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$149+ Cheap flights from Monterey (MRY) to Chicago (CHI)

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 3/11. Fares are subject to change and may not be available on all flights or dates of travel.
MRY — CHI
Dec 2 — Dec 91
Tue 12/2
Tue 12/9
1 adult, Economy
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Cheap flight deals from Monterey to Chicago

Discover tips and strategies to find the most affordable flight options for your journey from Monterey (MRY) to Chicago (CHI). 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 2, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$288
(KAYAK)

One-way from

$149
(Alaska Airlines)

Popular in

November

Cheapest in

August

Average price

$1,124
Provider with most accurate pricing for Monterey Regional-Chicago (CHI) flight deals.
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Provider most trusted by Cheapflights users for Monterey Regional-Chicago (CHI) flights.
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From Monterey Regional to Chicago (CHI)
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One-way flight from Monterey Regional to Chicago (CHI)
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Highest demand for flights based on searches. 21% potential increase in price ($161 potential increase over avg. RT price).
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Cheapest flight prices on average. 9% potential price decrease ($50 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 Monterey to Chicago

Cheapest flights from Monterey to Chicago
Explore the most affordable flight options available from Monterey to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on November 2, 2025.

This KAYAK deal was found by Cheapflights users on 11/1. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/36:00 amMRY - ORD
1 stop6h 09mAlaska Airlines
Tue 12/93:05 pmORD - MRY
1 stop10h 24mAlaska Airlines
Deal found 11/1$288
This American Airlines deal was found by Cheapflights users on 11/1. 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 12/312:45 pmMRY - ORD
2 stops8h 50mAmerican Airlines
Tue 12/910:24 amORD - MRY
2 stops10h 17mAmerican Airlines
Deal found 11/1$309
This KAYAK deal was found by Cheapflights users on 11/1. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/36:00 amMRY - ORD
1 stop6h 09mAlaska Airlines
Mon 12/83:05 pmORD - MRY
1 stop10h 24mAlaska Airlines
Deal found 11/1$311
This KAYAK deal was found by Cheapflights users on 11/1. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/46:00 amMRY - ORD
1 stop6h 09mAlaska Airlines
Tue 12/93:05 pmORD - MRY
1 stop10h 24mAlaska Airlines
Deal found 11/1$320
This Kiwi.com deal was found by Cheapflights users on 10/31. 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.
Mon 12/299:52 pmMRY - ORD
1 stop14h 25mMultiple Airlines
Thu 1/19:33 pmORD - MRY
2 stops25h 51mMultiple Airlines
Deal found 10/31$347
This Kiwi.com deal was found by Cheapflights users on 11/1. 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.
Mon 12/226:02 pmMRY - ORD
1 stop18h 15mMultiple Airlines
Thu 12/257:44 pmORD - MRY
2 stops27h 40mMultiple Airlines
Deal found 11/1$357
This Kiwi.com deal was found by Cheapflights users on 10/31. 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.
Mon 12/299:52 pmMRY - ORD
1 stop14h 25mMultiple Airlines
Sat 1/37:44 pmORD - MRY
2 stops51h 18mMultiple Airlines
Deal found 10/31$360

Cheapflights Fare Finder

 
Customize your flight search to find flights from Monterey to Chicago 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 2, 2025.
Use the filters below to find and compare flights from Monterey to Chicago that are best for you.

Fly from

Monterey

Fly to

Chicago

Route

Depart

Return

Price

MontereyChicago

MRY - ORD

MRYORD

Monterey Regional

Wed 12/3

6:00 am-2:09 pm

1 stop6h 09m

Chicago O'Hare Intl

Tue 12/9

3:05 pm-11:29 pm

1 stop10h 24m

$288

MontereyChicago

MRY - ORD

MRYORD

Monterey Regional

Wed 12/3

12:45 pm-11:35 pm

2 stops8h 50m

Chicago O'Hare Intl

Tue 12/9

10:24 am-6:41 pm

2 stops10h 17m

$309

MontereyChicago

MRY - ORD

MRYORD

Monterey Regional

Wed 12/3

6:00 am-2:09 pm

1 stop6h 09m

Chicago O'Hare Intl

Mon 12/8

3:05 pm-11:29 pm

1 stop10h 24m

$311

MontereyChicago

MRY - ORD

MRYORD

Monterey Regional

Mon 2/23

2:25 pm-1:04 pm

1 stop20h 39m

Chicago O'Hare Intl

Sat 2/28

9:00 am-1:56 pm

1 stop6h 56m

$321

MontereyChicago

MRY - ORD

MRYORD

Monterey Regional

Tue 3/10

6:00 am-1:59 pm

1 stop5h 59m

Chicago O'Hare Intl

Tue 3/24

7:00 am-1:35 pm

1 stop8h 35m

$333

MontereyChicago

MRY - ORD

MRYORD

Monterey Regional

Wed 3/11

2:40 pm-11:10 pm

1 stop6h 30m

$149

MontereyChicago

MRY - ORD

MRYORD

Monterey Regional

Wed 12/17

6:00 am-2:09 pm

1 stop6h 09m

$159

MontereyChicago

MRY - ORD

MRYORD

Monterey Regional

Mon 1/12

6:07 pm-5:10 pm

1 stop21h 03m

$177

MontereyChicago

MRY - ORD

MRYORD

Monterey Regional

Fri 12/12

6:00 am-2:09 pm

1 stop6h 09m

$181

MontereyChicago

MRY - ORD

MRYORD

Monterey Regional

Sat 1/10

3:14 pm-11:37 pm

1 stop6h 23m

$184

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/31

Showing 1-10 of 16 results
1
2

Compare providers for flights from Monterey to Chicago

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 Monterey to Chicago in November.
ProviderPrice AccuracyTrust Score*
eDreamsPrice Accuracy3 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*1 star

*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 Monterey-Chicago flights, users find the pricing of eDreams to be most consistent on Cheapflights vs. eDreams Users can find the same prices on Monterey-Chicago flight deals on Cheapflights vs. eDreams >95% of the time. Price accuracy is based on data collected from Monterey-Chicago flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Monterey-Chicago 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 Monterey-Chicago 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 Monterey to Chicago

Have a flexible travel schedule? Discover the best time to fly to Chicago from Monterey 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 Monterey to Chicago

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

Currently, December is the cheapest month in which you can book a flight from Monterey to Chicago (average of $111). Flying from Monterey to Chicago in March is currently the most expensive (average of $194). 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 MRY to CHI?

Find hourly flight availability from Monterey to Chicago. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated November 2, 2025.

A simple way to save on the total cost of your ticket is to fly from Monterey to Chicago in the afternoon. If you’re flexible enough to do this you can expect to save up to 12% on your trip compared to booking a flight in the morning.

Reviews of airlines servicing Chicago

Get insights into the airlines that provide service to Chicago. 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 Chicago. Reviews last updated November 2, 2025.
Read through reviews of airlines operating flights from Monterey to Chicago, such as United Airlines and American Airlines. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
United Airlines
7.4
Good
8,997 reviews

Boarding

7.7

Crew

8.1

Food

6.6

Comfort

7.3

Overall

7.4

Entertainment

7.1

Reviews

1 / 20
8.0
Excellent

Anonymous,Oct 2025

YUL - ORD

Crew and customer service are 5 stars. I had a lot of luggage for a very long trip and they were nothing but helpful and found solutions to every problem. It was my first time flying with United, and they really are the friendly skies. Leg room however, on 2/3 flights was terrible. Same for entertainment: There was only a seat-mounted screen on 1/3 flights. It would have been nice to have on the longest leg of the journey.
United Airlines
7.4
Good
8,997 reviews
United Airlines
7.4
Good
8,997 reviews

Boarding

7.7

Crew

8.1

Food

6.6

Comfort

7.3

Overall

7.4

Entertainment

7.1

Reviews

1 / 20
8.0
Excellent

Anonymous,Oct 2025

YUL - ORD

Crew and customer service are 5 stars. I had a lot of luggage for a very long trip and they were nothing but helpful and found solutions to every problem. It was my first time flying with United, and they really are the friendly skies. Leg room however, on 2/3 flights was terrible. Same for entertainment: There was only a seat-mounted screen on 1/3 flights. It would have been nice to have on the longest leg of the journey.
American Airlines
7.2
Good
11,034 reviews
United Airlines
7.4
Good
8,997 reviews

Boarding

7.7

Crew

8.1

Food

6.6

Comfort

7.3

Overall

7.4

Entertainment

7.1

Reviews

1 / 20
8.0
Excellent

Anonymous,Oct 2025

YUL - ORD

Crew and customer service are 5 stars. I had a lot of luggage for a very long trip and they were nothing but helpful and found solutions to every problem. It was my first time flying with United, and they really are the friendly skies. Leg room however, on 2/3 flights was terrible. Same for entertainment: There was only a seat-mounted screen on 1/3 flights. It would have been nice to have on the longest leg of the journey.

Related info for your journey

Find useful and relevant information for your journey from Monterey to Chicago. 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 from for flights from Monterey to Chicago?

    Most people fly from Monterey Regional (MRY) if they book a flight from Monterey to Chicago. On average, Monterey Regional has 0 outbound flights to Chicago per day from 2 airlines. Monterey Regional is conveniently located just 3.2 mi from Monterey’s city center.

  • How long is the flight from Monterey to Chicago?

    Departing from Monterey to Chicago will take you 6h 09m. The distance from Monterey to Chicago is about 1839 mi. This flight may include one or multiple stops.

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

    Our cheapest airline available from Monterey to Chicago is American Airlines. Our recent data shows that you can find tickets from as low as $268 on this airline. An additional option worth looking into is United Airlines, starting at $443. American Airlines is currently priced 53% below the average price you’ll pay for this route.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Monterey to Chicago 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 Monterey to Chicago?

    Currently, December is the cheapest month in which you can book a flight from Monterey to Chicago (average of $111). Flying from Monterey to Chicago in March is currently the most expensive (average of $194). 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

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
Lansing
Hammond
Porter
Benton Harbor

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Top 2 airlines flying from Monterey to Chicago

Discover the top 2 airlines that operate flights from Monterey to Chicago. 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 2, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$268Average$449FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$443Average$676FlexibilityNo cancel feeOn-time69%

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