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Monterey

$180+ 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 8/15. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — MRY
Aug 26 — Sep 21
Wed 8/26
Wed 9/2
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 July 27, 2026.

This Kiwi.com deal was found by Cheapflights users on 7/27. 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.
Fri 10/236:50 am
ORD
-
MRY
1 stop10h 01m
Multiple Airlines
Mon 10/264:31 pm
MRY
-
ORD
2 stops27h 03m
Multiple Airlines
Deal found 7/27$314
This Kiwi.com deal was found by Cheapflights users on 7/23. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/51:02 pm
ORD
-
MRY
1 stop26h 41m
Multiple Airlines
Mon 11/93:07 pm
MRY
-
ORD
1 stop12h 28m
Multiple Airlines
Deal found 7/23$347
This Alaska Airlines deal was found by Cheapflights users on 7/22. 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.
Tue 8/182:20 pm
ORD
-
MRY
1 stop11h 38m
Alaska Airlines
Tue 8/252:43 pm
MRY
-
ORD
1 stop20h 39m
Alaska Airlines
Deal found 7/22$349
This American Airlines deal was found by Cheapflights users on 7/22. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/188:20 am
ORD
-
MRY
2 stops9h 18m
American Airlines
Tue 8/2512:40 pm
MRY
-
ORD
1 stop7h 20m
American Airlines
Deal found 7/22$354
This United Airlines deal was found by Cheapflights users on 7/22. 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 9/93:56 pm
ORD
-
MRY
1 stop7h 14m
United Airlines
Tue 9/153:38 pm
MRY
-
ORD
1 stop7h 21m
United Airlines
Deal found 7/22$359
This American Airlines deal was found by Cheapflights users on 7/24. 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 9/86:00 am
ORD
-
MRY
1 stop7h 42m
American Airlines
Tue 9/1512:50 pm
MRY
-
ORD
1 stop8h 53m
American Airlines
Deal found 7/24$360
This Jetabroad deal was found by Cheapflights users on 7/26. 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 Jetabroad is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/91:03 pm
ORD
-
MRY
2 stops12h 56m
Alaska Airlines
Wed 9/166:01 am
MRY
-
ORD
2 stops15h 58m
Alaska Airlines
Deal found 7/26$362
This Kiwi.com deal was found by Cheapflights users on 7/23. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/67:00 am
ORD
-
MRY
1 stop8h 43m
Multiple Airlines
Mon 11/93:07 pm
MRY
-
ORD
2 stops28h 27m
Multiple Airlines
Deal found 7/23$363
This Alaska Airlines deal was found by Cheapflights users on 7/22. 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 9/98:00 am
ORD
-
MRY
2 stops17h 59m
Alaska Airlines
Tue 9/152:43 pm
MRY
-
ORD
1 stop20h 39m
Alaska Airlines
Deal found 7/22$364
This Orbitz deal was found by Cheapflights users on 7/27. 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.
Fri 10/232:14 pm
ORD
-
MRY
2 stops10h 43m
Alaska Airlines
Mon 10/266:00 am
MRY
-
ORD
2 stops15h 59m
Alaska Airlines
Deal found 7/27$369

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 July 27, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$342
(Kiwi.com)

One-way from

$180
(Alaska Airlines)

Popular in

December

Cheapest in

July

Average price

$348
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
High demand for flights, 6% potential price rise
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($18 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in July 2026
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 July 27, 2026.
Use the filters below to find and compare flights from Chicago to Monterey that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

ChicagoMonterey

ORD - MRY

ORDMRY

Chicago O'Hare Intl

Tue 8/18

2:20 pm-11:58 pm

1 stop11h 38m

Monterey Regional

Tue 8/25

2:43 pm-1:22 pm

1 stop20h 39m

$349

ChicagoMonterey

ORD - MRY

ORDMRY

Chicago O'Hare Intl

Sat 10/24

4:20 pm-9:05 pm

1 stop6h 45m

Monterey Regional

Wed 10/28

2:05 pm-11:02 pm

1 stop6h 57m

$359

ChicagoMonterey

ORD - MRY

ORDMRY

Chicago O'Hare Intl

Tue 9/8

6:00 am-11:59 pm

2 stops19h 59m

Monterey Regional

Tue 9/15

2:43 pm-1:22 pm

1 stop20h 39m

$364

ChicagoMonterey

ORD - MRY

ORDMRY

Chicago O'Hare Intl

Thu 8/27

2:22 pm-11:59 pm

2 stops11h 37m

Monterey Regional

Mon 8/31

6:01 am-7:21 pm

1 stop11h 20m

$364

ChicagoMonterey

ORD - MRY

ORDMRY

Chicago O'Hare Intl

Wed 9/9

6:00 am-11:59 pm

2 stops19h 59m

Monterey Regional

Wed 9/16

6:01 am-11:59 pm

2 stops15h 58m

$370
Quickest round-trip

ChicagoMonterey

ORD - MRY

ORDMRY

Chicago O'Hare Intl

Sat 8/8

6:00 am-11:42 am

1 stop7h 42m

Monterey Regional

Sat 8/15

2:05 pm-8:27 pm

Nonstop4h 22m

$384

ChicagoMonterey

ORD - MRY

ORDMRY

Chicago O'Hare Intl

Fri 10/9

2:21 pm-10:57 pm

1 stop10h 36m

Monterey Regional

Mon 10/12

6:00 am-6:53 pm

1 stop10h 53m

$389

ChicagoMonterey

ORD - MRY

ORDMRY

Chicago O'Hare Intl

Wed 9/9

7:20 am-2:06 pm

1 stop8h 46m

Monterey Regional

Tue 9/29

6:23 pm-6:20 am

1 stop9h 57m

$389

ChicagoMonterey

ORD - MRY

ORDMRY

Chicago O'Hare Intl

Mon 8/17

7:59 pm-2:28 pm

1 stop20h 29m

Monterey Regional

Thu 8/20

2:43 pm-11:59 pm

1 stop7h 16m

$393

ChicagoMonterey

ORD - MRY

ORDMRY

Chicago O'Hare Intl

Sat 1/23

2:54 pm-2:33 pm

1 stop25h 39m

Monterey Regional

Mon 1/25

6:00 am-1:54 pm

1 stop5h 54m

$421

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/23

Showing 1-10 of 22 resultsSorted by cheapest first
1
2
3

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 July.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice 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, November is the cheapest month in which you can book a flight from Chicago to Monterey (average of $410). Flying from Chicago to Monterey in December is currently the most expensive (average of $602). 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 July 27, 2026.

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Chicago to Monterey as you normally would.

Weekly flight availability from Chicago to Monterey

Explore weekly flight availability from Chicago to Monterey. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated July 27, 2026.

The most flights from CHI to MRY are scheduled on a Monday (1 on average). You will have fewer flight options on Monday, which is when the least amount of flights are scheduled (1 on average).

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

Airfare is below average for this route at the moment.
Chicago to Monterey flights typically cost between $439 and $593 in October.
The cheapest round-trip price found within the last 5 days was $314 on Multiple Airlines (Oct 23-Oct 26).

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 July 27, 2026.
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
10,041 reviews

Crew

8.1

Comfort

7.3

Overall

7.4

Entertainment

7.1

Boarding

7.7

Food

6.6

Reviews

1 / 20
10.0
Excellent

Tim,May 2023

ORD - DLH

Didn’t have to wait long for the plane and was in the lounge through that time could relax there made it nice.
United Airlines
7.4
Good
10,041 reviews
United Airlines
7.4
Good
10,041 reviews

Crew

8.1

Comfort

7.3

Overall

7.4

Entertainment

7.1

Boarding

7.7

Food

6.6

Reviews

1 / 20
10.0
Excellent

Tim,May 2023

ORD - DLH

Didn’t have to wait long for the plane and was in the lounge through that time could relax there made it nice.
American Airlines
7.1
Good
11,836 reviews
United Airlines
7.4
Good
10,041 reviews

Crew

8.1

Comfort

7.3

Overall

7.4

Entertainment

7.1

Boarding

7.7

Food

6.6

Reviews

1 / 20
10.0
Excellent

Tim,May 2023

ORD - DLH

Didn’t have to wait long for the plane and was in the lounge through that time could relax there made it nice.

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. 3 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 1 inbound flight from Chicago per day.

  • How long is the flight from Chicago to Monterey?

    Airlines like Alaska Airlines fly from Chicago to Monterey in about 11h 38m. 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 $268. Additional round-trip tickets that might be worth considering are offered by United Airlines and Alaska Airlines, with the lowest prices starting at $307 and $352, respectively. 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, November is the cheapest month in which you can book a flight from Chicago to Monterey (average of $410). Flying from Chicago to Monterey in December is currently the most expensive (average of $602). 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.

Top 3 airlines flying from Chicago to Monterey

Discover the top 3 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 July 27, 2026.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$268Average$509FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$307Average$459FlexibilityNo cancel feeOn-time69%
Alaska AirlinesCheapest$352Average$458FlexibilityNo cancel feeOn-time75%

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