

ORD

O'Hare Intl.

$333 Roundtrip, found 3 days ago

$333

Roundtrip

found 3 days ago

Select Spirit Airlines flight, departing Sun, Jul 6 from San Diego Intl. to O'Hare Intl., returning Mon, Aug 4, priced at $333 found 3 days ago