$156 Cheap flight deals from Chicago (CHI) to Seaside (MRY)

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This Weekend's Flight Deals from Chicago to Seaside

This weekend's flight prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.

Sun, Apr 5 - Wed, Apr 8
ORD
O'Hare Intl.
MRY
Monterey Peninsula
$524 Roundtrip, found 4 days ago
$524
Roundtrip
found 4 days ago
Select Alaska Airlines flight, departing Sun, Apr 5 from O'Hare Intl. to Monterey Peninsula, returning Wed, Apr 8, priced at $524 found 4 days ago

Airfares from $156 One Way, $302 Round Trip from Chicago to Seaside

Prices starting at $302 for return flights and $156 for one-way flights to Seaside were the cheapest prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.

Sat, Apr 25 - Wed, Apr 29
ORD
Chicago
MRY
Monterey
$302 Roundtrip, found 3 days ago
$302
Roundtrip
found 3 days ago
Select Alaska Airlines flight, departing Sat, Apr 25 from Chicago to Monterey, returning Wed, Apr 29, priced at $302 found 3 days ago
Tue, Apr 7 - Tue, Apr 14
ORD
Chicago
MRY
Monterey
$317 Roundtrip, found 2 days ago
$317
Roundtrip
found 2 days ago
Select Alaska Airlines flight, departing Tue, Apr 7 from Chicago to Monterey, returning Tue, Apr 14, priced at $317 found 2 days ago
Sat, Apr 25 - Wed, Apr 29
ORD
Chicago
MRY
Monterey
$323 Roundtrip, found 3 days ago
$323
Roundtrip
found 3 days ago
Select Alaska Airlines flight, departing Sat, Apr 25 from Chicago to Monterey, returning Wed, Apr 29, priced at $323 found 3 days ago
Sat, Apr 25 - Wed, Apr 29
ORD
Chicago
MRY
Monterey
$324 Roundtrip, found 3 days ago
$324
Roundtrip
found 3 days ago
Select Alaska Airlines flight, departing Sat, Apr 25 from Chicago to Monterey, returning Wed, Apr 29, priced at $324 found 3 days ago
Sat, Apr 25 - Wed, Apr 29
ORD
Chicago
MRY
Monterey
$328 Roundtrip, found 3 days ago
$328
Roundtrip
found 3 days ago
Select American Airlines flight, departing Sat, Apr 25 from Chicago to Monterey, returning Wed, Apr 29, priced at $328 found 3 days ago

Seaside economy flight packages

Price found within the past 48 hours. Click for updated prices.
Carmel Mission Inn
3.5-star property

Carmel Mission Inn

8.8/10 Excellent! (1,743 reviews)

May 13 - May 16

3 night stay

Chicago (CHI) to Monterey (MRY)

American Airlines • Non-stop roundtrip • Coach
Price was $780, price is now $643 per person
$643
per person
found 20 hours ago
A little over priced for the property. Walls a are paper thin, and they nickel and dime you the etire way.

Reviewed on Jul 28, 2025

Carmel Inn And Suites
2.5-star property

Carmel Inn And Suites

7.6/10 Good! (1,004 reviews)

Apr 27 - May 2

5 night stay

Chicago (CHI) to Monterey (MRY)

United • Non-stop roundtrip • Coach
Price was $929, price is now $830 per person
$830
per person
found 15 hours ago
The room had inadequate lighting. Too dark to read. The breakfast was not good. In a town with excellent bakeries, fresh pastry and fruit and some decent coffee would have been far preferable to the bad coffee, cereal and granola bars we got. The TV was old and had no APPs available. A bit more attention to detail could elevate this hotel without much effort.

Reviewed on Feb 3, 2024

Alila Ventana Big Sur
4.5-star property

Alila Ventana Big Sur

9/10 Wonderful! (338 reviews)

May 13 - May 16

3 night stay

Chicago (CHI) to Monterey (MRY)

American Airlines • Non-stop roundtrip • Coach
Save 100% on your flight
Price was $5,080, price is now $4,126 per person
$4,126
per person
found 20 hours ago
Return visit to enjoy Big Sur and celebrate my Birthday. Front desk show genuine interest to make certain your stay is exceptional. Kudos to Amanda among others. Among the many positives, we signed up for the photography hike with Alfonso. He is multitalented with an excellent understanding of photography and ability to communicate that knowledge. Fantastic-we learned more practical tips that have stepped up the quality of our shots and editing.

Reviewed on Jun 23, 2016

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More About Flying To Seaside from Chicago

Route Information for Flights from Chicago to Seaside

Origin Airport IATA Code
CHI
Destination Airport IATA Code
MRY
Distance
Direct Flight Airlines
Earliest Flight Arrival
Latest Flight Arrival

Chicago to Seaside

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Fare, taxes & fees: Fares include all taxes and fees, except baggage fees. Rates shown reflect fares found by other Orbitz users over the past 7 days. Due to rapidly changing airline prices & seat availability, these fares may no longer be available.

Refunds/changes/cancellations: Itinerary changes, if permitted for the fare, will have a $30 service fee charged by Orbitz. Additional airline charges may apply.

Other conditions: Schedules, fares and rules are subject to change without notice. Seats are limited and may not be available on all flights/dates or in all markets. Lower fares may be available. Fares will not be honored retroactively or in exchange for any wholly/partially unused ticket. Tickets are non-transferable and non-refundable. Fare rules are provided for the selected itinerary before booking.