$533 Cheap Flights from Chicago (MDW) to Monterey (MRY)

View $533 flight on Wed, Nov 5, 2025Opens in a new window

Popular airlines from Chicago Midway Airport (MDW) to Monterey Peninsula Airport (MRY)

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Cheap Flights from Chicago to Monterey (MDW-MRY)

Prices were available within the past 7 days and start at $533 for one-way flights and $1,000 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Delta
Mon, Feb 9 - Fri, Feb 13
MDW
Chicago
MRY
Monterey
$1,000 Roundtrip, found 3 days ago
$1,000
Roundtrip
found 3 days ago
Select Delta flight, departing Mon, Feb 9 from Chicago to Monterey, returning Fri, Feb 13, priced at $1,000 found 3 days ago
Delta
Mon, Feb 9 - Fri, Feb 13
MDW
Chicago
MRY
Monterey
$1,078 Roundtrip, found 3 days ago
$1,078
Roundtrip
found 3 days ago
Select Delta flight, departing Mon, Feb 9 from Chicago to Monterey, returning Fri, Feb 13, priced at $1,078 found 3 days ago
Delta
Mon, Feb 9 - Fri, Feb 13
MDW
Chicago
MRY
Monterey
$1,095 Roundtrip, found 3 days ago
$1,095
Roundtrip
found 3 days ago
Select Delta flight, departing Mon, Feb 9 from Chicago to Monterey, returning Fri, Feb 13, priced at $1,095 found 3 days ago
Delta
Sat, Jan 17 - Mon, Jan 26
MDW
Chicago
MRY
Monterey
$1,143 Roundtrip, found 4 days ago
$1,143
Roundtrip
found 4 days ago
Select Delta flight, departing Sat, Jan 17 from Chicago to Monterey, returning Mon, Jan 26, priced at $1,143 found 4 days ago
Delta
Sat, Jan 17 - Mon, Jan 26
MDW
Chicago
MRY
Monterey
$1,153 Roundtrip, found 4 days ago
$1,153
Roundtrip
found 4 days ago
Select Delta flight, departing Sat, Jan 17 from Chicago to Monterey, returning Mon, Jan 26, priced at $1,153 found 4 days ago
Delta
Mon, Feb 9 - Fri, Feb 13
MDW
Chicago
MRY
Monterey
$1,173 Roundtrip, found 3 days ago
$1,173
Roundtrip
found 3 days ago
Select Delta flight, departing Mon, Feb 9 from Chicago to Monterey, returning Fri, Feb 13, priced at $1,173 found 3 days ago
Delta
Mon, Feb 9 - Fri, Feb 13
MDW
Chicago
MRY
Monterey
$1,175 Roundtrip, found 3 days ago
$1,175
Roundtrip
found 3 days ago
Select Delta flight, departing Mon, Feb 9 from Chicago to Monterey, returning Fri, Feb 13, priced at $1,175 found 3 days ago
Delta
Thu, Nov 6 - Sat, Nov 8
MDW
Chicago
MRY
Monterey
$1,194 Roundtrip, found 3 days ago
$1,194
Roundtrip
found 3 days ago
Select Delta flight, departing Thu, Nov 6 from Chicago to Monterey, returning Sat, Nov 8, priced at $1,194 found 3 days ago
Delta
Sat, Jan 17 - Mon, Jan 26
MDW
Chicago
MRY
Monterey
$1,200 Roundtrip, found 4 days ago
$1,200
Roundtrip
found 4 days ago
Select Delta flight, departing Sat, Jan 17 from Chicago to Monterey, returning Mon, Jan 26, priced at $1,200 found 4 days ago
Delta
Sat, Jan 17 - Mon, Jan 26
MDW
Chicago
MRY
Monterey
$1,202 Roundtrip, found 4 days ago
$1,202
Roundtrip
found 4 days ago
Select Delta flight, departing Sat, Jan 17 from Chicago to Monterey, returning Mon, Jan 26, priced at $1,202 found 4 days ago

Frequently asked questions

How much does a flight from Midway Intl. Airport (MDW) to Monterey Peninsula Airport (MRY) cost?
Snag a cheap one-way flight from $533 or cheap return flight from $1,000 from Midway Intl. Airport (MDW) to Monterey Peninsula Airport (MRY) with Expedia. Enter your travel dates and sort by "Price (lowest to highest)" to see our cheapest flight deals on this route.
What is the cheapest month to fly from Midway Intl. Airport (MDW) to Monterey Peninsula Airport (MRY)?
Flying in February may help you find better deals, as it's the cheapest month for flights between MDW and MRY. You'll typically find the lowest fares during the off-season.
What is the cheapest airline that flies from Midway Intl. Airport (MDW) to Monterey Peninsula Airport (MRY)?
To find the cheapest airline that'll fly you from MDW to MRY, use Expedia's filter tool. Customize your search based on your travel style, such as preferred carriers and cabin class. You can then sort your results by "Price (lowest to highest)" to list the most affordable options first.
How many flights per day from Midway Intl. Airport (MDW) to Monterey Peninsula Airport (MRY)?
You'll have to take a flight with a layover when traveling from Midway Intl. Airport (MDW) to Monterey Peninsula Airport (MRY). Direct flights don't operate daily on this route. However, simply filter your search to include one or two stops to find an option that works for you.
What day of the week has the most flights from MDW to MRY?
Friday is usually the busiest day for flights, while Tuesday is often the quietest.* Keep in mind that flight schedules can vary depending on a number of factors, such as the time of year and carrier.*Busiest/quietest day to travel is based on Expedia flight demand through January to December 2024.
What is the best time to fly from Midway Intl. Airport (MDW) to Monterey Peninsula Airport (MRY)?
To touch down at Monterey Peninsula Airport (MRY) without delays, book a flight that leaves Midway Intl. Airport (MDW) before 3 PM. The chance of cancellations is 22% higher, on average, for departures after this time.**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 Midway Intl. Airport (MDW)?
Compare your flight options from Midway Intl. Airport (MDW) to Norman Y. Mineta San Jose Intl. Airport (SJC). This is the only Monterey airport you can arrive at if you're taking a direct flight.
Is it cheaper to buy a plane ticket from Midway Intl. Airport (MDW) to Monterey Peninsula Airport (MRY) last-minute?
Booking your flight from MDW to MRY shortly before your trip is typically more expensive. However, if there's some wiggle room with your travel dates and times, you could score a cheap last-minute fare.
Is it cheaper to book a MDW to MRY flight and hotel package?
Compared with arranging flights and hotels separately, booking a MDW to MRY flight and hotel package with Expedia could lead to significant savings. Better yet, having it all in one place takes the hassle out of planning your trip. Just pick your flights and select from our extensive range of stays, then personalize your trip with extras like tours and car rentals.
Can I cancel or change the date of my flight from Midway Intl. Airport (MDW) to Monterey Peninsula Airport (MRY)?
If you booked your MDW to MRY flight in the last 24 hours, you may be able to modify or cancel it without fees. Depending on the airline and the ticket type you purchased, additional charges may apply for changes beyond that time. Airline policies and contact information can be found in your itinerary or confirmation email. Or, visit our Customer Service portal if you want more information.

Travel information

Origin airport
Midway Intl.
Destination airport
Monterey Peninsula
Roundtrip price
$1,000
Distance
1848 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 February. 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 $533 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.