$129 Cheap Flights from Monterey (MRY) to Chicago (ORD)

View $129 flight on Tue, Dec 16, 2025Opens in a new window

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

  • notification illustration

    Be in the know

    Get alerts if flight prices drop or rise*
  • deals illustration

    Book smarter

    Save up to 30% on select hotels after you book a flight*
  • trophy illustration

    Earn twice

    Earn your airline miles on top of our OneKeyCash
    Learn about One Key

Cheap Flights from Monterey to Chicago (MRY-ORD)

Prices were available within the past 7 days and start at $129 for one-way flights and $242 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Hawaiian Airlines
Wed, Jan 7 - Tue, Jan 20
MRY
Monterey
ORD
Chicago
$242 Roundtrip, found 2 days ago
$242
Roundtrip
found 2 days ago
Select Hawaiian Airlines flight, departing Wed, Jan 7 from Monterey to Chicago, returning Tue, Jan 20, priced at $242 found 2 days ago
Bargain Flight
Sat, Feb 21 - Sat, Feb 28
MRY
Monterey
ORD
Chicago
$246 Roundtrip, found 2 hours ago
$246
Roundtrip
found 2 hours ago
Select Bargain Flight flight, departing Sat, Feb 21 from Monterey to Chicago, returning Sat, Feb 28, priced at $246 found 2 hours ago
Hawaiian Airlines
Fri, Dec 12 - Tue, Dec 16
MRY
Monterey
ORD
Chicago
$250 Roundtrip, found 1 day ago
$250
Roundtrip
found 1 day ago
Select Hawaiian Airlines flight, departing Fri, Dec 12 from Monterey to Chicago, returning Tue, Dec 16, priced at $250 found 1 day ago
Hawaiian Airlines
Wed, Jan 7 - Mon, Jan 19
MRY
Monterey
ORD
Chicago
$252 Roundtrip, found 2 days ago
$252
Roundtrip
found 2 days ago
Select Hawaiian Airlines flight, departing Wed, Jan 7 from Monterey to Chicago, returning Mon, Jan 19, priced at $252 found 2 days ago
Bargain Flight
Sat, Dec 13 - Tue, Dec 16
MRY
Monterey
ORD
Chicago
$258 Roundtrip, found 1 day ago
$258
Roundtrip
found 1 day ago
Select Bargain Flight flight, departing Sat, Dec 13 from Monterey to Chicago, returning Tue, Dec 16, priced at $258 found 1 day ago
American Airlines
Thu, Jan 29 - Tue, Feb 3
MRY
Monterey
ORD
Chicago
$258 Roundtrip, found 9 hours ago
$258
Roundtrip
found 9 hours ago
Select American Airlines flight, departing Thu, Jan 29 from Monterey to Chicago, returning Tue, Feb 3, priced at $258 found 9 hours ago
United
Thu, Jan 29 - Tue, Feb 3
MRY
Monterey
ORD
Chicago
$259 Roundtrip, found 9 hours ago
$259
Roundtrip
found 9 hours ago
Select United flight, departing Thu, Jan 29 from Monterey to Chicago, returning Tue, Feb 3, priced at $259 found 9 hours ago
American Airlines
Tue, Jan 27 - Tue, Feb 3
MRY
Monterey
ORD
Chicago
$260 Roundtrip, found 10 hours ago
$260
Roundtrip
found 10 hours ago
Select American Airlines flight, departing Tue, Jan 27 from Monterey to Chicago, returning Tue, Feb 3, priced at $260 found 10 hours ago
Alaska Airlines
Sat, Dec 13 - Tue, Dec 16
MRY
Monterey
ORD
Chicago
$262 Roundtrip, found 1 day ago
$262
Roundtrip
found 1 day ago
Select Alaska Airlines flight, departing Sat, Dec 13 from Monterey to Chicago, returning Tue, Dec 16, priced at $262 found 1 day ago
American Airlines
Tue, Dec 30 - Mon, Jan 5
MRY
Monterey
ORD
Chicago
$263 Roundtrip, found 23 hours ago
$263
Roundtrip
found 23 hours ago
Select American Airlines flight, departing Tue, Dec 30 from Monterey to Chicago, returning Mon, Jan 5, priced at $263 found 23 hours ago

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

October is typically the cheapest month to fly

From $252 - $503 per traveler.

Alternative airports near Chicago

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

Select flight to Midway Intl. MDW. Closest option available. Average driving time to city center is 16 minutes. Flights from $1,636
MDW
Midway Intl.
Closest
Average driving time to city center16 min
Flights from $1,636
Flights from Monterey (MRY) to Chicago (ORD)
Origin airport
Monterey Peninsula
Destination airport
O'Hare Intl.
Airlines serving
Alaska Airlines, American Airlines, Hawaiian Airlines, United
Roundtrip price
$242
Distance
1840 mi

Monterey to Chicago Flights

The cheapest times to fly from Monterey to Chicago

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 Monterey to Chicago are during the month of January. You can find some of the cheapest flights from Monterey to Chicago with Expedia's search tool and vast selection of airlines.

 

The best time to book a flight from Monterey to Chicago

Sunday is one of the best days to book for cheap flights from Monterey to Chicago: 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 Monterey to Chicago

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 Monterey to Chicago in 2025. You can also book with separate airlines for your outbound and return journeys, from $129 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 Monterey to Chicago 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 Monterey to Chicago 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.

 

Frequently asked questions

How much does a flight from Monterey Peninsula Airport (MRY) to O'Hare Intl. Airport (ORD) cost?
Secure a cheap one-way flight from $129 or cheap return flight from $242 from Monterey Peninsula Airport (MRY) to O'Hare Intl. Airport (ORD) with Expedia. Enter your travel dates and sort by "Price (lowest to highest)" to see our cheapest flight offers on this route.
What is the cheapest month to fly from Monterey Peninsula Airport (MRY) to O'Hare Intl. Airport (ORD)?
The cheapest month to fly from MRY to ORD is January, when there's less demand. Off-peak months are generally when airlines offer lower prices between these airports.
Which airlines fly direct from Monterey Peninsula Airport (MRY) to O'Hare Intl. Airport (ORD)?
There are no direct flights from Monterey, CA (MRY-Monterey Peninsula) to O'Hare Intl. Airport (ORD). However, you'll find other airports that have nonstop flights. Begin your journey at Norman Y. Mineta San Jose Intl. Airport (SJC) and travel straight to Chicago without layovers.
What is the cheapest airline that flies from Monterey Peninsula Airport (MRY) to O'Hare Intl. Airport (ORD)?
To find the cheapest airline flying from MRY to ORD, use Expedia's filter tool. Customize your search based on what's important to you, such as preferred carriers and flight duration. You can then sort your results by "Price (lowest to highest)" to discover the cheapest flight right away.
How many flights per day from Monterey Peninsula Airport (MRY) to O'Hare Intl. Airport (ORD)?
Direct flights from Monterey Peninsula Airport (MRY) to O'Hare Intl. Airport (ORD) aren't available daily, so you'll have to take a flight with a layover. Explore your options with Expedia's filter tool. Enter your travel dates and click on either "1 Stop" or "2+ Stops."
What day of the week has the most flights from MRY to ORD?
Generally you'll find the most flight options available on a Friday. Tuesdays are often the quietest.* However, this can change based on the time of year, carrier and other factors.*Busiest/quietest day to travel is based on Expedia flight demand through January to December 2024.
What is the best time to fly from Monterey Peninsula Airport (MRY) to O'Hare Intl. Airport (ORD)?
To avoid possible delays on the Monterey Peninsula Airport (MRY) to O'Hare Intl. Airport (ORD) route, aim to travel before 3 PM. Departures after this time have a 22% higher chance of cancellation.**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.
Is it cheaper to buy a plane ticket from Monterey Peninsula Airport (MRY) to O'Hare Intl. Airport (ORD) last-minute?
Waiting until just before your departure to book your flight from MRY to ORD generally means paying more. While you may come across some last-minute offers, they aren't always guaranteed. Be flexible with your itinerary for a better chance of getting a bargain.
Is it cheaper to book a MRY to ORD flight and hotel package?
Booking a MRY to ORD flight and hotel package tends to be cheaper than booking separately. With Expedia, you can enjoy the ease of organizing your travels all in one place. Pick from our wide range of hotels and then add activities, car rentals and flights to your booking. Bundle everything together, and you could save hundreds of dollars.
Can I cancel or change the date of my flight from Monterey Peninsula Airport (MRY) to O'Hare Intl. Airport (ORD)?
In most instances, you're able to cancel or reschedule your MRY to ORD flight. However, there may be additional fees, especially if you booked over 24 hours ago. Check your itinerary for the airline's rules and fees on flight changes, or if you'd like further details, visit our Customer Service portal.

Explore a world of travel with Expedia

*Available to One Key members.