How long is the flight from Monterey to Chicago?

Departing from Monterey to Chicago will take you 6h 07m. 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 $276. American Airlines is currently priced 41% below the average price you’ll pay for this route.

In terms of precipitation, rainfall in Chicago ranges from 1.7 - 4.9 inches per month. August is typically the wettest month, when rainfall can reach 4.9 in. January is typically the driest time to visit Chicago when rainfall is around 1.7 in.

If weather is an important factor for your trip to Chicago, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 73.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 23.0 F).

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.

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.

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.

$139+ Flights from Monterey to Chicago

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

Airfare is below average for this route at the moment. Monterey to Chicago flights typically cost between $409 and $675 in January. The cheapest round-trip price found within the last 3 days was $279 on Alaska Airlines (Jan 20-Jan 24).

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Cheap 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 December 18, 2025.

Wed 12/176:00 amMRY - ORD

1 stop6h 09mAlaska Airlines

Mon 1/53:37 pmORD - MRY

1 stop10h 10mAlaska Airlines

Deal found 12/16

$469

Wed 12/313:02 pmMRY - ORD

1 stop21h 35mAlaska Airlines

Sun 1/48:58 pmORD - MRY

1 stop28h 49mAlaska Airlines

Deal found 12/16

$570

Thu 12/186:00 amMRY - ORD

1 stop7h 04mAmerican Airlines

Tue 12/235:00 amORD - MRY

1 stop9h 24mAmerican Airlines

Deal found 12/16

$593

Wed 12/2410:32 amMRY - ORD

1 stop6h 23mUnited Airlines

Wed 12/318:18 pmORD - MRY

2 stops15h 30mUnited Airlines

Deal found 12/17

$619

Wed 12/2412:35 pmMRY - ORD

1 stop6h 44mUnited Airlines

Sat 1/33:42 pmORD - MRY

2 stops20h 47mUnited Airlines

Deal found 12/17

$622

Best flights from Monterey to Chicago
Discover carefully curated flight deals from Monterey to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated December 18, 2025.

Tue 1/203:14 pmMRY - ORD

1 stop6h 23mAlaska Airlines

Sat 1/243:44 pmORD - MRY

1 stop9h 42mAlaska Airlines

Deal found 12/16

$279

Thu 1/89:52 amMRY - ORD

1 stop6h 07mAmerican Airlines

Sat 1/1012:10 pmORD - MRY

1 stop8h 55mAmerican Airlines

Deal found 12/16

$289

Mon 2/232:43 pmMRY - ORD

1 stop7h 16mAlaska Airlines

Sat 2/283:07 pmORD - MRY

1 stop10h 36mAlaska Airlines

Deal found 12/16

$289

Tue 1/203:14 pmMRY - ORD

1 stop6h 23mAlaska Airlines

Fri 1/233:44 pmORD - MRY

1 stop9h 42mAlaska Airlines

Deal found 12/16

$289

Thu 1/83:14 pmMRY - ORD

1 stop6h 23mAlaska Airlines

Sat 1/109:00 amORD - MRY

1 stop7h 37mAlaska Airlines

Deal found 12/16

$289

Sat 2/146:00 amMRY - ORD

1 stop6h 58mAlaska Airlines

Wed 2/188:20 amORD - MRY

1 stop17h 23mAlaska Airlines

Deal found 12/17

$290

Sat 1/176:00 amMRY - ORD

1 stop15h 37mAlaska Airlines

Wed 1/219:00 amORD - MRY

1 stop7h 37mAlaska Airlines

Deal found 12/15

$290

Mon 2/232:43 pmMRY - ORD

1 stop7h 16mAlaska Airlines

Fri 2/273:07 pmORD - MRY

1 stop10h 36mAlaska Airlines

Deal found 12/16

$298

Last-minute flights from Monterey to Chicago
Discover last-minute flight deals from Monterey to Chicago. Data last updated December 18, 2025 and is based on user searches.

Wed 12/176:00 amMRY - ORD

1 stop6h 09mAlaska Airlines

Mon 1/53:37 pmORD - MRY

1 stop10h 10mAlaska Airlines

Deal found 12/16

$469

Thu 1/13:02 pmMRY - ORD

2 stops12h 00mAlaska Airlines

Mon 1/58:58 pmORD - MRY

1 stop19h 27mAlaska Airlines

Deal found 12/17

$554

Sun 1/48:02 pmMRY - ORD

1 stop8h 27mAlaska Airlines

Wed 1/73:44 pmORD - MRY

1 stop9h 42mAlaska Airlines

Deal found 12/17

$369

Thu 1/83:14 pmMRY - ORD

1 stop6h 23mAlaska Airlines

Sat 1/109:00 amORD - MRY

1 stop7h 37mAlaska Airlines

Deal found 12/16

$289

Thu 1/89:52 amMRY - ORD

2 stops10h 26mAmerican Airlines

Sat 1/1010:10 amORD - MRY

2 stops10h 55mAmerican Airlines

Deal found 12/16

$330

Sat 1/176:00 amMRY - ORD

1 stop15h 37mAlaska Airlines

Wed 1/219:00 amORD - MRY

1 stop7h 37mAlaska Airlines

Deal found 12/15

$290

Sat 1/176:40 amMRY - ORD

2 stops12h 35mUnited Airlines

Wed 1/215:16 pmORD - MRY

1 stop6h 43mUnited Airlines

Deal found 12/16

$447

Tue 1/203:14 pmMRY - ORD

1 stop6h 23mAlaska Airlines

Sat 1/243:44 pmORD - MRY

1 stop9h 42mAlaska Airlines

Deal found 12/16

$279

One-way flights from Monterey to Chicago
Search for one-way flight options from Monterey to Chicago. Find affordable one-way fares based on user searches. Data last updated December 18, 2025.

Sat 1/103:14 pmMRY - ORD

1 stop6h 23mAlaska Airlines

Deal found 12/16

$139

Sat 1/1012:52 pmMRY - ORD

2 stops8h 52mAmerican Airlines

Deal found 12/16

$145

Sun 1/114:22 pmMRY - ORD

1 stop6h 01mAmerican Airlines

Deal found 12/16

$149

Tue 3/246:00 amMRY - ORD

1 stop5h 59mAlaska Airlines

Deal found 12/17

$184

Wed 12/2412:35 pmMRY - ORD

1 stop6h 44mUnited Airlines

Deal found 12/16

$185

Sun 1/185:00 amMRY - ORD

1 stop7h 55mUnited Airlines

Deal found 12/17

$195

Mon 4/277:25 pmMRY - ORD

1 stop9h 03mAmerican Airlines

Deal found 12/16

$203

Wed 12/312:30 pmMRY - ORD

1 stop6h 44mUnited Airlines

Deal found 12/17

$230

Sun 2/83:14 pmMRY - ORD

2 stops19h 56mAlaska Airlines

Deal found 12/16

$263

Fri 3/272:25 pmMRY - ORD

1 stop7h 33mAlaska Airlines

Deal found 12/17

$272

Tue 12/302:30 pmMRY - ORD

1 stop6h 44mUnited Airlines

Deal found 12/17

$286

Mon 12/296:00 amMRY - ORD

1 stop6h 37mAlaska Airlines

Deal found 12/17

$293

Find flight deals from Monterey to Chicago

Most accurate provider	eDreams 3 stars
Most trusted provider	eDreams 3 stars
Round-trip from	$279 (Alaska Airlines)
One-way from	$139 (Alaska Airlines)
Popular in	June
Cheapest in	March
Average price	$542

Provider with most accurate pricing for Monterey Regional-Chicago (CHI) flight deals.

Search Deals

Provider most trusted by Cheapflights users for Monterey Regional-Chicago (CHI) flights.

Search Deals

From Monterey Regional to Chicago (CHI)

Search Deals

One-way flight from Monterey Regional to Chicago (CHI)

Search Deals

Highest demand for flights based on searches. 15% potential increase in price ($86 potential increase over avg. RT price).

Search Deals

Cheapest flight prices on average. 4% potential price decrease ($21 potential savings vs. average RT price).

Search Deals

Average for round-trip flights in December 2025

Search Deals

Fly from

Fly to

Route

Depart

Return

Price

MontereyChicago

MRY - ORD

MRYORD

Monterey Regional

Tue 1/20

3:14 pm-11:37 pm

1 stop6h 23m

Chicago O'Hare Intl

Sat 1/24

3:44 pm-11:26 pm

1 stop9h 42m

$279

MontereyChicago

MRY - ORD

MRYORD

Monterey Regional

Thu 1/8

9:52 am-5:59 pm

1 stop6h 07m

Chicago O'Hare Intl

Sat 1/10

12:10 pm-7:05 pm

1 stop8h 55m

$289

MontereyChicago

MRY - ORD

MRYORD

Monterey Regional

Mon 2/23

2:43 pm-11:59 pm

1 stop7h 16m

Chicago O'Hare Intl

Sat 2/28

3:07 pm-11:43 pm

1 stop10h 36m

$289

MontereyChicago

MRY - ORD

MRYORD

Monterey Regional

Tue 1/20

3:14 pm-11:37 pm

1 stop6h 23m

Chicago O'Hare Intl

Fri 1/23

3:44 pm-11:26 pm

1 stop9h 42m

$289

MontereyChicago

MRY - ORD

MRYORD

Monterey Regional

Thu 1/8

3:14 pm-11:37 pm

1 stop6h 23m

Chicago O'Hare Intl

Sat 1/10

9:00 am-2:37 pm

1 stop7h 37m

$289

MontereyChicago

MRY - ORD

MRYORD

Monterey Regional

Sat 2/14

6:00 am-2:58 pm

1 stop6h 58m

Chicago O'Hare Intl

Wed 2/18

8:20 am-11:43 pm

1 stop17h 23m

$290

MontereyChicago

MRY - ORD

MRYORD

Monterey Regional

Sat 1/17

6:00 am-11:37 pm

1 stop15h 37m

Chicago O'Hare Intl

Wed 1/21

9:00 am-2:37 pm

1 stop7h 37m

$290

MontereyChicago

MRY - ORD

MRYORD

Monterey Regional

Mon 2/23

2:43 pm-11:59 pm

1 stop7h 16m

Chicago O'Hare Intl

Fri 2/27

3:07 pm-11:43 pm

1 stop10h 36m

$298

MontereyChicago

MRY - ORD

MRYORD

Monterey Regional

Sat 1/10

3:14 pm-11:37 pm

1 stop6h 23m

$139

MontereyChicago

MRY - ORD

MRYORD

Monterey Regional

Sun 2/8

3:14 pm-11:37 pm

1 stop6h 23m

$149

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/16

Showing 1-10 of 16 results

Compare providers for flights from Monterey to Chicago

Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Monterey to Chicago in December.

Provider	Price Accuracy	Trust Score*
eDreams	Price Accuracy3 stars	Trust Score*3 stars
FlightHub	Price Accuracy3 stars	Trust 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 $107). Flying from Monterey to Chicago in November is currently the most expensive (average of $210). 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?

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.

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

Reviews of airlines servicing Chicago

Read through reviews of airlines operating flights from Monterey to Chicago, such as Alaska Airlines, United Airlines, and American Airlines. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.

Alaska Airlines

8.0

Very good

11,474 reviews

Reviews

1 / 20

2.0

Mediocre

Art,Dec 2025

SAN - OGG

It was a five hour flight and my seat did not recline. I have had three back surgeries and I’m solid bone for my L3 vertebrae all the way to my tailbone. My body has never hurt so much. There was no TV on this flight and only a small can of soda was free.

Alaska Airlines

8.0

Very good

11,474 reviews

Alaska Airlines

8.0

Very good

11,474 reviews

Reviews

1 / 20

2.0

Mediocre

Art,Dec 2025

SAN - OGG

United Airlines

7.4

Good

9,092 reviews

Alaska Airlines

8.0

Very good

11,474 reviews

Reviews

1 / 20

2.0

Mediocre

Art,Dec 2025

SAN - OGG

American Airlines

7.2

Good

11,053 reviews

Alaska Airlines

8.0

Very good

11,474 reviews

Reviews

1 / 20

2.0

Mediocre

Art,Dec 2025

SAN - OGG

Related info for your journey

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 07m. 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 $276. American Airlines is currently priced 41% 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 $107). Flying from Monterey to Chicago in November is currently the most expensive (average of $210). 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

Lansing

Merrillville

Hammond

Porter

Benton Harbor

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Top 2 airlines flying from Monterey to Chicago

Airline	Cheapest	Average	Flexibility	On-time
American Airlines	Cheapest$268	Average$450	FlexibilityNo cancel fee	On-time71%
United Airlines	Cheapest$276	Average$664	FlexibilityNo cancel fee	On-time69%

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$139+ 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 1/10. Fares are subject to change and may not be available on all flights or dates of travel.

Find cheap flights from Monterey to Chicago with Cheapflights

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Cheap flight deals from Monterey to Chicago

Cheapest flights from Monterey to ChicagoExplore 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 December 18, 2025.

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 December 18, 2025.

Find flight deals from Monterey to Chicago

Most accurate provider

Most trusted provider

Round-trip from

One-way from

Popular in

Cheapest in

Average price

Cheapflights Fare Finder

Use the filters below to find and compare flights from Monterey to Chicago that are best for you.

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 December.

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.

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?

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 December 18, 2025.

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

Reviews of airlines servicing Chicago

Read through reviews of airlines operating flights from Monterey to Chicago, such as Alaska Airlines, United Airlines, and American Airlines. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.

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?

How long is the flight from Monterey to Chicago?

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

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

How can I find direct flights from Monterey to Chicago?

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

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

Traveling to a place near Chicago?

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Alternative routes for Monterey to Chicago

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Top 2 airlines flying from Monterey to Chicago

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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 December 18, 2025.