Flights from Monterey to Chicago

Cheapest flights from Monterey

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, Jul 9 - Sat, Jul 12

SJC

Norman Y. Mineta San Jose Intl.

ORD

O'Hare Intl.

$185 Roundtrip, found 15 hours ago

$185

Roundtrip

found 15 hours ago

Select Spirit Airlines flight, departing Wed, Jul 9 from Norman Y. Mineta San Jose Intl. to O'Hare Intl., returning Sat, Jul 12, priced at $185 found 15 hours ago

Tue, Aug 5 - Tue, Aug 12

SFO

San Francisco Intl.

ORD

O'Hare Intl.

$188 Roundtrip, found 3 days ago

$188

Roundtrip

found 3 days ago

Select Hawaiian Airlines flight, departing Tue, Aug 5 from San Francisco Intl. to O'Hare Intl., returning Tue, Aug 12, priced at $188 found 3 days ago

Wed, Aug 6 - Wed, Aug 6

SFO

San Francisco Intl.

ORD

O'Hare Intl.

$191 Roundtrip, found 5 days ago

$191

Roundtrip

found 5 days ago

Select Alaska Airlines flight, departing Wed, Aug 6 from San Francisco Intl. to O'Hare Intl., returning Wed, Aug 6, priced at $191 found 5 days ago

Tue, Aug 5 - Wed, Aug 6

SFO

San Francisco Intl.

ORD

O'Hare Intl.

$197 Roundtrip, found 3 days ago

$197

Roundtrip

found 3 days ago

Select Hawaiian Airlines flight, departing Tue, Aug 5 from San Francisco Intl. to O'Hare Intl., returning Wed, Aug 6, priced at $197 found 3 days ago

Tue, Jul 8 - Tue, Jul 15

SFO

San Francisco Intl.

ORD

O'Hare Intl.

$197 Roundtrip, found 15 hours ago

$197

Roundtrip

found 15 hours ago

Select United flight, departing Tue, Jul 8 from San Francisco Intl. to O'Hare Intl., returning Tue, Jul 15, priced at $197 found 15 hours ago

Tue, Aug 5 - Wed, Aug 6

SFO

San Francisco Intl.

ORD

O'Hare Intl.

$197 Roundtrip, found 3 days ago

$197

Roundtrip

found 3 days ago

Select American Airlines flight, departing Tue, Aug 5 from San Francisco Intl. to O'Hare Intl., returning Wed, Aug 6, priced at $197 found 3 days ago

Thu, Sep 25 - Sat, Oct 4

SJC

Norman Y. Mineta San Jose Intl.

ORD

O'Hare Intl.

$205 Roundtrip, found 5 days ago

$205

Roundtrip

found 5 days ago

Select Spirit Airlines flight, departing Thu, Sep 25 from Norman Y. Mineta San Jose Intl. to O'Hare Intl., returning Sat, Oct 4, priced at $205 found 5 days ago

Tue, Aug 5 - Thu, Aug 7

SFO

San Francisco Intl.

ORD

O'Hare Intl.

$207 Roundtrip, found 3 days ago

$207

Roundtrip

found 3 days ago

Select Hawaiian Airlines flight, departing Tue, Aug 5 from San Francisco Intl. to O'Hare Intl., returning Thu, Aug 7, priced at $207 found 3 days ago

Tue, Aug 5 - Wed, Aug 6

SFO

San Francisco Intl.

ORD

O'Hare Intl.

$217 Roundtrip, found 3 days ago

$217

Roundtrip

found 3 days ago

Select Alaska Airlines flight, departing Tue, Aug 5 from San Francisco Intl. to O'Hare Intl., returning Wed, Aug 6, priced at $217 found 3 days ago

Tue, Jul 8 - Tue, Jul 15

SFO

San Francisco Intl.

ORD

O'Hare Intl.

$217 Roundtrip, found 15 hours ago

$217

Roundtrip

found 15 hours ago

Select Hawaiian Airlines flight, departing Tue, Jul 8 from San Francisco Intl. to O'Hare Intl., returning Tue, Jul 15, priced at $217 found 15 hours ago

Tue, Sep 30 - Tue, Oct 7

SJC

Norman Y. Mineta San Jose Intl.

ORD

O'Hare Intl.

$224 Roundtrip, found 5 days ago

$224

Roundtrip

found 5 days ago

Select Spirit Airlines flight, departing Tue, Sep 30 from Norman Y. Mineta San Jose Intl. to O'Hare Intl., returning Tue, Oct 7, priced at $224 found 5 days ago

Fri, Sep 26 - Sat, Oct 4

SJC

Norman Y. Mineta San Jose Intl.

ORD

O'Hare Intl.

$225 Roundtrip, found 5 days ago

$225

Roundtrip

found 5 days ago

Select Spirit Airlines flight, departing Fri, Sep 26 from Norman Y. Mineta San Jose Intl. to O'Hare Intl., returning Sat, Oct 4, priced at $225 found 5 days ago

Tue, Aug 5 - Wed, Aug 6

SFO

San Francisco Intl.

ORD

O'Hare Intl.

$227 Roundtrip, found 3 days ago

$227

Roundtrip

found 3 days ago

Select Delta flight, departing Tue, Aug 5 from San Francisco Intl. to O'Hare Intl., returning Wed, Aug 6, priced at $227 found 3 days ago

Tue, Jul 8 - Tue, Jul 15

SFO

San Francisco Intl.

ORD

O'Hare Intl.

$227 Roundtrip, found 15 hours ago

$227

Roundtrip

found 15 hours ago

Select Delta flight, departing Tue, Jul 8 from San Francisco Intl. to O'Hare Intl., returning Tue, Jul 15, priced at $227 found 15 hours ago

Tue, Jul 8 - Tue, Jul 15

SFO

San Francisco Intl.

ORD

O'Hare Intl.

$232 Roundtrip, found 15 hours ago

$232

Roundtrip

found 15 hours ago

Select United flight, departing Tue, Jul 8 from San Francisco Intl. to O'Hare Intl., returning Tue, Jul 15, priced at $232 found 15 hours ago

Sun, Sep 7 - Sun, Sep 14

SFO

San Francisco Intl.

ORD

O'Hare Intl.

$233 Roundtrip, found 5 days ago

$233

Roundtrip

found 5 days ago

Select Frontier Airlines flight, departing Sun, Sep 7 from San Francisco Intl. to O'Hare Intl., returning Sun, Sep 14, priced at $233 found 5 days ago

Sat, Sep 6 - Thu, Sep 11

SFO

San Francisco Intl.

ORD

O'Hare Intl.

$244 Roundtrip, found 5 days ago

$244

Roundtrip

found 5 days ago

Select Frontier Airlines flight, departing Sat, Sep 6 from San Francisco Intl. to O'Hare Intl., returning Thu, Sep 11, priced at $244 found 5 days ago

Sun, Sep 7 - Sun, Sep 14

SFO

San Francisco Intl.

MDW

Midway Intl.

$252 Roundtrip, found 5 days ago

$252

Roundtrip

found 5 days ago

Select Frontier Airlines flight, departing Sun, Sep 7 from San Francisco Intl. to Midway Intl., returning Sun, Sep 14, priced at $252 found 5 days ago

Sat, Jul 5 - Wed, Jul 16

SFO

San Francisco Intl.

ORD

O'Hare Intl.

$257 Roundtrip, found 15 hours ago

$257

Roundtrip

found 15 hours ago

Select Delta flight, departing Sat, Jul 5 from San Francisco Intl. to O'Hare Intl., returning Wed, Jul 16, priced at $257 found 15 hours ago

Tue, Jul 8 - Tue, Jul 15

SFO

San Francisco Intl.

ORD

O'Hare Intl.

$955 Roundtrip, found 15 hours ago

$955

Roundtrip

found 15 hours ago

Select JetBlue Airways flight, departing Tue, Jul 8 from San Francisco Intl. to O'Hare Intl., returning Tue, Jul 15, priced at $955 found 15 hours ago