$149 Cheap Flights from Chicago (ORD) to Monterey (MRY)

View $149 flight on Tue, Feb 3, 2026Opens in a new window

Popular airlines from Chicago O'Hare Intl. Airport (ORD) to Monterey Peninsula Airport (MRY)

Cheap Flights from Chicago to Monterey (ORD-MRY)

Prices were available within the past 7 days and start at $149 for one-way flights and $260 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

American Airlines
Mon, Jan 5 - Tue, Jan 6
ORD
Chicago
MRY
Monterey
$260 Roundtrip, found 5 days ago
$260
Roundtrip
found 5 days ago
Select American Airlines flight, departing Mon, Jan 5 from Chicago to Monterey, returning Tue, Jan 6, priced at $260 found 5 days ago
Hawaiian Airlines
Wed, Jan 7 - Fri, Jan 9
ORD
Chicago
MRY
Monterey
$260 Roundtrip, found 5 days ago
$260
Roundtrip
found 5 days ago
Select Hawaiian Airlines flight, departing Wed, Jan 7 from Chicago to Monterey, returning Fri, Jan 9, priced at $260 found 5 days ago
American Airlines
Mon, Jan 5 - Tue, Jan 6
ORD
Chicago
MRY
Monterey
$263 Roundtrip, found 5 days ago
$263
Roundtrip
found 5 days ago
Select American Airlines flight, departing Mon, Jan 5 from Chicago to Monterey, returning Tue, Jan 6, priced at $263 found 5 days ago
Hawaiian Airlines
Wed, Dec 3 - Thu, Dec 11
ORD
Chicago
MRY
Monterey
$269 Roundtrip, found 6 days ago
$269
Roundtrip
found 6 days ago
Select Hawaiian Airlines flight, departing Wed, Dec 3 from Chicago to Monterey, returning Thu, Dec 11, priced at $269 found 6 days ago
Hawaiian Airlines
Sat, Dec 13 - Tue, Dec 16
ORD
Chicago
MRY
Monterey
$278 Roundtrip, found 2 days ago
$278
Roundtrip
found 2 days ago
Select Hawaiian Airlines flight, departing Sat, Dec 13 from Chicago to Monterey, returning Tue, Dec 16, priced at $278 found 2 days ago
Hawaiian Airlines
Sat, Dec 13 - Wed, Jan 7
ORD
Chicago
MRY
Monterey
$280 Roundtrip, found 4 days ago
$280
Roundtrip
found 4 days ago
Select Hawaiian Airlines flight, departing Sat, Dec 13 from Chicago to Monterey, returning Wed, Jan 7, priced at $280 found 4 days ago
Hawaiian Airlines
Wed, Jan 7 - Sat, Jan 17
ORD
Chicago
MRY
Monterey
$290 Roundtrip, found 3 days ago
$290
Roundtrip
found 3 days ago
Select Hawaiian Airlines flight, departing Wed, Jan 7 from Chicago to Monterey, returning Sat, Jan 17, priced at $290 found 3 days ago
Alaska Airlines
Wed, Jan 21 - Sun, Jan 25
ORD
Chicago
MRY
Monterey
$291 Roundtrip, found 5 days ago
$291
Roundtrip
found 5 days ago
Select Alaska Airlines flight, departing Wed, Jan 21 from Chicago to Monterey, returning Sun, Jan 25, priced at $291 found 5 days ago
Hawaiian Airlines
Wed, Jan 7 - Fri, Jan 23
ORD
Chicago
MRY
Monterey
$292 Roundtrip, found 3 days ago
$292
Roundtrip
found 3 days ago
Select Hawaiian Airlines flight, departing Wed, Jan 7 from Chicago to Monterey, returning Fri, Jan 23, priced at $292 found 3 days ago
United
Mon, Mar 2 - Fri, Mar 6
ORD
Chicago
MRY
Monterey
$293 Roundtrip, found 5 days ago
$293
Roundtrip
found 5 days ago
Select United flight, departing Mon, Mar 2 from Chicago to Monterey, returning Fri, Mar 6, priced at $293 found 5 days ago

Find the cheapest month to fly from Chicago (ORD) to Monterey (MRY)

October is typically the cheapest month to fly

From $230 - $691 per traveler.

Alternative airports near Monterey

Prices were available within the past 7 days. Prices and availability are subject to change.

Select flight to Monterey Peninsula MRY. Cheapest and Closest option available. Average driving time to city center is 6 minutes. Flights from $539
MRY
Monterey Peninsula
CheapestClosest
Average driving time to city center6 min
Flights from $539

Frequently asked questions

How much does a flight from O'Hare Intl. Airport (ORD) to Monterey Peninsula Airport (MRY) cost?
Lock in a cheap one-way flight from $149 or cheap return flight from $260 from O'Hare Intl. Airport (ORD) to Monterey Peninsula Airport (MRY) with Expedia. Enter your travel dates and sort by "Price (lowest to highest)" to find our cheapest flight offers on this route.
What is the cheapest month to fly from O'Hare Intl. Airport (ORD) to Monterey Peninsula Airport (MRY)?
Flying in January is a great way to save, as it's the cheapest month for flights between ORD and MRY. You'll typically find the lowest prices during off-peak months.
What is the cheapest airline that flies from O'Hare Intl. Airport (ORD) to Monterey Peninsula Airport (MRY)?
Use the filter tool on Expedia to compare airlines and find the cheapest carrier that'll fly you from ORD to MRY. Then, sort your results by "Price (lowest to highest)" to pick 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.

Travel information

Origin airport
O'Hare Intl.
Destination airport
Monterey Peninsula
Airlines serving
Alaska Airlines, American Airlines, Hawaiian Airlines, United
Roundtrip price
$260
Distance
1840 mi

Book with confidence

Chicago to Monterey Flights

The cheapest times to fly from Chicago to Monterey

On average, Thursday can be the cheapest time to fly, according to data from the Airlines Reporting Corporation (ARC), one of the world's biggest databases for global airline sales. The data reveals that you could save up to 16% by flying on a Thursday—the cheapest day to travel on average—instead of a Sunday—the most expensive. Some of the most affordable flights from Chicago to Monterey are during the month of January. You can find some of the cheapest flights from Chicago to Monterey with Expedia's search tool and vast selection of airlines.

 

The best time to book a flight from Chicago to Monterey

Sunday is one of the best days to book for cheap flights from Chicago to Monterey: Tickets reserved on a Sunday cost between 6% and 13% less than those reserved on a Friday, according to ARC data. The data also suggests booking early can also lead to cheaper airfares. You could save 24% by buying your tickets for domestic flights at least a month in advance and 10% by booking international flights 2 months in advance.

 

How to find cheap round-trip tickets from Chicago to Monterey

Being flexible with your dates and using Expedia's Price Drop Protection and Price Tracking features are some of the best ways of finding a cheap ticket from Chicago to Monterey in 2025. You can also book with separate airlines for your outbound and return journeys, from $149 one-way. Expedia also offers Price Drop Protection, so if the cost of your airfare goes down after booking, you'll receive a credit for the difference*. This is available for a small fee, and is free to One Key Gold and Platinum tier members.

 

Expedia's Price Tracking feature means you can stay on top of airfares without manually checking every day. It sends you automated price alerts for cheap Chicago to Monterey flights and uses historical data to indicate when the best time to book is. Download Expedia's free app to activate this handy tool in a few easy taps.

 

You could also save big by booking one of Expedia's vacation packages. Bundling together your Chicago to Monterey airfare with your accommodations and car rental is often cheaper than booking everything separately. There’s also One Key, Expedia's generous rewards program. Join for free and you could earn One Key cash on most bookings to save on future adventures.

 

*Terms apply.

 

Disclaimer: ARC The statistics are based on average round-trip ticket prices between January and August 2023. The percentages you see are averages.

 

Chicago to Monterey Flights

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*Available to One Key members.