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Monterey

$139+ 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 1/31. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — MRY
Jan 7 — Jan 141
Wed 1/7
Wed 1/14
1 adult, Economy
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Cheap 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 December 8, 2025.

This United Airlines deal was found by Cheapflights users on 12/7. 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 12/177:10 amORD - MRY
1 stop8h 23mUnited Airlines
Wed 12/315:05 amMRY - ORD
1 stop7h 50mUnited Airlines
Deal found 12/7$380
This American Airlines deal was found by Cheapflights users on 12/7. 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 12/1710:24 amORD - MRY
2 stops10h 17mAmerican Airlines
Wed 12/3112:54 pmMRY - ORD
1 stop9h 22mAmerican Airlines
Deal found 12/7$385
This United Airlines deal was found by Cheapflights users on 12/7. 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 12/247:10 amORD - MRY
1 stop8h 35mUnited Airlines
Thu 1/15:05 amMRY - ORD
1 stop6h 14mUnited Airlines
Deal found 12/7$399
This United Airlines deal was found by Cheapflights users on 12/7. 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 12/257:10 amORD - MRY
1 stop8h 35mUnited Airlines
Wed 12/312:30 pmMRY - ORD
1 stop6h 44mUnited Airlines
Deal found 12/7$414
This United Airlines deal was found by Cheapflights users on 12/7. 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 12/257:10 amORD - MRY
1 stop8h 35mUnited Airlines
Thu 1/112:35 pmMRY - ORD
1 stop8h 25mUnited Airlines
Deal found 12/7$424
This Alaska Airlines deal was found by Cheapflights users on 12/5. 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.
Wed 12/248:39 amORD - MRY
1 stop7h 46mAlaska Airlines
Tue 1/66:00 amMRY - ORD
1 stop6h 37mAlaska Airlines
Deal found 12/5$432
This United Airlines deal was found by Cheapflights users on 12/6. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/319:10 pmORD - MRY
1 stop14h 38mUnited Airlines
Wed 1/78:20 pmMRY - ORD
1 stop7h 24mUnited Airlines
Deal found 12/6$463
This Alaska Airlines deal was found by Cheapflights users on 12/5. 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.
Wed 12/248:39 amORD - MRY
1 stop7h 46mAlaska Airlines
Mon 1/53:02 pmMRY - ORD
1 stop6h 57mAlaska Airlines
Deal found 12/5$473
This American Airlines deal was found by Cheapflights users on 12/7. 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.
Thu 12/1812:44 pmORD - MRY
1 stop8h 04mAmerican Airlines
Sun 1/47:18 pmMRY - ORD
1 stop8h 16mAmerican Airlines
Deal found 12/7$474

Find 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 December 8, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$260
(Kiwi.com)

One-way from

$139
(Alaska Airlines)

Popular in

December

Cheapest in

November

Average price

$744
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. 5% potential increase in price ($30 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($16 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 2025
Search Deals

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 December 8, 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

Sat 2/14

8:20 am-2:06 pm

1 stop7h 46m

Monterey Regional

Wed 2/18

2:43 pm-11:59 pm

1 stop7h 16m

$279

ChicagoMonterey

ORD - MRY

ORDMRY

Chicago O'Hare Intl

Sat 1/10

3:44 pm-11:26 pm

1 stop9h 42m

Monterey Regional

Tue 1/13

3:14 pm-11:37 pm

1 stop6h 23m

$279

ChicagoMonterey

ORD - MRY

ORDMRY

Chicago O'Hare Intl

Tue 2/3

9:00 am-2:37 pm

1 stop7h 37m

Monterey Regional

Sat 2/7

3:14 pm-11:37 pm

1 stop6h 23m

$279

ChicagoMonterey

ORD - MRY

ORDMRY

Chicago O'Hare Intl

Mon 2/9

9:00 am-2:37 pm

1 stop7h 37m

Monterey Regional

Sat 2/14

6:00 am-2:58 pm

1 stop6h 58m

$289

ChicagoMonterey

ORD - MRY

ORDMRY

Chicago O'Hare Intl

Thu 1/15

3:44 pm-11:26 pm

1 stop9h 42m

Monterey Regional

Tue 1/20

3:14 pm-11:37 pm

1 stop6h 23m

$289

ChicagoMonterey

ORD - MRY

ORDMRY

Chicago O'Hare Intl

Sun 1/11

3:44 pm-11:26 pm

1 stop9h 42m

Monterey Regional

Sat 1/17

3:14 pm-11:37 pm

1 stop6h 23m

$289

ChicagoMonterey

ORD - MRY

ORDMRY

Chicago O'Hare Intl

Wed 1/28

9:00 am-2:37 pm

1 stop7h 37m

Monterey Regional

Mon 2/2

3:14 pm-11:37 pm

1 stop6h 23m

$289

ChicagoMonterey

ORD - MRY

ORDMRY

Chicago O'Hare Intl

Mon 2/2

9:00 am-2:37 pm

1 stop7h 37m

Monterey Regional

Sat 2/7

3:14 pm-11:37 pm

1 stop6h 23m

$289

ChicagoMonterey

ORD - MRY

ORDMRY

Chicago O'Hare Intl

Tue 2/10

9:00 am-2:37 pm

1 stop7h 37m

Monterey Regional

Sun 2/15

6:00 am-2:58 pm

1 stop6h 58m

$289

ChicagoMonterey

ORD - MRY

ORDMRY

Chicago O'Hare Intl

Wed 2/4

9:00 am-2:37 pm

1 stop7h 37m

Monterey Regional

Sun 2/8

3:14 pm-11:37 pm

1 stop6h 23m

$289

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/7

Showing 1-10 of 20 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 December.
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 November 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 December 8, 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 December 8, 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
9,089 reviews

Boarding

7.7

Crew

8.1

Comfort

7.3

Overall

7.4

Entertainment

7.1

Food

6.6

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
9,089 reviews
United Airlines
7.4
Good
9,089 reviews

Boarding

7.7

Crew

8.1

Comfort

7.3

Overall

7.4

Entertainment

7.1

Food

6.6

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
11,045 reviews
United Airlines
7.4
Good
9,089 reviews

Boarding

7.7

Crew

8.1

Comfort

7.3

Overall

7.4

Entertainment

7.1

Food

6.6

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 7h 46m. 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 $342 round trip. American Airlines is 51% 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 November 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

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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 December 8, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$276Average$542FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$342Average$502FlexibilityNo cancel feeOn-time69%

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