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Monterey

$138+ 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 10/6. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — MRY
oct. 16 — oct. 231
jeu. 10/16
jeu. 10/23
1 adult, Economy
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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 septembre 16, 2025.

Round-trip from

$276
(Hawaiian Airlines)

One-way from

$138
(Alaska Airlines)

Popular in

March

Cheapest in

November

Average price

$686
From Chicago (CHI) to Monterey Regional
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One-way flight from Chicago (CHI) to Monterey Regional
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Highest demand for flights based on searches. 15% potential increase in price ($99 potential increase over avg. RT price).
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Cheapest flight prices on average. 5% potential price decrease ($28 potential savings vs. average RT price).
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Average for round-trip flights in September 2025
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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 septembre 16, 2025.

This Hawaiian Airlines deal was found by Cheapflights users on 9/16. 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 Hawaiian Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 10/73:50 pmORD - MRY
1 stop9h 01mHawaiian Airlines
sam. 10/117:57 pmMRY - ORD
1 stop8h 27mHawaiian Airlines
Deal found 9/16$276
This American Airlines deal was found by Cheapflights users on 9/13. 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.
mar. 11/117:00 amORD - MRY
1 stop7h 41mAmerican Airlines
mer. 12/312:45 pmMRY - ORD
1 stop6h 16mAmerican Airlines
Deal found 9/13$277
This Kiwi.com deal was found by Cheapflights users on 9/14. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 9/299:00 amORD - MRY
1 stop13h 35mMultiple Airlines
ven. 10/310:10 pmMRY - ORD
1 stop11h 41mMultiple Airlines
Deal found 9/14$281
This Alaska Airlines deal was found by Cheapflights users on 9/15. 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.
jeu. 12/48:00 amORD - MRY
2 stops17h 34mAlaska Airlines
dim. 12/76:00 amMRY - ORD
2 stops14h 30mAlaska Airlines
Deal found 9/15$287
This Alaska Airlines deal was found by Cheapflights users on 9/15. 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.
sam. 12/133:05 pmORD - MRY
1 stop10h 29mAlaska Airlines
lun. 1/126:00 amMRY - ORD
1 stop5h 59mAlaska Airlines
Deal found 9/15$307
This American Airlines deal was found by Cheapflights users on 9/15. 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.
mer. 11/125:18 amORD - MRY
1 stop8h 23mAmerican Airlines
mar. 12/212:31 pmMRY - ORD
1 stop7h 52mAmerican Airlines
Deal found 9/15$318
This American Airlines deal was found by Cheapflights users on 9/14. 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.
mar. 10/75:00 amORD - MRY
1 stop8h 39mAmerican Airlines
ven. 10/104:07 pmMRY - ORD
1 stop6h 23mAmerican Airlines
Deal found 9/14$322
This Kiwi.com deal was found by Cheapflights users on 9/15. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jeu. 10/236:40 pmORD - MRY
2 stops28h 40mMultiple Airlines
lun. 10/279:19 pmMRY - ORD
1 stop20h 15mMultiple Airlines
Deal found 9/15$324
This American Airlines deal was found by Cheapflights users on 9/14. 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.
mar. 10/710:32 amORD - MRY
2 stops9h 55mAmerican Airlines
sam. 10/114:07 pmMRY - ORD
1 stop6h 23mAmerican Airlines
Deal found 9/14$327

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 septembre 16, 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

sam. 10/18

3:50 pm-10:51 pm

1 stop9h 01m

Monterey Regional

sam. 10/25

2:53 pm-11:59 pm

1 stop7h 06m

$276

ChicagoMonterey

ORD - MRY

ORDMRY

Chicago O'Hare Intl

jeu. 12/4

3:05 pm-11:34 pm

1 stop10h 29m

Monterey Regional

dim. 12/7

6:00 am-2:09 pm

1 stop6h 09m

$277

ChicagoMonterey

ORD - MRY

ORDMRY

Chicago O'Hare Intl

ven. 11/14

4:40 pm-9:37 pm

1 stop6h 57m

Monterey Regional

dim. 11/16

2:30 pm-12:59 am

1 stop8h 29m

$277

ChicagoMonterey

ORD - MRY

ORDMRY

Chicago O'Hare Intl

mar. 11/11

7:00 am-12:41 pm

1 stop7h 41m

Monterey Regional

mer. 12/3

12:45 pm-9:01 pm

1 stop6h 16m

$277

ChicagoMonterey

ORD - MRY

ORDMRY

Chicago O'Hare Intl

jeu. 11/13

3:40 pm-9:37 pm

1 stop7h 57m

Monterey Regional

dim. 11/16

2:30 pm-12:59 am

1 stop8h 29m

$277

ChicagoMonterey

ORD - MRY

ORDMRY

Chicago O'Hare Intl

lun. 9/29

6:15 am-8:35 pm

1 stop16h 20m

Monterey Regional

ven. 10/3

10:10 pm-9:28 pm

2 stops21h 18m

$306

ChicagoMonterey

ORD - MRY

ORDMRY

Chicago O'Hare Intl

lun. 10/6

3:50 pm-11:37 pm

1 stop9h 47m

$138

ChicagoMonterey

ORD - MRY

ORDMRY

Chicago O'Hare Intl

mar. 10/14

3:50 pm-10:51 pm

1 stop9h 01m

$138

ChicagoMonterey

ORD - MRY

ORDMRY

Chicago O'Hare Intl

dim. 10/5

8:49 pm-8:29 pm

2 stops25h 40m

$164

ChicagoMonterey

ORD - MRY

ORDMRY

Chicago O'Hare Intl

mar. 12/23

3:37 pm-11:38 pm

1 stop10h 01m

$179

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/15

Showing 1-10 of 16 results
1
2

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, January is the cheapest month in which you can book a flight from Chicago to Monterey (average of $376). Flying from Chicago to Monterey in June is currently the most expensive (average of $486). 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 septembre 16, 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 morning tend to be the most expensive. A flight in the afternoon could potentially save you up to 20% on airfare.

How much does it cost to fly round-trip from Chicago to Monterey?

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 septembre 16, 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
8,924 reviews

Comfort

7.3

Overall

7.4

Entertainment

7.1

Food

6.6

Crew

8.1

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
8,924 reviews
United Airlines
7.4
Good
8,924 reviews

Comfort

7.3

Overall

7.4

Entertainment

7.1

Food

6.6

Crew

8.1

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
10,000 reviews
United Airlines
7.4
Good
8,924 reviews

Comfort

7.3

Overall

7.4

Entertainment

7.1

Food

6.6

Crew

8.1

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 Hawaiian Airlines, Alaska Airlines, and United Airlines fly from Chicago to Monterey in about 6h 57m. The time it takes to get you to your destination can typically vary by up to 3h 32m. Chicago and Monterey are separated by a distance of 1839 mi. This flight may include one or multiple stops.

  • 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 $268. 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, January is the cheapest month in which you can book a flight from Chicago to Monterey (average of $376). Flying from Chicago to Monterey in June is currently the most expensive (average of $486). 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

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Alternative routes for Chicago to Monterey

See prices for flight routes from nearby airports that may be better suited for you.
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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 septembre 16, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$268Average$552FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$358Average$532FlexibilityNo cancel feeOn-time69%

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