HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Monterey

$130+ Cheap flights from Chicago (CHI) to Monterey (MRY)

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 12/31. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — MRY
Nov 22 — Nov 291
Sat 11/22
Sat 11/29
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Chicago to Monterey with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

Cheap flight deals from Chicago to Monterey

Discover tips and strategies to find the most affordable flight options for your journey from Chicago (CHI) to Monterey (MRY). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated October 23, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$242
(Alaska Airlines)

One-way from

$130
(Alaska Airlines)

Popular in

March

Cheapest in

November

Average price

$463
Provider with most accurate pricing for Chicago (CHI)-Monterey Regional flight deals.
Search Deals
Provider most trusted by Cheapflights users for Chicago (CHI)-Monterey Regional flights.
Search Deals
From Chicago (CHI) to Monterey Regional
Search Deals
One-way flight from Chicago (CHI) to Monterey Regional
Search Deals
Highest demand for flights based on searches. 13% potential increase in price ($88 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 5% potential price decrease ($28 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in October 2025
Search Deals

Find flight deals from Chicago to Monterey

Cheapest flights from Chicago to Monterey
Explore the most affordable flight options available from Chicago to Monterey. Find the lowest fares from popular airlines and budget airlines, with prices last updated on October 23, 2025.

This American Airlines deal was found by Cheapflights users on 10/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/115:00 amORD - MRY
1 stop9h 41mAmerican Airlines
Wed 12/34:23 pmMRY - ORD
1 stop6h 08mAmerican Airlines
Deal found 10/21$261
This Alaska Airlines deal was found by Cheapflights users on 10/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/122:54 pmORD - MRY
1 stop10h 38mAlaska Airlines
Tue 12/211:23 amMRY - ORD
1 stop9h 07mAlaska Airlines
Deal found 10/22$289
This American Airlines deal was found by Cheapflights users on 10/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/125:00 amORD - MRY
1 stop9h 41mAmerican Airlines
Tue 12/212:31 pmMRY - ORD
1 stop7h 52mAmerican Airlines
Deal found 10/20$315
This Alaska Airlines deal was found by Cheapflights users on 10/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/192:54 pmORD - MRY
1 stop10h 38mAlaska Airlines
Sat 11/227:46 pmMRY - ORD
1 stop8h 42mAlaska Airlines
Deal found 10/23$339
This Alaska Airlines deal was found by Cheapflights users on 10/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/119:20 amORD - MRY
1 stop16h 12mAlaska Airlines
Wed 12/36:00 amMRY - ORD
2 stops22h 21mAlaska Airlines
Deal found 10/21$344
This United Airlines deal was found by Cheapflights users on 10/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/117:10 amORD - MRY
1 stop8h 14mUnited Airlines
Sun 11/162:30 pmMRY - ORD
1 stop8h 29mUnited Airlines
Deal found 10/21$351
This Orbitz deal was found by Cheapflights users on 10/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/182:54 pmORD - MRY
1 stop10h 38mAlaska Airlines
Mon 11/246:00 amMRY - ORD
1 stop15h 32mAlaska Airlines
Deal found 10/23$369
This United Airlines deal was found by Cheapflights users on 10/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/124:40 pmORD - MRY
1 stop6h 57mUnited Airlines
Tue 12/22:33 pmMRY - ORD
2 stops20h 38mUnited Airlines
Deal found 10/22$370

Cheapflights Fare Finder

 
Customize your flight search to find flights from Chicago to Monterey that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated October 23, 2025.
Use the filters below to find and compare flights from Chicago to Monterey that are best for you.

Fly from

Chicago

Fly to

Monterey

Route

Depart

Return

Price

ChicagoMonterey

ORD - MRY

ORDMRY

Chicago O'Hare Intl

Wed 2/25

7:45 am-11:25 pm

2 stops17h 40m

Monterey Regional

Wed 3/4

6:00 am-11:59 pm

2 stops15h 59m

$242

ChicagoMonterey

ORD - MRY

ORDMRY

Chicago O'Hare Intl

Wed 2/18

7:45 am-11:25 pm

2 stops17h 40m

Monterey Regional

Wed 2/25

6:00 am-11:59 pm

2 stops15h 59m

$242

ChicagoMonterey

ORD - MRY

ORDMRY

Chicago O'Hare Intl

Sun 1/11

9:00 am-2:37 pm

1 stop7h 37m

Monterey Regional

Sat 1/17

6:00 am-11:55 pm

2 stops15h 55m

$251

ChicagoMonterey

ORD - MRY

ORDMRY

Chicago O'Hare Intl

Tue 3/10

9:00 am-1:56 pm

1 stop6h 56m

Monterey Regional

Wed 3/11

2:40 pm-11:10 pm

1 stop6h 30m

$260

ChicagoMonterey

ORD - MRY

ORDMRY

Chicago O'Hare Intl

Tue 2/10

10:57 am-6:32 pm

1 stop9h 35m

Monterey Regional

Sun 2/15

4:29 pm-12:36 am

1 stop6h 07m

$260

ChicagoMonterey

ORD - MRY

ORDMRY

Chicago O'Hare Intl

Tue 3/10

7:45 am-1:35 pm

1 stop7h 50m

Monterey Regional

Wed 3/11

2:40 pm-11:10 pm

1 stop6h 30m

$260

ChicagoMonterey

ORD - MRY

ORDMRY

Chicago O'Hare Intl

Tue 11/11

7:00 am-12:41 pm

1 stop7h 41m

Monterey Regional

Wed 12/3

4:23 pm-12:31 am

1 stop6h 08m

$261

ChicagoMonterey

ORD - MRY

ORDMRY

Chicago O'Hare Intl

Wed 11/12

2:54 pm-11:32 pm

1 stop10h 38m

Monterey Regional

Tue 12/2

11:23 am-10:30 pm

1 stop9h 07m

$289

ChicagoMonterey

ORD - MRY

ORDMRY

Chicago O'Hare Intl

Wed 12/31

8:39 am-2:25 pm

1 stop7h 46m

$130

ChicagoMonterey

ORD - MRY

ORDMRY

Chicago O'Hare Intl

Thu 1/29

3:25 pm-11:26 pm

1 stop10h 01m

$130

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/20

Showing 1-10 of 18 results
1
2

Compare providers for flights from Chicago to Monterey

Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Chicago to Monterey in October.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy2 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars
eDreamsPrice Accuracy3 starsTrust Score*3 stars

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

  • Most accurate provider: When it comes to deals on Chicago-Monterey flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Chicago-Monterey flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Chicago-Monterey flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Chicago-Monterey flights, Cheapflights users trust FlightHub the most. FlightHub has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Chicago-Monterey flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

Best time to book a flight from Chicago to Monterey

Have a flexible travel schedule? Discover the best time to fly to Monterey from Chicago with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from Chicago to Monterey

What is the cheapest month to book a flight from Chicago to Monterey?

Currently, October is the cheapest month in which you can book a flight from Chicago to Monterey (average of $80). Flying from Chicago to Monterey in December is currently the most expensive (average of $207). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

What is the cheapest time of day to fly from CHI to MRY?

Find hourly flight availability from Chicago to Monterey. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated October 23, 2025.

One of the essential ways to save on airfare from Chicago to Monterey is to remain as flexible as possible. Flights that are in the evening tend to be the most expensive. A flight in the afternoon could potentially save you up to 60% on airfare.

Reviews of airlines servicing Monterey

Get insights into the airlines that provide service to Monterey. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Monterey. Reviews last updated October 23, 2025.
See what other customers who have flown with United Airlines and American Airlines from Chicago to Monterey have to say. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
United Airlines
7.4
Good
8,995 reviews

Comfort

7.3

Entertainment

7.1

Food

6.6

Crew

8.1

Overall

7.4

Boarding

7.7

Reviews

1 / 20
8.0
Excellent

Ruth,Dec 2024

ORD - AMS

United Airlines flights seem to always use a bus to/from the boarding gate to the plane. Can they not get their own gate? This time there was no lift when leaving the plane and people in wheelchairs somehow had to climb down the steps to the ground to get to the bus. I udon’t know how some managed that!
United Airlines
7.4
Good
8,995 reviews
United Airlines
7.4
Good
8,995 reviews

Comfort

7.3

Entertainment

7.1

Food

6.6

Crew

8.1

Overall

7.4

Boarding

7.7

Reviews

1 / 20
8.0
Excellent

Ruth,Dec 2024

ORD - AMS

United Airlines flights seem to always use a bus to/from the boarding gate to the plane. Can they not get their own gate? This time there was no lift when leaving the plane and people in wheelchairs somehow had to climb down the steps to the ground to get to the bus. I udon’t know how some managed that!
American Airlines
7.2
Good
11,032 reviews
United Airlines
7.4
Good
8,995 reviews

Comfort

7.3

Entertainment

7.1

Food

6.6

Crew

8.1

Overall

7.4

Boarding

7.7

Reviews

1 / 20
8.0
Excellent

Ruth,Dec 2024

ORD - AMS

United Airlines flights seem to always use a bus to/from the boarding gate to the plane. Can they not get their own gate? This time there was no lift when leaving the plane and people in wheelchairs somehow had to climb down the steps to the ground to get to the bus. I udon’t know how some managed that!

Related info for your journey

Find useful and relevant information for your journey from Chicago to Monterey. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What airport do you fly into for flights to Monterey from Chicago?

    Monterey Regional (MRY), located 3.2 mi from the city center, is the airport you fly into when you book flights from Chicago to Monterey. 2 airlines have flights to Monterey Regional from Chicago on a regular basis. Booking flights from Chicago to Monterey Regional should not be difficult; the airport handles an average of 0 inbound flights from Chicago per day.

  • How long is the flight from Chicago to Monterey?

    Airlines like Alaska Airlines fly from Chicago to Monterey in about 17h 40m. The time it takes to get you to your destination can typically vary by up to . Chicago and Monterey are separated by a distance of 1839 mi.

  • What are the cheapest airlines flying from Chicago to Monterey round-trip?

    Flying on American Airlines is currently your cheapest option to Monterey, with prices starting at $276. Another option worth looking into is United Airlines, starting at $358 round trip. American Airlines is 50% cheaper than the average price of flights available within the next 90 days to this destination.

  • Can I find deals for flights from Chicago to Monterey that include hotel bookings?

    Yes. In addition to deals on Chicago to Monterey flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Chicago to Monterey?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Chicago to Monterey.

  • Can I find deals for business class flights from Chicago to Monterey?

    Yes. Cheapflights offers flight deals from Chicago to Monterey by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Chicago to Monterey?

    Currently, October is the cheapest month in which you can book a flight from Chicago to Monterey (average of $80). Flying from Chicago to Monterey in December is currently the most expensive (average of $207). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Chicago to Monterey

See prices for flight routes from nearby airports that may be better suited for you.
O'Hare Intl to Las Vegas flights
O'Hare Intl to Los Angeles flights
O'Hare Intl to San Francisco flights
O'Hare Intl to Ontario flights
O'Hare Intl to Santa Ana flights
Midway to Las Vegas flights
O'Hare Intl to San Diego flights
St. Louis to Las Vegas flights
Midway to Los Angeles flights
O'Hare Intl to Palm Springs flights
Midway to San Francisco flights
O'Hare Intl to Burbank flights
O'Hare Intl to San Jose flights
O'Hare Intl to Sacramento flights
Rockford to Las Vegas flights
St. Louis to Los Angeles flights
O'Hare Intl to Reno flights
Midway to San Diego flights
St. Louis to San Francisco flights
Midway to Ontario flights
Midway to Santa Ana flights
O'Hare Intl to Oakland flights
Midway to San Jose flights
Midway to Palm Springs flights
St. Louis to San Diego flights
Midway to Sacramento flights
O'Hare Intl to Long Beach flights
Peoria to Las Vegas flights
Midway to Oakland flights
St. Louis to Ontario flights
O'Hare Intl to Santa Barbara flights
Moline to Las Vegas flights
St. Louis to Burbank flights
Midway to Burbank flights
St. Louis to Santa Ana flights
Decatur to Las Vegas flights
Moline to San Diego flights
St. Louis to San Jose flights
St. Louis to Sacramento flights
Midway to Reno flights
Bloomington to Las Vegas flights
Midway to Long Beach flights
St. Louis to Long Beach flights
Moline to Los Angeles flights
O'Hare Intl to Monterey flights
O'Hare Intl to Medford flights
St. Louis to Palm Springs flights
O'Hare Intl to Fresno flights
Midway to Fresno flights
Moline to Ontario flights

Top 2 airlines flying from Chicago to Monterey

Discover the top 2 airlines that operate flights from Chicago to Monterey. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated October 23, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$276Average$508FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$358Average$517FlexibilityNo cancel feeOn-time69%

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.