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

Our cheapest airline available from Monterey to Chicago is Alaska Airlines. Our recent data shows that you can find tickets from as low as $345 on this airline. Additional options worth looking into are American Airlines and United Airlines, starting at $508 and $516 round-trip. Alaska Airlines is currently priced 41% below the average price you’ll pay for this route.

What are the cheapest airlines to fly from Monterey to Chicago one-way?

To fly one-way, consider booking your trip with Alaska Airlines, which is currently one of the cheapest options available, starting at $168. Hawaiian Airlines flights start at $276 while deals on United Airlines start at $347 one-way.

What is the cheapest day to fly from Monterey to Chicago?

Travelers seeking maximum savings on their Monterey to Chicago flight should consider departing on Friday at noon when fares are most often at their lowest. Wednesday afternoons flights should be avoided if possible as fares are typically the most expensive at this time.

What is the cheapest day to fly round-trip from Monterey to Chicago?

Sunday flights are found to be more expensive to fly from Monterey to Chicago. This shouldn’t discourage you from searching, as you can still find great deals by being flexible with your options. Use our search form to find deals on tickets to Chicago.

How far in advance should I book a flight from Monterey to Chicago?

Travelers have found it’s best to book a flight 35 days in advance to save up to 74% compared to booking the same week of travel. As your travel date approaches, the cost of this flight route may potentially increase. While opting to book 35 days out may not be an option for all, there are still additional ways to secure a deal in the near future. You might find a flight from Monterey to Chicago 1-2 weeks in advance for as low as $387, or $538 for flights within the next 24 hours.

What is the cheapest month to fly from Monterey to Chicago?

February can be a great time to fly to Chicago from Monterey with a flight ticket averaging about $340. Cheapflights users have found deals in the month of February for as cheap as $183. The most expensive prices can be found in the month of December.

Most accurate provider : When it comes to deals on Monterey-Chicago flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Monterey-Chicago flight deals on Cheapflights vs. FlightHub >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 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 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.

$168+ Flights from Monterey to Chicago

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Cheap flight deals from Monterey to Chicago

Most accurate provider	FlightHub 3 stars
Most trusted provider	FlightHub 2 stars
Round-trip from	$345 (Alaska Airlines)
One-way from	$168 (Alaska Airlines)
Popular in	January
Cheapest in	February
Average price	$520

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. 11% potential increase in price ($78 potential increase over avg. RT price).

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Cheapest flight prices on average. 5% potential price decrease ($30 potential savings vs. average RT price).

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Average for round-trip flights in April 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 April 22, 2025.

Sat 5/246:43 pmMRY - ORD

1 stop8h 57mAlaska Airlines

Tue 5/277:51 pmORD - MRY

1 stop24h 12mAlaska Airlines

Deal found 4/22

$345

Sat 7/56:00 amMRY - ORD

1 stop7h 45mAmerican Airlines

Sat 7/125:00 amORD - MRY

1 stop8h 28mAmerican Airlines

Deal found 4/22

$508

Sat 8/162:14 pmMRY - ORD

1 stop13h 25mUnited Airlines

Wed 8/208:49 amORD - MRY

2 stops14h 59mUnited Airlines

Deal found 4/22

$516

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 April 22, 2025.

Sat 5/246:43 pmMRY - ORD

1 stop8h 57mAlaska Airlines

Tue 5/277:51 pmORD - MRY

1 stop24h 12mAlaska Airlines

Deal found 4/22

$345

Sat 7/56:00 amMRY - ORD

1 stop7h 45mAmerican Airlines

Sat 7/125:00 amORD - MRY

1 stop8h 28mAmerican Airlines

Deal found 4/22

$508

Sat 8/162:14 pmMRY - ORD

1 stop13h 25mUnited Airlines

Wed 8/208:49 amORD - MRY

2 stops14h 59mUnited Airlines

Deal found 4/22

$516

Last-minute flights from Monterey to Chicago
Discover last-minute flight deals from Monterey to Chicago. Data last updated April 22, 2025 and is based on user searches.

Fri 5/211:22 amMRY - ORD

1 stop8h 37mAlaska Airlines

Wed 5/77:19 pmORD - MRY

1 stop17h 26mAlaska Airlines

Deal found 4/21

$670

Wed 5/78:10 amMRY - ORD

2 stops12h 57mUnited Airlines

Sun 5/118:45 amORD - MRY

2 stops13h 55mUnited Airlines

Deal found 4/22

$612

Sat 5/246:43 pmMRY - ORD

1 stop8h 57mAlaska Airlines

Tue 5/277:51 pmORD - MRY

1 stop24h 12mAlaska Airlines

Deal found 4/22

$345

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 April 22, 2025.

Tue 5/206:43 pmMRY - ORD

1 stop8h 57mAlaska Airlines

Deal found 4/22

$168

Fri 8/14:03 pmMRY - ORD

1 stop25h 43mMultiple Airlines

Deal found 4/22

$256

Fri 6/276:46 pmMRY - ORD

1 stop8h 54mHawaiian Airlines

Deal found 4/22

$276

Fri 6/272:14 pmMRY - ORD

2 stops22h 30mUnited Airlines

Deal found 4/22

$347

Cheapflights Fare Finder

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

Fly from

Fly to

Route

Depart

Return

Price

MontereyChicago

MRY - ORD

MRYORD

Monterey Regional

Sat 5/24

6:43 pm-5:40 am

1 stop8h 57m

Chicago O'Hare Intl

Tue 5/27

7:51 pm-6:03 pm

1 stop24h 12m

$345

MontereyChicago

MRY - ORD

MRYORD

Monterey Regional

Sat 7/5

6:00 am-3:45 pm

1 stop7h 45m

Chicago O'Hare Intl

Sat 7/12

5:00 am-11:28 am

1 stop8h 28m

$508

MontereyChicago

MRY - ORD

MRYORD

Monterey Regional

Sat 8/16

2:14 pm-5:39 am

1 stop13h 25m

Chicago O'Hare Intl

Wed 8/20

8:49 am-9:48 pm

2 stops14h 59m

$516

MontereyChicago

MRY - ORD

MRYORD

Monterey Regional

Tue 5/20

6:43 pm-5:40 am

1 stop8h 57m

$168

MontereyChicago

MRY - ORD

MRYORD

Monterey Regional

Fri 8/1

4:03 pm-7:46 pm

1 stop25h 43m

$256

MontereyChicago

MRY - ORD

MRYORD

Monterey Regional

Fri 6/27

6:46 pm-5:40 am

1 stop8h 54m

$276

MontereyChicago

MRY - ORD

MRYORD

Monterey Regional

Fri 6/27

2:14 pm-2:44 pm

2 stops22h 30m

$347

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/22

Most accurate provider: When it comes to deals on Monterey-Chicago flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Monterey-Chicago flight deals on Cheapflights vs. FlightHub >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 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 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, August is the cheapest month in which you can book a flight from Monterey to Chicago (average of $245). Flying from Monterey to Chicago in March is currently the most expensive (average of $321). 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 evening. If you’re flexible enough to do this you can expect to save up to 38% on your trip compared to booking a flight at noon.

Rainfall in Chicago by month

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.

Temperature in Chicago by month

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).

Reviews of airlines servicing Chicago

Alaska Airlines

8.0

Very good

9,906 reviews

Reviews

1 / 20

10.0

Excellent

Cheri,Jan 2025

FAT - SEA

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them

Alaska Airlines

8.0

Very good

9,906 reviews

Alaska Airlines

8.0

Very good

9,906 reviews

Reviews

1 / 20

10.0

Excellent

Cheri,Jan 2025

FAT - SEA

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them

Hawaiian Airlines

7.9

Good

2,392 reviews

Alaska Airlines

8.0

Very good

9,906 reviews

Reviews

1 / 20

10.0

Excellent

Cheri,Jan 2025

FAT - SEA

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them

United Airlines

7.4

Good

8,683 reviews

Alaska Airlines

8.0

Very good

9,906 reviews

Reviews

1 / 20

10.0

Excellent

Cheri,Jan 2025

FAT - SEA

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them

American Airlines

7.2

Good

10,000 reviews

Alaska Airlines

8.0

Very good

9,906 reviews

Reviews

1 / 20

10.0

Excellent

Cheri,Jan 2025

FAT - SEA

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them

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.
What are the cheapest airlines flying from Monterey to Chicago round-trip?
Our cheapest airline available from Monterey to Chicago is Alaska Airlines. Our recent data shows that you can find tickets from as low as $345 on this airline. Additional options worth looking into are American Airlines and United Airlines, starting at $508 and $516 round-trip. Alaska Airlines is currently priced 41% below the average price you’ll pay for this route.
What are the cheapest airlines to fly from Monterey to Chicago one-way?
To fly one-way, consider booking your trip with Alaska Airlines, which is currently one of the cheapest options available, starting at $168. Hawaiian Airlines flights start at $276 while deals on United Airlines start at $347 one-way.
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, August is the cheapest month in which you can book a flight from Monterey to Chicago (average of $245). Flying from Monterey to Chicago in March is currently the most expensive (average of $321). 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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Lansing

Valparaiso

Chesterton

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Top 2 airlines flying from Monterey to Chicago

Airline	Cheapest	Average	Flexibility	On-time
United Airlines	Cheapest$388	Average$676	FlexibilityNo cancel fee	On-time69%
American Airlines	Cheapest$401	Average$487	FlexibilityNo cancel fee	On-time71%

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$168+ 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 5/20. 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

1. Tell us where you want to go

2. Select your favorite providers

3. Compare prices and book

Cheap flight deals from Monterey to Chicago

Most accurate provider

Most trusted provider

Round-trip from

One-way from

Popular in

Cheapest in

Average price

Find 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 April 22, 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 April 22, 2025.

Cheapflights Fare Finder

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

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 April 22, 2025.

Rainfall in Chicago by month

Plan your trip to Chicago by taking into account the average rainfall totals by month.

Temperature in Chicago by month

Plan your trip to Chicago by taking into account the average temperature totals by month.

Reviews of airlines servicing Chicago

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?

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

What are the cheapest airlines to fly from Monterey to Chicago one-way?

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 Monterey?

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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 April 22, 2025.