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.

Sat, Oct 11 - Wed, Oct 15

SFO

San Francisco Intl.

ORD

O'Hare Intl.

$197 Roundtrip, found 6 days ago

$197

Roundtrip

found 6 days ago

Select United flight, departing Sat, Oct 11 from San Francisco Intl. to O'Hare Intl., returning Wed, Oct 15, priced at $197 found 6 days ago

Sat, Oct 11 - Wed, Oct 15

SFO

San Francisco Intl.

ORD

O'Hare Intl.

$197 Roundtrip, found 6 days ago

$197

Roundtrip

found 6 days ago

Select American Airlines flight, departing Sat, Oct 11 from San Francisco Intl. to O'Hare Intl., returning Wed, Oct 15, priced at $197 found 6 days ago

Sat, Oct 11 - Wed, Oct 15

SFO

San Francisco Intl.

ORD

O'Hare Intl.

$197 Roundtrip, found 6 days ago

$197

Roundtrip

found 6 days ago

Select United flight, departing Sat, Oct 11 from San Francisco Intl. to O'Hare Intl., returning Wed, Oct 15, priced at $197 found 6 days ago

Sat, Oct 11 - Sun, Oct 12

SFO

San Francisco Intl.

ORD

O'Hare Intl.

$207 Roundtrip, found 6 days ago

$207

Roundtrip

found 6 days ago

Select United flight, departing Sat, Oct 11 from San Francisco Intl. to O'Hare Intl., returning Sun, Oct 12, priced at $207 found 6 days ago

Sat, Oct 11 - Wed, Oct 15

SFO

San Francisco Intl.

ORD

O'Hare Intl.

$214 Roundtrip, found 6 days ago

$214

Roundtrip

found 6 days ago

Select American Airlines flight, departing Sat, Oct 11 from San Francisco Intl. to O'Hare Intl., returning Wed, Oct 15, priced at $214 found 6 days ago

Thu, Nov 20 - Mon, Nov 24

SFO

San Francisco Intl.

ORD

O'Hare Intl.

$217 Roundtrip, found 3 days ago

$217

Roundtrip

found 3 days ago

Select United flight, departing Thu, Nov 20 from San Francisco Intl. to O'Hare Intl., returning Mon, Nov 24, priced at $217 found 3 days ago

Sat, Oct 11 - Wed, Oct 15

SFO

San Francisco Intl.

ORD

O'Hare Intl.

$225 Roundtrip, found 6 days ago

$225

Roundtrip

found 6 days ago

Select United flight, departing Sat, Oct 11 from San Francisco Intl. to O'Hare Intl., returning Wed, Oct 15, priced at $225 found 6 days ago

Thu, Aug 21 - Tue, Aug 26

SFO

San Francisco Intl.

ORD

O'Hare Intl.

$227 Roundtrip, found 4 days ago

$227

Roundtrip

found 4 days ago

Select Delta flight, departing Thu, Aug 21 from San Francisco Intl. to O'Hare Intl., returning Tue, Aug 26, priced at $227 found 4 days ago

Sat, Oct 11 - Wed, Oct 15

SFO

San Francisco Intl.

ORD

O'Hare Intl.

$231 Roundtrip, found 6 days ago

$231

Roundtrip

found 6 days ago

Select American Airlines flight, departing Sat, Oct 11 from San Francisco Intl. to O'Hare Intl., returning Wed, Oct 15, priced at $231 found 6 days ago

Wed, Nov 19 - Wed, Dec 3

SFO

San Francisco Intl.

ORD

O'Hare Intl.

$240 Roundtrip, found 4 days ago

$240

Roundtrip

found 4 days ago

Select Hawaiian Airlines flight, departing Wed, Nov 19 from San Francisco Intl. to O'Hare Intl., returning Wed, Dec 3, priced at $240 found 4 days ago

Sat, Oct 11 - Wed, Oct 15

SFO

San Francisco Intl.

ORD

O'Hare Intl.

$241 Roundtrip, found 6 days ago

$241

Roundtrip

found 6 days ago

Select Alaska Airlines flight, departing Sat, Oct 11 from San Francisco Intl. to O'Hare Intl., returning Wed, Oct 15, priced at $241 found 6 days ago

Sat, Oct 11 - Wed, Oct 15

SFO

San Francisco Intl.

ORD

O'Hare Intl.

$242 Roundtrip, found 6 days ago

$242

Roundtrip

found 6 days ago

Select United flight, departing Sat, Oct 11 from San Francisco Intl. to O'Hare Intl., returning Wed, Oct 15, priced at $242 found 6 days ago

Sat, Oct 11 - Wed, Oct 15

SFO

San Francisco Intl.

ORD

O'Hare Intl.

$245 Roundtrip, found 6 days ago

$245

Roundtrip

found 6 days ago

Select Alaska Airlines flight, departing Sat, Oct 11 from San Francisco Intl. to O'Hare Intl., returning Wed, Oct 15, priced at $245 found 6 days ago

Thu, Nov 20 - Mon, Nov 24

SFO

San Francisco Intl.

ORD

O'Hare Intl.

$246 Roundtrip, found 3 days ago

$246

Roundtrip

found 3 days ago

Select United flight, departing Thu, Nov 20 from San Francisco Intl. to O'Hare Intl., returning Mon, Nov 24, priced at $246 found 3 days ago

Thu, Nov 20 - Mon, Nov 24

SFO

San Francisco Intl.

ORD

O'Hare Intl.

$248 Roundtrip, found 3 days ago

$248

Roundtrip

found 3 days ago

Select United flight, departing Thu, Nov 20 from San Francisco Intl. to O'Hare Intl., returning Mon, Nov 24, priced at $248 found 3 days ago

Tue, Aug 19 - Tue, Aug 26

SFO

San Francisco Intl.

ORD

O'Hare Intl.

$249 Roundtrip, found 4 days ago

$249

Roundtrip

found 4 days ago

Select Hawaiian Airlines flight, departing Tue, Aug 19 from San Francisco Intl. to O'Hare Intl., returning Tue, Aug 26, priced at $249 found 4 days ago

Tue, Nov 18 - Mon, Nov 24

SFO

San Francisco Intl.

ORD

O'Hare Intl.

$257 Roundtrip, found 3 days ago

$257

Roundtrip

found 3 days ago

Select Delta flight, departing Tue, Nov 18 from San Francisco Intl. to O'Hare Intl., returning Mon, Nov 24, priced at $257 found 3 days ago

Mon, Jul 28 - Wed, Jul 30

SFO

San Francisco Intl.

MDW

Midway Intl.

$401 Roundtrip, found 6 days ago

$401

Roundtrip

found 6 days ago

Select Frontier Airlines flight, departing Mon, Jul 28 from San Francisco Intl. to Midway Intl., returning Wed, Jul 30, priced at $401 found 6 days ago

Sat, Nov 22 - Mon, Dec 1

SFO

San Francisco Intl.

ORD

O'Hare Intl.

$417 Roundtrip, found 4 days ago

$417

Roundtrip

found 4 days ago

Select Sun Country Airlines flight, departing Sat, Nov 22 from San Francisco Intl. to O'Hare Intl., returning Mon, Dec 1, priced at $417 found 4 days ago

Sat, Nov 22 - Mon, Dec 1

SFO

San Francisco Intl.

ORD

O'Hare Intl.

$987 Roundtrip, found 4 days ago

$987

Roundtrip

found 4 days ago

Select JetBlue Airways flight, departing Sat, Nov 22 from San Francisco Intl. to O'Hare Intl., returning Mon, Dec 1, priced at $987 found 4 days ago