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Monterey

$114+ 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 12/11. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — MRY
Dec 6 — Dec 131
Sat 12/6
Sat 12/13
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 November 6, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$238
(KAYAK)

One-way from

$114
(Kiwi.com)

Popular in

March

Cheapest in

November

Average price

$358
Provider with most accurate pricing for Chicago (CHI)-Monterey Regional flight deals.
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Provider most trusted by Cheapflights users for Chicago (CHI)-Monterey Regional flights.
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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. 13% potential increase in price ($90 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 November 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 November 6, 2025.

This Alaska Airlines deal was found by Cheapflights users on 11/5. 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.
Sat 12/63:05 pmORD - MRY
1 stop10h 24mAlaska Airlines
Mon 12/86:00 amMRY - ORD
1 stop6h 09mAlaska Airlines
Deal found 11/5$258
This United Airlines deal was found by Cheapflights users on 11/5. 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.
Thu 11/278:47 amORD - MRY
1 stop6h 37mUnited Airlines
Tue 12/212:40 pmMRY - ORD
1 stop6h 28mUnited Airlines
Deal found 11/5$259
This American Airlines deal was found by Cheapflights users on 11/5. 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.
Sat 12/68:11 amORD - MRY
2 stops9h 41mAmerican Airlines
Mon 12/84:23 pmMRY - ORD
1 stop6h 08mAmerican Airlines
Deal found 11/5$264
This Alaska Airlines deal was found by Cheapflights users on 11/4. 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 12/38:55 amORD - MRY
1 stop16h 34mAlaska Airlines
Tue 12/96:00 amMRY - ORD
1 stop6h 09mAlaska Airlines
Deal found 11/4$270
This Alaska Airlines deal was found by Cheapflights users on 11/4. 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 12/28:59 pmORD - MRY
1 stop28h 30mAlaska Airlines
Mon 12/86:00 amMRY - ORD
1 stop6h 09mAlaska Airlines
Deal found 11/4$290
This Expedia deal was found by Cheapflights users on 11/6. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/143:05 pmORD - MRY
1 stop10h 24mAlaska Airlines
Tue 12/166:00 amMRY - ORD
1 stop6h 09mAlaska Airlines
Deal found 11/6$303
This Kiwi.com deal was found by Cheapflights users on 11/5. 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.
Thu 11/208:10 amORD - MRY
2 stops38h 49mMultiple Airlines
Mon 11/249:49 pmMRY - ORD
1 stop19h 50mMultiple Airlines
Deal found 11/5$311
This Alaska Airlines deal was found by Cheapflights users on 11/6. 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.
Sat 12/208:58 pmORD - MRY
1 stop28h 49mAlaska Airlines
Thu 12/258:02 pmMRY - ORD
1 stop8h 27mAlaska Airlines
Deal found 11/6$335
This American Airlines deal was found by Cheapflights users on 11/5. 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 11/111:28 pmORD - MRY
1 stop7h 13mAmerican Airlines
Wed 12/34:23 pmMRY - ORD
1 stop6h 08mAmerican Airlines
Deal found 11/5$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 November 6, 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

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

$258

ChicagoMonterey

ORD - MRY

ORDMRY

Chicago O'Hare Intl

Sat 12/6

3:05 pm-11:29 pm

1 stop10h 24m

Monterey Regional

Mon 12/8

6:00 am-2:09 pm

1 stop6h 09m

$258

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

6:00 am-1:59 pm

1 stop5h 59m

$258

ChicagoMonterey

ORD - MRY

ORDMRY

Chicago O'Hare Intl

Sun 2/22

9:00 am-1:56 pm

1 stop6h 56m

Monterey Regional

Sat 2/28

2:25 pm-11:59 pm

1 stop7h 34m

$258

ChicagoMonterey

ORD - MRY

ORDMRY

Chicago O'Hare Intl

Fri 1/16

4:10 pm-9:18 pm

1 stop7h 08m

Monterey Regional

Mon 1/19

8:20 pm-5:44 am

1 stop7h 24m

$259

ChicagoMonterey

ORD - MRY

ORDMRY

Chicago O'Hare Intl

Thu 11/27

8:47 am-1:24 pm

1 stop6h 37m

Monterey Regional

Tue 12/2

12:40 pm-9:08 pm

1 stop6h 28m

$259

ChicagoMonterey

ORD - MRY

ORDMRY

Chicago O'Hare Intl

Mon 12/8

5:25 pm-10:28 pm

1 stop7h 03m

Monterey Regional

Sat 12/13

12:45 pm-11:40 pm

2 stops8h 55m

$264

ChicagoMonterey

ORD - MRY

ORDMRY

Chicago O'Hare Intl

Tue 2/24

2:00 pm-11:25 pm

2 stops11h 25m

Monterey Regional

Sat 2/28

2:40 pm-11:10 pm

1 stop6h 30m

$264

ChicagoMonterey

ORD - MRY

ORDMRY

Chicago O'Hare Intl

Wed 12/3

8:55 am-11:29 pm

1 stop16h 34m

Monterey Regional

Mon 12/8

6:00 am-2:09 pm

1 stop6h 09m

$270

ChicagoMonterey

ORD - MRY

ORDMRY

Chicago O'Hare Intl

Tue 12/9

8:55 am-11:29 pm

1 stop16h 34m

Monterey Regional

Sat 12/13

6:00 am-2:09 pm

1 stop6h 09m

$270

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/5

Showing 1-10 of 24 results
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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 November.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy2 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*1 star
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 eDreams to be most consistent on Cheapflights vs. eDreams Users can find the same prices on Chicago-Monterey flight deals on Cheapflights vs. eDreams >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 eDreams the most. eDreams 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 $203). 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 November 6, 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 November 6, 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
9,007 reviews

Food

6.6

Comfort

7.3

Boarding

7.7

Overall

7.4

Crew

8.1

Entertainment

7.1

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
9,007 reviews
United Airlines
7.4
Good
9,007 reviews

Food

6.6

Comfort

7.3

Boarding

7.7

Overall

7.4

Crew

8.1

Entertainment

7.1

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
11,040 reviews
United Airlines
7.4
Good
9,007 reviews

Food

6.6

Comfort

7.3

Boarding

7.7

Overall

7.4

Crew

8.1

Entertainment

7.1

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 and Hawaiian Airlines fly from Chicago to Monterey in about 6h 56m. 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 $203). 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 November 6, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$276Average$545FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$358Average$530FlexibilityNo cancel feeOn-time69%

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