Flights from Chicago to San Gregorio

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.

Wed, Sep 3 - Tue, Sep 9

ORD

O'Hare Intl.

OAK

Oakland Intl.

$185 Roundtrip, found 22 hours ago

$185

Roundtrip

found 22 hours ago

Select Spirit Airlines flight, departing Wed, Sep 3 from O'Hare Intl. to Oakland Intl., returning Tue, Sep 9, priced at $185 found 22 hours ago

Thu, Sep 4 - Mon, Sep 8

ORD

O'Hare Intl.

OAK

Oakland Intl.

$186 Roundtrip, found 22 hours ago

$186

Roundtrip

found 22 hours ago

Select Spirit Airlines flight, departing Thu, Sep 4 from O'Hare Intl. to Oakland Intl., returning Mon, Sep 8, priced at $186 found 22 hours ago

Tue, Sep 2 - Tue, Sep 9

ORD

O'Hare Intl.

OAK

Oakland Intl.

$192 Roundtrip, found 22 hours ago

$192

Roundtrip

found 22 hours ago

Select Spirit Airlines flight, departing Tue, Sep 2 from O'Hare Intl. to Oakland Intl., returning Tue, Sep 9, priced at $192 found 22 hours ago

Thu, Sep 4 - Mon, Sep 8

ORD

O'Hare Intl.

OAK

Oakland Intl.

$197 Roundtrip, found 22 hours ago

$197

Roundtrip

found 22 hours ago

Select Spirit Airlines flight, departing Thu, Sep 4 from O'Hare Intl. to Oakland Intl., returning Mon, Sep 8, priced at $197 found 22 hours ago

Tue, Sep 2 - Fri, Sep 5

ORD

O'Hare Intl.

OAK

Oakland Intl.

$199 Roundtrip, found 22 hours ago

$199

Roundtrip

found 22 hours ago

Select Spirit Airlines flight, departing Tue, Sep 2 from O'Hare Intl. to Oakland Intl., returning Fri, Sep 5, priced at $199 found 22 hours ago

Thu, Sep 4 - Mon, Sep 8

ORD

O'Hare Intl.

OAK

Oakland Intl.

$204 Roundtrip, found 22 hours ago

$204

Roundtrip

found 22 hours ago

Select Spirit Airlines flight, departing Thu, Sep 4 from O'Hare Intl. to Oakland Intl., returning Mon, Sep 8, priced at $204 found 22 hours ago

Fri, Sep 5 - Sat, Sep 6

ORD

O'Hare Intl.

OAK

Oakland Intl.

$204 Roundtrip, found 22 hours ago

$204

Roundtrip

found 22 hours ago

Select Spirit Airlines flight, departing Fri, Sep 5 from O'Hare Intl. to Oakland Intl., returning Sat, Sep 6, priced at $204 found 22 hours ago

Thu, Sep 4 - Mon, Sep 8

ORD

O'Hare Intl.

OAK

Oakland Intl.

$214 Roundtrip, found 22 hours ago

$214

Roundtrip

found 22 hours ago

Select Spirit Airlines flight, departing Thu, Sep 4 from O'Hare Intl. to Oakland Intl., returning Mon, Sep 8, priced at $214 found 22 hours ago

Thu, Aug 7 - Tue, Aug 12

ORD

O'Hare Intl.

SFO

San Francisco Intl.

$217 Roundtrip, found 6 days ago

$217

Roundtrip

found 6 days ago

Select Hawaiian Airlines flight, departing Thu, Aug 7 from O'Hare Intl. to San Francisco Intl., returning Tue, Aug 12, priced at $217 found 6 days ago

Thu, Sep 4 - Mon, Sep 8

ORD

O'Hare Intl.

OAK

Oakland Intl.

$220 Roundtrip, found 22 hours ago

$220

Roundtrip

found 22 hours ago

Select Spirit Airlines flight, departing Thu, Sep 4 from O'Hare Intl. to Oakland Intl., returning Mon, Sep 8, priced at $220 found 22 hours ago

Thu, Sep 4 - Mon, Sep 8

ORD

O'Hare Intl.

OAK

Oakland Intl.

$225 Roundtrip, found 22 hours ago

$225

Roundtrip

found 22 hours ago

Select Delta flight, departing Thu, Sep 4 from O'Hare Intl. to Oakland Intl., returning Mon, Sep 8, priced at $225 found 22 hours ago

Wed, Aug 6 - Tue, Aug 12

ORD

O'Hare Intl.

SFO

San Francisco Intl.

$227 Roundtrip, found 6 days ago

$227

Roundtrip

found 6 days ago

Select Hawaiian Airlines flight, departing Wed, Aug 6 from O'Hare Intl. to San Francisco Intl., returning Tue, Aug 12, priced at $227 found 6 days ago

Thu, Sep 4 - Mon, Sep 8

ORD

O'Hare Intl.

OAK

Oakland Intl.

$232 Roundtrip, found 22 hours ago

$232

Roundtrip

found 22 hours ago

Select Alaska Airlines flight, departing Thu, Sep 4 from O'Hare Intl. to Oakland Intl., returning Mon, Sep 8, priced at $232 found 22 hours ago

Sat, Sep 6 - Tue, Sep 9

MDW

Midway Intl.

SJC

Norman Y. Mineta San Jose Intl.

$257 Roundtrip, found 3 days ago

$257

Roundtrip

found 3 days ago

Select Delta flight, departing Sat, Sep 6 from Midway Intl. to Norman Y. Mineta San Jose Intl., returning Tue, Sep 9, priced at $257 found 3 days ago

Sat, Sep 6 - Tue, Sep 9

MDW

Midway Intl.

SFO

San Francisco Intl.

$257 Roundtrip, found 3 days ago

$257

Roundtrip

found 3 days ago

Select Delta flight, departing Sat, Sep 6 from Midway Intl. to San Francisco Intl., returning Tue, Sep 9, priced at $257 found 3 days ago

Wed, Sep 3 - Fri, Sep 5

ORD

O'Hare Intl.

SFO

San Francisco Intl.

$257 Roundtrip, found 3 days ago

$257

Roundtrip

found 3 days ago

Select Delta flight, departing Wed, Sep 3 from O'Hare Intl. to San Francisco Intl., returning Fri, Sep 5, priced at $257 found 3 days ago

Thu, Sep 4 - Mon, Sep 8

ORD

O'Hare Intl.

OAK

Oakland Intl.

$261 Roundtrip, found 22 hours ago

$261

Roundtrip

found 22 hours ago

Select Alaska Airlines flight, departing Thu, Sep 4 from O'Hare Intl. to Oakland Intl., returning Mon, Sep 8, priced at $261 found 22 hours ago

Sat, Sep 6 - Mon, Sep 8

MDW

Midway Intl.

OAK

Oakland Intl.

$267 Roundtrip, found 22 hours ago

$267

Roundtrip

found 22 hours ago

Select Delta flight, departing Sat, Sep 6 from Midway Intl. to Oakland Intl., returning Mon, Sep 8, priced at $267 found 22 hours ago

Tue, Sep 2 - Sun, Sep 7

ORD

O'Hare Intl.

SFO

San Francisco Intl.

$297 Roundtrip, found 3 days ago

$297

Roundtrip

found 3 days ago

Select American Airlines flight, departing Tue, Sep 2 from O'Hare Intl. to San Francisco Intl., returning Sun, Sep 7, priced at $297 found 3 days ago

Fri, Sep 5 - Mon, Sep 8

MDW

Midway Intl.

SFO

San Francisco Intl.

$326 Roundtrip, found 3 days ago

$326

Roundtrip

found 3 days ago

Select Frontier Airlines flight, departing Fri, Sep 5 from Midway Intl. to San Francisco Intl., returning Mon, Sep 8, priced at $326 found 3 days ago