$156 Cheap Flights from Chicago (ORD) to Monterey (MRY)

View $156 flight on Wed, May 28, 2025Opens in a new window

  • Plan, book, fly with confidence

  • trending down icon
    Be in the know
    Get alerts if flight prices drop or rise*
  • bex rewards loyalty icon
    Book smarter
    Save up to 30% on select hotels after you book a flight*
  • one key icon
    Earn twice
    Earn your airline miles on top of our OneKeyCash
    Learn about One Key
Find available prices by choosing your travel dates.

Cheap Flights from Chicago to Monterey (ORD-MRY)

Prices were available within the past 7 days and start at $156 for one-way flights and $335 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Hawaiian Airlines
Tue, Jun 3 - Tue, Jun 10
ORD
Chicago
MRY
Monterey
$335 Roundtrip, found 6 hours ago
$335
Roundtrip
found 6 hours ago
Select Hawaiian Airlines flight, departing Tue, Jun 3 from Chicago to Monterey, returning Tue, Jun 10, priced at $335 found 6 hours ago
Hawaiian Airlines
Tue, May 27 - Wed, May 28
ORD
Chicago
MRY
Monterey
$340 Roundtrip, found 2 days ago
$340
Roundtrip
found 2 days ago
Select Hawaiian Airlines flight, departing Tue, May 27 from Chicago to Monterey, returning Wed, May 28, priced at $340 found 2 days ago
Alaska Airlines
Sat, Jun 7 - Wed, Jun 11
ORD
Chicago
MRY
Monterey
$345 Roundtrip, found 1 day ago
$345
Roundtrip
found 1 day ago
Select Alaska Airlines flight, departing Sat, Jun 7 from Chicago to Monterey, returning Wed, Jun 11, priced at $345 found 1 day ago
American Airlines
Wed, May 28 - Sat, May 31
ORD
Chicago
MRY
Monterey
$345 Roundtrip, found 3 hours ago
$345
Roundtrip
found 3 hours ago
Select American Airlines flight, departing Wed, May 28 from Chicago to Monterey, returning Sat, May 31, priced at $345 found 3 hours ago
Alaska Airlines
Fri, May 30 - Tue, Jun 3
ORD
Chicago
MRY
Monterey
$349 Roundtrip, found 5 days ago
$349
Roundtrip
found 5 days ago
Select Alaska Airlines flight, departing Fri, May 30 from Chicago to Monterey, returning Tue, Jun 3, priced at $349 found 5 days ago
Alaska Airlines
Tue, May 27 - Fri, May 30
ORD
Chicago
MRY
Monterey
$350 Roundtrip, found 4 hours ago
$350
Roundtrip
found 4 hours ago
Select Alaska Airlines flight, departing Tue, May 27 from Chicago to Monterey, returning Fri, May 30, priced at $350 found 4 hours ago
Hawaiian Airlines
Sat, Jun 7 - Mon, Jun 9
ORD
Chicago
MRY
Monterey
$355 Roundtrip, found 6 hours ago
$355
Roundtrip
found 6 hours ago
Select Hawaiian Airlines flight, departing Sat, Jun 7 from Chicago to Monterey, returning Mon, Jun 9, priced at $355 found 6 hours ago
American Airlines
Thu, May 29 - Mon, Jun 2
ORD
Chicago
MRY
Monterey
$359 Roundtrip, found 5 days ago
$359
Roundtrip
found 5 days ago
Select American Airlines flight, departing Thu, May 29 from Chicago to Monterey, returning Mon, Jun 2, priced at $359 found 5 days ago
Alaska Airlines
Sat, May 17 - Sat, May 24
ORD
Chicago
MRY
Monterey
$362 Roundtrip, found 6 days ago
$362
Roundtrip
found 6 days ago
Select Alaska Airlines flight, departing Sat, May 17 from Chicago to Monterey, returning Sat, May 24, priced at $362 found 6 days ago
United
Wed, Jun 4 - Mon, Jun 16
ORD
Chicago
MRY
Monterey
$386 Roundtrip, found 3 days ago
$386
Roundtrip
found 3 days ago
Select United flight, departing Wed, Jun 4 from Chicago to Monterey, returning Mon, Jun 16, priced at $386 found 3 days ago

Frequently asked questions

How much does a flight from O'Hare Intl. Airport (ORD) to Monterey Peninsula Airport (MRY) cost?
Discover the latest flight deals from ORD to MRY by entering your preferred travel dates and searching on Expedia. Easily compare prices by departure date if you have flexibility with your schedule and use handy filters to explore prices for your preferred journey. As a member of One Key™, our free loyalty program, you can use Price Tracking to watch fares and receive notifications if prices go up or down.
What is the cheapest month to fly from ORD to MRY?
The cheapest flights from ORD to MRY are usually during off-peak season, when demand is lower. To save money, avoid flying during public holidays, school breaks and major local events.
What is the cheapest airline that flies from ORD to MRY?
Use the filter tool on Expedia to compare airlines and find the cheapest carrier that’ll take you from ORD to MRY. Sort your results by “Price (lowest to highest)” to snap up a great deal.
How many flights per day from O'Hare Intl. Airport (ORD) to Monterey Peninsula Airport (MRY)?
There are no daily nonstop flights available from O’Hare Intl. Airport (ORD) to Monterey Peninsula Airport (MRY). But you can choose flights with layovers. Filter your search on Expedia to include one or more stops, and you’ll be soaring above the clouds in no time.
What day of the week has the most flights from ORD to MRY?
You’ll usually find Tuesday the quietest day for flights, while Fridays tend to be the busiest.* However this can change from season to season and during public holidays or peak travel times.*Busiest/quietest day to travel is based on Expedia flight demand through January to December 2024.
What is the best time to fly from O'Hare Intl. Airport (ORD) to Monterey Peninsula Airport (MRY)?
To avoid potential delays on the O’Hare Intl. Airport (ORD) to Monterey Peninsula Airport (MRY) route, travel before 3 PM. Later departures are 22% more likely to be canceled.**Most reliable time of the day and month to travel recommendation is based on January through August 2024 flight status data sourced from OAG’s global flight data platform.
What airports do you fly into for Monterey from O'Hare Intl. Airport (ORD)?
Norman Y. Mineta San Jose Intl. Airport (SJC) is the only airport in Monterey with direct flights from O’Hare Intl. Airport (ORD). Browse the options and find cheap fares on Expedia.
Is it cheaper to buy a plane ticket from O'Hare Intl. Airport (ORD) to Monterey Peninsula Airport (MRY) last-minute?
Last-minute fares from ORD to MRY are generally more expensive. To secure the lowest rates, start looking for flights as soon as possible. That said, if you’re flexible with your travel plans, it’s possible to find a cheap ticket right before you leave.
Is it cheaper to book an ORD to MRY flight and hotel package?
You’ll typically save money by booking an ORD to MRY flight and hotel package compared to booking separately. In fact, travelers could save hundreds of dollars by bundling with Expedia. And it’s easy to manage it all in one convenient place. Once you’ve chosen your ideal accommodations and flights, consider adding extras including tours, car rentals and activities.
Can I cancel or change the date of my flight from O'Hare Intl. Airport (ORD) to Monterey Peninsula Airport (MRY)?
If you reserved your ORD to MRY flight within the last 24 hours, you may be able to modify or cancel it without fees. Depending on the airline and the fare type you purchased, additional charges may apply for changes beyond this timeframe. Airline policies and contact information can be found in your itinerary or confirmation email. Or, go to our Customer Service portal if you want more information.
*Available to One Key members.